Here’s Your Sign: How to Know It’s Time to Work With a Coach

I know you’re capable. You’ve built teams, made hard calls, and kept things running when it mattered most. But sometimes the weight of leadership grows heavier than it should. Decisions that used to feel clear start looping, and the pace just feels…never-ending. Relentless.

It might feel like asking for help means you’ve failed, but I promise that’s not true. Getting coaching isn’t a sign that you couldn’t make it alone. Far from it. It’s a way to create space in high-stakes environments so you can think clearly and move decisively.

What might be keeping you from reaching out

Tell me if this sounds familiar:

• “I should be able to handle this alone.”

• “I’m not sure what a coach would actually do.”

• “I don’t have time to explain everything.”

• “Is the return on investment for coaching worth it?”

I understand every one of those thoughts because I’ve had them too. Earlier in my career, I kept saying yes to bigger roles, running on five hours of sleep and the so-called routine of “highly successful people.” From the outside, it looked great. But on the inside? I felt isolated and out of alignment.

The turning point came when I finally clarified the direction and values I wanted for my career—and found the community that supported them. That clarity changed how I work, how I rest, even how I show up for others.

Why the idea that you should “handle it alone” is misleading

Independence is celebrated in leadership culture. From an early career stage, we’re praised for being self-starters and for “figuring it out.” That mindset can be useful when you’re building skills and proving yourself.

But at senior levels, the very independence that helped you rise can quietly work against you. Complex decisions involve people, systems, and trade-offs that no one person can fully see. Carrying every challenge alone can eventually narrow your perspective and slow your progress.

Again: seeking support isn’t a sign of weakness—it’s a strategic skill. The best leaders I know build a network of advisors, peers, mentors, and, often, a coach. They don’t outsource responsibility but instead they create the right conditions to think clearly and lead well.

Signs you’re ready for a coach’s support

Here are patterns I often see when a leader is ready for coaching. Any sound familiar?

You’re stuck in decision loops

You start spinning on the same options, unable to give real weight to pros and cons. Choices that once took an hour stretch into days. Sometimes you commit and then second-guess.

You feel alone in the big calls

You can be surrounded by people and still feel isolated. The quiet story in your head says, “No one really understands this call but me.” That feeling makes it feel riskier to share ideas and can create even more distance.

You’re moving fast without a clear why

People are often praised for how fast they can move and come up with solutions. But if priorities aren’t clear, moving faster usually creates confusion and extra rework instead of real progress.

Your progress feels heavy

Despite long hours, your momentum slows. A task that once took an afternoon now takes a full day. It’s tempting to blame the season or the team, but often it’s a sign your own energy is depleted.

You keep revisiting the same work

Projects loop back for revisions because you’re carrying too many threads to land a decision you trust.

Recognizing the signs is a good thing

If you postpone getting support until you’re burned out or in crisis, the impact is greater and lasts longer. Decision-making declines when you’re exhausted, and it takes far more time to regain energy and focus than it would to address the early warning signs.

Your team is affected too. When a leader is depleted, meetings drag, priorities shift unpredictably, and communication loses clarity.

Think of a car that’s overdue for maintenance—you can keep it running for a while, but small issues turn into costly repairs the longer you wait.

Seeking help before reaching that stage is a practical part of responsible leadership.

What coaching can give you

When people ask what coaching actually offers, I describe it as a focused space to think and act with clarity.

Here are a few of the most valuable outcomes my clients notice:

• A thinking partnership—not someone to hand you answers, but a dedicated space to hear your own thinking, challenge it, and act from alignment.

• Clarity on priorities—separating signal from noise so you know what matters right now.

• Renewed energy and presence—a subtle but steady shift that your team will notice.

Coaching isn’t a dramatic overnight change. It works over a period of time to help you think more clearly and make decisions with confidence. Much of the real progress happens between sessions as you test new approaches and bring insights back to the next conversation.

What to expect in a first coaching session

If you’re curious about how a first session works, think of it as a focused conversation to clarify what’s on your mind and where you’d like to go next. We outline priorities together and create a simple rhythm for exploring challenges and capturing insights.

For a fuller picture of how I structure ongoing coaching, check out my article on what it’s like to work with me: A Thinking Partner for High-Performing Leaders.

When you’re ready to begin

You don’t have to carry everything alone. Coaching offers a pause—a chance to realign your energy and make decisions you actually trust. If any of these signs sounded familiar, I invite you to join my newsletter by signing up below or check out my LinkedIn for more reflections and practical tools for navigating leadership with clarity.

And if you’re ready for coaching, set up your free clarity session with me today.