Hiring a Coach is a Significant Investment. Here are Some Practical Thoughts and Questions to Ask Before You Invest

Craig Stanland
4 min readJul 13, 2021

Finding the right coach/mentor isn’t easy.

Especially as the number of coaches flooding the marketplace increases exponentially — seemingly every day.

And they all seem to have the answer/holy grail/silver bullet.

So who do you work with?

Before we get to that, you have to know that deciding to work with a coach is a huge step (one of the best I’ve ever made) that goes beyond merely a financial investment — which can be significant.

It also requires a mental, spiritual and emotional investment.

To truly work with a coach requires a great deal of work. You get out of the relationship what you put in. This means you’ll also be investing your most precious resources:

Your Time. Your Energy. Your Attention.

Here are some questions and thoughts to ponder before investing in a coach.

Are you making a decision from an elevated state of negative emotions?

Meaning, are you anxious or desperate? Do you feel like you have to act RIGHT NOW? Otherwise, you’ll miss your opportunity?

If so. Take a breath. Go for a walk. Break the pattern. Get yourself back to neutral. I’ve found for myself that any decisions made from an elevated state of emotion don’t pan out well for me.

Decisions made from neutral come from a place of discernment. And discernment is power.

Empower yourself to make the best decision for yourself.

What is the best possible outcome I can imagine from working with a coach?

Does this coach have the skillsets to get me to that outcome?

What personal experience are they drawing upon to coach in the field they are coaching in?

I don’t know about you, but I wouldn’t get on a rocketship with someone who’s only read about space travel.

I want the person who’s been to space and come back — even if they don’t know a drop of physics.

Craig Stanland

I write about my journey from corporate success to federal prison and finding joy, mission, meaning, and fulfillment beyond professional and financial success.