10 questions you should always ask once a month


Though the original blog article is meant for entrepreneurs (read here), I believe that a few of the questions would apply to you if you are a manager as well. (Of course, only IF your organisation gives you the liberty to take decisions and implement initiatives. 🙂 ) I have split it up into two parts. The first set applies better to the “managers” but the entrepreneurs would have the tougher job of answering both the sets! 😛

Set One:

  • In one sentence, what does your product do and who buys it?
  • In one sentence, why does someone buy your product?
  • What one thing is most responsible for preventing sales?
  • What’s one thing you could do to get more feedback from customers, potential customers, or sales you’ve lost?
  • If you were forced to hire someone today, how would you define her job such that she would contribute enough revenue to cover her expense?
  • What initiatives could be done half-assed without significant impact?
  • If you could get one solid hour of advice from a guru you respect, what would you discuss and what would be the goal of the meeting?

Set Two:

  • If you had zero revenue from now on, on what date would you run out of money?
  • If someone handed you $100,000 today, how would you spend it to maximize future profits?
  • Which of your business operations do you hate?

These are a brilliant set of questions which brings clarity of thought and clarity of thought is something which is at a great risk always when you are dealing with a highly fluid situation like building a new organisation or spearheading a new product launch.


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Avishek Gupta

I help drive sustainable development by financing the growth of professionally managed entrepreneurial ventures that solve key social and environmental problems. Having financed and observed over 250 ventures from close quarters, I understand the challenges that such ventures face in scaling up. I have the knowledge of process, financing and technology solutions that can help overcome those challenges. Separately, I have the experience of building businesses that finance early/growth stage companies. Most recently, I was involved with growing Caspian Debt to a full-fledged operating company from an initial 3 member fund investments team.

2 thoughts on “10 questions you should always ask once a month”

  1. I completely agree they apply to management. Indeed, with some modifications it applies to anything in life! Particularly the general notion that it’s more important to be intentional and thoughtful than to have a plan.

  2. Hi Jason,
    Yes, Indeed! It takes some time to think through and answer these questions but it is of immense value in the longer run. According to me, asking it once a month or for that matter being religiously regular about asking these questions is the key!

What do you think?