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Empowering Questions to Ask Your Business Coach (Month-to-Month)

Updated: Jan 17

One of the top reasons why many executives hire business coaches is to use them as a sounding board. Having someone there to hear ideas and then offer feedback can help leaders make important decisions and steer their business to success.

A group of business owners having a meeting in the wilderness
Who says you can't have meetings in the wilderness?

If you’ve invested in Business Coaching, chances are you may not be using your coach in this particular way. While you may have sought out a coach for ongoing feedback, it’s easy to get sidelined with projects or other "fires" and forget that you still need to develop ongoing communication with your coach to see the maximum benefit. Even if you think you know the answer, it's always a great tool to bounce it off your business coach first!

To help make the most out of your relationship, consider some of the best questions you can ask your coach each month. Even if you don’t have a specific problem you need help with, these questions can guide you toward new strategies and ongoing improvement.


Where Do You See My Strengths and Weaknesses?

Asking about your strengths and weaknesses as a leader is one of the best questions to ask a business mentor. Your coach is there to provide an unbiased view of your business and leadership, and this question can help you see yourself in a new light.

Small business woman lifting weights in the gym.
Weaknesses can turn into strengths

Hearing about your weaknesses is sometimes a heavy weight to lift against our pride. Let's face it, as entrepreneurs we have a bit more confidence than the average person and criticism can sometimes sting. However, as a business leader we should exhibit humility as a functional act as well as inspiration for our teams.

That being said, after you’ve worked with your coach for a few months, they’ll likely have a good idea of your strengths and weaknesses. Asking this question can help you determine how your self-awareness might affect your business. Your coach may have noticed weaknesses that you weren’t aware of in the past as well as strengths you can put more focus on.

It is not uncommon for a business owner to be surprised at the response. Regardless, it's extremely important to remember that any weakness can be exercised into a strength!

The answer to this question gives you a better understanding of what you should prioritize as a business leader both as a person and as a business.

How Can I Get Out of My Comfort Zone?

Your comfort zone might not be something you have thought to ask in terms of business ownership. It's also no small assumption that discussing your comfort zone can sometimes be a difficult topic. However, it’s a highly important topic to address. Through analyzing your comfort zone and stepping outside of it, you can move toward business growth and innovation.

baby bird hiding inside the bloom of a pink tulip

Emerging from your shell isn’t an easy thing to do on your own. With your advisor, you can learn small steps to move away from what you’ve been doing in the past. Often, they might give you specific activities that you can easily do to help you see that there isn’t anything to fear.

For example, if you aren’t comfortable with networking, your coach might ask you to schedule at least one lunch date per week with a new connection. Networking one-on-one may prove easier than attending big events and help you branch out.

If you find yourself saying something along the lines of "We've always done it this way." then you likely have a comfort zone that is holding your business back. Saying 'you've always done it this way' is never a valid reason to continue doing something. It also happens to be one of the worst things you can say to your business coach!

As a solid, practical example of how 'always doing it a way' limits your business: As your business grows older, so too do your customers. Their tastes and values can change over time. You'll also need to secure the next generation of customers whom also will have evolved needs and expectations from what you've always done. You must modify and revolutionize your business to both attract the next generation AND to maintain the current, aging customer base.

How Should I Define Success This Month?

Achieving success is a painfully obvious important aspect of any small business. Business advisors will often help you tackle your goals step by step instead of maintaining your focus only on a big-picture mission.

A infographic showing a path to success

Through defining success monthly, you can also learn how to better deal with business failure. What didn’t work last month allows you to optimize, rethink or try again.