Article
Why Startup Founders Are So Challenging to Coach—and How to Do It Right
October 10, 2024
Coaching startup founders is not for the faint of heart. These are individuals who are fiercely independent, relentlessly driven, and often unwilling to slow down long enough for reflection. Yet, if you can crack the code, the impact can be profound—not just for the founder, but for the entire organization. So why is it so tough to coach founders, and more importantly, how can you do it effectively?
Why Founders Are So Tough to Coach
- Independence Is in Their DNA
Founders have built their companies by trusting their instincts and defying the odds. This fierce independence often makes them resistant to feedback, especially when it comes from someone they perceive as an outsider. In their minds, if they’ve gotten this far, they must be doing something right. - They Don’t Have Time for You
With a relentless pace of work, founders are under constant time pressure. They’re balancing product development, investor meetings, and hiring decisions. Slowing down to reflect or develop themselves often feels like a luxury they can’t afford. - Confidence—Sometimes to a Fault
Many founders are incredibly confident, which is a double-edged sword. This self-assurance has helped them push through challenges, but it can also make them blind to their weaknesses. They’re often too busy driving forward to look in the rearview mirror and see the gaps in their own leadership. - Fear of Letting Go
Founders often have difficulty with delegation. The company is their baby and letting go of control—whether it’s handing off responsibilities or being open to coaching—can feel like a loss of identity or influence. The fear of losing what made them successful in the first place often makes them resistant to change.
How to Coach Startup Founders Effectively
To coach founders successfully, you need more than just a set of coaching tools—you need to adapt to their world and bring real-time, action-oriented feedback. Here’s how:
- Deliver Tough, Data-Driven Feedback in Real-Time
Founders are data-driven by nature. If you want to get through to them, your feedback must be grounded in hard data or real-world impact. Use metrics, 360-degree feedback, or even operational outcomes to show them how their behavior is impacting the company. Don’t shy away from tough feedback; founders respect honesty, especially when it’s backed by data. If you can tie your insights to the bottom line, they’ll listen. - Balance Challenging Them and Supporting Them
Founders crave challenge, but they also need support. It’s a delicate balance. If you only push, they’ll resist or shut down. If you only support, they won’t grow. The best approach is to challenge their thinking in a way that provokes curiosity rather than defensiveness. Help them see blind spots while simultaneously offering solutions or pathways to improvement. Founders need to feel like you’re on their side, pushing them to be better while understanding the enormous pressure they’re under. - Offer Best Practice Insights, Especially to Inexperienced Founders
Not all founders come from business backgrounds. Some are first-time CEOs with brilliant ideas but little experience managing people or scaling operations. For these founders, bringing best practices from other startups or industries is invaluable. Share insights on delegation, leadership, and operational excellence. Help them build frameworks and processes where they may have gaps. Show them how seasoned entrepreneurs solve problems, and they’ll respect your practical, action-oriented advice. - Adjust to Different Founder Profiles
Founders are not a monolith. Some may be visionary and creative but disorganized; others may be highly technical but struggle with people management. Your coaching needs to be tailored to the specific strengths, weaknesses, and personalities of each founder. A one-size-fits-all approach won’t work. Whether you’re dealing with a highly extroverted, charismatic leader or a more introverted, analytical founder, understanding their individual challenges is key to breaking through. - Tap into the Conscious and Unconscious Motivations
Founders are driven by a mix of conscious ambitions (like scaling the business or disrupting an industry) and unconscious motivations (such as fear of failure, control, or the need for recognition). A skilled coach will dig into these deeper drivers. Ask probing questions to uncover what’s really motivating their decisions, behaviors, and resistance. Often, the very traits that make them successful—like their independence or drive—are also rooted in personal fears or unmet needs. Understanding this dynamic can unlock a new level of growth for the founder.
Best Practices for Coaching Founders
- Use Real-Time Feedback Loops: Don’t wait until the end of a session to give feedback. Founders operate in real-time, so your feedback should follow suit. Point out issues as they arise, and relate them to immediate outcomes.
- Focus on Quick Wins First: Founders need to see results. Focus on immediate, tangible improvements early on to build trust and credibility. Once they see that your coaching delivers, they’ll be more open to deeper, longer-term development.
- Be Direct, but Empathetic: Founders don’t have time for sugar-coating, but they also need to feel understood. Be brutally honest but do it in a way that shows you’re invested in their success. Empathy goes a long way in building trust, especially with leaders who often feel isolated.
- Drive Accountability:
Founders can be notoriously unorganized, which means accountability is key. Set clear goals, track progress, and hold them to their commitments. Many founders respect structure and metrics when it helps them grow.
The Bottom Line
Coaching startup founders is a tough, high-stakes game, but when done right, it can transform both the leader and the company. The key is to adapt to their fast-paced, independent mindset while delivering real-time, data-driven feedback. Challenge them to grow, support them through their struggles, and understand the deep motivations that drive their behavior. If you can master this balance, you’ll not only coach a founder—you’ll elevate a leader who can scale their vision to new heights.
Founders need coaches who can match their intensity, provide actionable insights, and help them unlock their potential—whether they realize it or not. If you’re up for the challenge, the rewards will be exponential.
share this
Related Articles
Related Articles
Founders live in a world of chaos. It’s exhilarating, intense, and downright terrifying. You’re constantly shifting between the thrill of new ideas and the crushing weight of responsibility. Every decision feels like a life-or-death moment for your company, and the stress is unrelenting. Yet, amid this madness, there’s one thing that determines whether you’ll thrive or crash and burn: personal grounding.
Scaling Beyond Genius: The Unseen Work of Building a Billion-Dollar Startup
In a recent Founders Keepers newsletter entitled “When Their Moral Compass Fails, Leaders Fail: How Greed, Power, and Pressure Can Destroy Founders” I discussed how the pressure of investor demands, and the corrosive effects of power and greed can erode a founder’s moral compass. These challenges are not limited to startup founders; they affect leaders across all industries. However, our research on nearly 2,000 executives, including the top 200 leaders who emerged as the “best” based on 360-degree feedback ratings, provides a critical insight: the best leaders are unwavering models of integrity and values. This is not just an ideal to aspire to—it’s a requirement for sustainable success. When leaders prioritize integrity and live by a clear set of values, they build trust, inspire their teams, and create a foundation for enduring impact. This post will delve into what it means to lead with integrity, how the best leaders embody these principles, and actionable steps you can take to align with these ideals. Integrity: The Cornerstone of Leadership Integrity in leadership is about much more than honesty. It encompasses consistency between words and actions, ethical decision-making, and a commitment to doing what is right, even in the face of adversity. Leaders with integrity act as a moral compass for their organizations, guiding decisions and behavior through a clear ethical lens. Our research on the best leaders revealed several defining characteristics of integrity in leadership: Consistency in Actions and Words: The best leaders “walk the talk,” ensuring their actions align with their stated values. This predictability fosters trust and reduces organizational uncertainty. Ethical Decision-Making: These leaders prioritize ethical considerations, making decisions that align with their values rather than taking shortcuts for short-term gains. Accountability: They own their mistakes, modeling humility and responsibility for their teams. Take Howard Schultz, the former CEO of Starbucks, as an example. Schultz demonstrated integrity by prioritizing ethical sourcing, offering healthcare benefits to part-time employees, and fostering a culture of respect and inclusion. His leadership not only built a globally respected brand but also created an environment where employees felt valued, and customers felt connected to the company’s mission. According to a comprehensive review of the literature, leaders who demonstrate integrity cultivate stronger trust among their teams, improve morale, and enhance overall organizational performance. The ripple effects of their behavior extend to organizational reputation, customer loyalty, and financial success. Values as the Leader’s Guiding Light Values are the principles that define what is most important to an individual or organization. For leaders, values serve as a decision-making framework, shaping their behavior and influencing their teams. Leaders who model and promote core values create a strong organizational culture where employees feel aligned and inspired. In our study of the best leaders, the following behaviors stood out: Leading by Example: The best leaders don’t just articulate values; they embody them. Their behavior demonstrates the standards they expect from others. High Standards of Conduct: These leaders maintain impeccable personal and professional standards, setting a tone that permeates their teams and organizations. Promoting Organizational Values: By aligning their behavior with the organization’s mission and vision, these leaders reinforce the importance of shared values. Brian Chesky, CEO of Airbnb, exemplified these principles during the COVID-19 pandemic. Faced with difficult decisions, Chesky ensured that laid-off employees received generous severance packages and career support. His transparent and empathetic approach reinforced Airbnb’s values and preserved the company’s reputation during a challenging time. The literature supports these findings, emphasizing that when leaders align personal and organizational values, it leads to increased job satisfaction, higher productivity, and reduced turnover. Trust: The Currency of Leadership Integrity and values contribute to the most critical currency a leader possesses: trust. Leaders who consistently demonstrate integrity earn the confidence of their employees, stakeholders, and customers. This trust forms the foundation of effective collaboration, open communication, and organizational resilience. Our research showed that trust was a hallmark of the best leaders. They were described as dependable, reliable, and fair. Their actions consistently reflected their commitments, which inspired loyalty and respect. Paul Polman, former CEO of Unilever, is a shining example of how integrity builds trust. Polman led Unilever with a focus on sustainability and social responsibility, proving that profitability and ethical practices can coexist. His leadership attracted like-minded stakeholders, enhanced the company’s reputation, and set a benchmark for ethical corporate governance. Building trust, however, is not a one-time effort. It requires continuous reinforcement through ethical behavior, transparency, and accountability. As one executive in our study remarked, “Trust takes years to build, seconds to break, and forever to repair.” The Downside of Losing Integrity The stakes for leaders who fail to model integrity are high. Our review of business failures, including infamous cases like Enron and Theranos, highlights how a lack of ethical leadership can lead to catastrophic outcomes. Leaders who compromise their values for short-term gains risk not only their reputations but also the viability of their organizations. The Enron scandal was rooted in accounting fraud and ethical violations by top executives who prioritized personal gain over organizational integrity. Similarly, Elizabeth Holmes of Theranos allowed ambition to override honesty, leading to the downfall of a once-promising company. These examples underscore the importance of ethical leadership in avoiding reputational and financial disaster. Expanding the Legacy: The Ripple Effects of Integrity Leaders who model integrity extend their influence far beyond their immediate teams. They create a ripple effect that shapes organizational culture, industry standards, and even societal expectations. A consistent pattern in our research is that ethical leaders inspire ethical behavior at all levels of the organization, amplifying their impact. For instance, Satya Nadella’s leadership at Microsoft has transformed the company culture from one of cutthroat competition to collaboration and innovation. By prioritizing empathy, inclusion, and a growth mindset, Nadella has demonstrated how values-driven leadership can rejuvenate a global organization and inspire employees worldwide. This ripple effect is not accidental; it requires intentional effort to embed integrity into every aspect of leadership. Leaders must ask themselves: How can I ensure my values are reflected in the decisions I make, the systems I design, and the culture I cultivate? Actionable Steps for Leading with Integrity So, how can leaders ensure they remain models of values in the face of challenges? Here are actionable strategies based on our research and the broader literature: Clarify Your Core Values: Take time to reflect on your principles and create a personal mission statement. Ensure your values align with your organization’s mission. Lead by Example: Demonstrate your values through consistent actions. Be the behavior you wish to see in your team. Be Transparent: Openly communicate your decisions and the values guiding them. Transparency builds trust and accountability. Own Your Mistakes: When you fall short, acknowledge it. Use failures as an opportunity to model humility and resilience. Seek Feedback: Regularly solicit input from your team to understand how your behavior aligns with your values. This fosters self-awareness and continuous improvement. Promote Organizational Values: Reinforce the importance of shared values by embedding them into your organization’s culture and decision-making processes. Practice Ethical Decision-Making: Develop a habit of evaluating decisions through an ethical lens. Ask yourself how your choices align with your values and their impact on others. Amplify Your Influence: Leverage your position to mentor others, advocate for ethical practices, and inspire your industry to prioritize integrity. An Inspiring Legacy The best leaders are not only successful but also admired for their integrity and values. Their influence extends beyond organizational performance to leave a lasting legacy of trust, inspiration, and ethical conduct. As leaders, we must constantly ask ourselves: What kind of legacy are we building? In the words of one of the best leaders from our study, “Leadership isn’t about being in charge; it’s about taking care of those in your charge.” By prioritizing integrity and living by our values, we can inspire those around us and build organizations that stand the test of time. As you reflect on this, revisit the challenges I outlined in Founders Keepers —the pressures, greed, and power that can erode integrity. Let this serve as a reminder to stay grounded in your values and lead with unwavering commitment to what is right. Success is fleeting, but integrity endures.
