10 Powerful Business Coaching Questions You Want Your Coach to Ask You

Ken Larson

Ken Larson

The right coaching questions go way beyond just solving some basic problems for your business. The most effective coaching questions will make you think and reflect deeply on what you’re doing, while evoking bigger questions about your company and its purpose. After your introspection, the answers you end up with can radically change your company’s foundation, culture, communication style, and overall performance. 

As a result, you and your team should come to a coaching meeting ready to answer the big business coaching questions while staying open to thought-provoking discussions and ideas from your coach. This guide will cover the top questions a business coach should ask you to bring out the best your company has to offer, whether you’re a small, medium, or big business.


1) What Is Your Vision for Success?

“Success” is a tricky word by nature, as its definition changes from person to person. That’s what makes this the most important questions your business coach can ask you — defining success for your company puts all of your team on the same page. With such a wide possibility of definitions, getting to the answer will take some purposeful thought.

Many business coaches ask you and your team to draw a mind map of many vital parts to help you with this step. These components often consist of your targets, goals, and other similar milestones you picture for your business. To tie these factors together, you and your team can then write a strong story of your targets and goals as if you’ve already achieved them. For instance, if you aim to increase your income by 15% in the next three years, write about what you did to get there, step by step. 

Doing so helps you and your team understand what it will take to reach that goal. Mentally, you’ll knock it down from impossible to completely possible. You all place yourselves in the mindset of a company that is ready and more than capable of achieving its objectives

2) What Is Your Foundation Made of?

Your business foundation is, fundamentally, what drives you and your team to get up and work hard every day. Without a solid foundation, your team will lack motivation, which will make them put in less-than-favorable efforts. A business coach should ask you a series of questions that will shine a light on where your foundation stands. 

Through this process, you should also get insight on what you need to do to achieve the goals you’ve set for it. The following questions are the most common ones you may face: 

What Are Your Core Values?

Your core values are much more than catchy buzzwords to put up on the wall. They act as a guiding compass for your business and its people; common purposes to refer back to when you need to make a decision, whether small or big. Business coaches can help you uncover your core values, which often run much deeper than you may have thought. 

Many businesses make the mistake of only using a few words that sound good, and failing to put these values into use. For example, if you choose words like “integrity” or “respect” but don’t explain how your company reflects those values, they may appear meaningless to both your employees and your customers. 

Discussing what inspires your company to make its decisions is a great starting point to discover your values. Moreover, think about whether you and your team successfully demonstrate your chosen values on a day-to-day basis. A company with strong core values will live and breathe them. 

What Are Your Core Competencies? 

Your core competencies are what give your business an advantage over your competitors. Reexamine your company’s skills and abilities to figure out what makes you stand out and what makes your products and services unique. Is it the high quality of your goods? Your exceptional marketing campaigns? Or perhaps your unparalleled customer service?

If you need some inspiration, take another look at your mission and vision to remember why you started your business and why you believed your company would succeed. You can also ask loyal customers why they choose to come back to you time and again. 

What Is Your Mission?

A business coach can help clear up the difference between your company’s vision and mission — two words that are often used interchangeably. While a vision will define what your company hopes to achieve down the line, a mission describes what your company is doing every day to achieve that vision. Breaking down your daily tasks into actionable statements helps your team find greater value in their work.

What Is Your BHAG (Big Hairy Audacious Goal)? 

You have your three-year goals, but your BHGA, or big hairy audacious goal, will be the ultimate goal you have for yourself in 10 to 25 years. This goal is meant to be large and invigorating, without a need for a step-by-step analysis. Instead, it acts as a source of inspiration for you and your team.

A coach will ask you to dare to dream the impossible and come up with a target that will act as your company’s ultimate source of motivation for the upcoming years. Think of something as big and bold as climbing Mount Everest or going to the moon.

What Is Your Brand Promise?

Your brand promise will act as the final piece of the foundation puzzle. It’s the benefit you promise to give your customers over every interaction they have with your company. You may already have solid ideas of what you aim to give every customer, but outlining the promises into sentences will show your brand’s confidence and focus. 


3) What Are You Measuring? 

A coach will ask about how you will measure your goals and targets, both financially and otherwise. What do your current measurements tell you? Are the numbers giving you the information you need, or do you need to reconsider what and how you’re measuring? How often do you measure, and who is accountable for the results you get? 

Your leading and lagging indicators are of utmost importance here. What approach are you taking to identify and measure the indicators that tell if you’re ahead of target, behind schedule, or going at the right pace?

Many businesses have a hard time figuring out exactly which leading and lagging indicators to focus on, putting their energy into factors that end up being less important on a long-term scale than they’d like. Simply changing your leading indicator can lead to a bigger and more influential change in a lagging indicator, affecting your bottom line overall. 

And if a particular metric isn’t helping you drive the business forward… STOP IT!


4) What Are the Potential Roadblocks that You Foresee?

Coming up with plans for dealing with potential roadblocks will prepare you for when challenges arise — as they always seem to. A coach may even come up with other possible challenges you might meet down the road, opening your mind to hurdles you may have never considered. Once you’ve got a list of roadblocks figured out, perform a risk mitigation analysis to see how you can handle them all.

You will need to take the following steps:

  1. Analyze: This step consists of asking as many questions as possible. How big is the risk? What departments or aspects of your business can this risk affect? What would the biggest effects be if the risk becomes a reality?
  2. Evaluate: Look over your list of risks and decide which would have the biggest effects and which would have the lowest. Doing so can help you figure out who would need to get involved for different issues, along with their timeline to sort it out and who else will be affected in the meantime.
  3. Contain and Monitor: Containing a risk involves discussing possible solutions with team members who are most likely to run into it. Make sure that these members monitor the situations that could cause each risk, as a preventative measure. 

Consider that risks can also be opportunities to continue improving your business, by giving you and your team chances to learn and grow in the face of adversity. 

And remember… EVERY challenge has an opportunity inside it – find these and leverage them!


5) What Will I See You Repeatedly Do that Aligns with Your Purpose, People, and Plans? 

A coach is interested in whether you walk the walk and talk the talk. It’s one thing to have figured out the fundamental aspects of your company, but it’s another to see if you’re putting your beliefs into practice. 

What example are you setting for your team right now? Is it in continuous alignment with your values, or are you sending a contrasting message? If that is the case, a coach can work with you to figure out how to present yourself as the example you’d like to set. They’ll help your team — and, by extension, your business — practice what it preaches.


6) How Would You Define Your Culture? 

Company culture affects the workplace much more than many believe. In fact, employees who don’t enjoy their company’s culture are 24% more likely to quit and seek employment elsewhere. As a result, making sure you have a clearly defined culture is one of the most important contributing factors in retaining employees.

Your company culture will consist of the relationship your colleagues have with each other, as well as your company’s overall shared values, ethics, and ideals. If a coach were to observe your team for a month, would they find that the team performs daily, consistent actions that suggest a healthy work culture? 

Consider the opposite. Weak company culture often consists of low employee engagement, a high turnover rate, constant miscommunication, and unhealthy competition. If you find that you’re suffering from any of these issues, it may be time to refine your company’s culture.

A coach will work with you to improve it and close the gap between what you want your culture to look like and what it is now. For instance, you can work on increasing employee recognition, one-on-one time, and encouraging employee authenticity. Remember the key acronym “CCO,” or Chief Culture Officer. It’s your duty to bring culture alive to the workplace. 

Culture eats strategy for breakfast!

7) How Would You Grade the Health and Performance of Your Leadership Team? 

The strongest leaders have the strongest leadership teams. All leadership team members need to fit two criteria: fit for your culture, and a top performer. These are your A-players. A fit member will be good at what they do. They will have a range of knowledge and skills they bring to their role that is incredibly valuable to their overall drive and mission. To be an A-player, they have to be open to any disagreements from other members. During these disagreements, they remain open to change, compromise, or negotiation without affecting their performance and drive. 

A coach will help you grade your leadership team’s performance and help you figure out how you can improve it, if you need to. Usually, improvement will consist of coaching up or coaching out. After all, there is a difference between team members who are capable of completing the job but struggling to do it and members who lack the motivation to do their role correctly and would be better off in a different team. 

Coaching up

To coach up employees who need improvement, make sure you demonstrate your belief in them, first and foremost. Be honest about the issue at hand and examine what potential barriers may be holding the employee back. Sometimes, all it takes is a little extra training. Ask the employee for feedback, as they may be able to come up with a solution themselves. 

It can help to follow up on an agreed-upon date and time to see how they’re doing, and to remind them that you care about their progress. Don’t tell them what to do… ask them what they think first. If they figure it out for themselves, they will own the actions and results and it will be easier for you to hold them accountable.

Coaching out

Coaching out takes the same level of transparency and belief in the employee as coaching up. This time, you’ll show that you really believe the employee will have a better opportunity in a different position. Lay out the expectations of the role and the issues that the employee has had with meeting them. 

Ask for input as well, and give them options when you can. Perhaps the employee would be better suited for another position at your company, or perhaps it’s for the best that they leave the role voluntarily.

This isn’t easy, especially if there’s an emotional and/or long term attachment. But remember… “the needs of the many (business) outweigh the needs of the few”.


8) How Would You Define and Assess Your Leadership Skills and Abilities? 

Besides assessing the quality of your leadership team, you must also assess your own skills and abilities as a leader. There are two big business coaching questions to address here: What your biggest strength is, and what your biggest weakness is (aka challenge). 

Identifying Your Number One Strength

Identifying your top strength helps you understand what you excel at and gets you thinking about ways you can leverage it. If you need help with this self-evaluation, you can ask your team, boss, or even customers to tell you what they think your strengths are. 

Getting third-party feedback can shine a light on your working and leadership style, or it can confirm what you’re already thinking about your abilities. 

Identifying Your Number One Weakness (aka challenge)

Recognizing your biggest weakness is one of the greatest steps you can take towards improving yourself as a leader. Once again, you can ask for third parties’ feedback on areas where you can improve. 

Any type of weakness, such as a tendency to miscommunicate or micromanage, gives you the opportunity to make an important choice. How will you mitigate this weakness or delegate the duties associated with it? Most importantly, in what ways can this weakness be an opportunity to grow? A coach can help turn a weakness into an exciting and energizing opportunity for you and your team in the workplace.

How effective and efficient are you?

Are you a living example? And are you exercising the “4D”? 

  1. Do only what you can do.
  2. Delegate to others to both create space for yourself and engage you people on a deeper level.
  3. Delay what’s not urgent, but may become so in the future.
  4. Dump the stuff that simply doesn’t advance your effectiveness and efficiency.


9) How Healthy and Up-to-Date Are Your Systems, Processes and Tools?

Since we’re in a digital work era, it’s vital to make sure you have the most up-to-date tools for your team. Business coaches are experts in keeping up with the latest and greatest business trends, processes, and tools. As such, they can offer the best ideas on how to lead and manage your hybrid workforce. They can also check that you are optimizing the following: 

1. Meetings

Virtual meeting systems have advanced exponentially in recent years. In fact, employees spend five times more time in meetings than they did before the start of the COVID-19 outbreak. Nowadays, there are countless features that virtual meeting systems offer you and your team that greatly boost your productivity and overall meeting success:

  • Noise reduction
  • Translation
  • Polling
  • Reaction emojis
  • Screen sharing
  • Digital whiteboards
  • Meeting transcription
  • File sharing
  • Chatting
  • Automatic recording 

Some meeting platforms include all of these features, but if you shop around, you may find platforms that only offer the features that you would find most useful.

2. Collaboration 

To greatly increase employee organization, efficiency, and — by extension — satisfaction, you will need to invest in top-notch collaboration software. Instead of having employees toggle back and forth between various tabs and applications all day long or send incorrectly formatted files and documents, you can centralize your team’s efforts in the same location. 

Even better, your team can communicate in one place, rather than needing to search through emails or messages to find the one important message for their current task. The best collaboration software will also let you integrate workspaces you might use, like Microsoft Teams or Google Docs, if you’d still like to use your usual system in place. 

3. Automation 

Automation has many benefits for your business, beyond just improving productivity. For example, it can vastly improve your accuracy by cutting down human errors, saving you time and finances. You can also use automation in various departments, like HR, marketing, or sales. For example, your HR reps can automate email replies instead of typing out the same response to the same simple questions. Or your marketing department could automate all social media posts, so they all publish when they’re supposed to. 


10) How Would You Assess the Health and Performance of Your Organization’s Communications? 

A coach will ask you to complete a thorough assessment of your company’s communications. Examine your communications both on an everyday and a long-term scale. What are your meeting rhythms? If you have daily meetings, do they serve a purpose or do they tend to become open conversations that don’t really get anything done? These same questions apply to weekly or monthly meetings, as well. After all, effective meetings should result in an actionable plan, goal, or target to pursue and an idea of how to get there no matter how often they occur. 

If your company has annual planning retreats, you may have to ask yourself if your retreats are advancing your team’s overall culture, performance, and accountability. If the answer isn’t a resounding “yes,” you can work with a coach to figure out what you need to leverage to make your retreats a complete success.

Business Coaching and Your Company

In the end, a business coach is there to guide you and your team on your way to success, whatever it may mean for your company. Good guidance starts with thought-provoking and deep questions that may challenge the foundation of your business — always aiming to help improve it. Both small business coaching questions and large corporation coaching questions do exactly that.

Whether you’re meeting with a coach for the first time or planning to schedule more coaching sessions for your team, it’s best to go into a coaching meeting as prepared as possible. You can continue to educate yourself on what coaching means for your team by checking out Champion PSI’s article on business and executive coaching. A little preparation can go a long way in bringing out the best of what your business has to offer. 

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