Stigma vs. Strategy: Why Smart CEOs Get Coached

“You’ve been successful in the roles you’ve held. But now, you’re playing a new game… You are now the leader who needs to get extraordinary results.”

— Mike, CEO and TVG Coaching Client

At some point in every leader’s career, the old playbook stops working.

The role gets bigger. The stakes get higher. The problems become more complex and ambiguous. And the instincts that once led to success? They don’t quite land the same.

These are inflection points—moments when a leader either levels up or stalls out and hits their limit. They’re also the moments when Executive Coaching can be most valuable.

The Stigma: “Why Would I Need a Coach?”

When this CEO stepped into the top job at a PE-backed company, he was already successful. He had a track record of results, deep technical expertise, and many years of leadership under his belt.

So, when the firm recommended a coach, something he had never experienced before, his first reaction wasn’t enthusiasm.

“There’s a stigma around having a coach. Many executives think, ‘I’ve been successful for decades, why would I need a coach now?’”

This is a sentiment we hear often. Coaching is sometimes seen as remedial. Something reserved for people in trouble or needing “fixing.”

That perception, while understandable given how coaching was historically leveraged, is outdated.

The Shift: From “Fixing” to High Performance

While coaching may have once been associated with “jerk fixing,” today it’s more often a strategic investment in growth.

For Mike, he had to shift his mindset to viewing this as a resource and an investment in his leadership skill—seeing coaching as a critical support function that could help him lead through complex, novel, and high-stakes situations.

This is how the best leaders and organizations view coaching: As a strategic tool to support high performance.

→ Want a refresher on what Executive Coaching entails? Here’s a quick read.

At The Violet Group, we work with leaders who are already delivering—but who know the next level will require more from them. More self-awareness. More adaptability. More strategic focus. And more trust in the people around them.

As Mike shared:

"...the truth is, we have no problem hiring a coach to improve our golf swing, learn a language, or train for a marathon. Why not the most demanding role of our careers?”

Mike’s Story: Letting Go of the Old Playbook

The challenge for Mike was not a lack of capability or experience, but a need to calibrate his approach to a new context and a different set of expectations. Specifically, this involved focusing on value creation, raising the bar on performance, and empowering people to work with greater autonomy.

As a former engineer and hands-on operator, he had built his success by being in the details. But as CEO, that approach was becoming a liability. He was too in the weeds with his team, which hindered their capacity to grow into their roles and operate at the level needed.

We see this often through a transition like this—it’s the classic 'what got you here won’t get you there' scenario. In one role, you’re rewarded for your detail orientation, diligence, and hands-on approach. In the next, those same strengths can unintentionally limit your team and create unsustainable habits that slow everyone down.

Fortunately, Mike leaned into this insight. He understood the need to operate and think differently. To zoom out, lead more strategically, and trust his team to own the day-to-day operations. This became a key focus in our coaching sessions: Checking in on how and where he might need to pull back, set clearer expectations, and empower others to deliver.

As he shared: “You’ve been successful in the roles you’ve held. You’ve overcome challenges, built teams, and delivered results. But now, you’re playing a new game. The pace of private equity. The weight of debt and direct investment. The responsibility to not just participate in the ecosystem, but to sustain and grow it. You are now the leader who needs to get these results.”

Once we got started, the real work began. Together, we:

• Reflected on his leadership identity in this new context

• Surfaced blind spots and habits limiting his team’s performance

• Engaged his senior team to build shared language and accountability

• Observed live meetings to surface real-time team dynamics

• Built a clear plan with goals aligned to key stakeholders

He did the work. He stayed open. And it paid off.

“What Stefanie and The Violet Group have done is help me step into the role of CEO with more clarity, more conviction, and a deeper understanding of how to build trust—both within myself and with my team.”

This is what high-impact coaching looks like.

 → Curious how to get the most out of a coaching engagement We wrote a guide for first-time coaching clients.

The Outcome: Confidence, Clarity, and Credibility

Six months later, Mike was a full supporter of Executive Coaching. The skepticism was gone and he saw how having space for confidential reflection and discussion could positively influence his day-to-day leadership behaviors and habits.

In his words:

“A great coach won’t give you the answers. But they’ll ask the right questions. They’ll offer perspective. They’ll hold the mirror up when others can’t or won’t. And they’ll help you become the leader your team, and your business, needs you to be.”

And in our view? Coaching doesn’t give you all the answers. It’s not intended to simply tell you what to do, rather, it helps you ask better questions, gives you space to reflect and cement your learnings, and ensures you’re appropriately challenged and held accountable to the goals you’ve set.

Final Thought from a CEO

“My wish for other leaders? Don’t wait until the pressure builds. If you’re stepping into a new challenge, make sure you have a coach who can help you win.”

If you’re facing a new level of complexity—or supporting someone who is—let’s talk. Contact us here.

Coaching isn’t about fixing what’s broken, it’s about winning at the next level. And the smartest leaders know, that’s not stigma—it’s strategy.