Five Approaches to Effective Decision Making

There are many approaches to making an effective decision

A man is sitting at a desk with a laptop and a computer.

Decision Making: A Critical Leadership Skill

Making effective decisions is crucial to a leader’s success. However, given the pressure to make decisions quickly, often without having all of the data necessary, it is easy to make the wrong choice. "On an important decision one rarely has 100% of the information needed for a good decision no matter how much one spends or how long one waits," said author and educator Robert K. Greenleaf. Although it is true that we don’t know what we don’t know, when you have a difficult decision to make, try to assess what information you lack, and how to obtain it.

It’s Too Easy to Make Bad Decisions A McKinsey study found that 72% of senior executives thought their companies frequently made more bad decisions than good decisions. This stunning finding should be a wake-up call to all executives to create and prioritize an effective decision-making process for your team or organization. Daniel Kahneman, who won the Nobel Prize for his research on decision-making, concluded that irrationality often trumps rationality in decision making. His research showed that 95% of all decisions are impaired by reasoning that engages in fallacies and systematic errors due to our use of mental shortcuts and rules of thumb that cloud our judgment.

Among the most effective antidotes to faulty decision making is to include the perspective of others who have different expertise, complementary functional or domain knowledge, or who can provide more objectivity or perspective on a leader’s decision. This includes not only your immediate team, but our network of colleagues, former mentors, and so on.

Do I Make The Decision Myself or Involve Other? Who you bring in to help you make a decision depends not only on who is available, but also on the nature of the problem you are trying to solve. They need to have deep knowledge or experience that will add critical facts and perspective to your analysis and help you identify alternatives, implications, risks, or other factors you might have overlooked.

Deciding Too Fast vs. Deciding Too Slow Of course, adding more people to the discussion is likely to slow things down. And there is no denying that including your team or other experts may add to the complexity of the decision or result in intense discussion and differences of opinion. But sometimes slowing down and being more thoughtful and deliberate is just what you need. “If there Is time to reflect, slowing down Is likely to be a good idea,” says Daniel Kahneman. Taking the time to gather evidence from as many relevant places as you can, brainstorming with knowledgeable people, and carefully weighing all the information rather than making a too-hasty decision could save you from making a huge error that could cost a lot of money, or even cost you your job or damage the organization’s chances of succeeding.

“There are times when delaying a decision has benefit. Often, allowing a set period of time to mull something over so your brain can work it through generates a thoughtful and effective decision.” - Nancy Morris, author of Procrastinate Now

So, what is a leader to do when there is pressure to make decisions quickly, but you know that your own biases and lack of complete information have the potential to lead to disastrous results? Is there a best way to make decisions?

This blog will take the position that there is no single best way to make decisions. Different circumstances and different types of decisions require different approaches.

In what follows, I will discuss five basic ways decisions can be made, what situations call for each approach, and the tradeoffs of different approaches. But first I will summarize the general benefits of including others in the decision-making process. Why Should I Involve My Team?

You must admit that making decisions by yourself is efficient and uncomplicated when you don’t have to consider others’ perspectives and concerns. When time is short, it is an attractive alternative. But solo decision making can easily lead to being heavily influenced by the leader’s biases, blind spots, reactivity, and focusing on too few options and too narrow a perspective.

By contrast, increasing the diversity of thoughts and opinions can generate more alternatives and innovative solutions. Bringing together the right group of people who have different skills, experience, viewpoints, functional perspectives and styles can create synergy that, in turn, can lead to dynamic discussions that yield new insights, more relevant facts and more objectivity.

Team Participation Is Empowering and Increases Buy-in Involving your team in decisions is not only good for you and for the success of the decision process, but also good for the team: it demonstrates that you value their viewpoints and makes them feel more engaged and likely to feel both appreciated and trusted. It suggests to them that you value their skills, knowledge and ideas. Both experience and research have shown that involvement in decision-making dramatically increases buy-in and ultimately elicits more support from team members when it comes to implementation. Participation in the process can increase their feeling of being invested in the decision and in their jobs and improves engagement and alignment. Gallup research also suggests that this can increase employee retention and reduce burn-out.

Team Participation Helps Grow Leaders Being engaged in a well-managed decision process can also help team members develop their judgment and their own leadership capability, by exposing them to the process of gathering facts and opinions, weighing alternatives, and the discipline of working in partnership with others to come up with the best solution for the problem at hand.

Team Participation Fosters Cohesiveness This experience of collaboration with the leader and other team members fosters team cohesiveness and increases a sense of shared identity because they are working to solve problems together rather than operating in and focusing on their functional silos. The feeling of accountability to the group grows as they take on greater responsibility for arriving at the decision.

Team Participation Shows A Willingness To Share Power But remember, when you decide to involve your team in making decisions, you are deciding to share power and the decision may not always be the one you had in mind at the beginning. It tests your willingness to let go of control and let others be leaders. Ultimately this can result in better quality decisions and greater engagement, but it will test your ego’s need to have the answer and be right all the time. It will challenge your willingness to trust others.

When should you involve your team in decisions?

1. When creating your strategy or long-term goals

2. When you realize that you have been too “top down” in your leadership style and need to be more open to input and do a better job of listening to feedback and ideas

3. When you have made some bad decisions in the past because you went off on the mountain and talked to God and came down with a solution that proved to be faulty

4. When you realize you have missed important information, leading to bad judgment

5. When trusting your gut rather than using a rational, systematic decision process led to bad results, hiring mistakes, confirmation bias, blindness to critical facts or alienation of team members

6. When you have received feedback that you are viewed as not trusting your team

7. When you need broad alignment and buy-in to ensure coordinated implementation

8. When the decision is consequential, difficult, complex or ambiguous and you could benefit from the collection of diverse viewpoints and facts

9. When you want to help team, members develop by exposing them to facts, ideas and decision disciplines

10. When you believe that the experience of collaboration and problem solving together and with the leader will foster team cohesiveness, encourage shared learning and increase a common sense of identity

Guidelines for Team Decision Making

• Be sure to involve the right people. The experience, skills and knowledge necessary to produce the best insights differs with each decision. The more diversity of perspective, the better. Including people based only on their seniority or their role can provide too narrow a perspective. Consider bringing in an expert regardless of their role or a person from outside who has domain knowledge relevant to the decision.

• Let the members of your team know which of these leadership styles you are going to use. If you are aiming for consensus, each person’s opinion and perspective is vital and must be brought out. If you are going to make the decision yourself based on some input from the team, it will be good for them to know this from the start.

• Consider setting up a meeting that is specifically designed to focus on this decision rather than trying to fit it into your usual staff meetings that often get hijacked by information exchange and reporting rather than high-level problem solving.

• Consider your time constraints and deadlines. Do you have time to involve others and gather additional viewpoints and alternatives? Do you have enough information, and the right information, to make a good quality decision?

• Be sure you carefully define the problem you are trying to solve rather than jumping too quickly into finding solutions. If you define the problem too narrowly, focus on a symptom rather than the broader root cause, or jump quickly to a single solution, the danger is that you will focus the team on the wrong thing and reach the wrong conclusion.

• Actively draw in ideas and viewpoints from all team members. Start with knowledgeable experienced team members and those with expertise in the problem area but consider also including opinions from the more junior before turning to your most senior people or expressing your own opinion. Patiently listen and be the last to weigh in.

• Try to create an environment where team members feel safe being open and honest and saying what they really think.

• Draw people out. Ask questions that surface alternative views, areas of concern, and problems that might prevent success. Invite team members to challenge each other’s opinions, including yours. Try to get the team to generate multiple possible solutions rather than locking in on one solution too soon. “That’s a good idea. What other angles can we come up with?”

• Take the time to look at the most important side effects that might negatively impact the outcome you are seeking. Ask everyone to consider: What could go wrong? It is important for a leader to discuss the proposal with people who are likely to disagree with it or uncover its drawbacks.

• Two common types of biases frequently have a negative effect on management decision, confirmation bias and over-confidence bias. Confirmation bias involves giving too much weight to information that supports your existing beliefs, conclusions or recent experience and discounts information that contradicts them. Overconfidence bias occurs when you overestimate your ability and fail to consider the risks that could lead to failure.

• It’s important to be aware and cautious about the potential problems and dangers, but equally important for you to dwell on the factors that could lead to succeeding in achieving your objective. And share that vision with your team.

• Play communication traffic cop. Ensure that people are listening, paying attention when others are speaking, are not interrupting, are being respectful of others’ views, and are building on each other’s ideas rather than trying to prove they are right.

• Don’t let certain team members dominate the discussion or dominate it yourself. Especially when your aim is consensus, it’s vital that everybody has a chance to state their views.

The following discussion considers various ways to make decisions, some involving other people and some not. There are many ways to get to the right answer.

5 Approaches To Making Leadership Decisions

1. The leader decides and informs the team Although in general it is always helpful to draw your team into the decision-making process, gathering their input and opinions, sometimes circumstances demand an immediate choice of direction: the decision is time-sensitive, and you need to take action now! You simply don’t have time to explore all the factors and ramifications with your team, so you need to decide and move forward on your own.

This unilateral approach to making a decision works best when the leader has sufficient information as well as some expertise in the relevant domain or domains. It can also be useful for low-impact decisions and simple, routine, administrative decisions which don’t require much input or deliberation. It’s relatively safe for you to use this mode when you know your team is likely to support and implement the decision despite having no input. Whenever possible, leaders should share their insights, analysis, and rationale for proposed changes with their team, even though their proposal might meet resistance and challenge from team members. Leaders do need to seek buy-in, but there are times when they need to take a direction even in the face of resistance. This partly depends upon the level of experience, domain expertise, and insight possessed by other team members.

Leaders frequently have insights and the ability to see around corners, making connections and spotting patterns sooner than the rest of the team. This is particularly true of visionary entrepreneurs. When the leader is working with a junior team and is many steps ahead of them, sometimes he or she doesn’t have time to bring the others along and must make a unilateral decision. The danger is that this can become a default pattern and may get in the way as the sophistication of the team increases and the complexity of decisions becomes greater and greater.

Elon Musk and Steve Jobs are exceptionally creative visionary leaders, who saw things other people missed. On the other hand, not everybody is Elon Musk and Steve Jobs. A lot of leaders justify autocratic leadership by citing Jobs and Musk and concluding that this is the way to be a leader. It’s one way – but unless you are so ridiculously brilliant that people are willing to put up with your arrogance, bossiness, intolerance, etc., it’s not a great way to lead, because you will have trouble retaining top people, you are likely to make biased decisions, and you will alienate people whose support you need. When the decision is yours alone, you run the risk of deciding without having all the important and relevant information and the benefit of your team’s experience. When there is no team interaction and team members are deprived of offering their input, they may resent the decision you’ve made and not support it. People on the team may feel disempowered and offended: “Why didn’t you ask for our input? Why were we excluded?” And because they didn’t have input in the decision, getting their buy-in may be problematic.

The one-person decision-making process is definitely efficient, and avoids time spent (or lost, depending on your perspective) to discussion and debate, but in doing that, it bypasses the group problem solving and brainstorming that can bring fresh and creative ideas to any situation.

And remember, when the decision is unilaterally yours, it is subject to your personal biases and blind spots. And when you are the sole decider, you are also solely accountable for the outcome!

2. The leader gathers input then decides Midway between the unilateral approach to decision making and the effort to broaden participation and generate consensus is the procedure where the leader consults with team members, solicits input of ideas and opinions, and then makes the final decision. This approach is effective when you are ultimately going to be the Decider. The whole team does not have to come to agreement on the best way to proceed, but you feel their input will be valuable and you want to hear their ideas. You realize that people from different backgrounds bring a variety of experience and understanding to bear on each situation, and you want to take advantage of what they know. As the leader, either speak with team members individually to gauge their position, or facilitate a group discussion of issues, pros and cons, possible outcomes from different courses of action, and so on. For this collaborative approach to work, team members need good communication skills, and must be open to lively discussion of ideas. It requires a leader able to facilitate a thorough exploration and discussion, and willing to absorb and process the information and then make decisions. Encourage team members not to just rubber-stamp your views, but to bring their own experience and perspective to the table. It can be helpful if someone is willing to be the “devil’s advocate” and question or even oppose your views for the sake of clarifying the issues.

But team members must be clear that although their input is solicited and viewed as valuable, in the end the leader is going to have the final say.

One advantage of this decision-making model is that even though you as the leader are ultimately responsible for whatever decision is made, the group input and involvement can take some of the pressure off your shoulders. That is good for you, and good for team members; if they feel they have some skin in the game they will be more energized and willing to work toward the desired outcome.

3. Consensus Consensus decision making is a method enabling a team or group to reach a decision by discussion and mutual agreement. Participants have a chance to contribute their ideas and opinions. Instead of the final decision being based on a vote, letting the majority get their way, the whole team commits to finding a solution that they can all support or at least live with. This approach encourages all team members to get involved and have some say in the decision.

It is an attempt to avoid having an individual team member or a minority feel like they have lost, that their concern or point of view is over-ridden or cancelled and that they cannot or will not support the final decision. To avoid this, the entire team as well as the leader must be willing to make a genuine effort to find solutions or alternatives that address the concerns and needs of all members. That means that you need to have input – and ultimately acceptance, support, and alignment – from all team members. The key is communication, an open flow of ideas and views among team members, including the leader.

There is a difference between consensus and a decision that is unanimous. In a unanimous decision, all the participants are in full agreement and accord. It’s 100 percent. If you have succeeded in creating a culture in which everyone feels that it’s safe to be fully honest, this kind of unanimity will be rare; there will almost always be some doubts, disagreements, and viewpoints that could not be reconciled. Consensus means that everyone has agreed to put their remaining differences aside, and a decision has been reached that everyone can and will support in order to move forward. Aiming for consensus can generate a thorough discussion of issues and produce innovative alternatives. Done well, it may involve long discussions and require surfacing and balancing diverse and sometimes opposing opinions and demands. Team members must have access to all relevant data. To reach consensus, the team needs to be able to work collaboratively and systematically together, and you need to be a skilled facilitator. Be careful to involve everyone, and don’t allow the loudest voices to control the discussion. The higher the level of involvement by team members, with everyone working together through all the discussion and deliberation and arriving at consensus, the more support you will ultimately have for implementation. Because of the broader base of individuals contributing to the discussion, the danger of narrow, silo-based focus of a small part of the team dominating the discussion and the outcome is reduced.

Consensus building is an effective, democratic way to create alignment and solidarity among team members, but it is not the right approach for every situation. It is probably not the way you want to proceed in emergencies or high-pressure, time-sensitive situations. Striving for consensus can take a lot of time and energy and will not be the most effective approach when you are facing a deadline, or a crisis and decisions need to be made in a hurry.

So, what should you do if there is a time crunch, you need to make a decision in the next 24 hours, and you don’t want to shut team members out of the decision-making process? In that case, decide which team members have the most expertise relevant to the problem, or who will be most involved in implementation of the decision, and talk to them. If you can’t get consensus of the whole team, at least get the solid support of this select group. If the consequences of making a bad decision are significant and you need to be sure that you have considered all the ramifications, consensus with careful consideration is probably the right approach. But if the cost of missing an opportunity is high, you may need to move faster, and consensus isn’t the right solution.

When you do need to act quickly, it is a good idea to designate an agreed-upon decision maker for every meeting. The approach is then called “consultative decision-making”. This could be you as the leader, or a trusted team member. You strive to gather the facts, generate discussion of ideas and alternatives and listen to concerns and opinions of team members who disagree with you and others. You want lively discussion of the issues and you want to hear the opinion of experts or those with domain knowledge. But the team doesn’t need to come to a consensus decision. Once the discussion of facts, viewpoints and alternatives is sufficient, the designated decision-maker steps in and makes the call. “Thanks for your input, I’ll let you know what I decide.”

“You want to make sure that everyone participates…. You want to get to the best idea. Your job as a CEO . . . is not to forge a consensus, but to run a process where the best idea emerges." – Former Google CEO Eric Schmidt, quoting legendary Silicon Valley executive coach Bill Campbell.

4. Consensus with fallback If it seems likely that two factions in your organization will not be able to compromise and reach consensus and a clear path forward, then it’s a good idea to pre-set a course of action that you will take if the team cannot come to an agreement and you are required to step in and make the decision. Let everyone know that this is what will happen if they cannot reach accord.

Setting a time limit may be necessary. If the leader fails to set limits, the discussion may go on endlessly without coming to an acceptable conclusion. A time limit puts pressure on the team, which can be a good thing or not. On the plus side, pressure can catalyze the process by pushing people to make concessions and compromises, particularly on issues that are not of central importance to them. Find out what concerns are most important to each of the disagreeing parties, and their willingness to compromise on issues that are less important.

On the other hand, the team may feel rushed and that they don’t have enough time for proper consideration of the relevant factors. Conflicts may surface, and fundamental disagreements may not be worked through, with the result that alignment within the team, and of the team with the organization, may not be complete.

5. The leader delegates to the team or sub-group of the team Sometimes it may be that you and your immediate team are not the best people to solve the problem. It may be a specialized marketing or engineering question that requires expertise other than yours. Who on your team can you turn to, who can be trusted to dig deeply into the issue and come to an informed decision, or make a knowledgeable recommendation?

If, as is often the case with the founders of start-ups, you are accustomed to being on top of all decision making, don’t panic, use this as an opportunity to let go of some responsibilities and decisions, and delegate to others the power to choose a direction, or at least to analyze the data and bring their suggested solution to you.

The key is to remain calm under pressure, trust the team you have built, and use the data available to make the best possible decisions. – Brent Gleeson, former Navy Seal, founder of TakingPoint Leadership

There will come a time when letting go of the reins will be necessary – there is just too much going on in too many areas of your growing organization for you to keep up with it all. It will not be easy for you but doing so will ultimately set you free to use your time and talents for other matters and builds confidence and leadership ability in team members. You may even have to look outside your organization to consultants who specialize in dealing with the kind of situation you are facing.

The danger here is that delegating fails to make use of the talents and expertise of the entire team. It limits team interaction. When fewer people are involved, there is more chance for an individual’s personal biases to cloud their vision. And because not everyone is involved in the decision, it doesn’t build broad and strong commitment to implementation of whatever decision is made.

This issue is of special relevance to entrepreneurs, who frequently have to make decisions in areas where they would be better off delegating, but they have limited funds and thus limited personnel. So, they themselves become central and crucial for all decisions, even on minor issues that would be best pushed downward. For major matters, if you feel the need to reach out beyond your team, you can solicit advice and suggestions from former colleagues who may have dealt with similar dilemmas, or from teachers or mentors.

I was working 12 hours a day with 10 hours of work that easily could have been outsourced. I had never been in a situation where I didn’t want to do all the work myself. One day, I needed four things done by the end of the week and realized I didn’t have the time. That’s when I hired my first employee. . . I never looked back. I hired three more freelancers and ended up hiring one of them full-time within the first month. I now have five full-time employees. [Will Ellis, Founder of Privacy Australia.] When should you use these different leadership styles?

Each of these five styles or modes of leadership has its appropriate time and place. You are likely more comfortable with one or two of them, but to become the most effective leader you can be, it will be helpful to become familiar with all of them, and to be flexible and adaptable enough to shift from one to another as circumstances demand. This is sometimes referred to as “conditional leadership.” For example, a less-experienced team might need a strong guiding hand and a more authoritarian or leader-centric style, while a team of accomplished people can be trusted with a more democratic or even laissez-faire style where they are mostly on their own once tasks and roles are well understood.

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.

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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 company

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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