Have you felt like something feels off every time you meet with your leadership coach, and you can’t quite put your finger on it?
You’re trying to grow. You’re showing up to every session. But the chemistry isn’t there, and you’re worried about wasting time, money, and energy on something that’s supposed to make you stronger as a leader.
If that’s where you are, this article is for you. Our goal is simple: to help you understand why this happens, what you can do about it, and how to get the kind of coaching support that truly moves you forward. Because coaching can be powerful, but only when the relationship supports real growth.
Here’s what we’re going to cover:
- How to know if your coach isn’t the right fit
- Why connection issues happen, even with experienced coaches
- What to do before making a change
- How to talk openly about what’s not working
- When it makes sense to switch coaches or formats
- How HR leaders can support employees in the same situation
How Do I Know if My Leadership Coach Isn’t a Good Fit?
Many leaders struggle to name why a coaching relationship isn’t clicking. They just feel uneasy or disconnected during sessions. Here are some common signs things might be off:
- You feel judged or misunderstood. A good coach should challenge you, but you shouldn’t feel criticized or shut down.
- You’re not seeing progress. If you’ve been meeting for months with no noticeable change in behavior, clarity, or confidence, something is likely misaligned.
- You don’t look forward to the sessions. You might feel drained, annoyed, or indifferent before a meeting. That’s usually a sign of fit, not motivation.
- The conversation always stays surface-level. If your coach can’t get past polite check-ins, they may not have the right approach for your learning style.
- Their approach feels too rigid or too loose. Some leaders want structure, while others want open reflection. If you need one and get the other, frustration can build quickly.
Why Am I Not Connecting with My Leadership Coach?
We want to make this clear: a mismatch doesn’t mean you failed! Leadership coaching is deeply personal, and several things can get in the way of connection. Understanding why the mismatch exists can help you decide what to do next.
Some common reasons are:
- Mismatched communication styles. Some coaches ask a lot of questions. Others give more direction. Neither is “wrong,” but one might feel more natural for you.
- Different views on leadership. If your coach sees leadership one way and you see it another, conversations might feel tense. Sometimes this feeling is productive; other times it’s too much.
- Life or work stress is making it hard to engage. Sometimes the issue isn’t the coach, but rather your own time, bandwidth, or burnout.
- Unclear expectations on both sides. If your goals or success measures weren’t defined up front, it’s tough to feel aligned.
Is It Normal to Not Click with a Leadership Coach Right Away?
Yes. Early coaching sessions can feel awkward while you’re building trust. But there’s a difference between early discomfort and actual misalignment.
Normal discomfort can look like feeling a bit vulnerable, not knowing exactly what to share, and/or needing a few sessions to find rhythm.
A deeper mismatch can look like constant miscommunication, feeling talked over or misunderstood, and/or no meaningful progress after several sessions.
If you’re unsure where you fall, track how you feel before and after each session for 3-4 weeks and see what patterns show up.
What Should I Try Before Deciding to Switch Coaches?
Before making a change, try a simple reset. This keeps you from walking away too quickly and helps you get the best outcome no matter what you decide.
1. Clarify your goals.
Go back to the beginning and ask yourself: What do I really want from coaching right now?
More confidence? Influence? Communication skills? Better team leadership?
Then, write it out. If your goals have shifted since you began, your coach might not even know they need to adjust.
2. Revisit expectations.
Many leaders assume their coach will take the lead, but coaching only works when expectations are shared out loud.
This includes:
- How you want to receive feedback
- How structured you want sessions to be
- How progress should be measured
3. Look at the format of your sessions.
Are the sessions too long? Too short? Too spread out? Sometimes it’s the format—not the coach—that’s the barrier.
4. Ask for a small experiment.
Try one new adjustment. Maybe it’s a different agenda style, homework between sessions, or a targeted skill focus. If that small shift creates a big difference, it’s a sign the coaching relationship can still work.
How to Have a Hard Conversation with Your Coach About What Isn’t Working
It’s normal and healthy for the conversation to feel uncomfortable. In fact, coaches expect feedback because it helps them adapt and serve you better.
Here’s a simple script you could use: “I want our coaching relationship to be helpful, and I think a few things are missing for me. Can we talk about adjusting our approach so it better fits how I learn and what I’m trying to accomplish?”
Keep your conversation centered on your goals, learning style, and what would help you feel supported. Most coaches respond well and appreciate clarity.
What If the Coaching Style Doesn’t Match My Learning Style?
This issue comes up more than people talk about. A coach’s style might be thoughtful and experienced but not aligned with how you naturally grow.
If you’re an analytical thinker, you may want structure, frameworks, and problem-solving.
If you’re relational, you may want open conversation, trust-building, and reflection.
If you’re action-oriented, you may want clear next steps and accountability.
If your misaligned at the start, it doesn’t necessarily mean someone is wrong. It just means the partnership might not be the right shape for what you need today.
Should I Try a Different Coaching Format (Cohort or Workshop)?
If 1:1 coaching feels slow or heavy, you might benefit from formats that are more interactive or experiential.
Cohort-based programs offer structure, shared accountability, and community energy. Workshops or intensives are useful if you want hands-on practice instead of long-term commitment and reflection.
Sometimes the issue isn’t the coach, but the isolation of 1:1 work. A blended approach can work great too.
Explore the differences between cohorts and workshops >>
When Is It the Right Decision to Switch to a New Leadership Coach?
Switching might be the best decision if:
- You’ve tried to reset the relationship
- You’ve given honest feedback
- You still feel stuck or unseen
A stronger coaching match will push you without making you feel unsafe, stretch your thinking, and help you build real results you can measure.
How Do I Choose a Better-fit Leadership Coach Next Time?
Here are questions worth asking during your next discovery call:
- “Who do you coach best, and who are you not the right fit for?”
- “How do you adapt coaching for different learning styles?”
- “What happens if we’re not connecting after a few sessions?”
- “Can you walk me through your approach to accountability?”
A good coach will answer these honestly and with confidence. You might even vet a few coaches and create a simple comparison chart to rank them by style, format, industry familiarity, approach, client testimonials, etc.
What If I’m an HR Leader and My Employee Isn’t Clicking with Their Coach?
This situation is more common than you might think. The biggest mistake HR leaders make is assuming the employee will “work it out.”
Instead, try:
- Checking in privately
- Asking about goals, not feelings
- Offering a reset or format change
- Keeping psychological safety front and center
Please know that a coaching mismatch doesn’t always reflect poorly on the employee. Treat it as an operational adjustment, not a performance issue.
How Do I Make Leadership Coaching Worth the Investment?
Leadership coaching is an investment of time, money, and emotional energy. To get the value you want, focus on these three things.
1. Track progress weekly.
This can be as simple as answering: What shifted for me this week?
2. Discuss ROI directly with your coach.
A good coach will welcome the conversation!
3. Choose the format that matches the season you’re in.
Sometimes you need depth. Sometimes you need momentum. Sometimes you need peers. When you align the format, coach, and goals, you feel the value quickly.
Where to Go From Here
You deserve leadership coaching that fuels your growth, not something that drains it. A mismatch with your coach doesn’t mean you’re difficult or uncoachable; it usually means the fit isn’t right or the expectations weren’t clear.
Now you know how to spot the signs, how to try resetting the relationship, and how to choose the right type of support moving forward.
If you want clarity on the best coaching approach for your situation, or you’re ready to find a new coach altogether, don’t hesitate to reach out to us online. We’re happy to talk through your goals, challenges, and how we can help you move forward.