50 Questions Every SMB Should Answer Before Next Year

Are You Ready for Next Year?

INTRODUCTION

At ThinkQSi, we help business leaders cut through noise, uncover what’s really holding their company back, and make smarter decisions before problems turn into crises. Our work sits at the intersection of clarity, operations, and execution.

These 50 questions are designed to give you an unfiltered look at where your business stands today financially, operationally, culturally, and strategically. Use them to evaluate your year, pressure-test your assumptions, and pinpoint the areas that need attention before the new year begins.

This isn’t theory. This is the same lens we use when we diagnose companies and design practical, high-impact solutions that restore stability and accelerate growth.

Take your time. Be honest. Let the questions do the work. Your answers will tell you more about your business than any dashboard ever will.

SECTION 1 – DIRECTION, CUSTOMERS, AND SALES (12 questions)

A. Strategy and Direction (6)

1.        Did we hit our revenue, margin, and growth targets this year? Where did we overperform or underperform?

2.        Do we clearly understand why we achieved (or missed) those results beyond “the market” or “the economy”?

3.        Has our market, customer behavior, or competitive landscape changed in ways our current strategy does not reflect?

4.        Do our vision and mission still accurately describe who we are, who we serve, and where we’re going or are they just words on a slide?

5.        What were our three most successful strategic moves this year? What did we learn from them that we must scale next year?

6.        Which initiatives did not deliver as expected, and what are the underlying reasons (timing, resourcing, ownership, wrong bet)?

B. Customers and Revenue (6)

7. Did we gain or lose customers this year? Which specific clients did we lose, and do we know exactly why?

8. What is our current customer retention rate by key segment, and where is churn or down sell most concerning?

9. Where did we succeed in increasing wallet share with existing clients? What did we do differently in those relationships?

10. Do we have a structured way to capture customer feedback (surveys, interviews, reviews) and act on it or only react when there’s a problem?

11. Which client relationships are at risk going into next year, and what is our concrete plan to stabilize or grow them?

12. How many high-potential opportunities did we walk away from or lose because of capacity, price, terms, or internal misalignment?

SECTION 2 – EXECUTION, PEOPLE, AND PROJECTS (14 questions)

A. Sales and Delivery Alignment (6)

13. Is our sales process clearly defined, documented, and followed from lead to close to handoff?

14. Do sales, operations, and delivery regularly review pipeline and capacity together, or do they work in silos?

15. How often do deals fail, stall, or shrink because we cannot deliver on time, to scope, or at the promised quality?

16. Are salespeople telling us why they can’t close certain deals (pricing, product gaps, lead quality, delivery reputation) and are we listening?

17. Do we differentiate clearly between business development, sales/closing, and account management roles? Are those responsibilities staffed and measured appropriately?

18. When was the last time senior leaders or the owner personally met with top clients to hear their perspective on our performance?

B. Operations and Project Management (5)

19. Do we have a central view of all key projects and initiatives—owners, timelines, risks, and status or is information scattered across teams?

20. Do we have a Project Management Office (even part-time or fractional) to track, prioritize, and de-risk projects across the company?

21. Where did operational bottlenecks, rework, or quality issues lead to missed deadlines, margin erosion, or unhappy clients this year?

22. How often did we say “yes” to work we were not fully equipped to deliver—and what did that cost us in time, money, or reputation?

23. What 2–3 process improvements would remove the most friction for our teams and customers next year?

C. People, Talent, and Culture (3)

24. What was our employee retention rate this year, and are we losing the right people or the wrong ones?

25. Where did we struggle to hire or keep the talent we needed, and what reasons did candidates or employees give us (comp, culture, role clarity, growth)?

26. Are there ongoing conflicts or disconnects between teams or departments? What are the common themes behind those clashes (priorities, incentives, communication, leadership)?

SECTION 3 – MONEY, RISK, AND VISIBILITY (12 questions)

A. Finance and Budget (6)

27. Did we have a clear budget for this year, and did we meet, exceed, or miss it in revenue, costs, and profit?

28. Where did we consistently overspend or underspend, and what does that tell us about our planning accuracy?

29. Do we have regular visibility into cash flow, not just P&L. How many times were we surprised by cash constraints this year?

30. Are next year’s revenue and profit targets grounded in pipeline, capacity, and market reality or are they wishful thinking?

31. Can we identify our most profitable clients, products, and services and our least profitable ones?

32. Where did we invest this year (tools, people, marketing, vendors), and what ROI did we actually see?

B. Contracts, Vendors, and Risk (6)

33. Do we have a central, up-to-date list of all client contracts with key terms, pricing, and renewal dates?

34. Which client contracts are up for renewal in the next 3–6 months, and do we have a plan to retain, renegotiate, or expand them?

35. On the vendor side, where are we overpaying, under-utilizing services, or stuck in auto-renewals we no longer need?

36. When was the last time someone systematically reviewed contract terms (SLAs, penalties, auto-renewals, price escalators, data/privacy provisions)?

37. Are there legal, compliance, or data security risks embedded in our current contracts or operations that leadership may not fully see?

38. Where are we most exposed if a key client, vendor, or partner changes terms or walks away next year?

SECTION 4 – BRAND, SYSTEMS, AND NEXT YEAR’S PLAN (12 questions)

A. Marketing, Brand, and Communication (5)

39. Does our current website, marketing collateral, and messaging accurately reflect who we are today and who we want to be next year?

40. Is our online presence (website, LinkedIn, other platforms) active, consistent, and aligned with our positioning or outdated and neglected?

41. Who owns our communication strategy (internal and external), and is it coordinated across leadership, sales, and marketing?

42. Are we measuring the effectiveness of marketing (leads, conversion, cost per lead/acquisition), or just tracking activity and impressions?

43. When was the last time we refreshed case studies, client stories, or proof points that support our credibility with new prospects?

B. Systems, Data, and Reporting (4)

44. As founder/CEO, do you receive simple, timely reports on the few metrics that matter most—or do you have to chase information?

45. Are core systems (CRM, finance, project management, HR) integrated enough to provide a single version of the truth, or are teams working from disconnected spreadsheets?

46. What key business questions can we not answer quickly today, such as “Where do we lose margin?” or “Which clients are truly profitable?”

47. Where are manual processes or shadow systems creating risk, duplication, or delays?

C. Next Year’s Focus and Q1 Plan (3)

48. Based on everything we’ve learned this year, what are the 3–5 things we must do differently next year to change our trajectory?

49. What are our non-negotiable priorities for Q1 and what will we deliberately postpone or stop doing to create capacity for them?

50. Who will own turning these answers into a concrete 12‑month plan with clear accountabilities, timelines, and a cadence to review progress?

NEXT STEPS

If this checklist surfaced gaps, concerns, or opportunities you want to explore, let’s talk.

ThinkQSi works directly with founders and executives who want clarity, operational discipline, and real progress not noise, not buzzwords, not more chaos.

Whether you need help diagnosing your operations, improving processes, planning for next year, or deciding your next strategic move, we’re here to support you.

You don’t have to solve everything alone.
A conversation might be the most valuable step you take before the year ends.

PS: If you like to receive a copy of the checklist in pdf format, please message us. 

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Insights from Anwer Qureishi, Thought Leader & Entrepreneur
Ready to accelerate growth? Schedule a Consultation with Anwer Qureishi, Founder, Q&S International (ThinkQSi).