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How to Interview Your Future Business Coach in 2023

Updated: Jun 10

Finding, hiring, and developing a relationship with a good business advisor can be tricky work. You absolutely want to make sure we're entrusting both ourselves and our business to the right person.

group of dragon boat rowers over clear water where you can see the bottom

We've put together a list of important questions to ask your potential business advisor before getting in too deep. These questions are a great starting place to finding out if the potential coach will be a good fit for your business.

For each item, we will include how we operate here at Out of the Box Advisors to help you give some perspective.


1. Are you collaborative?

In asking this question, we discover if the business coach will explain choices they make and include us in any potential decision-making.

a group of small business owners working in a meeting with a business coach

As a business owner, we may want the option of being more, and sometimes less, involved in certain decisions. We may feel comfortable allowing the coach to do what they do best and sitting back OR we may want to have them to provide reasoning behind the actions before we undertake any projects.

This one really comes down to your business' needs or your personal preference. Most coaches can handle adapting to whichever mode works best for you, but you'll want to establish the expectations up front.

Out of the Box Approach:

Unlike most "consultants" (check out this article to learn the difference between coach and consultant!), our coaches at Out of the Box Advisors focus on training the business owner how to do the specific tasks needed to succeed. We want to cultivate independence for our clients!

2. Do you know the industry?

Certain industries may need more or less specialty, especially depending on why you're bringing in a business coach. Advisors come in all packages: Some dedicated to working in very specific industries -and- Some that are multi-talented and have the ability to adapt to a variety of industries.

high rise office with a view of a city and employees working at their desks

However, about 90% of all the problems a small business will face will be the same across all industries. Typically the industry specific items are of the less priority type. If you think you must have someone with specific industry experience you're likely narrowing down your coach search a bit too much.

Sometimes getting a fresh perspective can also bring new life into your business, regardless of industry!

Out of the Box Approach:

As business coaches who focus on small to medium sized companies, we strongly advocate for a multi-industry approach. We feel that your industry has much less to do about your success than focusing on core business principles.

3. What is your work process?

How the advisor works is key to understanding if y'all would work well together.

a process flow written on a whiteboard with some sticky notes also

Do they work in a whirlwind of to-dos or do they prefer to focus on one task or project at a time, for example? Do they work in a way that is hands-on or hands-off? Ask similar probing questions to get a solid grasp of their processes.

Some business owners might not care how it gets done, just that it gets done, but that's up to you! Either way, establishing an understanding of the process that your potential business coach uses is critical to the value they will bring.

Out of the Box Approach:

Like many other small business coaching firms, we have coaches that can match just about every style. We encourage our clients to communicate their expectations and then we will pair them with a coach that works for them.

4. What is the biggest challenge a small business like mine might face in the coming year?

a small business coach free climbing a cliff face on a darker day

This question allows them to demonstrate how up-to-date the coach is on changes in the small business environment.

They should be able to let you know if tariffs are going to impact your company or if the changes in Google's advertising algorithm is going to set you behind the competition.

Use this question more of a test to the coach than it is for general information. However, make sure that you research their answer as well. There's a 50/50 chance you will disagree with their answer. But what if they were right? Keep and open mind

If you're hiring someone to help run your business, they should know how to help!

Out of the Box Approach:

Because we primarily focus on small, local businesses we have a solid handle on most issues. For example, our answer to this question in 2023 would be hiring and retaining employees, hands down.

5. How do you determine success as a business coach?

man with his fist raised in celebration for reaching the top of a mountain
Success is Different For Everyone

Benchmarks, metrics, goals - Knowing what the consultant will use to guide the company and decide the level of success is important. If you value different things, that could mean disconnect between you and your advisor.

Your average business coach or owner will likely look at revenues as their key metric of success. However, that is not always the case. Especially in terms of non-profits whose goal may be delivering on their mission.

The key to this question is to dive past the stereotypical responses. If the coach says Revenues, ask them for another response. Keep on pressuring them as far as you need. Make sure they have a vision for success beyond the basic.

Out of the Box Approach:

Success can be a fickle thing. For a small business owner, success is rarely about just the money. Often it is the realization of a dream or vision. Our approach is to focus on what drove you to creating your business in the first place and then helping you get there.

6. What is your payment structure?

This is a super important question, and the "why" it speaks for itself.

Do you pay them on a per project basis? Do they receive a bonus or other compensation depending on target metrics? Are you paying per hour, or per project?

a tip can with some stickers on it by the register at a local coffee shop
Always tip your barista!

Almost every business coaching firm has a different methodology. Some charge for structured "programs" that they run you through (think something like a school course). Other only work hourly and bill you similar to that of an attorney. Make sure that you research their payment structures and find one that works best for you.

Important Note: The benefits of business coaching is rarely tangible in nature. Sure some items can translate directly into revenues, but most have indirect impacts on success. For example, management training from your coach can help improve morale in the workplace. Ultimately this will lead back to sales, but it is indirect in nature. Make sure you consider this when interviewing a business coach.

Out of the Box Approach:

Like we said above, every coaching firm is different. Our payment structures work similar to that of a yoga studio. You pay for sessions individually, in packs, or monthly. It really comes down to preference and your budget.

7. What happens if we wish to terminate our contract?

Another important question that will help you avoid trouble, is what happens if you want to end the relationship with the advisor? Are you locked in for a certain number of years, or is it a monthly contract?

a young business owner signing a contact with their business coach
Be wary of contracts

It might even be an amicable ending of service, but knowing what happens in the end is certainly important in maintaining good working relationships, should future projects arise.

We recommend that you both ask them directly, but also ask that they send you any contracts up front. This way you will have plenty of time to make an educated decision on which coach and contract is best for your business.

Out of the Box Approach:

We do not operate on long term contracts at Out of the Box Advisors. Our pricing model is similar to that of a yoga studio. You prepay for sessions and then you work with your coach at your own pace without having to worry about being obligated to a contract.

8. Why should I hire you?

Last, but certainly, not least, is why should you hire this person? What can they offer you and your business?

two young kids dressed as super heroes jumping to pretend to fly.
Heroes, all!

Be direct. If they are a skilled business coach, they should readily and easily answer this question. If they are unable to sufficiently answer here it should tell you much more about their skills in helping you grow.

Try being specific. Something like 'What makes you uniquely suited to help us grow and success over that of XYZ competitor?' It will net you a reliable answer one way or another. Plus, it'll show them that you are well aware that you have options in your business coaching coice.

Out of the Box Approach:

Our answer here would be: We helped our clients grow their revenues by 19.1%, on average, in 2023. While we can guarantee a specific number for growth for you business, we can guarantee that the knowledge our coaches will impart to you will be invaluable to your success!


group of business owners cheersing their lattes
Meet us over a cup of coffee and see for yourself what we can do for your business!

Overall, finding the perfect business advisor can be tough and tricky work, but it doesn't have to be!

Out of the Box Advisors offers a free preliminary consultation, if you're ready, schedule a chat - the coffee is on us!

Don't forget to check out our other blog post on how a business advisor can help save your company time, money and sanity!

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