Your Guide to Getting the Most Out of a Coaching Relationship
If you've decided to hire a coach, congratulations. You're already in rare air. Most people stay stuck where they are because they never ask for help. But if you're ready to invest in coaching, the next step is knowing what to ask.
Coaching isn't about hand-holding. It's about unlocking new levels. As a business and leadership coach who’s sat across from hundreds of high-performers, I can tell you: The questions you bring to the table matter just as much as the goals you bring.
Let’s break down the top 10 questions you should ask your coach to maximize your results, build a true partnership, and ensure your time and money are well spent.
You want a coach who isn’t just going to talk in circles. You want results. This question helps you understand if your coach is outcome-driven and whether they’ll hold you accountable. You’ll also get a peek into how they define progress: Is it mindset? Revenue? Team culture? All of the above?
Heather’s POV: If your coach can’t tell you how they measure success, that’s your first red flag. Clarity here sets the tone for the entire relationship.
Some coaches are generalists. Others (like me) have sat in the sales seat, built the business, and lived through the chaos. Ask your coach what experience they have in your industry or role. You don’t need an exact match, but you do need someone who gets your world.
Spoiler alert: You will hit a wall. It might be mindset, burnout, hiring, or a plateau in your business. Ask your coach how they handle it. Do they have tools? Do they challenge you? Will they pivot with you or keep repeating the same script?
Heather’s POV: Real coaching means adapting, not just following a one-size-fits-all playbook.
A good coach doesn’t tell you what to do. They help you see clearly so you can decide. The goal is to grow your confidence, not your dependence. Ask how your coach will help you sharpen your decision-making muscle.
Coaches are not babysitters. But they are powerful accountability partners. Will they follow up on your goals? Do they use tools or trackers? Will they call you out when you’re playing small? You need to know this upfront.
Heather’s POV: If you don’t want to be challenged, you don’t want a coach. You want a cheerleader.
Growth doesn’t live in comfort. Ask your coach how they’ll stretch you. Will they have you role-play? Track numbers? Speak in front of your team? Build something you’ve been avoiding?
You don’t hire a coach to feel safe. You hire one to get somewhere you’ve never been.
Business is messy. Life is messy. A great coach builds grace and grit into the process. You want to know if they’ll adjust your plan, reset expectations, or help you re-center. This is especially important if you’re juggling multiple roles or hitting a rough patch.
Great coaches come with more than good vibes. They bring frameworks. Systems. Checklists. Templates. This is especially important for entrepreneurs or sales professionals who need structure to scale.
Heather’s POV: My clients don’t just get calls. They get systems, trackers, templates, and a battle-tested roadmap.
You’re not a robot. You’re a whole human with a life outside of business. If your coach only cares about numbers and ignores your health, relationships, or mental bandwidth, that’s a problem. Ask how they support you as a whole person.
Some coaches are gentle. Others are direct. Some are high-energy. Others are methodical. Neither is wrong, but you need a style that motivates you—not frustrates you.
Ask them: Are you going to listen first, or dive in with strategy? Do you give homework? Are you more supportive or more challenging?
Heather’s POV: My clients know I’m direct—but always with heart. I’m here to call you up, not call you out.
Hiring a coach is a bold move. But it’s also one of the smartest ways to shorten the learning curve, build momentum, and design a business that actually feels good to run.
But coaching is not a magic pill. It’s a partnership. And the best partnerships start with powerful questions.
So whether you’re new to coaching or ready for your next level—bring the questions
