For many leaders, working with a coach feels like stepping into unknown territory. They’ve heard coaching can be valuable, but what actually happens in those conversations? More importantly, how do you ensure it’s worth your time?
If you’re new to executive coaching, you’re not alone. Many leaders we work with are engaging in coaching for the first time. They often arrive with questions—and a healthy dose of skepticism. So, let’s pull back the curtain and explore how to maximize the value of your coaching engagement.
A Story: The Leader Who Almost Missed the Value
A few years ago, I worked with a senior leader—we’ll call him Jake—who was stepping into a much larger role. His company proactively offered him an executive coach (a nod to forward-thinking companies that invest in leadership development—a smart move). While he agreed, he wasn’t sure how to make the most of the coaching experience.
In our first sessions, Jake approached coaching the way he approached most things: efficiently, analytically, and with a “just tell me what to do” mindset. He expected answers and prescriptive guidance, not realizing that coaching is about unlocking the answers already within him.
It took a few conversations, but once he leaned in—reflecting, challenging his own assumptions, and applying insights between sessions—his growth accelerated.
By the end of our engagement, Jake admitted, ‘I almost treated this like a box to check—I had no idea how much I’d gain.’
Here’s what he learned—and what you can take with you if you want to make the most of your own coaching experience, too.
Come With a Focus—But Stay Open-Minded
Coaching works best when you bring real challenges, live issues, and clear aspirations to the table. Maybe you want to lead more effectively through change, build stronger relationships, or navigate a new leadership role with confidence. But coaching isn’t about rigid problem-solving—it’s about expanding how you think, see yourself, and lead.
The best coaching engagements strike a balance: You come with a focus but remain open to discovering new perspectives along the way.
→ Before each coaching session, ask yourself: What’s the most important leadership challenge I’m facing right now? What would make the biggest difference if I could improve it?
Commit to Doing the Work Between Sessions
Coaching isn’t just about what happens in the meetings—in fact, most of the work happens between them. Real growth comes from applying insights in real time, experimenting with new behaviors and strategies, and reflecting on what you learn.
Initially, Jake treated coaching sessions as standalone experiences. But once he started applying insights—trying a different approach in a high-stakes conversation, testing new ways of leading his team, and sharing reflections during our sessions—he saw immediate impact.
Often, I found myself validating his instincts and building upon what he was already doing. That alone was a powerful way to increase his confidence in his own capabilities. As a coach, seeing that confidence grow is a key indicator that the work is making an impact.
→ Try this: At the end of each coaching session, commit to one concrete action before the next meeting. Your coach will track it and follow up, holding you accountable. These small, intentional experiments compound into big results over time.
Share What You’re Working on With Your Team
Leadership growth doesn’t—and shouldn’t—happen in isolation. One of the most effective ways to accelerate your development is to let your team and key stakeholders know what you’re working on.
Why? Because when others understand the leadership behaviors you’re focused on improving, they can help hold you accountable, provide feedback, and recognize the shifts you’re making. This builds trust and ensures that your growth isn’t just something happening in coaching sessions—it’s something your team experiences in real time.
For example, Jake was working on becoming a more strategic leader instead of getting pulled into daily execution. Once he told his direct reports that he was intentionally stepping back to empower them more, they understood why he was changing his approach—and they were more willing to step up.
→ Try this: Identify one or two trusted colleagues (or your full team, depending on your role) and share what you’re working on. Say something like:
“One of my coaching goals is to delegate more effectively so I can focus on strategy. That means I’ll be handing off more decisions and resisting the urge to jump in. If you notice me backsliding, I’d love your feedback.”
Expect Discomfort—That’s Where Growth Happens
I’ll admit this is an overused piece of advice, but it’s often repeated for a reason: it's foundational to growth.
Good coaching challenges you. Great coaches create space to work through that discomfort. As a coach myself, I also have a coach, and I can tell you this: The moments when I felt like hiding my face or sinking in my seat were when I knew it was working. Those were the times I needed to sit up tall and work through the discomfort alongside my trusted advisor.
Back to you: Coaching pushes you to examine assumptions, stretch beyond old habits, and see yourself—and the situations you’re in—in new ways. That’s not always comfortable. In fact, it rarely is. But it’s where the real breakthroughs happen.
Jake had a moment mid-engagement where he felt stuck. He wanted a clear answer, and sure, I could have given him one—but that’s not what coaching is about. Instead, we sat with the complexity. I asked open-ended questions, letting him think out loud and make sense of his own perspective. Together, we arrived at the answers.
→ Mindset shift: When something feels uncomfortable in coaching, instead of resisting it, ask: What is this discomfort trying to teach me?
Be Honest and Open—With Yourself and Your Coach
The most effective coaching happens when leaders are willing to be honest—not just about what’s working, but about what’s hard and how they’re truly feeling. If you only bring the polished version of yourself to coaching, you limit what’s possible.
I tell every leader I work with that coaching is a “judgment-free” zone. I’ll support and challenge you, but it’s your space to be open and candid. Leadership is high pressure—it requires restraint, care, and thoughtfulness. A coaching partnership allows you to just say what’s on your mind without fear.
Some of the most transformative coaching moments happen when a leader says, “I don’t know how to handle this,” or “This is the part I don’t want to admit.” Those conversations unlock real change. And—this can’t be overstated—verbalizing these thoughts often provides clarity and relief, making challenges feel more manageable.
→ Consider this: What’s one thing you haven’t said out loud about your leadership challenges but that takes up space in your head? That’s likely where the most valuable coaching work begins.
Measure Progress in the Right Way
Coaching isn’t about quick fixes—it’s about sustainable growth. The biggest shifts often happen in how you think, not just in what you do. While external results (e.g., better team performance, clearer decision-making, stronger executive presence) matter, internal shifts are just as important.
Jake realized this when he handled a difficult conversation differently—not because he had memorized a script, but because he had fundamentally shifted how he approached leadership challenges. That’s the kind of transformation coaching is designed to create.
→ Ask yourself: How am I thinking differently about leadership now versus when I started? What new ways of showing up have I developed?
Final Thoughts: Coaching is an Investment—Make It Count
Coaching is a rare opportunity to step back, reflect, and sharpen your leadership in ways that day-to-day demands don’t always allow. The more you engage, experiment, and stay open, the more value you’ll gain.
If you’re stepping into coaching for the first time, approach it with curiosity. Trust the process. And most importantly, don’t treat it like a box to check—because, as Jake discovered, it can be one of the most powerful investments you make in yourself as a leader.
Elevating Leadership Starts with the Right Support
Let’s talk about how our executive coaching can help. Contact us to learn more.
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