Article

EXECUTIVE LEADERSHIP ACCOUNTABILITY

January 2, 2024

SETTING THE CONDITIONS FOR SUCCESS


Accountability is the glue that ties commitment to results.


It is the process of clarifying expectations and holding people responsible for getting the desired results.


It involves objectively measuring outcomes against established goals, while rewarding achievement and confronting poor performance.


If you do a Google search you will find that many sources define “Accountability” in terms of assigning blame when something goes wrong, or like a parent checking up on and correcting a problem child. One well-known book (Crucial Accountability by Patterson, Grenney et al) describes it as “resolving violated expectations, broken commitments, and bad behavior.” We have a different perspective.


To be accountable means to be reliable, to take responsibility, and to meet commitments. This is behavior that produces results. To hold people accountable means to expect them to follow through, to reward them if they do and to ask for explanations and remedy the situation if they do not.


Sure, there may be times when a leader needs to confront poor performance in a forceful way, and this chapter offers tips to help you do that effectively. But in our view, a more productive mindset sees accountability as a supportive collaboration, a partnership between leader and followers, rather than a parent-child relationship, to enable people to successfully meet their commitments and goals.


Organizations succeed or fail based upon their results. As a leader, it is your job to create an environment in which everyone understands that achieving excellence is expected, and everyone gets the resources and support they need for maximum accomplishment. And just as the talent in your organization are all accountable to you, you are accountable to investors and to your Board (once you have one) to build a dynamic, successful organization. 


This article will help you establish procedures so that:


  • responsibilities and expectations are clearly defined
  • people know what is expected of them
  • processes are in place to monitor progress toward achieving those goals and therefore “violated expectations and broken commitments” arise as little as possible. 


First: Be accountable to yourself


If you want people to be accountable to you and the organization, you have to first be sure that you are accountable yourself, that you take responsibility for your commitments and follow through. What are you going to commit to do, and what results are you going to deliver, in order to move things ahead?


Do you say in meetings that you will do X and Y, and then do them? Or do you let them slide? Either way – especially if you fail to follow through – people will notice. As I will remind you throughout the book, when you are the leader, people are watching you. What you do or don’t do, how you interact with others, how true you are to your word, how fair your decisions appear to be, set the tone for others’ behavior and for the organization’s culture. 


If you don’t do what you said you will do, no one will pay attention to the next goal and the consequences that you set. If you don’t take deadlines, target dates and meeting times seriously, nobody else will. So, follow through. If you lack discipline in meeting your commitments, the people who work for you will model that, and you will be a negative role model.   
 

Set goals for yourself, your team, and the organization.

 

Just as you will be asking your teams to set goals and monitor progress toward achieving them, you need to do the same for yourself. Goal-setting – especially writing down your goals and referring to them frequently – is a tried-and-true method of supporting achievement on a personal level as well as for organizations. (See box, “Goal Setting”) You will probably share your organizational aspirations with your team in goal-setting meetings, such things as:


  • growing sales revenue 
  • Increasing average revenue per user
  • reducing customer acquisition costs
  • reducing churn rate
  • more effectively monitoring burn rate
  • raising a Series B round at the highest possible valuation 
  • increasing monthly recurring revenue from new sales
  • increasing the accuracy of forecasts and performance in preparation for an IPO and ultimately, being profitable and going public. 
  • Improve the recruiting process and in order to acquire more experienced engineers

 

If you are comfortable being a little self-revealing, you might also share some personal goals:


  • “I aim to start all meetings on time. I realize that being late isn’t fair to others.”
  • “I will try to delegate more and empower people to make decisions, rather than trying to do everything myself.”


People appreciate this kind of honesty and vulnerability; admitting that you are human doesn’t detract from your leadership ability! When people realize that you have these goals, they will help you achieve them. If you make a point of wanting to start meetings on time, they are more likely to show up rather than straggle in a few minutes late. If you say you want to delegate, someone will come to you and quietly say, “You said you wanted to delegate more responsibility. I feel I could take on the XYZ project. Please consider it.” 


Goal Setting


Goal setting is a tool that many successful executives and leaders use to maximize their effectiveness. If you are not familiar with this practice, google “goal setting” and you will be confronted by (as of today) 22,500,000 hits with titles like, “10 tips for setting goals” and “The 4 secrets of goal setting.” Use those sources to make your own goal-setting system.


Here are a few things to keep in mind:
 

  1. Divide your goals into various areas of your life, such as Personal (which might include health, learning, exercise, relationships, getting more rest, etc.) and Work/Career (delegate more, be sure to regularly communicate strategic priorities, etc.) Goals for the organization will likely require a separate list, that you may wish to develop in collaboration with others.
  2. Write down your goals, and regularly check to see how you are progressing. Consider using goal setting or project management software.
  3. Simplify. For each goal area (personal, health, etc. ) list 2 or 3 things you’d like to achieve in a given time-frame. If your list is too long, your chances of success diminish.
  4. Compete with yourself. Set measurable goals and aim to meet or beat them. Even hard-to-measure goals, such as being more patient and helpful to others, can fit here: you will know when you fail to measure up and can take aim and try again.

How to hold people accountable: helpful attitudes and behaviors


The most important and necessary step in holding people accountable is to let people know what you want them to accomplish, and what is required of them in order to get there, what their responsibility is. For this, you have to be absolutely clear in yourself what you want to achieve, and then communicate it clearly. It all starts with you.


Here are some important tips:

Trust but verify: Communicate that you believe the person can succeed but also be clear that you will be meeting with them regularly to track progress. This is not about micro-managing. In a lot of early-stage companies, those who are heading up engineering, marketing etc. are not deeply experienced. They may be doing the job for the first time. They can easily get over their heads and get stuck. If employees are afraid to go to the leader/entrepreneur for help getting unstuck, the entrepreneur gets frustrated because the desired results aren’t coming, and if the situation persists, the person ultimately gets fired. The following steps will help you avoid this outcome.

Be organized and structured in your approach. Set up a plan, goals, clear deliverables, milestones, and a schedule of meetings. 
The key to accountability is a disciplined process of planning, goal setting, and fixing timetables to allow you to assess progress and troubleshoot.

Commit to actively helping and supporting your people.
To make accountability work, you have to commit to giving people whatever help they need in order to accomplish their goals. The amount of support will vary a lot. (See Sidebar below, Situational Leadership) The level of competence and experience a person has will dictate the level of direction and support that you need to give them. When you have an experienced “old pro,” you will not need to provide much support or direction – they might know their area better than you do, and a more laissez-faire approach will be appropriate. You can ask them to set goals, put together a plan, and then come to you with it.

On the other hand, less experienced people need a higher level of direction. If you ask them to put together a plan, they may not know where to start. You have to be more involved, both in the planning for a project, and in the various stages of execution, and you may need to bring in some more experienced people to help run the function.

Let them know you expect them to meet their commitments and take the process seriously. You cannot run an organization that is growing and scaling without having a way to be disciplined about meeting commitments.

Set high but reasonable goals. 
If you set stretch goals that are too high, people will get discouraged, or will not take them seriously. If you expect 100% accomplishment of all the goals, they will not aim high and will set goals that are easy to reach. Goal setting works best as a collaborative process, challenging people when they come to you with their plans and timelines, but not imposing goals that will make them feel like a failure if they don’t hit their targets.
 

Don’t be afraid to confront poor performance but avoid being overly aggressive and confrontational in your attempt to challenge them. If people perceive you as intimidating, they won’t be likely to come to you for advice when they’re stuck, and they may need that advice in order to proceed.

Tip: Remember, it’s a collaboration, a partnership to ensure that commitments are met, and it is up to you to set it up to be effective.

Expect that people’s progress may be gradual. Emphasize sustained momentum rather than getting frustrated with any backsliding or lack of rapid results. Patience can be difficult for an entrepreneur, who feels intense pressure due to limited funding and limited time to produce results. You know your runway is short. You know what your burn rate is and how many months you have left. You have critical deadlines when results must be delivered. There are times when things are moving too slowly, and times of crisis, that demand a sense of urgency.

However, even though the start-up leader must be continually aware of things like the organization’s burn rate, a successful startup is often a marathon rather than a sprint. A continuous sense of urgency can create burnout, over-focus on tactical firefighting, and bad, ill-considered decisions. So, this is not black and white. You don’t want to be the boy who cried “wolf!” because people will stop taking you seriously, they won’t believe your sense of urgency is real after a while. And you can’t always lead as if your hair is on fire.

It depends on the situation. If you are running out of funds and you have to get funding in the next three months, you’d better have a sense of urgency! But if you push people too hard, they won’t be able to sustain it and will burn out.

Be supportive and try to inspire commitment but don’t be overly concerned about being liked. It’s not a popularity contest. If people need a push, it’s your job to push. 


ASK YOURSELF . . .

Now that you can see some of the attitudes and behaviors that support greater accountability, take a few minutes for a self-assessment to see how well you hold people accountable as a leader and what you might need to learn or improve:


  • Do I hesitate to hold people accountable because I am avoiding conflict?
  • Have I told myself that it’s easier to do the job myself than to hold others accountable for doing it?
  • Have I made sure people understand goals, expectations and standards and measures of performance that I am going to hold them accountable for achieving?
  • Have we discussed what are acceptable and unacceptable levels of performance?
  • Am I coaching when I see substandard performance?
  • Am I giving enough praise and recognition for improvements in performance and accomplishments? Is the praise timely (soon after the event) and specific?
  • Am I being too sensitive, too nice, too laissez faire?
  • Am I willing to make tough decisions when poor performance persists?
  • Am I focused on results?
  • Is our compensation program (bonuses, promotions) tied to actual performance?
  • Do I understand the difference between holding people accountable for meeting their commitments and responsibilities, and micromanaging, looking over their shoulder and not giving them enough discretion for decision-making.?


Impact Of High Levels Of Accountability


The benefits for the organization of holding people accountable for their progress and achievements is huge. Our research shows that it is one of the most important factors in an organization’s success. Here are some of the payoffs we have seen: New ideas will be implemented more quickly because people are aligned behind common objectives.
 

  • The organization will more rapidly respond to trends and threats and be able to seize business opportunities
  • The organization will hit its targets and more efficiently achieve its goals
  • The organization will more quickly detect and correct errors and learn from mistakes that hamper success
  • The organization will gain a reputation as a meritocracy, and will attract and retain the best people in the industry
  • The organization will continue to develop new solutions and approaches that will allow it to adapt to changing business conditions

 

Key Elements of Accountability

[or, How to Hold People Accountable]


The remainder of this chapter is based on a simple model of key steps to promote greater accountability in your organization. While going through these steps, keep the following fundamental principles in mind:


The leader or manager’s job is to achieve desired results by working through others, and providing the necessary direction and support they need to succeed:

  • By collaboratively defining success 
  • Facilitating an environment in which employees can perform at their best
  • Providing whatever resources teams and individuals need to succeed 
  • Checking in with them often enough to provide necessary guidance 
  • Coaching when needed
  • Monitoring results periodically to keep projects on track
  • Recognizing, appreciating, and rewarding good work
  • Adjusting your leadership and coaching according to their level of competence 
  • Confronting poor performance and helping them correct mistakes and solve problems
Managing Accountability is a process.

Step One: Define Success, Set Clear Goals and Measurable Expectations


Setting goals and expectations and establishing measurable outcomes for each objective is the key to managing accountability. Make sure people understand the goals they are accountable for achieving, what they “own” and are responsible for. Everything flows from this. “Well begun is half done” - do this right and you’re on the road to success.

 

  • Define what success looks like. What are we striving for? Employees and team members must understand that they are expected to deliver results, and will be held accountable for achieving – or not achieving – their goals and objectives. 


Clear communication is crucial. People cannot read your mind, and they don’t always see things the way you do.


Communicate expectations in clear, specific language. Team members should be able to answer the question, “What exactly am I responsible for? How will I know if I have met expectations?" And that failing to meet their commitments has consequences: “People who don’t deliver on their commitments don’t last long at this company.”
 

Goals should be specific, measurable and verifiable by objective standards, and time specific. Write them down. State goals in terms of desired results and the actions needed to achieve them : what you want done and when you want it.

 

“Sudhir is very clear with team members when communicating his expectations and assigning duties and he holds them accountable for getting results. He insists that his people set objective and realistic goals and that they strive to achieve the desired results. ”  


Use the SMART formula for your goals. They should be:

S pecific

M easurable

A ctionable

R ealistic

T ime-related

 

Be crystal clear about deliverables, dates, and who owns what.


Goals should be attainable but still stretch people. They should have a 70-80% chance of success.


Ask, “How will we tell if the goal is accomplished?” What milestones will have been reached? What metrics will show us whether enough progress is occurring or that performance is up to expected to standards.


Ask, “What outcomes could we agree on as a measure of success?”


Be willing to adjust and reformulate goals as the project advances and new conditions arise.


“Joanna will take as much time as necessary to ensure you understand exactly what her expectations of you are. She will then expect you to give her your very best and will not hesitate to let you know if you are not. She is very fair and will work with you if needed.”
 

Set Milestones 

Stages of achievement image.

Milestones mark important stages of achievement of a project. Setting milestones provides a way to monitor progress and track where you are in the process of taking an idea from inception through various stages of development to completion. Project milestones help everyone involved recognize and work toward specific goals. They help ensure that projects are completed and delivered on time and turn out as expected and desired.


Setting milestones is like creating a roadmap, or better, a timeline, as each step is designated with a date. Successful achievement of predefined milestones indicates that a project is on track. Failure to meet a milestone indicates that a project is not proceeding according to plan.


Milestones do not have to be only for major steps; achieving a series of minor milestones gives the team a sense of momentum and boosts confidence.


Typical milestones:

  • Concept approval or approval of a design stage
  • Obtaining funding
  • Identifying staffing needs, hiring or assigning people for key roles
  • Completion of a project phase or stage
  • Product testing started/completed
  • Bugs fixed
  • Product operational


All projects should have at least 4 major milestones:

  1. requirements complete,
  2. design complete,
  3. code complete and test ready,
  4. product shipped/accepted/deployed.
     

Engage, don’t impose


Involve talent in goal-setting and creating milestones. Don’t just impose expectations. Get their understanding and input. Set expectations together, through dialogue.


Don’t micromanage. Try to establish a genuine partnership, an attitude of collaborative inquiry in setting and monitoring goals.

 

Avoid falling into a parent/child relationship of micromanaging – checking up on them too often or looking over their shoulder. When the leader micromanages, team members feel distrusted. Once everyone knows what is expected of them, back off and let them work. 

 

Micromanaging focuses on process and attempts to control it; accountability focuses on outcome and getting results.

Empower your team to succeed. You are interested in outcomes, not how people get there. Trust them to figure it out. They don’t have to do it your way in order to get good results.


“Genevieve is the exact opposite of a micro manager - which is exactly what makes her so effective. She gives a task and allows completion. She isn't so concerned about making sure it is done ‘her way’ but rather about making sure it is done. She provides responsibility to those below her which is appreciated.”


People are more motivated when they have a say in how goals are set and measured. Motivation rises when they feel that what they do matters, so remind them. Show them how their function and their team contributes to the success of the whole. Get their skin in the game. 

“It doesn’t make sense to hire smart people and then tell them what to do.

We hire smart people so they can tell us what to do.” – Steve Jobs

SITUATIONAL LEADERSHIP


The premise of Situational Leadership is that your leadership style should be adjustable and adaptable, relative to the level of “readiness” – competence and motivation – of the people you are responsible for leading. (Some call this “tailoring your message to your target audience.”) The takeaway: it is your responsibility as the leader to figure out the leadership style that will work best for specific talent and team members.


For example, with experienced, competent people who have bought into your goals, a more supportive and laissez-faire style works well, while neophytes will likely require more support and help setting direction, identifying goals, and even figuring out tactics to achieve those goals. 


There are many variations of this theory, perhaps the most well-known coming from Ken Blanchard and Paul Hersey, who designated four main styles:

  • Directing  – The leader makes the decisions, sets the objectives, directs others on what to do and how to do it, and then closely supervises. This is a very top-down approach, with mostly one-way communication, recommended for new employees or people with the lowest levels of both skill and prior experience.
  • Coaching  – Rather than dictate to employees, leadership “sells” their ideas and plans, explaining and persuading, allowing for discussion and input. This is effective for people with more experience and skill, but who may lack motivation or confidence.    Supporting  – Employees have more responsibility for decision making. Leaders are available to provide direction but give more attention to feedback and support.
  • Delegating – Leaders provide minimum guidance and follow-up, delegating authority to employees to make decisions and plan strategies for implementation. The more capability they demonstrate, the more autonomy you can give them. The highest level is empowerment: enabling employees to set their own work goals, make decisions, solve problems on their own, and take responsibility for the result.


“Ricardo recognizes his high performers and gives them flexibility in innovating and determining future paths for their projects and careers.”

Supportive vs Directive Behavior diagram.

S1 – Directing: The leader defines roles and sets goals, tells talent what tasks to do as well as how to do them. Communication is primarily top down and one directional. Effective for people with low competence.
S2 – Coaching/Selling: For people with greater competence than S1, the leader serves as motivator and coach.
S3 – Supporting/Facilitating:  A more collaborative relationship in which leader and followers share in decision making. Employees are more competent and aligned, but leader may still need to provide motivation or coach some skills.

S4 -  Delegating: Competent and motivated talent now need little direction or support from leaders, who can delegate tasks and stand back and let talent run with the ball.


Could conclude at the bottom,
“Leaders need as many people as possible who are in the bottom left quadrant: self-starting, capable, competent.” 

Step Two: Coach, Develop, and Support

Develop and support diagram.

One of the defining characteristics of entrepreneurs is that they have a high need for autonomy and independence. They are often non-conformists who do not like to be controlled or told what to do. As a result, when they take on a role as leaders – often their first time managing anything – they may fail to provide sufficient clarity about purpose and goals to their direct reports. But not everyone is an independent self-starter like they are. One of their lessons is to recognize that both individuals and the organization as a whole need the direction and support that only they, as the leader, can provide.


The amount of direction and support will vary, depending on how experienced and competent a person is. A more capable and experienced person needs less of your attention than someone who is new to the job or to the organization. (See Situational Leadership image below)

A diagram of situational leadership by hersey blanchard

The ideal is to have employees who are competent and self-directed. But even someone who is knowledgeable may lack motivation, and your job then becomes to light a fire under them, giving support and encouragement.


The main question you need to ask yourself is, How can I ensure that they have the best chance to achieve the goals we have set together? This is the underlying attitude that will make the collaboration effective and set people up for success.


  • Provide the Resources Needed for Success. Needed resources may include
  • More team members with experience and domain expertise
  • Funding necessary to get the job done
  • Information that will enable them to make good decisions and set the right priorities
  • Connections who can help, support, and mentor them
  •  Invest in training and developing the skills critical to achieving your strategic objectives
  • Make sure people are prepared to do the tasks assigned to them. Provide training where it is needed.
  • Don’t assume people will always figure it out on their own.
  • Successful leaders and their organizations are adept at setting goals and then helping employees attain those goals through training, coaching, and doing whatever it takes to move forward. Setting goals and then throwing people in the deep end of the pool with the hope that they will swim rather than sink – that they will figure it out and come through with results – is not an effective strategy. 
  • Make sure you have the right people – in the right roles
  • Is current talent capable not only of meeting present demands, but also scaling, growing the organization? If you see that some people are over their heads as growth and success transform the company, you may need to make some changes in personnel.
  • This is especially true if you do not have time to coach, train, and develop the people you have. Coaching everyone is not feasible, nor is it necessarily in the organization’s best interest, especially if the timeline is short.
  • Letting people go can be difficult for you if someone has been loyal and hard-working, perhaps part of the original team, yet is now struggling to keep up. Possible solution:  See if you can retain the person, but move him/her to a position better fitted to their capabilities, or bring in a more experienced person, from whom they can learn.
  • In addition to the right people, you need enough people. You may have one engineer developing a product or feature, but to get it out the door in the time frame you have set, you may need three.
     

Determine and allocate the financial resources that are needed


How are you going to pay for those additional engineers? (Or whatever else you need.) Obviously, budgets are a constraining factor. If the project is critical, you may need to find resources elsewhere, such as moving somebody off a non-critical project.  


Step Three: Monitor

A diagram of managing accountability is a process

Monitoring progress is a vital part of accountability. As the leader, you need to set clear, measurable goals, get the process of achieving those goals started, keep it moving along, and regularly monitor progress. Establish not only a final goal, but interim objectives to mark successful, partial progress.


Consider using OKR software to help set, align, and track progress, which can be very helpful in clarifying desired results, setting up timelines and delivery dates, and tracking progress. We’ll talk about OKRs more fully later in the chapter. Check in periodically, both in an informal way and through the objective measures and metrics you have established, to ensure that things are progressing, and be there to help if people are encountering difficulty. This does not mean interfering or micromanaging.


Tips for effective monitoring:


  • It is important to formally and informally review plans and progress. Set up regular meetings as a routine. Tip: Don’t only call meetings when there are problems.
  • If you feel it would be helpful, have employees send you progress reports at specified intervals. (See below)
  • Set up metrics and objective measures of success and progress. Establish benchmarks. Without data, how will you measure progress? 
  • Use tools such as OKR software to determine whether people are hitting the performance targets they have been assigned or have agreed to meet. 
  • Establish the expectation that you want to hear about problems before they become serious.
  • Create an atmosphere of trust, in which people feel you are there not to judge them but to help them be successful. Then they will not be afraid to come to the boss for help when they become stuck. Otherwise people may hide the difficulties they are encountering.


Important:  If problems are not brought up, and the employee continues to be stuck, the leader may become frustrated because expected results are not coming. This may erupt as anger and/or overly aggressive, combative, confrontational behavior. Try to avoid this, by building trusting relationships and encouraging people to bring up problems while they are still minor, rather than letting them grow.  On the other hand, a little “tough love” may sometimes be needed to help the person wake up to his/her responsibilities and get back in focus.


Progress Reports


Progress reports on ongoing projects, made accessible to all stakeholders, can provide continuing, transparent assessments of the project’s status. They are helpful for those directly involved in the project, for you as the leader, and for interested stakeholders who do not have ready access to the project or team.


One of the great benefits of progress reports is that they help to identify problems and risks early, so course corrections can be made in a timely way.


Written reports require some time for reflection and formulating ideas in more depth and detail than a verbal check-in, so we recommend them. Progress reports are not necessary in all cases, but If you feel you’d like to receive reports to be sure the goals you set are being met:
 

  • Establish a schedule for reports to be submitted
  • You may need to help design the format of the progress report and what it should include
  • Designing the report will take a little time, but once it’s done, subsequent reports will just be about filling in the needed information
  • If deadlines are missed, ask for an explanation of why, and how the individual or team plans to correct the situation

 


A typical Progress Report might include some or all of these topics:
 

  1. Key owners or project manager of each deliverable
  2. Project scope (example: one-year project involving 5 departments and $14 million) 
  3. Brief verbal summary including
  4. Current project status including percentage completed
  5. Major deliverables completed
  6. Milestones reached
  7. Key priorities for the upcoming week/month 
  8. Is the project on time and on budget? 
  9. Important decisions needed 
  10. Project performance rating: red, yellow, or green
  11. Green = on target (project deliverables are on track and delivery is on target for projected date)
  12. Yellow = at risk (project is X percentage complete and in X phase] 
  13. Red = off-track (project is delayed) 
  14. Key Milestones: milestones scheduled for achievement since the last report, and performance against those milestones
  15. Review: What is the impact of achievement or non-achievement of key milestones for the previous period?
  16. Budget: planned expenditure, actual expenditure, surplus, problems
  17. Timing: original planned completion date, current planned completion date, actual completion date (for a completed project)
  18. Brief summary of key accomplishments for the last period
  19. Important risks for next period?
  20. Additional issues

 

When a problem comes to your attention, try to understand what has happened.

  • Did the person know and understand what was expected?
  • Did you communicate expectations clearly?
  • Did they have an effective plan of action? 
  • Did they diagnose the problem accurately?
  • Did they exercise good judgment?
  • Did they not have the skill to solve the problem?

 
Help them analyze and understand the difficulty, but in most cases, you are not the person responsible for solving the problem, you are there to help and to brainstorm with them.

Organize a skip-level meeting.

 

If you feel the need for a broader perspective on issues within the organization, you might schedule a “skip-level” meeting, where you meet one on one with the people directly involved in a project, for example the engineers rather than just the head of engineering.


Leaders sometimes get isolated from the “grass roots” level of activity, especially in bigger companies, and this is never healthy.


Skip-level meetings should be seen as a common, generic phenomenon, so managers don’t feel they are being singled out to be checked up on. It is okay for them to sometimes attend these meetings, but you need to tell them, “Sometimes it’s important for you not to be there, so people feel free to speak their minds.” (See image, Questions to Ask at a Skip-level Meeting)

For Teams:


  • Are you getting the cooperation you need from other functions and teams?
  • What are some of the things your team has accomplished in the last few months that you feel most proud of?
  • What are the biggest challenges your team faces?
  • Are there any specific obstacles holding you back from achieving your goals? What could company leadership do to remove the obstacles and help you be more successful?
  • What can we do to more quickly and efficiently bring in needed talent?

 
For a one-on-one: 

  • What parts of your job give you the most satisfaction and feeling of accomplishment?
  • What do you like most about your job, and about working here? Least? 
  • Is it clear to you how your job fits into the company mission, vision, and strategy?
  • What could be done to make this a better place to work?
  • What are the areas of inefficiency you see, that get in your way?
  • What are your biggest sources of frustration?
  • What made you interested in joining our company? What were you most excited about when you started? Is it working out the way you hoped?
  • If you were CEO, what would you do differently, emphasize or de-emphasize?
  • Do you feel that people get enough recognition for work well done?
  • If you could change one thing about your job, or about the company, what would it be?
  • What are your personal career interests and aspirations? How can we help you fulfill them here?
  • If you encounter a problem you can’t solve, where do you go for help and support?

 

Learn about your people through surveys

 

To learn more about individuals in the organization, as well as about morale and engagement in the company as a whole, you can make use of various kinds of survey instruments.


Two examples:

  • 360 degree multi-rater feedback surveys - these gather assessments from an employee’s colleagues, supervisors, and subordinates to create a picture of their performance.
  • Engagement surveys - these gauge overall employee engagement, their job satisfaction, enthusiasm, and commitment to the organization, their trust in management and relationship with their manager, their sense of the company atmosphere, and so on.

 

 

Create a true meritocracy by objectively assessing performance and putting the most capable people in critical positions

 

One of the keys to keeping top talent is to create a meritocracy, using objective criteria to determine how well people are performing and living up to their commitments and responsibilities, and rewarding those who do well.


Advancement in the company, in a meritocracy, is not based on subjective evaluation, political clout, or whether you are the boss’s brother, but on whether you are actually delivering results.

Don’t expect people to do it your way

 

You are in the position you’re in because your way of doing things was successful. Your route up to the mountaintop is what got you there. But there are other routes. So it’s best to focus on results. Give people a chance to find their own way. Of course you will have processes in place to measure their success and redirect them if they’re heading toward a cliff, but as long as the needle is moving, and the metrics and milestones show that progress is being made, try to be open and supportive of alternatives.


Tip: Experienced, capable people do not want to be told what to do. You will lose them if you insist on micromanaging, or that everything be done your way.
 

Provide regular, honest feedback about performance

 

Discuss with people on every level what are acceptable and unacceptable levels of performance.


It is the responsibility of leaders and managers to provide people with direct feedback about their performance. People are usually eager to receive feedback. They want to know what they are doing well, and how they can improve.


“With James you always know how you are performing. You know the goals of the operation as well as your personal goals. Some people have a hard time with James because he is upfront and honest on your performance and most people aren't used to having this honest discussion. Many leaders beat around the bush on performance but James doesn't”.


This doesn’t mean they won’t get defensive if you let them know where they fall down and need improvement. But if you have objective data, such as from the 360, an engagement survey, and the fact that you talked to people at a skip-level meeting about their performance, they are likely to listen.


Based on whatever metrics you are using to monitor performance, offer praise and recognition for meeting their goals, and hold them accountable and offer suggestions for improvement when they don’t.


It is better to provide feedback early and often rather than letting problems grow and fester.


Giving feedback throughout the life of a project allows for adjustments when necessary, and prevents surprises at the end. A common failing, especially among inexperienced leaders, is that they tend neither to offer enough recognition for work well done, nor are they direct enough in confronting poor performance, giving forceful feedback when there is a problem. [See Step Four below, “Reward and Confront”]


 
Important: Be sure people really understand that your goal in pointing out mistakes and making suggestions is not to criticize but to help them improve their effectiveness. “We’re all in this together.”


 "
Heidi not only holds people accountable, but she also makes herself available – her door is always open for you to come and ask for help to achieve results. If she is not able to help, she will seek help from other resources.”


Don’t wait for end-of-quarter or year-end reviews to give feedback, when it is too late.
 

Check-ins


The “check-in” slots that you see between major phases in the Accountability model indicate times for the leader to check in with subordinates to ascertain how things are going. This can take the form of a meeting, whether one-on-one or with the team, or it can be as informal as running into each other in a hallway and asking, “How are things going with the ABC project?” or “What’s the latest on the product launch?” It’s good to schedule check-ins regularly and keep to the plan without allowing the latest “fire” to control your schedule.


When you check in:

  • Listen to what they’re doing
  • Ask probing questions, don’t just accept “Fine, it’s going great.” Find out if there are any challenges, if they are stuck, or what are the specifics of their latest progress 
  • Offer support if they are stuck or have questions
  • Challenge them: to raise the bar, to question processes, to make an effort to hit targets, to improve the level of output. Sometimes, with a high achiever, all you need to say is, “I think you could do a little better job on X,” or, “If you put in a little more time and thought, I think this could be improved,” or, “I’m sure you can find a way that you and your team could get this back on track,” or, “Can you think of a way to achieve this goal more quickly or efficiently?”

 

Check-ins are valuable at any point, to let the talent know your attention is on what they are doing, and for you to keep your finger on the pulse of the company.

Make a priority of managing your time.

 

If you are new to management and leadership, it may be difficult for you to switch from being a “doer” to being manager of a group of doers, but it is a necessary transition if you are going to survive without burning out. As time goes by and the company grows and scales, you will need to spend more time working on the company, rather than in the company.

A powerful system for increasing accountability: OKR = Objectives and Key Results

 

The OKR system, created by former Intel CEO Andy Grove and popularized by venture capitalist John Doerr, was designed to align all members of the team behind a common set of objectives. Each manager and his or her reports work together to establish objectives and key results. They set timelines and dates and set up metrics to track progress, milestones, and steps of achievement. The organization as a whole has strategic objectives and key results that it is looking to accomplish; each function has objectives and key results; and within the function all the talent – engineers, sales, etc. – have their individual objectives and key results.


Goals and results can be displayed openly at all-hands meetings for the entire organization to see. Many companies use a red light – yellow light – green light system, where teams that fail to move the needle toward achieving their objectives since the previous meeting get a red light, those who have moved forward to a measurable extent are rated with the yellow light, and those who reach their goals are colored green.


Nobody wants to stand up in front of the whole company and admit that for the third month in a row they have failed to make progress toward a key OKR. It’s a powerful form of social pressure to encourage individuals and teams to live up to their commitments, and to get the whole organization aligned behind the strategic objectives.


In a transparent system of accountability like OKR, people get rewarded and/or promoted because they hit their targets, not because of political favoritism. Likewise, when somebody gets fired for poor performance, it is obvious to everybody why it happened.


Ideally all members of the team feel accountable for specific results, not just to the boss, but also to each other. This adds greatly to the effectiveness of OKR as a tool for creating a culture of accountability.


Step Four: Reward and Confront

Managing Accountability is a process

My experience is that young entrepreneurs, particularly those with a tech/engineering background, are not strong either in rewarding and praising, or in dealing with conflicts and problems on the team or in the organization. They tend to be conflict averse. They love to solve problems, but not necessarily the human kind that may entail messy emotions, so even if they become aware that a conflict situation exists or is brewing, they may hold back and take no action until forced to by a crisis.   But there are always problems, and ultimately the leader is responsible for getting them fixed – not fixing them yourself, but making sure that issues get resolved and obstacles to progress and productivity are removed. The longer you let things slide, the more difficult it becomes to set them right. So whatever the difficulty, it’s best to deal with it as soon as possible.


“Ingrid rewards her people for their good work and also challenges them to do better, when she believes that their performance is below par. She holds each employee responsible for their own actions. She has rewarded me with a lunch for all the good work I have done. But when there is someone not meeting standards she has no hesitation in reprimanding them.”


Entrepreneurs are also frequently perfectionists with very high standards, and they expect everyone else to do as thorough and “perfect” a job as they do. So just as they are not great at giving critical feedback, they also do not freely offer recognition or praise or celebrate milestones for work well done.


But recognition and praise are extremely important to most people, and they are strong motivators to continue performing at a high level. People want to be respected and valued for their contributions.
Failure to offer praise and reward for people who deserve it, is counter-productive. It’s a missed opportunity for leadership. The research is clear: when people feel valued, productivity and satisfaction increase, and so does motivation.

Did you know this? Research has verified that the most effective ratio of praise to blame, positive to negative feedback, is 7 to 1. How well do you stack up to this formula for maximizing effectiveness?

Bottom line: leaders need to learn both to confront poor performance, and to praise progress and achievement.
“Dennis will be the first one to let you know you have not achieved the ideal result, but he will also be the first one to recognize achievement and he will be the first to congratulate you on it. I find that this is a great motivating tool and pushes employees to work towards their best.”


Tip: Whether you are delivering praise or questioning poor performance, do it yourself, live – not by email, not by delegating someone else to do it. Probably you will not want to do this (especially the tough stuff) but it will have a much greater impact if it comes from you. 

Be on the lookout for individuals who are doing things right, and reward them.

 
A lack of praise and recognition is a strong factor in making people unhappy with their jobs. A study by the Gallup organization showed that those who go unrecognized are 3 times more likely to quit. A study by Heaphy and Losada at the University of Michigan Business School found that the best performing teams used 6 times as many positive comments for every negative one, while the worst performing teams used 3 negative comments for every positive one. Excessive criticism dampens enthusiasm and commitment.


Many times, dependable, +-consistent and trustworthy people are taken for granted. Create heroes in every role by recognizing excellence at all levels.


Keep a close eye on everyone on your team and find something you like. Search for people doing things right rather than focusing on mistakes.


Help people understand how their efforts are contributing to the overall mission and strategy of the organization. Take time to show them the deeper meaning and purpose of their work.

There are many ways to show your appreciation

 

Money, in the form of salary increases and stock options, is a tried-and-true method of rewarding employees and team members for making a positive difference. But it is far from the only way.


In a book entitled, “1001 Ways to Recognize Employees”, author Bob Nelson suggests that the top two drivers of employee performance are: “I am able to make a difference at work” and “I have been recognized recently for what I do.” He found that money ranks a distant fifth place. 


Here are a few suggestions that will make your people feel appreciated and motivated:

  • Simplest of all: Offer a sincerely spoken “thank you”. Important: For praise to be most effective it needs to be specific. Tell the person what they did that was beneficial and what was the positive impact 
  • Recognize heroic efforts, people who have gone the extra mile or who have been essential to the success of an initiative or project. Send them an email or a handwritten note of appreciation, or arrange a personal meeting 
  • Offer a paid training or professional development opportunity of their choice
  • Take them to lunch 
  • Find an opportunity for a verbal shout-out in front of everyone
  • A promotion or a move to a different part of the company they are interested in exploring 
  • A gift card for Amazon, a favorite restaurant, or a store you know they like
  • Free tickets to a ballgame or concert 
  • For a significantly large contribution: a paid vacation
  • A voucher for a massage or an afternoon at a spa
  • Express interest in their personal life, partner, children
  • Offer a flexible work schedule, or some time off

 

For more ideas for rewarding your people, a quick Google search brings up, for example, “101 Ways to Reward Employees (Without Giving Them Cash)”, “52 Epic Ways to Reward Your Employees,” and many, many more.   Tip: Don’t offer praise unless it is truly deserved. Any insincerity will be noticed. Praise needs to be genuine and heartfelt and delivered with conviction and emotional connection. A passing, “Good job” means very little. Be specific in praising the behavior that you want to see repeated: “I thought the way you handled the situation with our big customer at the meeting last week was very effective, because you said XYZ and that addressed their concern.”

Reward managers and team leaders for challenging ineffective practices and outdated assumptions, and for finding more efficient ways to do things 

 

Encourage an organization-wide mindset of excellence and continual improvement. Develop a culture of discipline. Communicate to others that we will not be truly successful unless we focus our efforts on striving to be better – individually and as an organization.

Cultivate a learning organization that continually strives to improve and learn from successes, mistakes and failures

 

To deepen the knowledge and insights that lead to success, the most effective leaders and their organizations learn from their mistakes as well as their achievements. When projects fail to produce the desired results, try to understand what happened. Ask, “What did we do wrong,” in order to avoid making the same mistakes in future. You can also learn by analyzing your successes to see what worked and what you can carry forward from those victories into new projects. One effective tool is periodic debriefing.

Debriefing: Learn from your successes and failures

 
At the conclusion of a project or even at various stages of progress, conduct a debriefing with your people and discuss what worked and what did not work. Lessons can be learned from both. More than a mere discussion, a debriefing should probe more deeply, inquiring why things happened the way they did, and what can be done to retain positive elements and eliminate mistakes. Encourage people to take part in the discussion with openness and a desire to improve personal, team, and organizational performance.    Here are some suggestions for effective debriefing: 

  • Decide how often you want to conduct debriefing sessions, and stick to the schedule. Some teams hold a short session every morning (you may not need to participate that often) to review the previous day’s progress and set goals for the day. Once a week, or even once a month can work. One benefit of scheduling – people know it’s going to happen, and begin to gather their thoughts on what to share beforehand. 
  • It’s all about learning – not just rehashing, and never about blaming. The underlying thought should be: How can we do better? What can we improve?
  • Keep it relaxed and informal: but focused. 
  • Ask yourself and the team: 
  • Did we hit our objectives? This will be obvious if you set clear targets and established metrics. 
  • Why do you think we hit/missed the target? What did we do right? Where did we mess up? In almost all cases, there will be a mix of positive and negative factors. (We were aligned and focused, we put in the necessary time, we jumped in without sufficient planning, we weren’t strongly motivated, etc.) Try to come up with at least 4 or 5 reasons for how things turned out. 
  • If you reached or exceeded your goal, acknowledge and celebrate that, and thank team members for their contribution. 
  • Take responsibility for any ways you personally failed to meet your own targets or failed to provide adequate guidance and direction. If you do this at the beginning of the session – which means you have to think about it ahead of time – then others will be inspired to speak openly, and you will have a more fruitful discussion.
  • Write down, together, what you have discovered, and how you can apply it to future projects. Decide on action steps to implement your findings. Distribute this document to everyone involved 

 

How to give constructive criticism


  • Remember that both praise and criticism can be motivators
  • Be thoughtful of the person you’ll be speaking to, and weigh the risks and benefits before giving any negative feedback
  • Start by letting the person know that their contributions are appreciated. Then make a specific suggestion for how to improve their effectiveness. Avoid chit-chat; get to the point
  • Deliver criticism in private, behind closed doors – never in front of others
  • Never deliver a critique when you are angry or upset. Take time to cool down but still deliver constructive feedback as soon after the incident as possible. Difficult conversations can morph into lawsuits, so be very careful what you say
  • Focus on behavior that you have observed and avoid personally attacking the person. This will lead to defensiveness
  • Be specific about the behavior and the implications of this behavior to the organization
  • Tell the person that you still have confidence in them and their abilities but emphasize that their performance needs to change
  • Give them a chance to respond to your statements and really listen
  • Agree upon the future performance you expect
  • Establish a timeline for following up on their progress

 

Recognize that people from some backgrounds may not be comfortable confronting or being confronted with poor performance issues

 

  • It could be cultural: some cultures, such as Indian and East Asian, have more indirect ways of dealing with performance problems, compared to the more direct confrontational style of the West. There are also different corporate cultures, some more laissez-faire than others 
  • It could be personal: Some people are tougher than others in their ability to issue and receive strong critiques 
  • So be aware of who you are dealing with and moderate your approach – but that doesn’t mean you can avoid facing problems head on.


What to do when there is a performance problem

 

No matter how many precautions you take to set up clear expectations, give firm direction, and set people free to be creative, problems will arise. Results will lag; people will fail to ask for help when they need it; unexpected obstacles will come up and the project may get derailed.

Everybody Gets Stuck  “All people and all work units get stuck. Effective leaders recognize when their team is stuck and either figure out what to do to get it unstuck or get help from others to do so. Although it may be hard to admit that you need help, it is a fact of corporate life.” – Successful Manager’s Handbook , PDI Ninth House, 2010

When someone is stuck and is having difficulty moving forward on a project, or when there is a gap or discrepancy between what you expected and what gets delivered, go into a conversation about accountability with the intention to understand what happened, and to find a mutually workable solution to fix the problem and set up conditions so it won’t be repeated. Don’t be looking to assign blame, or to discipline the person (although that may in the end be necessary) but rather to understand. Try to have a scientific attitude of curiosity: What happened? Why?


Try the following steps to resolve the problem:

  1. Meet privately with the person. Advice from the Society for Human Resource Management (SHRM) suggests, “Treat the person respectfully, but don’t engage in small talk to put off the issue. Acknowledge immediately that this is going to be a difficult conversation about serious performance issues.” [reference: “11 Tips for Talking About Poor Performance: How to protect your organization when handling the hard stuff” By Jonathan Segal, https://www.shrm.org/hr-today/news/hr-magazine/0416/pages/11-tips-for-talking-about-poor-performance.aspx]
  2. You might begin by saying there seems to be a gap between expectations and performance. Does the person see that, and understand that there is actually a problem?
  3. If so, are they motivated to resolve it?
  4. Determine whether the problem is due to poor communication, faulty understanding about goals and objectives, lack of skill or knowledge, or they simply don’t have experience with the challenges they are facing 
  5. What have they tried, how have they attempted to deal with the problem?   
  6. Is it a one-time issue, or a repeating pattern?
  7. Does the person agree that a change in behavior or approach will help resolve the issue?
  8. Does the person feel he or she has what it takes to overcome the difficulty? 
  9. If the discrepancy is minor, ask the person to come up with a plan to get back on track, and put the plan in writing
  10. If the problem is major, ask the individual to meet with you to develop a plan for meeting their goals
  11. They might need coaching or formal training
  12. They might benefit from a mentor being brought in, or a consultant
  13. Seek knowledgeable advice. Find someone, within the company or in another organization, who has dealt successfully with this issue, and solicit their help. Ask them how they have handled this problem, what solutions have worked for them, etc. If you value your employee, the expense and time can be worth it. 
  14. Avoid being too quick to take the entire task back or assign it to someone else. Give them a chance to make it right – unless it’s obvious they are not able to.
  15. Monitor their progress on the new plan.
  16. Acknowledge positive steps made.
  17. Make yourself available for feedback and encouragement.

 

Tip:  Don’t fixate on problems so much that you neglect to acknowledge and reward achievements. 


Accountability and the Three Pillars of Leadership


Visionary Evangelist  – Visionary Evangelists are passionate about turning their vision into reality. They can therefore be demanding, and focused on their own agenda. They can also be prone to micromanagement because of their obsession with excellence and a desire to control all decisions about product. They usually believe their way is the best, or even the only way. Because they tend to be overly optimistic, their goals and timelines are often unrealistic.


Because they are extremely self-starting, they often fail to recognize that others need more support and direction. They tend to throw people in the deep end.


They have high expectations, but they often don’t take the time to define or communicate them. They set high goals for others (as well as for themselves) and get frustrated and sometimes angry when others don’t perform as well as they would like.


They often don’t follow through in a disciplined manner or set up a systematic process of check-in and monitoring to ensure that accountability happens.


They need to either learn to create those structures, or bring in a Chief Operating Officer or someone with a Manager of Execution profile to help them.


Relationship Builder – Relationship Builders are the most socially skilled. Naturally warm and friendly, they easily engage people in the goal-setting process, and try to generate a coherent, harmonious work environment.


  • They are free with praise and generous with support and coaching.


  • They create the kind of warm and friendly atmosphere that everyone likes to be around, but may lack a strong enough drive for successful outcomes. They tend to be overly informal and easy-going and don’t set up a clear expectation that people have to work hard and produce results.

    Because they strongly desire harmony and for everybody to get along, they tend to avoid confronting people when there are problems, such as failure to meet promised deadlines, and thus they may fail to hold people accountable.


  • They are often too trusting that people will keep their commitments, so they don’t monitor carefully or verify progress toward performance goals.


For Relationship Builders, whether they admit it or not, harmony and being liked are often more important than results. It is hard for them to be demanding and to make tough decisions when performance is sub-standard. Providing negative feedback, or disciplining people when it’s needed, is hard for them. Rather than deal with problems when they are small, they take a “wait and see” approach. Sometimes problems do sort themselves out, but often they only grow and become harder to deal with. 


Manager of Execution – Managers of Execution are the best of the Three Pillar types at holding people accountable. They are the most focused on results, and best organized. Their process is the most structured and methodical. They have an easy time setting goals, metrics, and milestones – it comes naturally to them.

  • They expect commitment and hard work from the people they’re delegating to. They take their responsibilities extremely seriously, and expect their people to do the same.

    The problem is that they can be so focused on driving for results that they can be insensitive to what people are experiencing and what may be in the way of their achieving results. They don’t really listen to the reasons why somebody may be struggling, or pay enough attention to internal barriers or motivation, they just want the job to get done.


  • They can be overly demanding and critical, only focusing on what’s lacking, what’s not being done – they give very little recognition for work well done, and very little praise.

    Like Visionaries, they are prone to micromanaging because they are worried about mistakes, and losing control, and are overly focused on the details.

    Rather than working collaboratively to create mutually acceptable goals, they tend to impose their goals. And they can be intimidating: they don’t create an environment that allows people to feel safe in sharing what they don’t know or that they are stuck.


  • They are often lacking in empathy and compassion.  And like Visionary Evangelists, they are strongly focused on doing it their way.

    In an “accountability conversation,” when performance is inadequate and results are lagging, the skill sets of Relationship Builders and Managers of Execution are most important.


Leaders need to be able to relate to employees in a non-threatening way to reach a resolution of problems, and at the same time to take a tough-enough line if a person has been lacking in motivation, effort, or application. 


Discover the transformative power of Dr. Rich Hagberg's leadership coaching, rooted in data-driven analysis. With decades of experience, Dr. Hagberg excels in enhancing self-awareness, balancing strengths and weaknesses, and fostering effective decision-making. His tailored approach helps founders build strong teams and navigate growth challenges seamlessly. Ready to elevate your leadership skills and drive your startup to success?


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When Should a Founder Bring in a COO? And why choosing the right type of COO could save or sink your
By Rich Hagberg September 28, 2025
One of the biggest dilemmas that founders face knowing when and why to bring in a Chief Operating Officer (COO) . Too early, and you risk creating bureaucracy before the business finds its footing. Too late, and the founder becomes a bottleneck, throttling growth and burning out teams. Get the wrong type of COO, and you’ll spark culture clashes or stifle innovation. I have had 4 COOs over my career. Their styles and capabilities were very different and the role I needed them to play differed dramatically based on the stage of the company. Some of them worked out beautifully and were the perfect complement to my founder tendencies and limitations. Some were a disaster. Here is what I learned. The COO is the most variable role in the C-suite. Some founders never hire one. Others go through three or four before finding the right fit. In many cases, the question isn’t if you need a COO—it’s what type of COO your company and your leadership style demand at this stage of growth. Let’s break this down. Why COOs Matter Founders are visionaries. They are idea machines, market spotters, and force-of-nature storytellers who rally talent and investors around a dream. But those same strengths often come paired with weaknesses: disorganization, impatience, lack of systems, and difficulty letting go of control. A strong COO is the counterweight. They turn vision into execution. They stabilize culture. They keep promises made to customers and investors. And, at the right time, they free the founder to do what only the founder can do—set direction, evangelize the mission, and keep the spark alive. But “COO” isn’t one job. It’s a category. And picking the wrong type is like forcing a square peg into a round hole. The Seven Archetypes of COOs 1. The Executor The backbone of day-to-day operations. They build systems, enforce discipline, and make the trains run on time. Best fit: Visionary founders who thrive on ideas but leave chaos in their wake. Stage: Early scaling, when the business needs process without killing momentum. Examples: Sheryl Sandberg at Facebook (balancing Zuckerberg’s vision), Gwynne Shotwell at SpaceX (stabilizing Musk’s whirlwind). 2. The Change Agent The fixer. Brought in when transformation is urgent—scaling fast, restructuring, or pulling out of crisis. Best fit: Founders who know the business has outgrown their own operational grip. Stage: Scaling into hypergrowth, or turnaround scenarios. Examples: Daniel Alegre at Activision Blizzard, leading cultural and operational overhaul. 3. The Mentor/Partner The grown-up in the room. A seasoned leader who steadies a first-time or young founder, often more coach than operator. Best fit: Visionary but inexperienced founders, often in the earliest stages of institutional growth. Stage: Transition from startup scrappiness to formal organization. Examples: Eric Schmidt at Google—while not COO by title, he played this role for Page and Brin. 4. The Heir Apparent The COO as CEO-in-waiting. They take on broad P&L responsibility, often shadowing the founder before succession. Best fit: Companies preparing for leadership transition. Stage: Later scaling into maturit Examples: Tim Cook at Apple before succeeding Steve Jobs. 5. The MVP Functionalist The specialist. A COO with deep expertise in one critical area—finance, product, supply chain, or sales. Best fit: Founders strong in vision but weak in a single domain essential to scaling. Stage: Startup to early scale. Examples: Prabir Adarkar at DoorDash, covering finance and operations. 6. The Complement to the CEO’s Gaps A tailor-made role. If the founder is a disorganized visionary, the COO is structured and disciplined. If the founder is technical but introverted, the COO is outward-facing and people-savvy. Best fit: Any founder aware enough to know their own blind spots. Stage: Anywhere, but especially scaling. Examples: Sandberg balancing Zuckerberg’s lack of operational rigor; Shotwell countering Musk’s volatility. 7. The Integrator/Hybrid The most complex type. They unify strategy, execution, culture, and talent at once—bridging across multiple functions. Best fit: Complex, multi-line businesses with global teams. Stage: Scaling into maturity. Examples: Angela Ahrendts at Burberry, integrating brand, culture, and operations before moving to Apple. Why Founder–COO Relationships Fail So Often If the COO role is so valuable, why do so many founder–COO relationships crash and burn? Boards are often gun-shy about hiring COOs because they’ve seen these partnerships implode. The reasons fall into several predictable buckets. 1. Lack of Role Clarity The fastest way to sabotage the relationship is leaving the COO’s job undefined. Who owns what decisions? Where does accountability lie? If the COO’s role overlaps with the founder’s, or isn’t communicated to the rest of the team, the COO quickly becomes either a glorified project manager or a powerless deputy. Both end badly. 2. Founder’s Inability to Let Go Many founders simply can’t let go. They want to approve every detail, revisit every decision, and undermine the very autonomy they hired the COO to exercise. A COO who feels second-guessed or constantly overruled either disengages or quits. 3. Misaligned Vision and Values Operational excellence isn’t enough if the COO doesn’t fully buy into the founder’s vision and cultural values. When the COO wants to optimize for stability while the founder is pushing disruption—or vice versa—the two end up pulling the company in opposite directions. 4. Trust and Emotional Reactivity Trust is fragile. If the founder is volatile under stress, or the COO isn’t skilled at navigating the founder’s personality, the relationship becomes brittle. Outbursts, defensiveness, or miscommunications erode psychological safety between them and ripple across the organization. 5. Succession Ambiguity and Power Tensions Is the COO being groomed as the future CEO—or not? Few questions create more tension. If expectations aren’t clarified up front, the COO may feel misled and the founder may feel threatened. Meanwhile, employees begin to compare the two and pick sides. Boards have seen this movie before, and it rarely ends well. 6. Unrealistic Expectations Founders and boards often expect the COO to “fix everything yesterday.” In reality, operational improvements take time—learning systems, culture, and people. When results don’t appear overnight, frustration builds. On the flip side, some COOs expect to make sweeping changes immediately, without respecting the founder’s legacy or the team’s tolerance for disruption. 7. Culture and Communication Breakdowns The founder and COO need structured ways to align—weekly check-ins, clear communication norms, and mechanisms to resolve disagreements. Without them, minor irritations accumulate into major grievances. Worse, the team sees open conflict at the top and begins to question who’s really in charge. 8. Identity and Ego Issues Let’s name the elephant in the room: many founders see hiring a COO as an admission of weakness. They sabotage the hire by bypassing the COO or contradicting them in front of the team. On the other side, ambitious COOs often chafe at being “Number Two.” If the relationship isn’t anchored in humility and respect, egos will clash. How Founders Can Prevent the Breakdown Knowing the pitfalls is only half the battle. Preventing them takes deliberate work: Define the COO’s mandate explicitly —what they own, what’s shared, and what stays with the CEO. Set up trust rituals early —regular one-on-one check-ins to surface tension before it festers. Align on vision and values —not just what you’re building, but how you’ll build it and why it matters. Clarify succession expectations —is this person a partner, a long-term No. 2, or a potential future CEO? Say it. Set realistic timelines —agree on milestones, but don’t expect magic overnight. Communicate clearly to the org —so employees understand who does what and aren’t caught in the crossfire. Hire for complementarity —choose a COO who fills your blind spots, not one who duplicates your strengths. The founder–COO relationship is like a marriage with the pressure of Wall Street, venture capital, and 200 employees watching. When it works, it’s transformative. When it doesn’t, it’s messy, public, and expensive. The Founder × Stage × COO Fit So how do you know when and which type of COO to bring in? Here’s the decision logic: Startup + Visionary Founder Needs an Executor or Mentor/Partner. Someone to turn chaos into motion without killing energy. Startup + Operator Founder May not need a COO yet. If they do, it’s usually a domain specialist (MVP Functionalist) to cover blind spots. Scaling + Visionary Founder Needs an Integrator or a Complement to gaps. Execution and people issues become bottlenecks. Scaling + Operator Founder May need a Change Agent or Heir Apparent. The role becomes about transformation or succession. Mature Company + Visionary CEO The COO role is succession-oriented (Heir Apparent) or complex integration (Hybrid). Mature Company + Operator CEO Sometimes no COO is needed; the CEO already runs operations. In other cases, the COO is simply the next CEO waiting in line. Takeaway Hiring a COO isn’t about “offloading work.” It’s about admitting what kind of company you’re really building, and what kind of leader you are. If you’re the spark but not the engine, you need an Executor. If you’re a force of change but leave wreckage behind, you need a Relationship-Builder complement. If you’re building for the long haul, sooner or later you need an Heir Apparent. The best founders aren’t the ones who try to do it all. They’re the ones who know when to step aside—just enough—to let someone else make the company stronger. Closing Thought In Founders Keepers, I often say: what got you here won’t get you there. The founder’s job is to create possibility. The COO’s job is to turn possibility into performance. The only real mistake is waiting until your company is already fraying before you decide which kind of COO you need. By then, the cost of waiting may be higher than you can afford. 
From Vision to Reality: How Founders Can Ensure Their Ideas Get Implemented
By Rich Hagberg September 21, 2025
The Founder’s Dilemma Founders are fountains of ideas. You see possibilities everywhere, you connect dots others can’t, and you can sell a vision with enough energy to light up a room. But there’s a problem: ideas don’t implement themselves. They need systems, people, and execution discipline. In my coaching of more than a hundred startup founders—and backed by data from 122 founder assessments—the same challenge comes up again and again: founders are world-class at generating ideas, but their companies stumble when those ideas aren’t translated into action. I have struggled with this tendency for my entire career. My creative ideas just keep bubbling up and my execution discipline and focus can’t keep up. I have the classic “shiny object” distraction problem shared by many founders. The irony? The very traits that made me a classic visionary evangelist—creativity, independence, impatience, and risk tolerance—are the same traits that made execution difficult. If you want your ideas to live beyond a brainstorming session, you must learn to do what feels unnatural: offload execution, delegate real authority, and empower others to carry your vision forward. Why Great Ideas Die Without Execution Most failed ideas don’t die because they weren’t brilliant. They die because: 1. The founder keeps ownership too long, trying to do everything personally instead of empowering others. 2. Delegation is fake, with tasks assigned but no real authority granted, leaving the founder still in control. 3. Priorities aren’t clear, so teams are overwhelmed by too many initiatives and unsure of what matters most. 4. Accountability is weak, with no consistent follow-up or consequences when commitments slip. 5. Founders love possibilities but resist discipline, avoiding the planning, sequencing, and focus execution requires. 6. Ideas are left open-ended, because founders generate endlessly but fail to converge on closure and completion. 7. Optimism turns unrealistic, as founders overestimate what’s possible and ignore what could go wrong. 8. Expectations aren’t communicated, leaving teams uncertain about roles, outcomes, and next steps. 9. They rush ahead without buy-in, moving too fast to bring others along and win their commitment. 10. They undervalue operators, failing to leverage managers of execution who can turn vision into systems. This is what I call the founder time bomb. Early success convinces you that your personal hustle is the engine of growth. But as the company scales, hustle becomes a bottleneck. Unless you shift, your best ideas will choke on lack of oxygen. Step 1: Translate Vision Into Tangible Priorities Your job as a founder isn’t to hand down a 37-slide vision deck and hope for the best. Your team needs clarity. That means breaking down your big idea into concrete, winnable battles. Set the “critical few” : Define 3–5 top priorities for the quarter. Outcome > activity : Don’t assign tasks, define the result (e.g., “Increase retention by 5%”). Overcommunicate : If you feel like you’re repeating yourself, you’re doing it right. One founder I coached changed his company trajectory by beginning every weekly meeting with just three priorities. The noise vanished. His team finally knew what mattered. Step 2: Practice Real Delegation, Not Fake Delegation Too many founders think delegation means assigning a task and then hovering over the person doing it. That’s not delegation—that’s micromanagement with extra steps. Real delegation means: Handing over ownership, not just chores. Giving the decision rights along with the responsibility. Accepting that “80% their way” may be better than “100% your way.” Here’s a phrase worth practicing: “You own this. You don’t need my approval.” Few sentences are harder for founders to say. Few sentences build more trust. Step 3: Build a Culture of Accountability Without Becoming a Tyrant Accountability is where many founders stumble. They either avoid conflict (hoping problems fix themselves) or they overreact when deadlines slip. Both extremes poison execution. Healthy accountability requires: Clear expectations : No hidden rules or shifting targets. Visible commitments : Public goals build peer pressure to deliver. Rhythms of review : Regular check-ins that aren’t nagging but structured. Consequences : Underperformance addressed quickly, not ignored. Accountability isn’t punishment—it’s support. It says, “I expect the best from you because I believe in you.” Step 4: Share Information Like Oxygen Execution thrives on information. Yet many founders hoard knowledge—sometimes out of habit, sometimes out of insecurity. Teams can’t execute if they don’t understand the why behind the what. Empowered teams need: Transparent dashboards : Everyone sees progress metrics. Context, not just orders : Explain reasoning, not just results. Accessible strategy docs : Kill the “founder black box.” When people understand the big picture, they stop running back to you for every decision. They start acting like owners. Step 5: Invest in Second-Line Leaders Scaling execution isn’t about having 50 great individual contributors—it’s about having 5 managers who can each lead 10 people effectively. Yet many founders neglect their managers, focusing instead on product or fundraising. Strong second-line leaders can: Translate your vision into plans. Coach their teams instead of doing the work themselves. Spot and develop talent below them. Your leverage point is not how many people you personally manage, but how many leaders you multiply. Step 6: Watch Out for Founder Autopilot Your instincts—boldness, independence, impatience—got you this far. But they can sabotage you at scale. I call this founder autopilot. It looks like: Jumping back into execution “just to speed things up.” Overloading the team with new initiatives before finishing the old ones. Cutting around your managers and making unilateral calls. The cure is self-awareness. Tools like 360 feedback and coaching help you notice when you’ve slipped back into heroic founder mode instead of scalable leader mode. Step 7: Celebrate Execution, Not Just Ideas Most founders glorify the spark of ideation but forget to recognize the grind of implementation. If you only celebrate creativity, you’ll get lots of brainstorming but little delivery. Shift the culture: Spotlight the team that launched, shipped, or solved—not just the one that dreamed. Tell stories of execution at all-hands meetings. Publicly recognize “builders,” not just “visionaries.” What you celebrate becomes what your team repeats. The Founder’s Evolution: From Genius to Builder of Builders The founder who can’t offload execution ends up as the bottleneck, exhausted and surrounded by frustrated employees. The founder who masters delegation and empowerment evolves into something much more powerful: a builder of builders. In my research, the difference between founders who scaled 10x and those who flatlined wasn’t idea quality. It was execution quality. The 10x founders learned to empower others, create accountability systems, and step back from doing everything themselves. The founder who shifts from “I’ll do it” to “I’ll ensure it gets done” makes the leap from fragile startup to durable company. Closing Thoughts Ideas ignite companies, but execution sustains them. If you want your vision to shape reality, you must resist the temptation to hold the reins too tightly. Translate vision into priorities. Delegate real authority. Build accountability and transparency. Develop leaders beneath you. And above all, celebrate execution as much as you celebrate ideation. That’s how founders ensure their ideas don’t die in the brainstorm stage but live on as products, services, and companies that change the world. 
When Loyalty Becomes a Liability: Why Founders Must Confront Team Obsolescence
By Rich Hagberg September 14, 2025
Every founder eventually faces a moment of reckoning. It doesn’t arrive with a clear announcement. It creeps in gradually, often disguised as small frustrations: projects slipping, team members complaining, or investors quietly losing confidence. And at the center of it all is a painful truth: The people who carried you through the chaos of the early days, the ones who slept on office couches, pulled all-nighters, and took pay cuts to bet on your dream—can no longer keep up. The company has grown. The stakes are higher. And the job has outgrown them. This is one of the hardest truths in entrepreneurship, and one most founders struggle to face. Instead of acting, they convince themselves: “She’ll grow into the role.” “He’s been with me since day one—I can’t let him go.” “Loyalty matters more than resumes.” But here’s the hard truth that separates founders who scale from those who stall: loyalty doesn’t scale. Competence does. The Startup Version of the Peter Principle The Peter Principle tells us that in large corporations, people rise to their level of incompetence. In startups, this principle plays out in hyper-speed. What made someone a hero in a five-person company, improvisation, raw hustle, and the willingness to do anything becomes a liability in a 50- or 500-person company. Think about the hacker who was indispensable in the garage. Brilliant at rapid problem-solving, he could patch servers at 3am and crank out features in a weekend. But leading a team of 50 engineers requires a totally different skill set: planning, delegation, recruiting, building processes. His improvisation becomes chaos. His genius turns into bottlenecks. Or the co-founder who thrived on energy and vision. In the early days, charisma and instinct were enough. But scaling requires a discipline around metrics, process, and accountability. What once looked like bold leadership now looks like reckless improvisation. Even the beloved “culture carrier”—the person who organized team offsites, boosted morale, and made the company feel like family—can become a roadblock. When decisions stack up and complexity explodes, loyalty and good vibes aren’t enough. What the company needs is a strategic operator, not just a glue person. This is what I call team obsolescence : the brutal, recurring reality that many early employees get outgrown by the job. The Head vs. Heart Conflict Why do founders struggle so much with this? It’s not because they’re blind. It’s because they’re human. The tension isn’t just intellectual—it’s emotional. Guilt and Indebtedness : Early employees bet on you before anyone else did. They turned down safer jobs, endured lower salaries, and staked their careers on your vision. Cutting them loose feels like betrayal. Psychologists call this the principle of reciprocity: the human drive to repay sacrifices. Founders feel they owe these people more than just a paycheck. Fear of Losing the Magic : Founders often worry that bringing in “outsiders” will ruin the scrappy, intimate culture that made the company special. This is a classic case of in-group bias. We trust the familiar, even when it’s no longer fit for purpose. Many founders cling to the idea that culture is fragile and must be protected from “corporate types.” Conflict Avoidance : Few people relish difficult conversations. Founders, especially those wired to inspire rather than confront, often procrastinate on hard personnel decisions. This is loss aversion at work: the immediate pain of conflict feels worse than the long-term risk of stagnation. Blind Loyalty Bias : Founders frequently overestimate an early employee’s ability to “grow into” a scaled role. This is the halo effect: past loyalty and past performance cast a glow that blinds you to current shortcomings. This is the founder’s head-versus-heart struggle. Rationally, you know the company has outgrown someone. Emotionally, you can’t let go. A Founder’s Story: When Friendship Meets Reality One founder I coached built his company with a close college friend. This friend was the first engineer, working nights and weekends to bring the product alive. He coded nonstop, patched outages at all hours, and was the reason the company survived its early chaos. By Series B, the company had 80 employees. Suddenly the role wasn’t about heroic coding; it was about systems, processes, and leading dozens of engineers. The founder knew his friend was drowning. Deadlines slipped. Senior engineers were frustrated. Investors raised eyebrows. But he kept saying, “He’s been with me since the beginning. I owe him.” Eventually, he faced reality. With coaching, he had the hard conversation: “You’re invaluable to this company, but the role has outgrown your strengths. Let’s find a place where you can thrive without being set up to fail.” The friend transitioned into a specialist role where his brilliance could shine without the weight of leadership. The company brought in a seasoned VP of Engineering. Painful as it was, the decision saved both the company and the friendship. This is the essence of true leadership: honoring loyalty without letting it sink the ship. The High Price of Avoidance The costs of avoidance aren’t abstract—they’re devastating. Execution Bottlenecks : An underqualified leader slows everything down. Projects drag, opportunities slip, and customers churn. It’s like trying to scale a skyscraper on a foundation built for a cottage. A-Players Walk : The best people won’t stay if forced to work under weak leaders. They leave, taking ambition and excellence with them. The company becomes a place where mediocrity thrives. Culture Corrodes : Protecting underperformers sends a loud signal: politics matter more than performance. Over time, resentment builds. High performers check out. Trust erodes. Investor Mistrust : Boards and investors notice quickly when execution falters. They start asking tough questions—not just about your team, but about your judgment as a founder. Founder Burnout : Perhaps the greatest cost: you, the founder, pick up the slack. Instead of scaling your vision, you spend nights fixing problems others should solve. Exhaustion sets in. Your energy, the one resource no one else can replace, gets depleted. What feels like an act of loyalty today can quietly strangle the company’s future. Another Case: The Culture Carrier I once worked with a founder whose operations manager was beloved by the team. She organized payroll, ordered office supplies, and planned offsites. She was the glue. But when the company hit 150 employees, the demands shifted. The job required scalable systems, compliance expertise, and strategic HR planning. She was still running things on spreadsheets and memory. People loved her, but they were increasingly frustrated with the chaos. The founder feared that replacing her would “destroy the culture.” Eventually, he hired a Head of People. But instead of cutting her out, he redeployed her into an employee experience role. She continued to be the cultural heartbeat of the company while freeing leadership to professionalize operations. The lesson: redeployment, when done thoughtfully, preserves loyalty without sacrificing competence. What Great Founders Do Differently The best founders I’ve studied don’t avoid this problem. They approach it with discipline and compassion. 1. They Diagnose Early They don’t wait until the crisis is obvious. They ask themselves, “If I were hiring for this role today, at this stage, would I choose this person?” If the answer is no, they don’t kick the can—they act. 2. They Separate Potential from Plateau Some people can grow. With coaching, training, and mentorship, they can rise to the next level. Others plateau quickly. Great founders don’t confuse the two. They invest in growth where it’s possible and cut losses where it’s not. 3. They Redeploy with Respect This isn’t about discarding people. The best founders move loyal employees into roles where their strengths shine—special projects, advisory positions, cultural leadership. Redeployment preserves respect and institutional knowledge while freeing the company to grow. 4. They Upgrade Before Crisis They don’t wait until the engine fails. They hire seasoned executives early, before execution falters. And they communicate clearly: every stage requires different skills. Honoring the past doesn’t mean guaranteeing the future. Leadership with Compassion The real test of a founder isn’t whether you can attract capital or inspire a team. It’s whether you can make the painful calls that protect the company’s future while respecting the people who got you started. True leadership is not about cold detachment. It’s about balancing head and heart: Gratitude means honoring contributions, celebrating sacrifices, and rewarding loyalty. Governance means making clear-eyed decisions about whether someone can perform at the next level. When founders confuse the two, they put sentiment ahead of survival. But when they balance both, they create companies that endure. One founder I know addresses this directly with his team: “Every stage requires new skills. Some of us will grow into them. Others will contribute in different ways. What matters is building a company that lasts.” That’s leadership with compassion—telling the truth while honoring the past. Why This Matters More Than Ever The startup environment today is more unforgiving than ever. Capital is tighter. Investors are quicker to act. The margin for error is smaller. In this climate, founders who delay tough calls are at greater risk than ever. Execution failures and cultural corrosion are spotted instantly by boards and competitors. The founders who scale are those who balance loyalty with realism—who act before the cracks widen into chasms. The Founder’s Real Test It’s easy to celebrate early wins and bask in loyalty. The real test is whether you can honor that loyalty without being trapped by it. Because here’s the paradox: The only way to truly honor early sacrifices is to build a company that endures. And that means making the call when loyalty becomes liability. Call to Action If you’re a founder facing this dilemma, don’t wait for the board to force your hand. Don’t wait for top talent to walk or investors to lose confidence. Confront it now. Diagnose honestly. Redeploy with respect. Upgrade before crisis. Be compassionate. Be decisive. Be clear-eyed.  Your team—and your company—will thank you later.
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