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Wanna grow your business?

Start with making time to ask yourself good questions about what growth means for you and how you want to achieve your desired results.

On a recent episode of the Bold Business Podcast, I talked with my fellow panelists about how much time it takes to ask strategic questions that drive your business forward.

Before we get to how much time this takes, we agreed that first you have to make the asking of those questions a priority so that like other important things it gets on your calendar and your to do list.

Then you have to treat the time you schedule with yourself to ask questions of and about your business as important as any other appointment you have.

In other words, make a standing appointment with yourself and keep it.

That’s where you start.

Not every question you ask will be a strategic question but with time and practice you’ll get better at asking good questions that lead to other good questions.

You can get better faster by

  1. Giving yourself grace: Making appointments with yourself to focus on what you and your business need can be a challenge. Sometime you won’t do it as consistently or frequently as you would like. Understand where you’re at and be flexible. Some planning time is better than none. Be flexible.

  2. Stop worrying about getting it ‘right’: There is no ‘right’ way to ask strategic questions or some magic set of questions you should be asking at any given time. In my experience, you can’t hack growth so just start thinking, reflecting and asking.

  3. Experimenting: Have an idea but you’re not sure if you’re on the right track? Find was to test it - fast and cheap. What did you learn? What new questions do you have?

  4. Engage others: Even solopreneurs have people they talk about business ideas with. Pull in your formal and informal advisors, employees, key vendors and anyone else who can help you ask better questions or source the answers to the questions you’re already asking.

It also helps to

  • Write things down. Thinking is great but writing things out helps you communicate them more clearly and helps you capture fleeting or incomplete thoughts.

  • Stop thinking about time management. Change your relationship to time and the amount of time you commit to being deeply curious about the current state of your business. To grow, you want to take action in an intentional way. That requires a commitment to whatever process you use to decide what choices to make and actions to take.

  • Don’t forget to act. Taking action gives you new information and raises new questions.

  • Remember, it takes the time it takes. It certainly takes whatever time you make to ask and answer the strategic questions that only you as owner can ask and answer. At different times it may require more time than you want or plan. And it takes the time it takes. So surrender to the need to make frequent and consistent time for strategic thinking and planning. Growth demands this time of you. You can’t grow in ways that are strategic, sustainable and profitable without investing time in the process.

To hear more musing on the topic of asking strategic questions, check out our entire #BoldBusinessPodcast episode on apple podcasts or watch the YouTube video below.


One great way to commit to making time to ask strategic questions to grow your business is to work with a coach. Ready? Let’s talk.

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