“Comfortably Uncomfortable”: Authentically Embracing Growth as a New CEO

During a recent coaching session with a seasoned-but-new CEO in the Edison portfolio, he mentioned to me that another new (and first-time) CEO had just sought him out for advice. When asked about the leadership nugget that had most helped him, he notably shared: learn to be uncomfortable; unlearn habits that have made you successful up until now; and learn new habits that will help you meet the challenges in the context of your new situation. 

Having coached executives through various opportunities and transitions, I can safely say that the very strengths and patterns which got them to their leadership role are those most likely to be modified or abandoned first once they’re “in the seat.” I’ve seen the brilliant operator who struggles to delegate. Or the decisive executor who can't build consensus. Or the visionary who gets bogged down in operational details. Whatever may have been part of their career development playbook, or brought them success along the way, might now very well be their greatest leadership liability. 

And so therein lies the stark and naked truth: if the same approach to leadership worked at every level and in every context, leadership development would be rather simple.  But we all know it isn’t.  

Let Discomfort Be Your Friend 

Question: When was the last time you felt genuinely uncomfortable in your leadership seat? 

Hopefully, just moments ago. Or even right now. If it's been a while, that might be telling you something. Having extensively coached PE-backed CEOs, I've found initial “comfort” to be an early warning sign. While it is by no means synonymous with poor performance, it might reflect a bit of a lost edge, or a reliance on established strengths rather than an openness and willingness to develop new ones. When your growth-stage company is entering unfamiliar waters – be it operational scaling, rapid talent acquisition, accelerated market expansion, or AI-infused work processes – any one or all of these challenges are very likely to demand a different version of you than the one who got to this place. What’s asked of you now to realize success in your new role is simply different.  

Unlearning: The Critical, Yet Often Bypassed, Leadership Skill  

Early on in my career, as I left the world of banking and finance and moved over into the world of media and publishing, the process of unlearning was a prominent and central theme. I went from a very left-brained, process-intensive culture to a right-brained, creative, political, and relational culture. Prior success certainly helped get me in the door, but what I really needed was to adapt and reframe. To unlearn. 

For many leaders aspiring to be successful in the world of growth stage leadership, unlearning is often the most daunting, and yet most crucial, adaptation.  

 Here are a few growth-stage CEO leadership and personality profiles who may serve to benefit from unlearning. Do you see yourself in any one of them?  

• The leader with a “tech expert” mindset. You made your career mark because of domain / area expertise. But now your job isn't to be the smartest person in the room about your product, market, or operational requirements. Your job is to be the bandleader and to orchestrate others' expertise. 

• The leader who was the “hero.” Throughout your career, you were the uber problem-solver. But, solving problems that should or could be handled two levels down can create organizational bottlenecks and stunt team growth, especially in a fast-moving, high-growth organization.  

• The leader who is the de facto control freak. Your instinct to personally review every significant decision might have served you well as a functional leader prior to making it to the top. As a CEO, it’s that same approach that will serve as a guaranteed path to personal, team, and organizational paralysis. 

• The leader who has cultivated a trusted and invaluable inner circle. Meritorious at face level, the aggressive timelines of PE firms demand talent capabilities beyond the individuals in your current network and will put your new selection skills to the test.  

Targeting and Building New “Muscles” for the Growth-Stage  

While it might be easy enough to spot the need or catalyst for change as a new PE-funded CEO, what are some of the new habits, or new “muscles” that can be targeted and built to help fully embrace your new leadership opportunity?  

• Intense stakeholder management. Like any great conductor, success in your new role requires you to align diverse, and sometimes divergent, stakeholders – investors, board members, customers, talent – each of whom rely on separate metrics, and operate on different timelines. Success requires diplomacy and relational astuteness.  

• Decision-making design. Rather than make all decisions, you now need to architect how decisions get made – creating clear frameworks that cleanly identify chains of command and authority thresholds, and that help enable quality of decision-making without your direct involvement. 

• Talent acceleration. You'll need to identify, attract, and integrate leadership talent at speeds that match the timelines of your investors. This may likely mean developing talent instincts beyond your current core area(s) of functional expertise. 

• Strategic and executional dexterity. While seemingly contradictory, PE-backed scenarios require leaders to both adjust strategies nimbly while also maintaining focused execution against investment theses. Can you establish the proper organizational framework to deliver against both? 

• Transparency. Becoming truly transparent in the midst of change and uncertainty can be difficult. But leading with openness, especially with respect to real challenges, helps build the trust necessary to rapidly scale. 

Your First 180 Days Roadmap 

1. Reflection and Learning

• Start first by asking yourself: "What leadership moves feel most natural to me?" These might quickly also qualify as your defaults, and might potentially become limitations. Consider the leadership approaches that defined your success along the way and note which one of these might not serve you well in your new context. Then ask your trusted colleagues: "What leadership habits have you seen consistently in me?" Their observations might reveal patterns you’re not able to easily see in yourself.  

2. Build Your Discomfort Muscle

• Like deliberate exercise, schedule weekly conversations with the people most likely to challenge your thinking, and not just validate it. Identify your knowledge gaps and deliberately spend time in those areas. Keep a decision journal, noting when your instincts conflict with input from the team. Any of these “inflection points” could be viable opportunities for growth. 

3. Redesign How Information Reaches You

• Your biggest risk isn't lacking information – it's receiving filtered information that reinforces existing biases. Audit your current information sources – are you hearing primarily from the same functions or perspectives? Create direct channels to frontline realities – the voices of regular, unfiltered customer and employee conversations. Institute a "bad news first" norm in every senior meeting. 

4. Create Learning Rituals

• Your calendar is a simple reflection of your priorities. If learning isn't baked in or scheduled, it likely won't happen with the consistency required to make any real or lasting difference. Block 90 minutes weekly for exposure to unfamiliar domains relevant to your business. Leverage your board to build a network of advisors from industries that differ from your background.  Read across multiple disciplines – the most valuable insights often come from unexpected sources.

5. Show Vulnerability as Strength

• When you openly acknowledge areas where you're working to develop new leadership “muscles”, you create a culture of psychological safety, which might encourage others to do the same. Share what you're trying to unlearn and what you're working to develop. Acknowledge when you notice yourself defaulting to old patterns.

6. Build Your Support System

• Leadership transitions are challenging. Don't navigate them alone. Find a coach. Develop relationships with other CEOs from organizations at similar growth stages. Create structured dialogue with board members about your leadership development. 

Remember this move into the CEO seat isn't a one-time transition – it's your new normal… at every stage.  

I’ve found the most effective growth-stage CEOs don't simply survive a period of discomfort; they systematically use discomfort to better themselves and fuel their performance. In discomfort are possibilities which wouldn’t otherwise exist were it not for an openness and willingness to evolve.  

The habits that brought you career success helped get you here. The courage to develop new ones will likely determine where you go next.