20 questions to assess the overall health of your business
Rate on a Scale of 0-5:
0 – I don’t know
1 – Far from it
2 – A little bit
3 – True but not consistent
4 – Yes, often
5 – Agree wholeheartedly



[ ] I love the lifestyle my business provides me
[ ] I love my business
[ ] I make good money
[ ] I am neither bored or anxious at work

Section Score [  ]


[ ] I have clear 1 year goals for the business
[ ] I track and adjust business strategy every month
[ ] I work on internal and external business strategy every week
[ ] Team members are aware and engaged in the progression of our business strategy

Section Score [  ]


[ ] The business has a clear market positioning strategy that is communicated and established
[ ] The business has a specific expertise and is/will be the best in the market at what we do
[ ] Our service approach is unique, delivers consistent results and could be considered intellectual property that adds value to the business
[ ] Our clients love our work and we receive most new business through in-bound/referral leads

Section Score [  ]


[ ] We have the right people to execute effectively on our market focus / service approach
[ ] We are strong at execution: always fulfill client projects on time and on budget
[ ] 60-70% of the total working time business wide is billable
[ ] I am aware of open projects status and profitability on a weekly basis

Section Score [  ]


[ ] My business earns healthy profit margin – 10-20% quarterly/annually
[ ] I get paid what I deserve or normal market rate on a regular basis from my business
[ ] I have a positive operating bank balance and rarely need to stress about cash flow
[ ] I am on top of bookkeeping / accounting with all tax filings up to date and paid

Section Score [  ]



For Each Section

0-5: Put immediate focus on this section of your business and set goals for improvement

5-10: Identify specific areas of weakness within this section and focus on improvement

10-15: Continue to develop this area of your business

15-20: An area of strength – maintain and tweak

Overall Assessment

0-20 Let’s be honest – this requires a step back to consider if you’re on the right path at all. Likely you need to pivot or reinvent this business entirely.

20-40 You have a lot of work to do in building a better version of your business. Step back and assess if it’s possible. If so, prioritize the areas, set goals, and dedicate 1 full day per week on strategies to improve. Potentially look for a mentor or professional help / perspective on how to move forward. Focus on your strengths and find opportunities to do more in those areas.

40-60 You’re likely on the right path, but need to identify specific areas of weakness and dedicate 10-20% of your week on strategies to improve. Look specifically at your positioning strategy. If you’re weak there, it’s hard to improve in other places.

60-80 You’ve got a nice business with the opportunity to do even better. 10% of your time per week on strategy to improve will benefit your business in a big way. Continually tweak the areas that need focus.

80-100 A great business. Continue to improve and move forward. If your business is this kick-ass then it means you likely spend at least 10% of your week on strategy – keep that up!



1. Your bank balance is consistently positive and you have a cash buffer to manage revenue fluctuations (this allows you to sleep well at night)

2. You feel you get paid a reasonable salary – about what you deserve for your role in the business and as a founder

3. You wake up every Monday morning looking forward to getting into work

4. You’re not bored with your business – consistently feeling like your challenged and learning more all the time

5. You don’t experience anxiety at work. That feeling like you can’t rise to the challenge or don’t have the knowledge tools to execute. You feel stress sometimes, but no anxiety

6. You have weekly and monthly reports that indicate the performance of your business – and you make decisions with them

7. Most or all of your business comes by referral or in-bound leads. Your marketing costs are minimal as a result

8. Clients are happy, budgets and timelines are consistently met

9. Your quarterly and annual net profit is +15%

10. You have time: to think, work well, lead your people, work on strategy and most importantly live the life you want to live and do the work you love