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How many questions do you ask in a day?

I already asked 1 question here! But trust me, it won’t be the last one for the day!

Not after Martin Gaedt, author of Rock Your Idea, challenged me to ask 44 questions indiscriminately, and see how difficult it is. In fact, he challenged the spell-bound audience at a recent session in Berlin.

Asking questions sometimes could be difficult. And some might even treat it as a sign of weakness. Some see it as a sign of looking for help. Or even vulnerability.

Actually, it’s a sign of strength. It empowers you with the knowledge, that you probably didn’t know existed. Your curiosity becomes that knowledge. I think, it’s vital for everyone to start asking questions. Even if we sometimes lack the courage to do so.

To sum Martin’s thought provoking talk on creativity through questioning, he brilliantly drove home the point that if we do same things for the same reasons we will end up with the same results.

However, to shake things up we have to start asking questions; without judgment, trivial or significant, big or small.


So I took up his lead and decided to jot down 44 questions that I’d ask all startup founders who have started to put the foot on the gas for sales acceleration.

(and as he had warned, it took me 2 mins for the first 10 questions and 20 mins for the last 10)

And my favorite question? #44 is something I’d ask more often now.

My 44 questions to a Startup Co-Founder on Sales

  1. What is the biggest sales challenge you are facing right now?
  2. What are you doing to work around your current sales challenges?
  3. How do you look up for help and ideas on those sales challenges?
  4. Who do you approach?
  5. What would a good solution to your sales challenge look like?
  6. How do you work on sales hiring?
  7. How do you find sales help?
  8. What do you need for growth, and specifically for sales right now?
  9. Who do you trust for sales advice?
  10. What do you need to see before you trust & believe someone’s sales advice will work for you?
  11. How do you address the issue of your particular context and general sales advice available on the internet?
  12. Why would you choose “trial  & error” approach rather than trust sales advice from an expert?
  13. Who are your mentors / network when you look for sales thought leadership?
  14. What do you think is the magic formula for growing your sales?
  15. What kind of events do you attend for sales knowledge?
  16. What kind of forums do you participate for sales knowledge?
  17. How did you hire your first sales rep? How will you hire your next one?
  18. In what ways does your sales rep over deliver? Where does he/she under-deliver?
  19. What traits do you look for in sales hiring?
  20. What kind of sales innovation you think should exist in your industry?
  21. What objectives do you set for your sales team / organization? And when?
  22. What metrics do you track? How do you know your metrics for sales goals are reached?
  23. Do you actively reach out to mentors & coaches for sales topics? If so, how often?
  24. How do you know your sales coach’s advice is working for you?
  25. What kind of mentors or coaches do you like to work with?
  26. What resource pool / help should exist for sales coaching that you did not find till now?
  27. What is most promising & satisfying thing about what you do in sales?
  28. How could you be better in what you do?
  29. What other skills, trainings and ideas you’d need to be more effective, better & faster in sales?
  30. What are you willing to give to someone who comes to you for sales advice?
  31. What area of sales knowledge have you mastered? (I mean you are the Yoda!)
  32. How would you know that you’ve made someone successful?
  33. What do you hate most about sales & selling?
  34. What are you skeptical about when it comes to sales advice offered by others?
  35. What was your finest sales deal / negotiation that you feel really proud of?
  36. How would you want to leave your legacy as a sales leader?
  37. Who is your peer group when it comes to friendly sales competition?
  38. Who challenges you in sales?
  39. What do you find boring in your role as a (sales) leader?
  40. What would make selling and sales a complete profession, if it is not about the money?
  41. How should a high performing, super contagious sales role model look like?
  42. Who left the biggest impression on your career and why?
  43. If not sales, what else would you be doing?
  44. Why are you talking to me right now? Or why are you reading this right now?

Now, what are yours?

It doesn’t matter what the topic is, just write those 44 questions down. To anybody! Even me! Write those 44 questions and share it with the world. Don’t forget to include Martin Gaedt (and even me ;))


by Deepanker Dua

Deep is the chief sales scientist at SalesChakra. As he experiments with sales acceleration at tech startups, he documents his learnings through this blog. An avid traveller, he has lived selling disruptive technologies in 4 continents, and speaks 5 international languages. Connect with him on Twitter @askdeepr and LinkedIn.