One of the best dialogues in the latest season of True Detective is when Jodie Foster, as Police Chief Liz Danvers says, “you’re asking the wrong question”!

As the owner and CEO of your growing business, you will have many challenges in front of you. To solve these challenges the key will be asking the right questions. Are you asking the right questions?

Of course, not every problem is worth chasing down. You will need to prioritize, to curate those that deserve your time.

Let’s look at a few priority challenges for every management team trying to scale a private company and explore the right questions. Use this list to tweak a version for your sector. We’ve built versions of this list for high tech manufacturing, software, staffing, biotech, travel, ad agencies and more. As CEO gather the team and ask them:

50 Right Questions

  1. Where is the business leaking value if we look at the business through the lens of a buyer? Our Saleability Test is a great place to start.
  2. Is our positioning understood by all stakeholders? Articulate your positioning statement that makes sense to all stakeholder, all members of staff, not just the c-suite, prospects, customers, partners, shareholders, bankers – everyone. Go test your positioning and ask for feedback.
  3. Are our product teams relentless tweakers? Are we allocating serious time to continuous product innovation?
  4. Are departmental objectives aligned with the big three (or 4 or 5) company objectives we want to achieve this year?
  5. Have we defined high priority projects and selected a cross-functional team with a leader to leverage those special talents?
  6. Are we continually looking for hidden gems in our talent pool that could do so much more (hint it’s nothing to do with experience)?
  7. How effective is our internal training process?
  8. Is the increase between last year’s EBITDA and this year’s forecast grounded in real life initiatives that we are controlling? What projects are going to drive us from A to B. (Hint it’s unlikely to be the same road map as articulated in the budget)?
  9. Are our sales and marketing teams knowledgeable about our competition? Cheats sheets should be kept up to date to ensure your competitive value proposition is kept relatively sharp. You must understand Why You Can Win.
  10. Are our top ten KPIs measuring the achievement of our goals? Build dashboards that grab the business by the jugular every day, week, and month (hint different dashboards)?
  11. Does the C-suite really understand the needs of the customers base? Are we abdicating responsibilities to the marketing and sales teams. Always intervene when you notice that customer’s needs are moving away from the service you are bringing to the market. Embed a Voice of the Customer system (VOC).
  12. Are we frequently communicating our story, the manifesto of the business, both internally and externally? If it does not feel like missionary work you’re not trying. Do not assume your vision has been translated into relevant actions by your managers. Continually validate.
  13. Are we evaluating the accuracy of our cash flow forecasts? 70% of businesses that go bankrupt are forecasting profit for the next three months.
  14. Does every meeting have clear next steps? So many businesses have wasted meetings with no follow through. After all that is all execution is.
  15. What is the credibility of our sales forecast over the last 8 quarters? How accurate are our weighted pipeline sales forecasts throughout the quarter compared to the result?
  16. Are there any large sales opportunities that we are relying on to close over the next 3 months?
  17. Is our production slot plan capable of building what is in the sales pipeline
  18. What supply chain issues could prevent us shipping our main products in the next 6 months?
  19. Do we have a compelling competitive value proposition in the current market?
  20. Can you name the 20 most popular pieces of content we published last year
  21. What is the cumulative return on investment % of our Google Ads?
  22. What are the trend lines over the last 3 years for online form sales inquiries and inbound sales calls?
  23. What are the 5 highest referral engines regarding traffic to our site?
  24. What is the acquisition cost of sales leads by marketing channel and the trend lines for all?
  25. What are the key drivers to transform the profitability of our business?
  26. What products/services are the most profitable?
  27. What are the main reasons for quarterly Gross Margin & Net Margin movements over the last 12 months?
  28. What are our most successful distribution channels?
  29. Which marketing campaigns have had the greatest ROIs over the last 24 months?
  30. What are the 10 key reasons reconciling last year’s pretax profit with this years forecast?
  31. What actions are required to improve our weekly cash generation?
  32. What are the absolute $ amounts and the annual cost growth % of all of our main suppliers over the last 5 years?
  33. What does that translate to, on a unit cost basis, again absolutes and % terms?
  34. Taking all cost lines as a % of sales, which % have grown the fastest and why?
  35. Which ratios would you use to measure productivity and illustrate your point using 3 years’ worth of data?
  36. What changes to our pricing model could improve our sales and profits?
  37. What best practices could improve our bottom line if they were to be rolled out across the group?
  38. Which multi-departmental projects have we executed over the last 3 years and what was the ROI% compared with the expectation. If nonfinancial objectives were set, then were they achieved?
  39. If you were to take a zero-based budget approach to our infrastructure, what recommendations would you make?
  40. Where are the greatest risks to our planned profit target for this year and what actions could be taken to reduce that risk?
  41. What IT systems that are currently being deployed are failing us, and why?
  42. What innovative technology investment would significantly improve our performance, anywhere in the business?
  43. What are biggest constraints holding back our business?
  44. What is the strategic rationale for our acquisition program?
  45. What’s the high-level post-acquisition integration plan for our top ten targets?
  46. What is our process for validating our post-acquisition integration strategy before we own the target?
  47. Who will drive our Integration Management Office (IMO)?
  48. Which businesses no longer fit our strategic objectives and are candidates for divestiture?
  49. What actions are required to ensure the divestiture candidates are saleable?
  50. Have we aligned shareholder objectives with company objectives?

I hope the list inspires you to produce your own “Right Questions”.

Ian is the founder of Boston based The Portfolio Partnership, a fractional senior management team of operators. We help owners “build businesses buyers love to buy” by deploying our successful playbooks. We seamlessly join your team to work on the right stuff.

As always if you found these insights useful, please share.

Ian@TPPBoston.com