Questions to Ask A Potential Mentor, Business Coach, or "Expert" BEFORE Hiring Them

Whether you are looking to start or grow a business, you will have many options along the way in terms of accelerating your path to success.

There are free resources like blogs and YouTube, paid educational products and programs like online courses, as well as coaches or consultants that work one-on-one with clients.

This is a good list of questions to consider whenever you decide to invest in a mentor, expert, or “guru”, whether you are only investing your time (to watch their free content, for example) or your hard earned money to learn from them.

However, since one-on-one coaches and consultants tend to be the most expensive option in terms of accelerating your success in business, it is absolutely crucial to choose the right person that fits your needs and goals (in addition to your budget!). 

Making the best choice for you will have a major positive impact on your business and could easily change the entire trajectory of your life. Because this decision is so important, I want to give you my own personal checklist I use to choose my own mentors, whether I am considering buying their paid course or hiring them to coach me individually.

But the most important thing-- and this is going to sound cliche-- is to listen to your GUT. 

Even if someone checks all the boxes but gives you a bad feeling or vibe-- that’s generally a huge red flag for me. Many “gurus” say what they think potential clients want to hear and then do a 180 when the actual work relationship begins and the clients check has been cashed.

So pay attention to your gut feeling when you consume free content or engage in a free consult and use this list and you should be able to move forward with your investment with absolute confidence and get GREAT results in turn.

1) WHAT IS YOUR EDUCATIONAL OR BUSINESS BACKGROUND?

Now, hear me out.

I am not saying that someone absolutely needs to have a Master’s degree in order to provide value to others. Experience goes much further than formal education but I do like to ask this or research it because I look for people to have knowledge in things I lack.

This is just ONE of ten questions so I don’t put ALL the weight of my decision on this one particular topic-- but it does factor in, especially if I’m stuck between a few options.

Here’s an example.

I have a master’s degree in economics and finance and it gives me a great foundation to help members of my online courses, in particular my Play Cafe Academy course, with the more technical parts of their business plans like cash flow projections, creating their prices, estimating their expenses, and things like that.

And that brings me to my next question to ask.

2) WHAT ARE YOUR BIGGEST STRENGTHS? CHALLENGES?

The mistake that SO many people make when choosing a mentor is that they choose someone exactly like them, which they assume means they’ll work well together.

And while that may be the case, choosing someone with the same background or same set of strengths as you will LIMIT the amount that person can teach you and the value they can bring to you-- and can therefore limit the amount you’ll be able to grow as a result of the relationship.

Instead of choosing someone with the same strengths, choose someone with the same VALUES.

For example, look for a potential mentor that has a set of skills that you lack (accounting/ finance, for example) so they’ll compliment you-- but make sure you both value the same things from a business-- like MORE time freedom (which we will also touch on later) and financial stability.

I’ll use my Play Cafe Academy course, which teaches entrepreneurs how to launch their own profitable indoor playground business, as an example again.

Many people going into that type of business are creatives or former teachers and have trouble with crunching those numbers, which make me a great fit as a mentor for those individuals seeking guidance.

However, since I am a numbers person and am not a trained teacher, I sought out more creative types to help me with that side of my business when I was getting started.

3) WHAT IS OR WAS YOUR ROLE IN YOUR BUSINESS?

Especially for brick and mortar businesses, this will be crucially important. But really anyone in business needs to ask this question, and here’s why.

SO many business owners I know (and in the indoor playground industry specifically!) wear busy like a badge of honor. 

For example, they take on ALL of the tasks of their business themselves, are their main or only employee, and generally work around the clock-- including weekends-- to keep their business afloat.

They are there at the check-in counter daily, planning their events, running errands, managing their books, etc. 

And if that is what you envision yourself doing as a business owner and want to hustle that hard-- that is absolutely your choice! If that’s the case, find someone with similar values and who lived that same “dream” life you envision as a business owner.

However, if you’re looking to be a bit more hands-off and set your systems and your business up so that you can delegate the most time-consuming tasks (or the tasks that aren’t in your “genius” zone that you don’t like completing yourself) then that person will likely lack experience in knowledge in that area and won’t be able to help.

To me, owning a business should mean MORE time freedom for you as the owner-- and I follow a specific system to ensure systems allow the owner to ONLY spend time in their “genius zone” that I mentioned before. 

My opinion is (and again this is my opinion!) that trying to do SO much yourself is NOT sustainable and will lead to your business feeling more like a JOB-- since you are completely tied to it and the amount of money you can make is dependent on the amount of time you work.

There are so many different philosophies around this topic so be sure to choose one that aligns with what YOU want out of your business. 

4) HOW UPDATED IS YOUR INFORMATION OR YOUR METHODS?

Unfortunately this IS a question you need to ask. I have noticed that many mentors across industries are teaching methods that are years or even decades old, and that they have not been active in their chosen industry in quite some time.

Unless someone is continually immersed in a particular industry, either as an owner or a consultant-- that they cannot possibly have the most current or up-to-date information or knowledge. 

Look for someone who is constantly learning and evolving their teachings and measuring their success.

5) DO YOU HAVE A SPECIFIC METHOD OR BLUEPRINT?

This question is important for SO many reasons.

First of all, not only does have a proven, documented system help the entire process along, but the clear documentation helps reduce the amount of time you will need to spend one-on-one with your mentor and therefore likely reduce the amount of money you need to spend.

This is one of  the reasons I chose to put my specific 8-step blueprint for launching a successful indoor playground into an online course.

Each module represents a step-- whether it be creating a business plan or developing a marketing strategy-- and the lessons are organized in the exact order that one should follow them to find the MOST success in the least amount of time.

Because I have all of this clearly outlined in a step-by-step manner, I can give people who purchase my course over 40 hours of value for a FRACTION of the cost that 40 hours would cost with a one-on-one consultant with that particular program.

Having a proprietary system also helps ensure that the success that other students or clients have seen can be replicated again and again. 

Creating specific plans for every client based on budget/ time can be very misleading when it comes to them providing case studies and testimonials, which we will discuss a bit later.

It’s much better to create a documented system and then empower your clients or students with the skills and knowledge they need to adapt that blueprint to their specific needs and vision for their business or life.

6) HOW MANY OTHERS HAVE YOU HELPED?

This is another question that I don’t put a HUGE amount of weight on, but do consider it important.

For example, if someone’s proprietary system is truly replicable and scalable-- then they should have the ability to impact HUNDREDS or even thousands of people in a concrete way.

Also, I have found that the more people someone is able to work with and impact-- the more powerful and extensive their knowledge becomes. 

If someone is a one-on-one consultant and only works with a dozen or so people a year, they will have less experience and knowledge than someone who is able to work with hundreds.

That’s one of the things I love MOST about my group coaching program that is an optional membership upgrade after someone has completed my Play Cafe Academy program.

There are over 130 members from all different walks of life and geographic areas, who all have slightly different (or totally different!) visions for their business and we ALL have different strengths.

I have learned more from collaborating with them daily for the last 18 months than I could have learned in 10 years helping people one-on-one, and for that I am truly grateful!

7) DO YOU HAVE VIDEO TESTIMONIALS OR REFERRALS?

Speaking of those a potential mentor has impacted-- ALWAYS ask for referrals, and ask if you are able to personally contact any.

While written testimonials can be helpful, they can be changed from the person’s original words or be faked entirely.

Not only will videos be more credible, but they are often much more powerful when making a decision.

I made sure to have several members inside my Play Cafe Academy program speak (on video!) on exactly HOW my system helped them AND describe the success they’ve been able to find-- and most even give tours of their facilities.

This helps potential students look for similarities in their success and see if it aligns with what they envision for themselves, and again often aids in their decision making.

8) DO YOU HAVE CASE STUDIES?

In addition to testimonials, case studies can also be very helpful.

Typically case studies are a deeper-dive into one specific client or student’s success.

For example, before I take on a client and run their Facebook and Instagram ads for them, I provide several specific and detailed case studies.

I include what the industry and business was, what the objective of the campaigns were, how much money was spent, and how much profit was made. With permission, I also include screen shots of the ads and more detail regarding the cost per conversion, and more technical things like that.

Not only does it help them make a decision on hiring me or not, but it also helps to set their expectations in terms of the type of work and results I am able to produce for them.

9) HOW DO YOU DELIVER YOUR COACHING OR MENTORSHIP SERVICES?

This is similar to the question about having a blueprint or specific system-- but it’s important to ask the question in this way also, in case your potential mentor does NOT have a documented and proprietary system.

If your client delivers all materials via phone or video calls, you are likely NOT getting the best “bang” for your buck-- and you will likely need to spend THOUSANDS of dollars to scratch the surface of the information you will need -- depending on the task they are helping you with-- since most one-on-one consultants charge by the hour.

That also means you are on THEIR schedule-- so if there are time zone differences or if they have a packed schedule (which is likely!) it will be difficult for you to access them.

I have also found that most consultants who do not have a system do their calls based on Q&A from their client-- which is problematic.

Someone just starting out in an industry likely does not even know WHAT to ask and may not spend the time asking the most important questions-- and therefore waste their money and time.

10) HOW LONG WILL I HAVE ACCESS TO YOU OR YOUR MATERIALS?

Also, if you only have access to that consultant if you continue to pay them-- then you will NOT be able to access any updates to their knowledge or advice or have any continued access to them after your time is up.

This is one of the reasons I am CONSTANTLY updating my courses and programs-- things change DAILY in many industries and giving my students access to the most cutting edge information (without charging them more!) is one of my core values as a business owner.

For example, I am re-recording many lessons as a result of the changing consumer preferences due to the COVID-19 crisis-- and ANYONE who has purchased my program will be able to access the new information.

Again, when it comes down to it-- choosing a mentor has to FEEL right to you. Even if there are some gaps based on these questions but it feels right to move forward-- that’s OK!

Many very successful business owners have made mistakes or missteps when choosing their first mentors-- but were able to quickly recognize it and correct their path.

But next time you are making a decision-- keep these 10 questions handy, and it will certainly reduce your risk!

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