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Leadership calendar    May 31, 2023

Leading By Letting Go

In a world where letting go and delegating day-to-day tasks happens without even a thought behind the unconscious click of a mouse or screen tap, why do some executive leaders struggle to let go and delegate as they build, grow, and run their companies?

Having just wrapped up an interesting call with a CEO client, I hit “send” on a dinnertime DoorDash order and stared at the on-screen confirmation. While doing so, I was struck by a thought:

I get it, clicking my screen to order dinner and leading an organization are not comparable. However, there are commonalities, and even parallels, in the choices one has to make, and where, when, or how to “hand off” tasks, roles and decisions, to do it transactionally or strategically, and how to apply common or learned behaviors and habits.

A few examples:

A successful entrepreneur shared his challenges with me after building two companies in the shipping and trade industry. One had failed. The other was sold for a large return. Despite his financial success, he was now working at a local bank. Apparently, he had lost most of his fortune through bad business and investment decisions. Surprisingly forthright, he commented that his failures were partly rooted in an inability to invite in and empower others with more expertise to help him make the right choices, especially at key moments along the journey.

Several coaching and advisory clients I’ve come across are first-time founders and/or CEOs. As they adapt their leadership style to growth mode, their “letting-go challenges” create a dilemma. Fueled by their own passion and commitment to problem solve and dig in, those urges often come into conflict with exceedingly greater demands of their time, especially externally. The outcome is commonly significant performance challenge for themselves, their hand-picked executive team, or the organization at large.

One growth-stage executive with whom I recently met spoke of a seminal moment with her supervisor, a C-level micro-manager fearful of being usurped or deemed expendable, especially in the current working climate. In the context of a larger team meeting, the COO specifically asked her for her thoughts and opinions on a revenue growth idea that she had shared with him in passing the prior day. As she re-described the idea, her direct boss accused her of insubordination. Why? He was not aware of the idea, was not involved in its birth, and needed to “approve” it. The COO paused the meeting and took both to an adjoining conference room where he made it clear that she did not need his approval or involvement. In fact, it would be easier to learn how to trust, delegate and support versus succumbing to the urge that being involved is the only path forward.

Letting Go Is Not Easy

Growth company CEOs face a daily challenge as they balance adjusted revenue targets, customer challenges, staffing challenges, and economic headwinds. And, as they reprioritize their time, focus and effort, their ability to let go and delegate becomes crucial in realizing sustained success, executive team performance, and -- at a minimum --improved mental health and endurance for all of those involved as part of the growth stage.

When conducting CEO and executive team assessments of potential investments for Edison Partners a primary focus of our conversations center around each leader’s personal, team and organizational leadership profiles. A key behavior that contributes to post-investment growth and adjusted priorities and approaches to scale, is the capability for the CEO and Executive Team to let go and delegate over time.

Undoubtedly, this transition is not without its’ hurdles. The process of letting go can be quite emotionally challenging, especially for founders who must now trust others with the vision they nurtured and continue to steward, while simultaneously confronting a fear of failure, loss of control, or the urge to do what they enjoy most – all of which can often “get in the way”.

So, what can a growth company CEO do proactively to improve his or her ability to let go? Here are a few actions to consider:

  1. Be clear about the skills, behaviors and capabilities needed on the executive team and recognize that who got you to this point is not always who will get you to the next level. Embrace the reality that others may be better suited than you across the many areas necessary to grow the company. You simply cannot do it alone.
  2. Be honest with yourself about your own strengths and limitations, biases for and against action, and your appetite and interest to be more self-aware of how you show up.
  3. Establish clear Executive Leadership Team (ELT) goals, values, and norms as a foundation of trust and accountability. Be open to feedback on how you contribute to, and hinder, your ELT’s performance.
  4. Be honest and intentional about performance expectations and decision-making authority at both the enterprise and functional level. While you certainly have the right, resist the urge to overrule, jump in, or usurp unless truly necessary (e.g.; a crisis, material customer or product challenges, an unplanned threat, etc.).
  5. Recognize that the behaviors intrinsic to growth CEO success are different and more diffused as you move from a “leader of people” to a “leader of leaders”, and influencing across a growing stakeholder network. In short, you are being held to a new standard of performance and behavior.
  6. Allow for mistakes and embrace failures (as you did early on in foundational mode). While a culture of experimentation and risk-taking are hallmarks of early-stage companies, letting go does not mean inhibiting those same or similar behaviors even if you are no longer the driver.
  7. Take a gradual approach and start with less crucial tasks or decisions. Allow for adjustments to help build trust and confidence within the team.
  8. Appreciate the impact of letting go. Recognize success and areas for improvement and reinforce those privately and publicly.

You Are Always Present

Ultimately, when coaching or advising CEOs and ELTs, I remind them that while letting go may be challenging, you are always present whether “in the room” or not. It really boils down to how present you want or need to be -- situationally, or as a matter of practice as you grow and scale the company:

At the head of the table where you display authority, clarity, direction, and inspiration?

Around the table where you act as a facilitator, inviter, enabler, debater, or questioner?

At the back of the room where you observe, support, encourage, and empower?

Outside the room where you trust your team to operate on their own, with intent and collective accountability?

Letting go is not really about “giving up” something; it’s far more about embracing a new vision of growth, about becoming more externally oriented, about clearing roadblocks and hurdles, and – in the end – gaining the strength of those inspired and empowered by you to achieve collective results.

Finally, as I went back and reflected on the CEO coaching conversation that inspired this post, I asked Chat GPT-4 for some help. Being a huge fan of “Succession” on HBO, I was interested in how lead Succession character, Logan Roy, might operate as a client in a similar situation. Here’s what Chat GPT-4 spit back at me. For all you Succession fans out there, enjoy!


A Letting Go Conversation with Logan Roy

Setting: an opulent, high-rise office, tastefully decorated with modern artwork and floor-to-ceiling windows, showcasing a breathtaking city skyline. LOGAN ROY (sharp, powerful) sits behind a sleek glass desk, engrossed in paperwork. Me, an executive coach with a calming aura, sits across from him, observing the scene:

ME (sympathetically): Logan, I appreciate you inviting me into your domain. How can I help you today?

LOGAN (gruffly): Cut the crap Steve. I've heard good things about you. They say you're some kind of expert at unraveling people's messed-up minds.

ME (smiling calmly): I prefer to think of it as helping leaders understand their blind spots and overcome their challenges. What seems to be troubling you?

LOGAN (reluctantly): Fine. It's this whole “letting go” thing. I built this company from scratch. It's my baby. But my children, these idiots, they're not stepping up like I need them to. And I can't just walk away.

ME (nodding): I understand the struggle, Logan. Succession can be a delicate process, especially for founders. Tell me more about your concerns.

LOGAN (agitated): Concerns? They can barely run a board meeting without me breathing down their necks. If I let them take the reins, we'll be bankrupt within a month. It's a family business, dammit! We need to stay together.

ME (sincerely): You value family loyalty, Logan. That's commendable. But perhaps there's a way to balance your desire to protect the company and your longing for a seamless transition.

LOGAN (irritated): Balancing? I'm not here to balance. I'm here to win! We're a media empire, Steve, not a knitting circle. I need to know they can handle the pressure before I loosen my grip.

ME (calmly): Winning is undoubtedly important to you, Logan, and rightfully so. But what if I told you that loosening your grip could actually increase your chances of winning in the long run?

Logan leans back in his chair, skepticism etched across his face.

LOGAN (confrontational): So, what's your real angle here, Steve? Are you just another yes-man like the rest of them?

ME (earnestly): I'm here to challenge you, Logan. To help you see things from a different perspective. You've built an incredible empire, but clinging too tightly to control may be limiting your potential. By empowering your children, you allow them to grow and succeed, and in turn, strengthen the company.

Logan's eyes narrow, contemplating my words.

LOGAN (softening): You think I'm holding them back?

Me (gently): It's possible, Logan. By fostering an environment of trust and autonomy, you create a space for innovation and fresh ideas. It's about leveraging their strengths while guiding them strategically.

LOGAN (resolute): Alright, Steve. Let's say I'm open to giving them more freedom. How do I even start? How do I stop myself from jumping in at every mistake?

Me (pensive): We can work on developing your ability to delegate effectively. Establishing clear goals, providing support and feedback, and giving them room to learn from their own mistakes are all crucial steps. But remember, Rome wasn't built in a day. Patience is key.

Logan leans forward, a mix of determination and vulnerability in his eyes.

LOGAN (confidently): Alright, Steve. Count me in.

Steve is an accomplished and mission-driven business leader, 2x former chief people officer, and trusted partner with the board, CEO, and executive team.  Known for his intentional, pragmatic, and values-driven leadership, Steve is a highly effective executive and team coach, advisor, and facilitator.