How to Find a Career Coach Who Actually Fits You (Not Just Your CV)
If you’re reading this, there’s a good chance something feels off.
On paper, things might look fine. You’ve got a decent job, a steady income, you’re respected.
But inside, you’re either restless, flat, or quietly asking yourself, is this it?
And that’s usually the moment men start Googling things like career coach, career coaching, career development coaching or career transition coach.
Not because you’re dramatic, or you’re failing, but because you’re finally admitting that brute forcing your way through another year of the same isn’t the answer.
The tricky part is, once you decide you want support, you’re hit with the next problem. How do you choose a career coach who actually fits you?
Not just your CV.
Not just the version of you that performs well at work.
You.
First, a truth men need to hear
Career coaching isn’t only for people who are lost.
It’s for people who are thinking and people who are growing, and realising the old version of success doesn’t fit anymore.
A lot of the men we work with are high achievers - founders, leaders, specialists. Men who’ve been “doing well” since their twenties. And yet they land here because:
They’ve been made redundant and need to figure out their next move.
They’re gunning for a promotion but feel stuck in the same loop.
They want a career change but have no head space to think through it.
They’re succeeding outwardly but feel empty inwardly.
They’ve lost confidence in their voice, presence, or direction.
That’s where career coaching for men comes in, not to tell you what to do, but to help you strip back the noise and hear yourself again.
Why choosing the right career coach matters more than you think
The wrong coach won’t ruin your life, but they can waste your time, your money, and your momentum.
Many men choose a coach the way they’d choose a consultant.
They look for credentials, experience, Impressive clients, industry background and a slick website. Great stuff. But none of that guarantees the coach will be right for you.
Because career coaching is not just a professional process, it’s personal. It’s someone you trust enough to be honest with. That makes you feel safe. So that you can bring all your stuff to the table and know it will be heard without judgment.
And that is where fit matters.
The right coach helps you:
Get clear on what you actually want
Understand what’s really driving the dissatisfaction
Break through the internal blockers you’ve normalised for years
Build a practical plan, not just a motivational one
Take action and stay accountable
Step 1: Get honest about what you actually need
Before you speak to anyone, pause and ask yourself a few uncomfortable but useful questions.
What is it that you want to change?
Is it the job itself?
The environment?
The leadership?
The lack of challenge?
The lack of purpose?
The pressure and burnout?
The feeling you’ve outgrown it?
The fear you’re wasting your time?
Are you looking for clarity, confidence, direction, or all three?
This matters because different coaches focus on different things.
If you’re craving a career change but don’t know where to start, a career transition coach might be what you need.
If you’re trying to progress into leadership and strengthen your presence, executive coaching may fit better.
If you’re a high performer who feels stuck, career development coaching can help you identify what’s next and why.
Step 2: Make sure they understand men
This isn’t about “male only” spaces for the sake of it.
It’s about the reality that many men:
Carry pressure quietly
Overthink, but don’t say it out loud
Tie self-worth to performance
Struggle to admit uncertainty
Avoid asking for help until they’re already running on empty
A good coach for men will understand how this shows up, and they’ll know how to work with you in a way that feels grounded, practical, and human.
Step 3: Ask questions that reveal fit quickly
When you book an introductory call, treat it like a fit check.
Here are some questions that might help you figure out which coach is right for you:
What’s your coaching style?
Do they listen
Do they challenge
Do they keep you accountable
Do they bring structure or keep it open
What does success look like in your coaching?
Career coaching should lead somewhere.
Even if the destination changes.
How do you help someone who doesn’t know what they want yet?
Truth is, a lot of us don’t quite known what we want, and that’s why we look for a coach, to help bring that clarity.
A good coach should have a process for helping you find clarity, not just “set goals”.
What happens between sessions?
Accountability is everything.
If the coach offers check ins, tools, reflection work, or structure, that often separates a good experience from a transformational one.
Step 4: Notice how you feel when you speak to them
This is the part men often ignore.
But it matters.
After your call, ask yourself:
Did I feel heard?
Did I feel rushed?
Did I feel judged?
Did I feel like I could be honest?
Did I feel clearer even after one conversation?
Did I feel like they were selling to me or supporting me?
The right coach makes you feel both safe and stretched.
Not pressured.
Not handled.
Not fixed.
Just understood, and moved forward.
What career coaching with The Midlife Man looks like
At The Midlife Man, our career coaching for men is built around clarity, confidence, and direction.
We work with men navigating change, uncertainty, transition and growth.
Some want a promotion, some are winding down and wanting to explore legacy, some want a career change, some want to stop feeling flat and start feeling purposeful again.
Our approach is practical, structured, and human.
We listen. We challenge. We hold you to account.
If you’re nervous about coaching, that’s normal.
We’ll bust a few myths and keep it simple.
Our goal is to help you get honest about what you want, then build the framework to go and get it.
Final word
A career coach won’t magic everything better, but the right one will help you stop ignoring the questions you’ve been avoiding. And if you’re in midlife, that matters.
Because time starts to feel different.
Not in a scary way.
In a clarifying way.
If you’re ready to explore career coaching start with one thing.
Find someone you can be honest with, not just someone who looks good on paper.
If you want to chat, you can book an introductory call, or drop us a note and we’ll come back to you within 24 hours.
