Coaching To Develop the Leadership Capability on Your Team

There’s a reason why founders are revered as the beating heart of their startups. Your creativity, vision, and grit are what bring the impossible to life. But let’s be real—your quirks and blind spots? Those can just as easily become the cracks that bring everything crashing down. As someone who’s studied, coached, and analyzed hundreds of founders, I’ve noticed a pattern. Certain personality traits that serve you beautifully in one stage of growth can utterly sabotage you in the next. It’s like you’re building the rocket while flying it, and some of the bolts (your tendencies) keep loosening along the way. So, let’s do some introspection. How do your strengths and weaknesses as a founder shape the trajectory of your startup through the seed stage, the traction stage, and the fast-growth stage? And more importantly—what can you do about it? Let’s dive in. Seed Stage: The Wild West of Startups Where the Chaos Begins The seed stage is where you, the founder, shine. It’s about taking your big, bold idea and turning it into something tangible—a minimum viable product (MVP). You’re fueled by creativity, adaptability, and risk-taking, which makes you the perfect pioneer for this uncharted territory. But here’s the catch: the same traits that make you a visionary can also make you a bit of a loose cannon. What You Need to Do: Talk to Customers (No, Really): Are you intellectually curious? Great. Use it to dig into what your customers actually want—not what you think they want. The startup graveyard is littered with the corpses of products that nobody needed. Iterate Quickly: Your adaptability is a gift—lean into it. Test your assumptions, pivot when necessary, and don’t let perfectionism slow you down. (Yes, we know you want your MVP to “wow,” but nobody expects a Picasso in Version 1.0.) Build a Nimble Team: Your charm and vision can attract talented people who want to join your mission. But be careful not to micromanage these early hires. Generalists thrive in this stage; just give them the space to do their thing. Where Founders Go Off the Rails: Overbuilding: Are you getting lost in complexity? Stop adding features nobody asked for and launch the dang thing. Ignoring Feedback: If your independent streak is whispering, “I know better,” pause. Arrogance has no place in customer discovery. Misallocating Resources: Sure, a sleek office might feel like success, but if you’re blowing cash on branding while your MVP is still duct-taped together, you’re doing it wrong. Provocative Question: How often do you really listen to customers versus listening to your own brilliant ideas? Be honest. Traction Stage: Scaling the Engine Now the Fun Begins You’ve found some traction. Customers like what you’re selling (yay!), and now it’s time to scale. This stage is all about systems, processes, and data—words that can strike terror into the hearts of visionary founders. What You Need to Do: Focus on Metrics: Are you tracking retention, revenue, and other KPIs? If not, start yesterday. Your big-picture thinking is great, but now it’s time to get granular. Expand the Team: This is when you need specialists. Let’s face it, you’re not great at everything (and that’s okay). Hire people who are better than you at execution and let them shine. Refine the Product: The MVP is evolving. Listen to your customers (yes, again) and improve it. Cut what isn’t working, even if you love it. Build the Brand: Use your charisma and social savvy to tell the world why your product matters. Just make sure you’re delivering on those promises. Where Founders Go Off the Rails: Micromanaging: If you’re charming but commanding, here’s a truth bomb: you might be the bottleneck. Delegation isn’t a dirty word; it’s your ticket to scalability. Premature Scaling: Are you hiring like crazy or expanding markets too soon? Slow down, tiger. Scaling chaos is a real thing. Avoiding Accountability: Struggling to hold people accountable? Your team sees it, and they’re frustrated. Don’t let this fester. Poor Market Positioning: Visionaries sometimes forget that clarity sells. If customers don’t “get” your value proposition, they won’t buy. Provocative Question Alert: Are you micromanaging because you don’t trust your team—or because you don’t trust yourself to let go? Fast Growth Stage: Scaling the Organization Welcome to the Big Leagues This is where your startup either becomes a rocket ship or implodes from its own momentum. Fast growth is exhilarating, but it’s also the stage where founders most often become the biggest problem. Why? Because the skills that got you here won’t get you there. What You Need to Do: Operationalize Growth: Your charming, scrappy, “figure-it-out” culture won’t scale without systems. Invest in hiring processes, customer support frameworks, and financial controls. Invest in Leadership: You can’t do it all, and you shouldn’t try. Bring in seasoned executives who know how to handle complexity. Empower them, don’t overshadow them. Evolve the Culture: Your early team loved the chaos; your new team needs structure. Create a culture that balances speed with sustainability. Think Strategically: Stop fighting fires and start thinking long-term. What partnerships, markets, or innovations will keep you competitive? Where Founders Go Off the Rails: Founder’s Syndrome: Let’s be blunt—if you’re struggling to let go of control, you’re the problem. Stop second-guessing your leadership team. Leadership Gaps: Are you hiring strong managers? If not, your teams will flounder. Weak leadership is a recipe for dysfunction. Operational Chaos: Scaling without systems is like building a skyscraper on sand. Get your house in order. Burnout and Retention Issues: If your team is burning out because you’re pushing too hard, you’re running a sprint when you should be running a marathon. Strategic Drift: Are you chasing shiny objects instead of staying focused? Your team needs clarity, not a thousand half-baked ideas. Provocative Question Alert: Are you holding onto control because you think no one else can do it—or because letting go scares the hell out of you? So, What’s the Takeaway? Here’s the hard truth: you are your startup’s greatest asset, but you’re also its most dangerous liability. Your strengths as a visionary, risk-taker, and pioneer are what make your startup possible. But if you’re not careful, your weaknesses—disorganization, micromanagement, avoidance of conflict—will eventually hold it back. Every stage of growth demands a different version of you. The scrappy hustler who dominated the seed stage might become a bottleneck in fast growth. The big-picture thinker who thrived in traction might struggle with the discipline of systems. Your ability to adapt, delegate, and evolve as a leader will determine whether your startup scales—or stalls. Let’s Debate: What’s the one personality trait you think holds most founders back? What’s harder: building a great product or building a great team? Are founders born or made? Drop your thoughts in the comments—I can’t wait to hear your stories, arguments, and maybe a few war stories from the trenches. And remember, growth isn’t just about your startup. It’s about you. Are you ready to evolve?

Don't Just lead - create a safe environment for dialogue

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.

Navigating the Highs and Lows: The Dual-Edged Sword of Ego-Driven Leadership

Securing second-round funding is often a pivotal milestone on the journey toward success. While innovative ideas and promising markets certainly capture investors' attention, one fundamental aspect consistently stands out as a critical factor: the strength and experience of the founding team. Behind every groundbreaking startup is a team with the vision, expertise, and determination to turn dreams into reality. Investors recognize that a strong team can navigate challenges, capitalize on opportunities, and drive sustainable growth. Let's delve into why team strength matters and explore the statistical evidence supporting its importance in securing second-round funding. Diverse Skill Set: The Engine of Innovation A diverse skill set within the founding team is akin to having a well-equipped toolbox for tackling the complexities of startup life. Startups require a range of talents spanning product development, marketing, sales, finance, and operations. According to research conducted by Harvard Business Review, teams with diverse backgrounds and skill sets are more innovative and better equipped to solve complex problems. Investors seek teams that complement each other's strengths and compensate for weaknesses, fostering a culture of collaboration and creativity. Startups with diverse teams are more likely to identify unique market opportunities, develop innovative solutions, and adapt to evolving industry landscapes. Relevant Industry Experience: Navigating the Terrain Experience is invaluable in the startup ecosystem, where uncertainty and rapid change are constants. Investors place great emphasis on founding teams with relevant industry experience, as they bring insights, networks, and best practices that can accelerate growth and mitigate risks. According to a study by CB Insights, startups founded by teams with industry experience are more likely to achieve higher levels of success and attract follow-on funding. Seasoned entrepreneurs understand market dynamics, customer needs, and competitive forces, positioning their startups for strategic advantage and sustainable growth. Track Record of Execution: Turning Vision into Reality Ideas are abundant in the startup world, but execution is the true currency of success. Investors scrutinize the track record of founding teams, seeking evidence of execution prowess and the ability to deliver results in the face of challenges. Startups that have demonstrated traction, achieved key milestones, and effectively allocated resources are viewed favorably by investors. According to data compiled by PitchBook, startups with proven execution capabilities are more likely to secure second-round funding and position themselves for long-term success. Investing in People, Investing in Success Team strength emerges as a decisive factor in securing second-round funding. Investors understand that while ideas may spark interest, it is the people behind those ideas who ultimately drive success. Startups with diverse teams, relevant industry experience, and a track record of execution stand poised to capture investors' attention and fuel their growth trajectory. As the startup ecosystem continues to evolve, the emphasis on team strength remains unwavering, underscoring the timeless adage: "Invest in people, and success will follow." For startups eyeing the next stage of growth and expansion, investing in team strength is not just a strategic imperative—it's the cornerstone of enduring success. Team strength emerges as a decisive factor in securing second-round funding. Investors understand that while ideas may spark interest, it is the people behind those ideas who ultimately drive success. Startups with diverse teams, relevant industry experience, and a track record of execution stand poised to capture investors' attention and fuel their growth trajectory. As the startup ecosystem continues to evolve, the emphasis on team strength remains unwavering, underscoring the timeless adage: "Invest in people, and success will follow." For startups eyeing the next stage of growth and expansion, investing in team strength is not just a strategic imperative—it's the cornerstone of enduring success. It is however important to understand that: What got you here, isn't going to get you there!. Being ready and willing to accept that there needs to be some measure of personal growth is what sets Founders who can scale, apart from those who won't.