Unlocking Business Potential: The Most Powerful (and Annoying) Coaching Questions You Can Ask YOURSELF, Today!

The Most Powerful (and Annoying) Coaching Questions You Can Ask YOURSELF, Today!

Today, we're talking about some of my favorite—and least favorite—business coaching questions. As a former teacher and now a business coach, I can tell you that asking yourself (or having your coach ask!) the right questions at the right time is pivotal for creating clarity, growth, and perspective in your business. The questions might seem (and actually ARE) annoying at times, but they are ALSO incredibly powerful. 

Let's explore these questions so you can start using them to transform your business.

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Why Not? Break Free from Self-Imposed Limits

One of the most impactful questions you can ask yourself is: "Why not?"

This tiny, simple question has the BIG power to challenge the soooo many of limitations you set for yourself. As business owners, we often ask "why" when considering new ideas or actions. However, we rarely ask "why not?"

For example, I recently found myself very reluctant to send an email series about something new I was selling to my entire list. When a colleague very wisely asked me, "Why not?" I realized there was no valid reason for my reluctance—only self-imposed barriers. All the reasons why not were MY reasons, and those reasons didn’t have anything to do with helping the people I was trying to serve.

This question helps uncover the rules we’ve set for ourselves that may not be necessary. It encourages you to explore possibilities you might otherwise dismiss. If you're holding back from trying something new, ask yourself: "Why not?" and see what opportunities unfold.

 Who Are You Trying to Avoid Disappointing?

Another critical question is: "Who are you trying to avoid disappointing?"

This question often brings out groans because it can brings up uncomfortable truths about us and our motivations. For example, if you’re struggling with pricing decisions, this question can help you identify the ways you might be trying to please someone else at the expense of your own value (not to worry, we’ve ALL done this!).

Understanding who you’re trying to avoid disappointing can clarify when and how your decisions are really alignment with your goals, or if they are being pressed on by outside and maybe unexpected pressures. This self-awareness is crucial for making decisions that honor your own needs and values rather than trying to meet others’ expectations.

What Is the Actual Problem You're Trying to Solve?

When tackling challenges, ask yourself: "What is the actual problem I'm trying to solve?"

Often, we jump into problem-solving mode without fully understanding the issue at hand. This question helps you articulate the REAL problem rather than jumping to solutions that may not address the core issue (and - BONUS - this question also lets you know when you’re jumping into solve a problem that actually isn’t a problem at all, BEFORE you do all that extra work!).

What Do You Need to Let Go of to Move Forward?

The question "What do you need to let go of to get where you're going?" can be tough but essential.

Growth often requires us to shed old habits, beliefs, or roles that no longer serve us. This might include letting go of outdated processes, thoughts about yourself, or even aspects of your identity.

For example, I’ve had to let go of side jobs and fears about not being accepted in the business world because of my unconventional (teaching!) background. The process of letting go can be (is!) uncomfortable, but it’s necessary for embracing the next version of yourself and achieving your goals. 

What Do You Actually Want?

Finally, ask yourself: "What do you actually want?"

This question might seem straightforward, but it’s often challenging to answer because we are not always trained to identify our own wants - we focus on what we need, and then move on to helping other people. Understanding what you truly want helps you shape your business and life in a way that matches up with your goals and values.



Many of us, especially women, are conditioned to focus on meeting others' needs or expectations either ahead of or to the exclusion of our own. However, your business should reflect what you WANT it to be, not just what others expect of it. 

Taking Action with Powerful Questions

These questions are more than just things to think about —they are tools for big-time self-discovery and business growth.

They will challenge you to confront self-imposed and sometimes secret rules, clarify your motivations, identify real problems, let go of outdated practices, and align with your actual wants.

If you find these questions useful and want more, coaching together might be for you - you can use the links at the top of the page to explore your options.

For more great (free!) content and to connect with a community of like-minded individuals, join the Facebook community, Uncomplicated Business for Teachers, Helpers, and Givers.