What Executive and Career Coaching Actually Is (And Who It’s For)

Executive and career coaching is one of those things everyone’s heard of, but very few people can clearly explain.

Some people think it’s therapy for work. Others think it’s paid advice from someone who’s been there before.

None of those are quite right.

If you’ve ever thought, “I might benefit from a coach” and stopped there, this is for you.

What Executive and Career Coaching Is

At its core, coaching is not about answers. It’s about thinking better.

A good coach helps you slow down just enough to see the real shape of the problem you’re dealing with, including the assumptions, tradeoffs, and blind spots that are easy to miss when you’re inside it.

A coach is there to help you:

• Get clear on what you actually want next, not what you think you should want, by balancing ambition, role expectations, and organizational needs

• Understand what’s getting in your way, including thinking patterns, incentives, and interpersonal dynamics

• Make deliberate decisions in ambiguous or high-stakes situations, where speed, clarity, and second-order effects matter

• Build confidence and conviction when the path forward isn’t obvious and others are taking cues from you

The work isn’t abstract. It’s grounded in what you’re dealing with right now.

What changes is how you think through it.

When Coaching Is Most Useful

Coaching tends to be most effective during moments of transition or ambiguity. It’s a good fit if:

• You’re uncertain about your next career step

• You feel capped or underutilized in your current role

• You’re navigating a change in scope, identity, or direction

• The decisions in front of you don’t have obvious answers

• You want to be more intentional instead of reactive

For executives, coaching usually shows up later than it should.  Things don’t feel broken, but the cost of being wrong has quietly increased:

• Headcount decisions ripple through teams.

• Strategic calls shape quarters, not weeks.

• Uncertainty doesn’t just affect you, it affects everyone downstream.

If execution is the bottleneck, coaching may not be the best first move.

What a Coaching Session Actually Looks Like

Most effective coaching sessions follow a simple arc, even if it doesn’t feel structured at the moment.

1. A Real Situation You’re Facing

Most start with something very practical and current. This might show up as:

• Your day-to-day work no longer fits, but you’re not sure what should come next

• You’re considering a new role, company, or direction while weighing responsibility to the people and systems you’re part of

• You want to grow your impact but don’t know which lever to pull

• You feel underutilized, capped, or misaligned, even though things look fine from the outside

2. Pressure Testing Your Current Thinking

From there, you and your coach unpack:

• The options you’re already considering

• The tradeoffs you’re making, whether you realize it or not

• The assumptions shaping your decisions

• The risks you might be avoiding

• What success would actually look like in this scenario

Most people are surprised here. Oftentimes, no one has slowed you down enough to really examine your thinking.

3. Deciding What to Do Next

You leave with one of three things:

1. A clearer decision

2. A stronger approach

3. A specific action to try

What Coaching Is Not

Coaching is not primarily about execution. If what you need right now is:

• Someone to help you do the work → consultant

• Someone to tell you what to do based on experience → mentor

• Someone to weigh in strongly on strategy or decisions → advisor

These are different needs and often require a different skillset.

That said, the best coaches often blend coaching with one of these disciplines. They know when to ask questions and when to offer perspective.

Why Finding the Right Coach Matters

One pattern I see over and over is this:

People know coaching could help, but they don’t spend enough time finding the right fit. Once they pick someone, they rarely switch, even as their role or problems change.

That’s a mistake.

The right coach depends heavily on where you are and where you’re trying to go.

If you’re moving from individual contributor to people leadership, you want someone who understands that transition.

• If you’re going from $1M to $5M, you want someone who’s lived that jump.

• If you’re rethinking your identity entirely, you want someone who won’t rush you to clarity.

Fit matters more than credentials.

Reflection Questions to Help You Get Oriented

These reflection prompts will help you think more clearly before starting a conversation with a coach.

Where Are You Today?

• What parts of your work energize you?

• What consistently drains you?

Where Are You Trying to Go?

• Are you clear on your next step and want help accelerating, or are you still figuring it out?

• If this time next year went really well, what would be different?

What Kind of Support Do You Want Right Now?

• Direction

• Accountability

• Skill building

• Confidence

• Practical advice

Just as important:

• What kind of support would not be helpful?

What Type of Coach Might Be Best?

• Do you want someone who’s walked your exact path or someone with a different perspective?

• What style works best for you? Direct, supportive, structured, exploratory, etc.?

How Do You Want to Work With a Coach?

• What cadence feels right, one on one, group, monthly, bi weekly?

• What budget range feels reasonable for you?

Clarity here makes everything downstream easier.

A Final Thought

Coaching isn’t about fixing you.

It’s about creating space to think clearly, make better decisions, and move forward with intention instead of momentum.

If that sounds like something you need, the next step isn’t finding the “best” coach. It’s getting clear enough to find the right one.

If you want help thinking that through or want me to help you find a coach who fits where you are right now, reach out.