Creating Buy-in

A group of business people are having a meeting in a conference room.

Getting Buy-in For Your Initiatives

Creating Buy-In

There’s a common understanding that executives are hired to make decisions. True enough. But they are also hired to insure that the decisions are implemented. Coming to a decision – choosing a direction, formulating a strategy or deciding on an action plan – is difficult enough in these complex times. Getting people to buy in – to understand, accept, and align behind the plan - is another matter.

Nobody creates a successful business alone

No matter how brilliant or visionary you are, how innovative your ideas or your product, you need other people to help you transform your vision into reality. Leaders get results by working through others.

You need cooperation and support for your initiatives from investors, employees, and other stakeholders if you are to lead successfully and accomplish your goals.

The authoritarian leadership style is a dinosaur

We no longer live in a world where the person at the top can dictate terms to followers and employees and automatically get his or her way. It doesn’t work like that. Leaders on every level operate in a complex web of relationships and inter-relationships. They have to work with people who have differing agendas, viewpoints, and leadership styles, and need to find ways of working together to achieve common goals.

So you need to create buy-in

One of the ongoing challenges you will face as a leader is creating buy-in – getting the people whose support you need as fired-up as you are about what you are creating together. People who take on your vision as their own, who will enthusiastically put in the hours and the focus because they believe in you and your objectives and truly want to see your idea come to life. The more your agenda becomes theirs, something they want to achieve because they believe in it, the better your chances of success.

How will you do it?

This will not happen by itself. How will you light the fire that will make people passionate about building the organization needed to realize your dream? How will you enlist the cooperation of those who are not passionate, but whom you need on your side?

And how will you avoid the pitfalls that get in the way?

Here are some ideas that are relevant both for specific projects that you want to pursue, and for the overall success of your organization.

Steps to create buy-in:

Determine what you want
Creating buy-in first requires knowing what you want (your goals, priorities, and needed resources). So, before trying to present your idea or suggest an action, it’s important to carefully think through your proposal. Ask yourself:

What is most important to you in this situation?
What is your primary goal or core agenda?
What do you need others to agree to or support, both immediately and in the future?
What actions or changes do you want to see?

Determine what you can give up

Differentiate between your “A” priorities and your “B” and “C” priorities.
What are you willing to give or trade to get what is most important to you?
Be clear about the relative importance of getting the current task accomplished or initiative supported, versus maintaining or building a long-term relationship with those you are trying to influence.

Prepare the ground – do your homework
If you need an individual or group to buy in to your idea or initiative, set up a meeting and prepare for it carefully. Don’t impulsively jump into action before you have your plan thought through.

Know what you want to achieve.

Get clear what points you want to make, and how you want to state them.
Make whatever notes you may need so you can give a thorough, cogent, and persuasive presentation.
Get your facts straight and know the details.
Do your homework so that your argument has credibility. This is how you want people to see you: “She is so knowledgeable that her ideas and proposals have immediate credibility.”

Anticipate the opposition
Before you meet, make a list of all the people your proposal will affect. Talk to key players to find out how they think and what they want:

What are their concerns, agendas, and motivations?
What do they care about the most?
How are they likely to react to your proposal?
Try to anticipate likely disagreements or any opposing views you may face. Adjust your presentation accordingly.

Try to understand the person or persons you want to influence

One factor that inexperienced leaders – and some who should know better – often fail to take seriously is learning all they can about the people they wish to influence. It’s a common, and very natural mistake to feel that your vision, your personal persuasive powers, and your position authority should be enough to bring others into alignment with what you want. But it isn’t.

Before you aim directly for buy-in, try to understand the situation from the point of view of the people you’ll be addressing. When you talk to them, explain your ideas but be in a listening mode. Pay attention to what they say, and adapt your approach based on what you learn they want and what the forces are that are acting on them. If you understand their world and have a bit of empathy for what they are facing, you will be more likely to see them as allies rather than as the evil opposition.

Clarify what you have to offer in exchange

The unspoken question people will almost always have when considering whether to buy in to someone else’s initiative is, “What’s in it for me?” So before you try to influence and persuade, it’s important to clarify not just what you want, but what you have to offer. What can you trade for something they want or need? Important: This is likely to be different for each stakeholder, so you need to get to know your people. It’s not always about money.

Here are some things people value:

Meaning: Being involved in a project that has broader meaning and significance
Challenge: The chance to work on a demanding, stimulating project or problem
Money: Making more of it
Growth: Expanding their territory of influence or their level of responsibility
Learning something that is useful to their career advancement
Acknowledgement or praise for their accomplishments, competence, or knowledge
Being listened to – feeling that their ideas and contributions are appreciated
Getting support for a pet project in the form of financial or other resources such as staff, equipment, or office space
Greater visibility in the organization, profession, or industry
The opportunity to work with a person they admire or respect
Receiving coaching or mentoring
Feeling that they are a valued part of a group or team

Action Plan for Creating Buy-In:

Build consensus with key people

Identify the stakeholders whose buy-in you most need, whose input may influence or even change your approach or your course of action. That usually means all of your direct reports and your peers, and if you're the CEO, your board members.

Talk with them, and listen to what they have to say. You want key players to get behind you, but the process of persuading almost always involves listening to their concerns before you try to convince them of your rationale. They may have insights you don't have or concerns you don’t know about until you reach out to them.

Note: Pretending to listen – going through the motions with no intention to take the other’s ideas seriously – is not listening. Most people can spot a phony.

Line up your support

In their book, Influence Without Authority, educators and consultants Allan R. Cohen and David L. Bradford suggest that you consider starting with

People you know or are pretty sure are supportive. “Early wins help.”
People whose support will bring others along with them.
People whose expertise can improve your case.
People who are likely to oppose you if you do not incorporate their demands.

Connect with employees and direct reports

Ultimately, you want buy-in from everyone, not just critical stakeholders. Depending upon the size of the company you may or may not have sufficient time to establish relationships with everyone, but do the best you can.

Easy ways to create rapport and build support

Preferably before you need people to support an initiative:

Invite people for a one-on-one, perhaps for coffee or to share an informal lunch.
Pause at somebody's work area and ask what they're working on, what is exciting to them, and what frustrates them. Ask: “How can I help? What do you need?”
If they are new in town – perhaps they’ve moved in order to work with you and your team - ask if they are comfortably settled, and how partners or family members are.
Take a minute to find common ground in personal interests – sports teams, music, etc. – and share your enthusiasm. “Did you see the game last night?” “Have you heard the new song?”

It doesn’t take a lot of time to show interest or say a kind word. Fostering positive, trusting relationships is an investment in creating buy-in.

On the other hand, if you only show up when you want something they will quickly get onto it, and their trust level will be damaged.

Influence, don’t push

The tendency among entrepreneurs is to focus almost exclusively on pushing their idea. But forcing things tends to create resistance. Creating buy-in is ultimately about influencing others, not making demands on them. It may require a little time to truly listen and take others’ concerns into consideration, but if you need to build support to get something done, or must work collaboratively with others over the long haul, it’s worth the investment.

Involve people in decision making

An effective way of creating buy-in with your team is to involve them in problem-solving and decision-making. Not every decision or problem requires consensus but involving people in problem solving, whether it's gathering relevant facts or getting suggestions for potential actions or approaches, is very useful. People love to feel that their opinions and insights are valued, i.e., that they are respected members of the team.

Keep people in the loop

Explain your decisions and share the rationale for your conclusions or actions. This helps people understand how you think about problems and empowers them to develop capability for independent decision-making. The more they can do that, the more you can trust them and the less you will feel the need to micromanage.

Inspiration generates buy-in

People need to know where the leader is leading them, and they need to feel that the destination is meaningful and attainable. Visionary Evangelists have a natural gift for painting a verbal and conceptual picture of their vision, delivered with enthusiasm, that draws people to want to follow their lead and makes them feel, “We can do this!”

Share your vision and keep it fresh

You have the big picture, and at least a partially developed long-term strategy, and you know what you need to have happen as you go forward. Your employees do not have this vision or understanding, unless you share it with them. One of the most powerful ways to generate buy-in is to paint that big picture, and repeatedly remind them of where you are going as an organization and how they can help.

Create an atmosphere of openness, not fear

If a leader is autocratic and intimidates or bullies people, it fosters the development of a culture of yes-men. Then you’ll never know what people are thinking, or what is really going on in your organization. If you want to elicit people’s best thinking and most committed action, you need to allow others’ voices to be heard. Create an atmosphere where people will bring forward their ideas. They will do that, if they believe you are really listening.

Try to take time for your people even when you feel you don’t have an y

A critical factor facing the entrepreneur that others may be blissfully unaware of is the sense of urgency he or she likely feels because funding is limited, the fuses are burning, and the runway is getting shorter. With this kind of pressure – with so much to accomplish in a short time frame – it feels impossible to take time soliciting people’s opinions and building support. Try to do it anyway.

Apologize if you screw up

If you snap at someone because of the pressure, apologize as soon as you can. “I’m sorry, the time crunch is getting to me. You didn’t deserve that. You’re doing a great job.” This will go a long way to soothe hurt feelings and build a stronger relationship with your team.

Model the values you expect others to follow

Creating buy-in starts with the first people you hire, and continues through all phases of the organization’s growth. You need to be sure that all the individuals are in alignment with the values and goals of your company. You can’t expect this to happen unless you make those goals and values clear, explain why they are important, and demonstrate them in your own behavior and relationships.

People will buy in to the project or plan if they trust the leader’s sincerity and are convinced he or she has the right people, resources, expertise, and managerial skill to bring the vision to life.

Integrity counts

People are naturally drawn to support and get behind a leader of integrity, who is trustworthy and respected. If a leader intentionally misleads people, chances are very strong that the truth will eventually come out, and from then on, trust and credibility will be damaged and the leader’s ability to get people to buy in will be undermined. Not being truthful and transparent, taking the easy way out of a difficult situation, may seem expedient in the moment, but this behavior ultimately amounts to self-sabotage.

People are not just “resources”

Many entrepreneurs are lacking in social awareness and may not consider the needs of others when they make decisions, or the impact their decisions will have on people. They see their employees as means to an end, as “resources,” they see them as part of a numbers calculation, but not as people. This may work for a little while, but it will fail in the long run.

Followers will be much more likely to buy in to the goals you set for the organization if they feel you are committed to their personal growth and advancement.

Be sure employees and team members are buying in from the get-go

Generating commitment and dedication will be an ongoing challenge for you as your organization evolves, new initiatives are on the table, and new people start appearing. It begins with finding, hiring, and inspiring the right people. For a startup it will be up to the entrepreneur, the one with the vision and passion, to craft a core leadership team whose members are not only expert in their area, but who share the vision and are on board with the goals and values that drive the company.

As you expand and need to take on more people, ask yourself:

Do they care about the company’s mission?
Do they understand the exceptionally hard work and long hours that will be required?
Do they see value in what the organization wants to create in the world?

You need to hear unambiguous Yes’s to these questions!

Obstacles to Creating Buy-in:

Communication Breakdown

One of the chief hang-ups preventing buy-in is that one or more of the parties has not clearly heard or fully understood the others’ position. From your side as the leader, you need to be sure

That your communication is clear, logical, data-driven when possible, and conveys the value of your initiative for all concerned, and
That you have truly listened and understood the opposing or counter-argument. Often, simply clarifying positions resolves opposition.

Clash of values/desires/expectations

If the positions are understood yet there is still a problem, look beneath the surface for different or opposing values, desired outcomes, or expectations. Clarify these as much as possible (this will require some time), and negotiate, trying to find ways for all parties to get something they value.

The hard sell doesn’t work

Most entrepreneurs are very strong-willed people who can be far more forceful and intimidating than they realize. Pushiness and bullying don't capture people's hearts, and without that deeper commitment, you can’t get the kind of motivation you need to sustain an effort.

Forcing compliance may work in the short run but not in the long run. Not only will people not put forth their best effort, they may come to resent you if they sense you are just pushing your own agenda.

Authoritarian leadership is a dinosaur

With reference to the Three Pillars model, creating buy-in is primarily a Relationship Builder skill set. Leaders who are accustomed to making demands without listening to their peers and subordinates are not good at it. If you don’t relate to people with at least some degree or warmth, caring, and approachability, you may find it hard to elicit support for your ideas, projects, and goals. Good relationship builders do have a natural advantage, but this is a skill that can be learned.

Summary and Recommendations for Creating Buy-In:

It’s not all about them

Contrary to what you might expect, creating buy-in is not only about persuading people to adopt your agenda. It actually starts with you: who you are, how you present yourself, and how you treat others. It requires knowing what you want - your goals, priorities, and resources.

Her combination of friendliness and professionalism helps her win over everyone.

Be clear on who you are and what you want

Before trying to present your idea or persuade others to get onboard with a plan or strategy, ask yourself, what is most important to you in this situation? Keep in mind your primary goal or core agenda. What do you need them to agree to or support, both immediately and in the future? What actions or changes do you want to see? What are your priorities? Think about what you are willing to give or trade to get what is most important to you.

Consider others’ needs, values, and priorities

Be aware that you may be working with people who have different goals and measures of success. Find out what they want and need. Learn what is driving them. Invest in understanding their needs and motivations in order to gain alignment and find mutually beneficial solutions.

He includes us at the inception of new initiatives. He really wants to know our thoughts.

Earn trust

If people sense that you are manipulating them and just going through the motions of openness to their input while pushing your own agenda, they're going to be much less likely to trust what you say. You build trust by being trustworthy – truthful, consistent, and ethical.

He is someone you feel you can trust. He has a reputation for sound decision-making and judgment. People just believe him.

He has earned the loyalty of his team by being clear, consistent, open, and reliable.

Listen and Adapt

Take the time to listen to your main stakeholders, discuss your proposed initiative, and reach consensus. You may need to adapt your approach based on learning what others want and what the forces are that are acting on them. Try to understand what is driving them and what or who may be influencing their goals and concerns.

He talks with all of his partners one-on-one on virtually every critical issue affecting the organization.

Her approach is very consultative, and she makes sure that she hears all viewpoints before she decides her next steps.

Ask for their support

Rather than make demands, ask for the support of all involved. Let them know that the success of what you are trying to achieve depends on their active and enthusiastic participation. Be sure they fully understand why this initiative is important, what is at stake, and how achieving the end you are proposing will benefit them as well as the organization.

I have seen him create buy-in by creating a sense of ownership in the whole project.
Everyone feels they have a stake in the success of the project.

Do your homework

Be prepared. Before talking to individuals or groups, think things through, know what you want to achieve, try to anticipate the opposition you may face, and make whatever notes you may need so you can give a powerful and persuasive presentation. Know not only what points you want to make, but how you want to state them. Get your facts straight and know the details.

What are you offering?

In return for their support and participation, what are you offering in exchange? Try to clarify what you can put on the table that may be of value, before sitting down to try to influence them. What can you trade for something they want or need? It could be expertise, information, or knowledge; it could be appreciation, gratitude, recognition, assistance, or support for a pet project; it could be financial or other resources like staff, equipment, or office space. Work toward a win-win solution.

See the Big Picture

Various stakeholders within your organization will have diverging agendas and demands. The bigger the organization, the more complex this becomes. You have to be the one who takes all the factions and points of view into consideration in order to come up with the solution that will be best for everyone. Don’t just charge ahead with your own plan before you truly consider what outcome the others are looking for, and what they will accept if they don’t get everything they want. And that goes for you, too.

Take a long-term view
Weigh the relative importance of getting the current task accomplished or initiative supported versus maintaining or building a long-term relationship with those you are trying to influence. You don’t want to win the battle and lose the war, alienating the other person or group. If there is a lot of opposition, ask yourself if you really need to win this one. They may be holding on to the status quo or have some other agenda that you need to overcome, or they might actually see consequences that you don’t.

Be open to their input. It will help a lot toward creating buy-in and achieving a positive outcome if you can show that you understand where they are coming from.

< Older Post

Newer Post >

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.

ALL ARTICLES

Article