The Barrel leadership team has been working with a CEO/business coach this year. One of the most valuable takeaways from our sessions with him are the questions he asks about our business. It’s humbling how often we don’t have a clear answer, but with each session, we’ve been able to improve our knowledge of the business and install systems to better retrieve answers in the future.

The following are 25 questions (not exhaustive by any means) that we’ve explored this year, some directly from our coach and others as our own follow-ups in digging deeper into our understanding of the business.

1. What does your agency do? What services does it offer?
2. How are you different / why should clients choose you?
3. Who are your top clients?
   1. Top 10%, top 25%
   2. What are the characteristics of your top clients (e.g. types of engagements/SOWs, industry vertical, rates, etc.)
4. What is your ideal client profile / who do you target?
   1. What is the market size you are going after / your total addressable market?
5. Who are your competitors? Who is the best in your space and why are they the best?
   1. What is keeping you from doing what they are doing?
6. What is your revenue and profits (last year, trailing 12 months)?
   1. How much revenue comes from repeat/existing clients vs. net new clients?
   2. How much revenue is recurring/retainer-based vs. project-based?
7. What are your revenue and profit goals for this year? This quarter?
8. How are you going to achieve your revenue and profit goals for this year? This quarter?
9. Where will the increase in revenue come from?
   1. How much from new clients vs. existing clients? How much from new service offerings vs. existing service offerings? How much from price increases?
   2. What activities will drive the increase in revenues? How are you tracking your efforts?
10. What are your marketing activities?
    1. What are you doing to generate leads?
    2. What channels are you active in?
    3. How do you measure the performance of your marketing activities?
11. What is your sales process? What are the steps from engaging with a lead through close?
12. What does your pipeline look like?
    1. How many leads, qualified leads, proposals, etc.?
    2. What is the weighted value?
13. How many leads do you get per week? Per month? Per quarter? Per year?
14. Where do your leads come from?
    1. What are your top lead sources? (read my blog post on lead sources)
    2. What can you do to get more leads from top sources?
    3. What can you do to get more leads from different sources?
15. What percentage of leads become qualified?
    1. What counts as a lead? How do you qualify leads? When does a lead get marked as qualified?
16. What is your win rate?
    1. Does it vary depending on the type of lead (e.g. new client, former client, existing client) or project?
    2. How long does it take to close a deal? Does it also vary on type of lead or project?
17. What is your average deal size?
    1. Does it vary depending on the type of lead (e.g. new client, former client, existing client) or project?
18. How much new business do you need to add each week to meet your goals for the quarter and for the year?
    1. How much of each type of lead or project would you have to add (if they vary)?
    2. What needs to change if you don’t meet your goals?
19. What is your gross margin? How does it break down across your services offering?
20. What does your org chart look like? Who is in charge of the sales function? Who is in charge of the delivery function?
21. What is your utilization rate? What is your utilization target?
    1. How do you calculate utilization? Does it include PTOs? What headcount does it include or exclude (e.g. FTEs or W-2s only)?
    2. What does revenue look like at full utilization?
    3. At what utilization rate are you breakeven / in danger of being negative?
22. What will be your starting revenue next year?
    1. How much churn do you expect?
    2. How much new business do you need to reach your revenue goal?
    3. How many leads and deals per month/week do you need to close in order to hit your goal?
23. What will be your profit goal next year?
    1. What happens to the cost structure as revenue grows?
    2. How will you change your cost structure to meet your goal?
24. What do you want to achieve over the next 3 years?
    1. Revenue and profit: growth rates and figures for each of the next 3 years.
    2. Also: client makeup, services offering, and org structure.
25. What will you do differently to achieve your goals over the next 3 years?
    1. What new sales and marketing activities will you have to engage in?
    2. What new markets might you target? How might your ideal client profile(s) evolve?

Bonus: If you hit your profit goals, how will you reinvest or use your profits? (see my post about cash reserves and capital allocation).

We’ve left every session remarking how we “got our asses kicked” because it feels very much like a tough workout in the gym – it’s constant exposure of our weaknesses and knowledge gaps, trying to get a handle of where we need to improve or try something different. Overall, it’s been an amazing experience and something I wish we had done a lot sooner.