80 Thoughtful Small Business Coaching Questions

As executive coaches, we understand the power of coaching questions. They can clear up your vision, reach your blind spots, and help you realize your big goals.

Sometimes, your business desperately needs change. But doubt and uncertainty can hold you back, which is why you need the right question to get the needed courage. Here are 80 thoughtful small business coaching questions to ask yourself.

What Are Some Good Coaching Questions?

good business coaching questions

Below are some of the most powerful business coaching questions for small business owners.

Having a Role Model

During your coaching session, a business coach might ask you about your role model in entrepreneurship.

  • Who is your role model?
  • Why do you respect them?
  • What do they do?
  • What do you want to do similar to them?
  • What do you want to do differently?

Visualizing Your Dream

Allow yourself to visualize your hopes and ideal life. If you're your own worst critic, these questions should help you operate from a positive mindset and gain the confidence you need. In other words, they'll force you to imagine a positive future in which it all works out.

  • What would success look like to you?
  • What would it feel like?
  • How would you describe your ideal life in as much detail as possible?
  • What relationships do you treasure the most in your life?
  • What would you do if you knew you couldn't fail? Are you scared of failure? It can be liberating to consider the world of possibilities that lies outside of it. Your answer will tell you what you should be doing.

Defining Core Values

As you know, it's best to align your talents and passions with your work. This way, it'll feel less like work, and you'll be more likely to make it. In "Essentialism: The Disciplined Pursuit of Less," Greg Mckeown encourages readers to do less but better. So, don't let outside forces drag you in any direction, but hone in on what's essential to you.

If you're just getting started, you can pinpoint what's essential to you, determine your niche and strength points, and get started with the following questions.

  • What are you passionate about?
  • As a small business owner, what do you want to accomplish?
  • What do you want your business to be known for?
  • What is the most important thing you do as a small business owner?
  • Who do you want to help?
  • What is the problem your business can solve?
  • What tools does your business provide to solve the problem?
  • How can it solve that problem?
  • How do your core values speak to that?
  • What does your avatar look like? Feel free to fetch a paper, and illustrate your avatar. This exercise will get you to envision its appearance, clothes, hair, smell, spouse, kids, and more. Understanding your desired personal life is crucial to finding your perfect niche.

Taking the First Step

taking the first step to asking your business coach the right question

Sometimes, turning your ideas into actual decisions is intimidating. But the right questions can encourage you to take action.

Looking Back

After taking a few strides, looking back to the beginning of your journey can give you the needed insight for your business's future. Also, it'll help you verbalize your current mindset. Accordingly, any mindset issues over money or business will resurface, and you can resolve them.

  • What was your original vision for your new business?
  • What is your vision now?
  • How has it changed over time?
  • How does your current role relate to your vision?
  • If you could go back to January, what career advice would you give your past self?
  • When was your business at its most successful?
  • When was your business at its least successful?
  • What has been working for you?
  • What hasn't been working for you?
  • Would you rehire that employee?

Making Weekly Calls

If you had a business coach, you would've probably had weekly calls with them in which they'd ask you some great coaching questions. If not, it helps to set time aside every week and have an internal monologue with these questions:

  • Did you reach your goals for the week?
  • What was a small win during this week?
  • What are the challenges you've faced this week?
  • How did you overcome them?
  • Are there any mistakes you've made this week?
  • What did you learn from them?
  • What are your goals for the next week?

Scheduling Periodic Check-Ins

Some people start strong but eventually lose motivation and regress, which is why you should always stop and evaluate where you are. It's best to recognize your obstacles, hold yourself accountable for your failures, and feel proud of your success. This way, you'll be better committed to the journey.

  • On a scale of one to ten, how satisfied are you with your business right now?
  • What are you dissatisfied with at present?
  • What are you already great at? Don't become too fixated on the future; learning to enjoy and appreciate where you're at is essential.
  • What can you do to be fully satisfied with your business?

Setting Goals

setting goals with a business coach

A big part of laser-focused coaching is goal setting. To start with, you need to set goals that are really yours (not projected by others). Then, you'll have to break them down into more attainable goals and create a step-by-step plan about how to succeed.

These are some of the best business coaching questions that'll help you gain clarity about the goals you should be achieving.

  • Using only three words, how would you sum up the business owner you want to become in six months?
  • Are there any particular skills that can help you become that version of yourself?
  • Are there any habits that are keeping you from becoming that version? You'd be surprised by how much your habits contribute to your outcome. So, categorize your patterns into personal, health, relationship, and leadership habits. Then, make a "stop doing" list with the bad ones.
  • Imagine yourself six months from now. You're thrilled with your achievements. What has prompted this sense of lasting fulfillment? This should help you focus on your main goals.
  • Where would you like to be in five years?
  • What part of that could you do right now? Big goals may be intimidating, which is why you need to break them down into smaller ones.
  • How are you working to achieve these goals in five years?
  • Which of your goals can you achieve alone, and which require assistance?
  • Are your goals quantifiable?One of the main mistakes companies make is setting vague goals. Being specific means you can track your progress and know when you've reached your goal.
  • How will you celebrate reaching that goal? Don't forget to appreciate how far you've come and celebrate your growth. Being grateful and proud of yourself throughout your journey makes the biggest difference.
  • If you were to improve in three areas, what would they be?
  • How can you improve in those areas?
  • What is stopping you from improving in those areas?

Making Decisions

two coaching clients thinking about the questions they will ask their business coach

If you fear making the wrong decision and second-guess yourself a lot, we might have the perfect questions. They'll turn the decision-making process into an inner dialogue and help you work through your limiting beliefs.

  • How do you typically go about decision making? As a CEO, you want to make sure you aren't just going through the motions of keeping your business running. Instead, you want to have intent and strategy; that's what makes you a leader.
  • What other decision strategies and methods could you use?
  • What would a great decision look like?
  • How will you implement that decision?
  • What information do you need before making the decision?
  • What is the best outcome for this decision?
  • What are your blind spots when it comes to the decision? Blind spots are the reason many car accidents happen. Similarly, they're the reason many business decisions go south. So, consider the data, knowledge, and experience you're lacking that can cause problems down the road.
  • A year from now, your decision has completely backfired. How did that happen?
  • What is the biggest problem that you face every day? Don't stop there, but understand why this problem hasn't been solved yet. Usually, there's a reason for that procrastination, such as a difficult decision that you're putting off.
  • Is there a small step that you could take right now to resolve it and improve your current state? You may feel overwhelmed and stuck, so try zoning in on one problem.

Managing Frustrations

business coach managing frustrations

Some of the most powerful questions to ask yourself are those that hit your pain points. They might help you put your feelings into words and understand why your business is suffering. This way, you can turn these problems into your own solutions and now that we have been utilizing virtual meetings. You can ask your coach all of these questions online.

  • What question do you not want to be on this list? Did something cross your mind when you read the word "pain points"? Did you secretly hope you wouldn't have to talk about it? Real change happens when we're honest about the real issues.
  • What are your biggest fears, and has any of them ever materialized?
  • What can you do to alleviate them?
  • If there's nothing you can do, how do you manage your negative emotions?
  • What is the biggest source of stress for you today?
  • What is one thing you can do to relieve it?

Sales Coaching Questions

a business coach helping a client with sales questions

Are you looking for small business coaching questions relating to sales? Answer the following to become more aware of your motivations, strengths, and weaknesses. Eventually, it can help you lead a better sales team. That's why these are amazingly thoughtful small business coaching questions to ask,

  1. When you consider the sales process, what is the most challenging aspect of it? Your response should help you discover your weaknesses and address them.
  2. What are your short-term and daily goals? To achieve your long-term goals, you need to divide them into smaller goals. Also, try devising a system to monitor your daily progress.
  3. What are the potential issues that could hurdle you? You're more likely to reach your sales goals if you're prepared for any problems. So, you'll greatly benefit from "if-then" responses. Feel free to ask for guidance, support, and any resources that can help you overcome these potential obstacles.
  4. What would your partner or prospects say about working with you? Remember that no one will know your answers other than you, so be transparent.
  5. This question should help you understand the perspective of your partner, prospect, or client. Of course, it's critical to take responsibility for any less-than-perfect behavior if you want to improve your relationship with others.
  6. Do you have an approximate budget for your project? Now that you can clearly see your project, you can calculate its approximate budget.
  7. How will you fund this project? It's essential to follow up project ideas with conversations about money and funding. Make sure you can produce your project's expected budget, and decide where you'll get the money from.
  8. How many calls and emails do you have to make this week? Knowing how many calls and emails are on your schedule for the week is insightful. For example, you might find yourself spending too much time on them, so think about how you can be more productive about such communications.

How to Make the Most Out of These Coaching Questions

a happy business coaching client

You can get the most value out of the questions we've mentioned with the following tips. Firstly, you have to be open to change. Businesses can't become better if they're left unchanged. If you're a person who dislikes change, it won't be easy to accept it. However, change is key, whether it's a structural or behavioral shift.

Secondly, hold yourself accountable. Accountability is necessary for the development of your small business. These questions might shed light on habits you need to change and decisions you need to make. Although it can be tempting to find excuses, accountability is the only acceptable attitude if you desire to see real change.

Thirdly, invest in your professional development. If these questions help identify your next steps, expect that they'll probably require funding. For example, you might need to expand your business by hiring more employees or get the ball rolling by doubling the number of products you put out.


What Makes a Good Coaching Question?

When coaching clients, we prefer open-ended questions that promote reflection. They usually start with "who," 'what," "when," "why," and "where." Coaches attempt to invoke their clients' curiosity, get them to think, bring attention to their underlying assumptions, promote creativity, help them focus, and invite them to ask more questions.

What Makes a Bad Coaching Question?

A bad coaching question is a close-ended one, and here's how you can spot it. For one, most rhetorical questions don't help much and can promote negative self talk. Also, solution-oriented questions are mostly close-ended. And be careful with "why" questions because you don't want this to become a self-grilling session.

Why Do You Need Powerful Business Coaching Questions?

The benefits of small business and sales coaching questions are limitless. For one, they allow you to get to know yourself on a more personal level and identify your passion, goals, and interests. Also, if you had a life coach, they'd make sure these questions empower you to make your own choices and take control over your life.

What Do You Ask Your Mentor or Business Coach?

A coaching relationship is one where you ask and answer questions. If you're hiring a coach, you can ask them if they can pinpoint your blind spots, areas of opportunity, strengths, missing skills, and more. Also, you can ask them what they'd do if they were you and listen as they explain how your next step is crucial to the process.

What Is the Best Coaching Question?

Don't buy into that idea that there's just one perfect question that'll propel a breakthrough or revelation. Although that may happen, coaching questions can benefit you as long as they allow your inner conversation to unfold naturally.

Final Words

Ultimately, asking small business questions can reap many benefits. Coaches don't cost as much as you would assume. As you've seen, the questions we've listed are diverse, covering your dreams, aspirations, strengths, weaknesses, frustrations, limiting beliefs, decision-making techniques, budgeting, victories, fails, and long and short-term goals.

Of course, some questions may speak to you more personally than others, which is why you don't need to answer all 80 of them. Instead, you can target the ones you know you need. This way, you can be honest with yourself, find purpose, know where and how to direct your energy, understand how your team can work effectively, and more! And now you will know a TONE of thoughtful small business coaching questions to ask any business coach.

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