In every industry, we see leaders at the top of their game who still struggle with one key decision: whether or not to engage in executive coaching. After decades of coaching high-performing professionals, I’ve heard every reason under the sun for why leaders won’t, don’t, or can’t say yes to coaching.
But here’s the truth: The timing will never be perfect. And if you’re waiting for a window to magically open, you’re actually closing the door on transformation.
The Timing Trap
The most common excuse I hear? “I don’t have time.”
Leaders are busier than ever. They’re short-staffed, managing reorgs, overseeing high-stakes projects, or prepping for earnings season. The list never ends. Maybe we hear this at our organization because our coaching process is front-loaded to deliver immediate value – through robust assessments, full day leadership development workshops, data collection, and deep reflection – it can feel like “too much” on an already full plate.
But here’s the twist: after those first few weeks, nearly every client says, “This is easier than I expected. I love it.” Because the ROI kicks in fast. One weekly session turns into a cadence of growth, insight, and, most importantly, measurable impact.
The “Not Now” Illusion
Closely related is the “not now” excuse. Maybe there’s a major transition underway. Maybe a key employee just left. Maybe you’re in “survival mode.” But if you’re a leader, chances are you’re always in the middle of something. The idea that someday there will be a calm moment to begin is, simply a myth.
The Cost Objection
Coaching can be expensive. And many companies, especially those recovering from a tough financial year, hesitate to invest. But the issue may be they often don’t understand what professional executive coaching can deliver.
We’re not talking about book recommendations or soft-skill seminars. We’re talking about a data-driven, behaviorally anchored methodology that increases trust, accountability, alignment, and execution. The kind of coaching that helps leaders stop micromanaging and start orchestrating. That moves teams faster. That improves delegation and communication, freeing leaders to lead at a strategic level.
Related: Measuring the ROI of Executive Coaching
Past Bad Experiences
Some leaders have worked with coaches who weren’t a fit or they didn’t deliver an impactful ROI, and it soured their perception. Maybe it felt like therapy. Or maybe it was too tactical. Worse yet, maybe it wasn’t measurable. Without clear outcomes and accountability, of course they walked away skeptical.
A good coach doesn’t just ask how you’re feeling. They show you the blind spots you can’t see. They track data, measure performance shifts, and create transformation from the inside out. Without that structure, you’re not really getting coaching – you’re getting a conversation.
“My Supervisor Is Already Coaching Me”
We also see this misconception: “My boss is coaching me. I don’t need more.”
But most managers who claim to “coach” are actually just directing, advising, or telling. Coaching is not telling someone how you would do it. It’s helping them discover new levels of self-awareness, uncover blind spots, avoid self-sabotage and coach how they can do it better, with authenticity and ownership. Coaching levels someone up – it doesn’t just create clones.
Lone Rangers and the DIY Myth
Then there’s the independent learner. The Lone Ranger who says “I can read a book. I can Google it.”
Sure, you can get tips from a book (in fact, that’s one reason I wrote my book Leading Lightly to enable individuals to jumpstart their progress). But performance breakthroughs don’t come from tactics alone. They come from self-awareness, behavioral shifts, and repetition. True change happens when someone challenges the wiring of your brain – often wiring you don’t even know is there.
One client, a high-performing VP in a tech organization, came to us believing his only issue was presence in meetings. On the surface, he was effective, detail-driven, and met his goals. But his team was disengaged. Through our coaching process, we discovered he was so over-indexed on execution that his team felt shut down before ideas could even take flight. He wasn’t just being efficient – he was unintentionally dismissive.
Coaching helped him radically shift his approach, opening space for collaboration and innovation. Within months, team performance and morale had measurably improved. He became known not just for getting results, but for cultivating talent. That behavioral shift was not going to come from reading a book.
Fear of the Mirror
Many leaders are simply afraid.
Afraid to fail. Afraid to look weak. Afraid of what they’ll see in the mirror when we start peeling back the layers. But here’s what they discover: Growth isn’t about shame. It’s about clarity. And when you finally understand the “why” behind your behaviors, performance accelerates at a level no checklist can provide.
Culture That Undermines Coaching
Some organizational cultures do not support coaching. They see it as fluff. Or worse, a checkbox for HR.
One company recently engaged JMA only because they feared losing a top SVP. They didn’t believe in coaching, but they believed in him. This VP was a right-hand leader to a C-suite executive, but internal feedback flagged key concerns around his interpersonal effectiveness. HR recommended coaching as a retention strategy. The C-suite leader reluctantly agreed, stating, “I think we might be wasting money, but we can try.”
Three months in, that same skeptical leader was astounded. Through coaching, the SVP had increased his emotional intelligence, developed nuanced awareness of how his tone and energy impacted others, and transformed how he led meetings and feedback sessions. He became known for balancing high performance with approachability. He was being discussed as a future EVP – something the CEO said was “unthinkable” without the intervention and the subsequent change in his interpersonal behavior.
Coaching Isn’t Just About You
When you change, everyone under you changes. That’s the beauty of the trickle-down effect of executive coaching. Everyone has better conversations, better clarity, better alignment. Teams move faster, own more, and execute with greater accountability.
Think of it like Tiger Woods changing his golf swing. He was already the best. But in the early 2000s, Woods recognized that his swing, though effective, was limiting his long-term dominance due to underlying flaws that could cause injury and inconsistency. With his coach, he made the bold decision to deconstruct and rebuild his swing from the ground up. It was an excruciating process. He lost tournaments. Critics doubted him. But over time, the payoff was undeniable. He returned stronger, more consistent, and more dominant than ever.
The same is true for leadership. The next level isn’t always about doing more. Sometimes, it’s about doing it differently – even if that means unlearning what’s worked in the past to unlock what’s possible in the future.
So, When Is the Right Time?
Now. Always now.
Because the cost of waiting isn’t just lost time. It’s lost potential. And in leadership, potential isn’t a luxury. It’s your job. It’s cementing future upward trajectory.
Ready to stop waiting and start transforming?