10+10 Business Breakthrough Questions to ask yourself EVERY year

We all start our businesses with passion, motivation, ambition and drive to make it a success.

We have clarity around why we are doing it, what we want to achieve and how we will do it. For some, this level of energy and focus remains constant. But for many of us we lose it. The challenges arise, the pressure mounts and the fog descends. We get caught up in the daily “doing” of our work, fighting fires and just trying to keep our head barely above water.

I have been working a lot lately with business owners who have been operating for 3 years or more. I’ve found incredible value in taking them through this business discovery process to help them rediscover their purpose, identify what’s working and what’s not and re-align their strategies for the future.

I highly recommend all business owners take the time each year to stop and ask themselves these 20 very simple breakthrough questions – you will be amazed how much creative thinking this inspires and how it can steer your brand in a fresh direction almost immediately!

Round 1 

  1. What was your original vision for your business or brand?
  2. Has that changed at all now?
  3. If so, how and why?
  4. What do you think you have done well in the business?
  5. What areas could be improved upon?
  6. What’s keeping you awake at night?
  7. What is your main channel for acquiring new clients right now?
  8. Has that always been the case?
  9. Which of your services or products generates the most income?
  10. Where do you think the biggest opportunity is?

Round 2

  1. How would you define “an ideal client” or project for your business?
  2. How do you want your ideal client to “feel” about you and your brand?
  3. Are your current clients having this experience of you and your brand right now?
  4. How do you currently balance working in the business vs on the business?
  5. Do you see your role changing in the business over time?
  6. What would be your ideal scenario in the future?
  7. Where would you like to see your business in 12mths time?
  8. In 3 years time?
  9. What do you not have the time or resources to do now that you feel would make a tangible difference to the business – in terms of productivity, profile and profitability?
  10. If you could do one thing right now that would make a difference to your business what would it be?

While all the insights gathered from this process are important, it’s the answers to Question 10 in both rounds which will reveal your current priorities. This can provide immediate guidance on steps you can take right now to make a difference to the future of your business.

For more information or to assist you in distilling these insights into a strategic plan for your business please contact


NB: Interestingly, this same set of questions can also be used to assist employees seeking clarity in their career direction. Just make the following substitutions:

  • the business = your career
  • client = organisation / career opportunities
  • products / services = skills / expertise / strengths

So powerful!!