What High-Performing Leaders Get Wrong About Executive Coaching

Executive coaching isn't about fixing problems. Former CIO Jessica Kral breaks down the four mechanisms that make it the highest-value development for leaders at the top.

I was talking to my executive coach, weighing how to deal with a challenge, when she asked me, "What do you want your legacy to be when you leave this role?"

The question caught me off guard. My response? "Oh. Whoa." And then I went quiet.

I was in my second CIO role. I'd always invested in my own development. I thought I was pretty good at challenging my own thinking. I hadn't expected to be stopped cold by a single question.

Some organizations have figured out that coaching is a strategic investment, not a remedial one. Most haven't. And even in the best development cultures, the leaders who are excelling often get promoted and left to navigate the next level largely on their own. The unstated assumption is that success means you've figured it out and don't need additional investment. For high-performing leaders, however, coaching isn't remediation. It's the highest-value development available.

The Paradox of Success

Success creates its own blind spot. The behaviors and thinking patterns that got you to the executive level have become so instinctual they're invisible—not because something's wrong with them, but because they've worked. You don't question what keeps delivering results.

There's a compounding factor at the top: the more senior you become, the fewer people are willing to tell you the truth. The feedback that shaped you earlier in your career becomes harder to come by precisely when the stakes are highest.

This is why elite athletes hire coaches. Serena Williams had been ranked No. 1 in the world and won 13 Grand Slams when she hired Patrick Mouratoglou. She went on to win 10 more. Atul Gawande, an accomplished surgeon, hired a coach after years of established practice because he recognized he couldn't see his own patterns from the inside. "Coaching done well may be the most effective intervention designed for human performance," he wrote in the New Yorker.

The best performers in high-stakes fields treat coaching as non-negotiable. So why don't the best performers in business?

Maybe because if you've reached the executive level, you're probably someone who already invests in development. You read the books, listen to the podcasts, take the courses, talk to advisors. You're always learning. But more input isn't always the answer.

Or maybe the stigma is the barrier: coaching is for when something's wrong. That assumption alone keeps many high performers from ever considering it.

Organizations struggle with this, too. Some have figured out that coaching is a strategic investment; most haven't. Even in the best development cultures, leaders who are excelling get promoted and left to navigate the next level on their own.

The paradox is that being at the top is precisely the reason you'd benefit most.

The Missing Relationship

There is a specific loneliness that comes with seniority, rarely acknowledged. You cannot show your team uncertainty without risking their confidence. You cannot always be fully candid with peers. You cannot always be vulnerable upward. Your external network, while broad, is often too political or surface-level to go deep with.

A coach may be the only relationship in a senior leader's life that is simultaneously professionally informed, completely confidential, non-hierarchical, and entirely focused on you. At the level where the stakes are highest, that turns out to matter enormously.

My client found out he was in line for a promotion. Instead of being excited, he was overwhelmed. He was already working at his limit. He knew if he admitted the overwhelm, he'd be seen as not having what it takes.

I asked, "What if a new role isn't more work… It's just different work?"

He visibly relaxed. We used our subsequent meetings to design experiments to shift from doing it all himself to focusing on what mattered most. That skill served him well when he got the promotion.

What Makes Coaching Work

Conventional development tools can expand your thinking. They can't see your patterns, hold them over time, or ask the question that stops you cold. Executive coaching can. Here's how.

1.    The Honest Mirror
Most relationships in a senior leader's life come with a competing agenda. Direct reports need you to provide clarity and confidence. Peers can also be rivals. Your boss just wants you to deliver. Your partner and friends don't have time. A coach has no stake in any of that. For many executives, it's the only relationship where they can have an unedited conversation fully focused on what they want to achieve—and where someone will ask what no one else will.

I worked with a client who was the go-to person for all the toughest challenges. She loved being the go-to and knew it had been a major factor in her last two promotions. But she also knew she was becoming a crutch for others, and it was impacting her ability to focus on her most important work. Her goal was to interrupt the pattern.

During a conversation, she made a passing mention of something that appeared to be another example of taking on someone else's challenge. I asked, "How is this new challenge related to your goal to focus on your most important work?"

She looked at me ruefully. "Ugh. I didn't even realize I was doing it again." We partnered on an approach to elegantly pass the challenge back to its rightful owner.

2.    Holding Patterns Over Time
A single insightful conversation is not the same as a relationship that remembers what you said three months ago and notices when you've returned to the same place. Coaching is longitudinal in a way that no leadership book, MBA course, or annual offsite can replicate. Someone is tracking your patterns in real time and real situations.

My client felt pressured by his new boss to influence a business partner in an inauthentic way. I reminded him of situations where he had successfully influenced outcomes authentically. "How might you apply your past success here?" He immediately smiled and said he knew exactly what to do.

3.    Development in Production
Most leadership development gives you something to store and apply later. Coaching works on your actual needs, your real stakeholders, your current decisions—not simulations or case studies.

My client was a newly promoted COO. We were focused on establishing her leadership brand when she had a crisis. We worked together on a communication approach consistent with her brand.

Two weeks later, she reported that while she wished there hadn't been a crisis, she felt proud she had shown up in a way that reinforced her brand.

4.    Targeting Thinking, Not Just Behavior
The most durable changes come from shifts in how you think, not adjustments in what you do. Most development tells you what to do differently. Coaching examines the assumptions underneath.

I had a client who was frustrated by reorganization news that meant he'd be working with a colleague he found difficult. I asked, "What would have to be true for the two of you to have an excellent working relationship?"

He paused, then grabbed his pen and started writing. "I'd been thinking this was something I just had to endure. It hadn't occurred to me to be proactive in shaping the way we'd work together." He left with a plan to approach his colleague.

No book or course can replicate what happens when someone sees you clearly and asks the right question at the right moment. That's what other forms of development can't touch.

Back to the Question

In the silence, as I reflected on my coach's question about legacy, I was transported back to sitting in a room listening to a speaker quote Maya Angelou. I couldn't remember the exact words, but I remembered the theme: People won't remember what you said or what you did; they'll remember how you made them feel.

Suddenly, I was looking at my challenge from a different altitude, and the next step became clear.

What would your answer be?