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

Updated: Apr 18

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.

Asking this question can also help you rethink what success means. If you’ve only been focused on KPIs and revenue, there may be a lot you’re missing. For example, what about more opaque items such as employee satisfaction or perhaps brand awareness? Clearly these two examples can lead to more revenues, but they are more indirect.

In fact, one of the purposes of this article is to help your maximize the benefit of having a business coach on your team. You clearly made or are making the decision to hire one based on the idea that they will provide you value that will ultimately translate into revenues. However, the line item breakdown of their work is more intangible than a KPI. More confidence, less stress, better sleep for the business owner for example.

Regardless of what you decide to define as success for each month, your business coach should be making sure that each one is a variation of a S.M.A.R.T goal. Even for those more opaque items, you can be creative to find a way to make them measurable. If you need a hand with some examples, we have a guide already waiting for you!

What Are Examples of Similar Challenges I’m Facing?

Each month, it can also help to ask for examples of other clients that can help guide you through specific experiences. If you have a certain challenge you’re facing, your coach may have advice based on their past experiences.

Two cars sitting side by side for comparison
The same, but different.

One of the best ways to learn is through others, and the right business mentor already has all the experience to help you through most challenges. Your advisor has likely faced the same thing or may have already worked through a similar challenge with another client.

Let's suppose that your business is within a home services industry such as pest control. You want to develop your marketing outreach to incorporate more complex email marketing campaigns. Chances are high, or guaranteed with our coaches, that they have extensive experience marketing similar businesses via many facets. Your coach may also have a roofer as a client, as an example, for which they just launched a successful email campaign. That experience would transfer from one business to another via your coach; leading to your own business' successful deployment.

Keep in mind that everyone and every business is different, but hearing about similar examples can help guide your decisions. One of our favorite things about being a small business coaching firm it that all small businesses typically encounter the same problems and we provide the knowledge for them to succeed rather than guess their way through a problem.

What Areas of My Business Should I Make a Top Priority?

Business owners, and especially small business owners, have to juggle a lot of shifting priorities. Without a coach, most business owners can’t always see what they should prioritize above other tasks. How many times have you looked at your website and you just know that it needs a redesign, but it always gets put off for one reason or another?

person writing on a glass, see through, wall with erasable markers about small business growth.

Only about 9% of business executives are very satisfied with their time allocation, showing that priorities are always difficult to navigate. Your coach has an outside view of your business, so he or she can tell you what to prioritize from an unbiased POV.

But back to that website example: perhaps the reason you keep putting off the redesign is because you feel it isn't an area for which you have strength. However, it's now reached 3+ years in age and its marketing effectiveness is minimal at best. This is a strong indicator that it should move up the priority list ASAP.

Prioritization will help you think more clearly. You can finally decide what to move off of your plate and what isn’t as important as you might have thought. Freeing up your time then allows you to focus more on your biggest goals.

Can You Recommend A Course or Book for Continuing Education?

The best business coaching programs are focused on continuing education. All along the way, you should be learning more about business and implementing what you’ve learned.

A library full of business owners studying hard for success
Study hard for success!

This question also has the added benefit of acting like a filter for your business that will sift out *ahem* lackluster business coaches. Bad business coaches may selfishly view giving you the tools to enhance your own skills as a threat to their own business. Any business coach worth their weight should be there to improve you as the business owner as well as the business itself. If your coach ever wavers on this question, then it's time to find a replacement!

While talking with your coach regularly is a form of continuing education in itself, you can also invest in courses, webinars and books. In fact, we wrote up quick-start book list for business owners if you're unsure where to begin. A quick, easy recommendation that always applies is to join your industry organization and partake in their provided resources.

After working with you and understanding your business, their recommendations will align with your specific needs. Many business consultants stay up to date with trends and continuing education, so they’ll usually recommend options they’ve enjoyed personally.

What New Skills Should I Invest In?

In the same vein as continuing education, it’s important to ask which skills are best to place your focus. Many business leaders already have skills to help them thrive, but they may need to be fine tuned.

A woman business owner climbing a mountain
Never limit your scope for new skills

For example, some of you might excel in the technical aspects of their business but need more help in fine tuning soft skills such as communication. Work with your coach to understand the skills they recommend for you. Once you have their feedback, you can use their advice to prioritize your efforts at work as well as your continuing education.

Also, don't be afraid to think outside the box with respect to new skills. As the image here implies, you could easily take up rock climbing as a new skill. Not only would something like this help you bleed off some stress, it also helps teach perseverance, a well desired trait of any leader.

Also, be sure not to let your ego get in the way of any recommendations. If you’re shocked that your coach wants you to focus on a specific skill, there may just be new ways you can use the skill you’re already great at.

How Should I Improve My Team?

In business, teams that are engaged show 21% more profitability. It’s no secret that a great company culture helps create better business success. While your mentor can help address your business strategies and scalability, they can also help with internal challenges.

A group rowing a crew boat
Work as a team, play as a team!

If you were to ask us about your team once a month, you can get great advice about team building activities and more. As always, your coach will use a third-party POV to point out where it looks like your culture could improve.

Quick tip: Every business should conduct employee satisfaction surveys of some kind regularly. While you may have the 'feel' of your team down, at the very least this could be a way to empower them to make suggestions for your business anonymously.

By focusing on your team monthly, this ensures that you aren’t leaving them in the dust. While your leadership and business strategies are important to discuss, your team is equally as important.

How Should I Improve My Leadership?

Many of the questions you might have already ask can help you answer this question. Yet, it’s always valuable to get straight to the meat and potatoes so to speak. Your leadership style as a business owner can make or break your success, so it’s important to evaluate it.

A business owner meditating
Work on your own happiness!

This question often revolves around you as a person. Your coach will likely ask a lot of prodding and potentially personal questions to help you really dive in to what makes you tick. There's a reason that many business coaches are also life coaches!

It is important to ask this question with an open mind so you’re readily available to make improvements. Your coach may suggest things you’ve never done before, but it’s important to make an effort toward change.

What Type of Help Should I Ask For?

Phone with text saying ask more on a pile of leaves
Don't be afraid to ask!

Everyone needs help. What often sets apart those who are successful with those who fail is their ability to seek help even when they don't think that they need it.

This question may seem redundant, but what it does is empower your business coach to enlighten you to problems you may not be aware exist. Asking this question month-to-month helps you flesh out ideas and/or guide you when you may find yourself lost for what needs to change within your business.

It's important to keep in mind the strengths that your business coach brings to the table with respect to this question. Most coaches are well versed in every aspect of the business. It happens to be one of our greatest strengths. So, don't hesitate to rely on them to help discover where you need help most.

Once your coach has a good understanding of your operations and team members, he or she can suggest where to fill any gaps. If one of your biggest challenges is in finance, it may be time to invest in an improved accounting system for example.

Make a Point to Ask Ongoing Business Questions

Business owner crossing marathon finish line
Business is a Marathon!

Your questions shouldn’t taper off after you’ve made your initial connection. A coach is there for ongoing support, and their advice can be more and more helpful as they work with you longer.

As they get more ingrained within the specifics of your business they will both understand more about things like culture, but also will be more tuned in to where you'll see the most gains. Essentially, the power and benefit that your mentor can provide increases over time.

Most likely you hired a business coach to help you tackle a very specific problem that was plaguing your business. Perhaps once your coach helped you through that problem that was the end of your relationship. But, we are guessing that during the process of solving that specific problem, several more were discovered. Make it a point to keep engaging with your coach over time to tackle problems as continuous improvement.

We recommend coming to your coaching sessions with a regularly prepared list of questions. There may be specific questions about what you’ve done the past month as well as a standard list that you can ask repeatedly.


Path to Excellence: Hire a Business Coach

Communicating openly with your coach helps you get the most out of your partnership. Through open communication, you’re opening the door wider for us to step in and help you succeed.

Out of the Box Advisors has been coaching small businesses for the past 10 years and counting. We have over 30 years of C-Suite business experience. We were founded to take that knowledge and empower the small business owner to achieve their dreams.

If you're still looking for the coach to help grow your small business, we offer free consultations to get your started on your growth journey! Schedule your free consultation using the button below!

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