Getting coaching matched to a real goal, not vague growth
Book an executive coach for a real, measurable goal, not vague growth. Match your specific challenge to a coach with credible track record.
Most people who seek an executive coach say they want to "perform better" or "develop as a leader"—language so broad it almost guarantees disappointment. A coach can't do much with a target like that. What separates a coaching engagement that shifts something real from one that feels like expensive chat is whether your goal is specific enough to measure and whether the coach you pick can credibly move that needle.
You need a goal sharp enough to know when you've reached it. Not "improve my leadership" but something like: "I'm losing good people on my team because I micromanage; I want to delegate key decisions within three months and keep those people." Or: "I'm promoted into a peer group where I don't know how to operate; I need to understand the unwritten rules and find my voice in that room." These are problems a coach can grip. They're also problems you can tell a prospective coach about and watch whether they nod knowingly or start pitching generic frameworks.
The gap between vague and concrete often reveals itself in how you describe your situation to a potential coach. If you find yourself struggling to explain what "better" looks like, you're not ready to book yet. Spend time thinking about what success would actually feel like. What would change? What would people notice? What decision would you make differently? Your answer doesn't need to be polished—it just needs to be real and particular to your context.
The match between your goal and the coach's track record
Once you have a goal, the coach you choose should have explicit experience with that kind of challenge. If your goal is navigating a critical relationship at work—say, repairing trust with your board after a mistake—ask the coach directly: "Have you worked with someone on this exact thing?" Not "Do you have experience with board dynamics?" but the specific flavour of it.
A coach who's spent years in financial services but has never worked with a founder in crisis mode may understand risk and pressure, but they won't know the particular loneliness of that role. Similarly, a coach strong with technical leaders moving into general management might flounder if your challenge is learning to lead in a matrix where you have no formal authority. The coach should be able to point to work they've done that mirrors yours, not just claim general competence.
This is why the screening conversation matters. You're not asking for their credentials—you're testing whether they can articulate back to you what makes your situation tricky and what their actual method would be. A coach who listens to your goal and immediately launches into their proprietary model is signalling they're going to fit you into their framework rather than build one around your reality.
From goal clarity to committing
Before you sign anything, agree on what done looks like. How will you know the coaching worked? What's the timeline? If your goal is to build trust with your team again, are you measuring that by their feedback, by decisions you make differently, by them applying for promotions internally? Nail this down together, because it keeps both you and the coach honest.
You should also ask what the coach expects from you between sessions. Real change doesn't happen in the room; it happens when you go back to work and apply something different. A coach who books you fortnightly but gives you nothing to actually do is wasting your time. The ones worth paying are the ones who'll push you to experiment, fail, and learn while you're working.
When you're ready to move forward, look for a coach on Strove who's worked on the specific challenge you're facing and who can explain their method clearly. The right match combines a concrete goal, a coach who's been there before, and accountability that goes both ways.
Common questions
- What makes a coaching goal specific enough to actually work?
- Your goal should describe a concrete change—not 'improve leadership' but 'I micromanage and lose good people; I want to delegate key decisions.' You should be able to measure it (what would people notice? what would you decide differently?) and know when you've reached it.
- How do I know if a coach has relevant experience for my challenge?
- Ask them directly: 'Have you worked with someone on this exact issue?' A strong coach will point to similar engagements and be able to articulate why your situation is tricky. If they launch into a generic model instead, they're fitting you into their framework rather than building one around you.
- Should I agree on success markers before I book?
- Yes. Discuss what 'done' looks like—whether that's feedback from your team, decisions you make differently, or timeline milestones. This keeps both of you clear on what you're paying for and holds the coach accountable alongside you.
- What should happen between coaching sessions?
- The coach should give you something to experiment with at work—a new approach, a conversation to have, a decision to make differently. Real change happens when you apply things back in your role, not just in the session room.
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