8 Essential Questions You Should Ask Before Hiring a Coach  – How to Choose a Great Coach and Avoid a Bad Fit

Before investing in a coach, you need to ensure they’re the right fit. An introductory conversation, often called a discovery session is your chance to assess their approach, philosophy, and how they can help you reach your goals.

Here are some important questions to ask—along with what to look for in their responses.

How do you tailor your coaching to each client?

Why it matters: You don’t want a cookie-cutter framework. A great coach adapts their approach to your specific challenges, strengths, and goals.

What to Look For: A coach who takes time to understand your unique situation, adapts their methods based on your needs, and doesn’t just follow a rigid playbook.

Red flag: If they rely on a one-size-fits-all system without customization.

What’s your coaching philosophy?

Why it matters: Some coaches focus on motivation, while others prioritize strategy, mindset, or execution. You need to know if their approach aligns with what you actually need.

What to Look For: A well-articulated philosophy that aligns with your values, goals, and preferred learning style.

Red flag: If they struggle to explain their philosophy or rely too much on surface-level tactics.

How do you help clients gain clarity on their biggest challenges?

Why it matters: Many people think they need help with execution when the real issue is a lack of clarity. A strong coach helps you define the right problem before jumping into solutions.

What to Look For: A coach who asks deep, thought-provoking questions and helps you uncover the real obstacles, not just the symptoms.

Red flag: If they immediately start offering solutions without understanding your deeper challenges.

Can you give me an example of a client you’ve helped in a similar situation as mine?

Why it matters: You want proof that they’ve successfully guided others through similar challenges. Their past work should inspire confidence in their ability to help you.

What to Look For: Specific success stories with clear outcomes that relate to your situation.

Red flag: If they lack specific examples or only offer vague success stories without tangible results.

How do you handle tough conversations and challenge clients?

Why it matters: Growth comes from being pushed outside your comfort zone. You need a coach who isn’t afraid to challenge your assumptions.

What to Look For: A coach who is firm but respectful, able to deliver hard truths with constructive feedback and support.

Red flag: If they avoid difficult conversations or focus on keeping clients comfortable rather than pushing for real transformation.

What’s your process for uncovering blind spots and creating clarity?

Why it matters: A coach’s real value comes from helping you see what you can’t on your own. You want someone skilled in asking the right questions and guiding breakthroughs.

What to Look For: A coach who challenges your assumptions, encourages new perspectives, and helps you navigate roadblocks with insight and strategy.

Red flag: If their approach is overly tactical without addressing deeper mindset or strategy issues.

What happens if I don’t see the results I’m looking for?

Why it matters: A great coach is committed to your progress. They should have a plan for adjusting the approach if things aren’t working.

What to Look For: A coach who is adaptable, willing to adjust strategies, and committed to helping you get results.

Red flag: If they place all responsibility on you without any flexibility or offer no alternative solutions when progress stalls.

 How do you handle a client that displays resistance?

Why it matters: Resistance is natural when facing change. A skilled coach will recognize when a client is pushing back due to fear, self-doubt, or limiting beliefs—and will have strategies to help them move forward.

What to Look For: A coach who sees resistance as part of the process, explores the root cause, and provides guidance to help you navigate through it.

Red flag: If they respond with frustration, pressure, or dismiss the resistance instead of exploring why it’s happening.

Final Thought:

The Right Coach Welcomes These Questions

An experienced, professional coach won’t shy away from these questions, they’ll embrace them. If a coach seems defensive, vague, or uncomfortable answering, it’s a sign to walk away.

Your investment in coaching should lead to clarity, action, growth, and actual results. Asking the right questions ensures you’re choosing the best coach for your journey.

Of course I welcome all of these questions and any others you can think to ask. 

If you are curious about working with me let’s talk. The first conversation is always free.

Use this link to schedule

https://calendly.com/mattisongrey/info-session