Business Management
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Executive Coaching: The Secret Weapon for Founders, CEOs, and CXOs

In today's rapidly evolving business landscape, the demands on founders, CEOs, and CXOs are increasingly complex. 65% of high-potential startups fail due to co-founder conflict. Legends like Garry Tan and many more have fallen prey to conflicts and getting burnt out in navigating such situations. But it doesn’t have to be that way. We uncover how founders like Steve Jobs, Sam Altman, Sheryl Sandberg, and more have leveraged executive coaching to 10x their output, and how you can too.


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In today's rapidly evolving business landscape, the demands on founders, CEOs, and CXOs are increasingly complex. From steering companies through explosive growth to making game-changing strategic calls and cultivating a winning culture - effective leadership has never been more crucial. 

Transitioning from a co-founder to CEO, staying true to your vision, and handling internal conflict are some common challenges when you’re tasked with steering the ship. Amid these multifaceted challenges, a growing number of successful entrepreneurs and executives are turning to an often-overlooked secret weapon: executive coaching.

65% of high-potential startups fail due to co-founder conflicts. A similar situation was faced by Garry Tan (CEO, Y-Combinator) in his early days, who eventually left his startup. But Garry opened up about how, in hindsight, the conflicts were avoidable. He often emphasises how important executive coaching has been for him. 

Garry and his team have been working closely with executive coaches for years.

The Power of an Unbiased Perspective

One of the most valuable aspects of executive coaching is the ability to gain an objective, external perspective. It's all too easy for leaders to become entrenched in their own thought patterns and blind spots, missing out on fresh ideas or potential pitfalls. An executive coach can provide that crucial impartial lens, challenging assumptions and offering new insights.

Sheryl Sandberg understands this well. The Meta COO in her book, Lean In, has shared extensively on her self-doubt and imposter syndrome. “The beauty of the impostor syndrome is you vacillate between extreme egomania and a complete feeling of: ‘I’m a fraud! Oh god, they’re on to me!” Sandberg writes. An outside view empowered her to push past limiting beliefs, and working with her media coach Bill McGowan helped her navigate this.

Unlocking Next-Level Leadership

From public speaking to conflict resolution, executive coaches can provide personalised guidance to help leaders elevate their communication and people management skills to the next level. Schmidt credited his executive coach, Bill Campbell, as being instrumental in his success at Google. In his book, "How Google Works," Schmidt said, "By having a coach, I gained an experienced sparring partner who could challenge my ideas and decisions in a trusted environment." Campbell helped Schmidt navigate the challenges of leading a rapidly growing company and encouraged him to empower his management team.

Navigating Mission-Critical Decisions

Every founder and CEO inevitably faces make-or-break strategic crossroads. Having an experienced executive coach as a sounding board during these crucial junctures can be invaluable. Sam Altman has emphasised how he was sceptical of executive coaching but working with Matt Mochary has significantly improved his output. But more so, the most impactful addition was helping Sam and his team stay put on the mission, “Matt’s coaching has brought me clarity, focus, organisation, less stress, and higher performance (from me and the team)” expressed Sam.

Cultural Catalysts

Exceptional company cultures don't emerge by chance; they are painstakingly shaped through conscious leadership. Microsoft's leadership, first Bill Gates and later Satya Nadella, have both relied on executive coaching. As Bill famously says “Everyone needs a coach. It doesn't matter whether you're a basketball player, a tennis player, a gymnast, or a bridge player. We all need people who give us feedback. That's how we improve.” Microsoft has truly lived up to it. 

An Investment in Sustainable Success

For leaders ready to embrace executive coaching, here are some key considerations -

Identify Your Aims: Clearly define your goals to find the right coach and maximise impact. 

Identifying areas requiring assistance is crucial. Some individuals may require assistance in managing stress or insecurities, while others may seek guidance in strategizing and maximising resource utilisation. In Google’s case, Eric Schmidt wanted an inclusive and collaborative work environment. On every Monday, Schmidt held a weekly staff meeting, but these meetings were typically agenda-driven and lacked engagement. A seemingly minor tactical shift, championed by Bill Campbell (Eric's coach), transformed the dynamic. For every meeting, everyone would share their weekend experiences through "trip reports," fostering a space for connection. This simple act of sharing stories and experiences helped strengthen interpersonal relationships between employees.

Take Action: Implement learnings iteratively and adapt as situations evolve.

Iterating and adapting are key to staying at the top in everything, not just in business. Tiger Woods is famous for having worked with many coaches to switch up his tactics and keep exceeding his performance. He was the world’s number 1  for 281 weeks straight: the longest streak ever. 

Embrace Vulnerability: Being open about fears and weaknesses allows tailored mentorship.

Even Steve Jobs took to executive coaching feeling the need to vent out and open up. Steve was coached by Bill Campbell and John Mattone. Mattone reveals that the sessions covered topics like the vulnerability decision, having a mindset of entitlement versus a mindset of duty, and having the courage to execute with pride, passion, as well as precision. 

Adopt a Growth Mindset: View coaching as an ongoing journey of development.

Oprah Winfrey has been working constantly with her executive coach Martha Beck for over 30 years. Beck helped Winfrey manage the stress of running her media empire and maintain work-life balance throughout her journey.

Executive coaching is not a cost. It's an investment. And investing in yourself is the best investment you can make.

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