20 Questions to Ask Before Taking Advice

I was on the phone the other day with an event pro who was at a crossroads in his planning company. Let’s call him Doug. He’d been in business for several years but recently things had been pretty slow. Revenues had plateaued, leads weren’t coming in, inquiries ghosted after hearing about pricing. He attended several conferences and workshops each year, took online courses, and listened to all the industry podcasts. 

Still, business wasn’t booming.

Doug didn’t know what to do: a) risk going further into debt but try to save the business, or b) admit defeat and head back to the 9-5 crowd.

The call broke my heart. Truly. I wanted to reach through the phone and give the poor guy a hug. He sure needed it.

Instead, I offered something even better.

Try Before You Buy

Prior to the call, we had emailed a bit about his situation. Doug told me he was giving the same information to a handful of other business coaches. Also, he was asking them some questions before committing to working with them.

I loved that Doug was doing some research on us, but his questions were hit or miss. Because he’d never worked with a coach before, he didn’t know what to ask.

If you’re like Doug and haven’t worked with a coach, read on. If you’ve worked with a coach but it didn’t work, maybe you didn’t pick the best one for you – and so read on.

A New Twist on 20 Questions

The more you know about your potential coach/mentor/consultant/instructor the more likely you are to see success. Here are some good questions to ask before you take someone’s advice about your business.

1. What areas would you consider yourself an expert in?
2. Why do you think you’re an expert in these areas?
3. How did you get your experience and training in the areas you’re expert?
4. Have you ever [insert what you want to do more/better]? (eg. sold a wedding, led a wedding team, executed a marketing strategy)
5. How long did you work in the wedding industry before coaching/mentoring?
6. Have you ever worked outside the wedding industry in a leadership position?
7. Have you ever worked for a company other than your own?
8. Is coaching/mentoring a side hustle or is this your full-time job?
9. Where did you learn to teach/train?
10. How would you describe your teaching/training style?
11. What kinds of personal success in [insert what you want to do more/better] have you seen using the methods you’re recommending?
12. Do you focus on mindset or tactics with your clients?
13. How long do clients typically work with you?
14. What specific knowledge do you have about my market (where I work)?
15. What specific knowledge do you have about my field (what I do)?
16. What specific knowledge do you have about my segment (mass market, premium, luxury, ultra-luxury)?
17. What are the different ways we can work together?
18. What way would you recommend we work together and why do you think that’s best for me?
19. What’s the biggest value you add to your clients’ businesses?
20. What happens if I don’t see the results I want?

Investing time and money into a coach is nothing to mess around with. It’s not just time and money you spend with the coach, it’s time and money you might lose if you pick the wrong person to lead you where you want to go.