The 21 Questions This SaaS Startup Genius Wants You to Ask Yourself


How is your SaaS start-up business doing so far?

This question can flood your head with answers like, “we haven’t seen growth so far”, “we’re losing more customers” or “we are losing money….”

Tweet this: Asking pertinent questions is part of growing your business.

Asking pertinent questions is part of growing your business. Sometimes, as a business owner, you’re likely to find yourself at your wits’ end on how to grow your business. This is when you’d need lots of inspiration, and it can typically come from any source if you pay attention. It could be Google, your employees, your competitors, your family or even Twitter followers!

This was the case with, James Kennedy. Over the weekend, the CEO took to Twitter to interact with his fellow SaaS entrepreneurs. When James posted, “I am planning a company retreat. What are some great questions we can work on as a company?” The tweet triggered a series of 21 mind blowing questions from start-up genius, Jason Cohen that I thought I should share with you.

Some of the most thought provoking questions include, “If you had a magic wand, what would you change?”, and “In the past 12 months, where have we wasted a lot of time and energy due to poor or missing internal communication? What can we do instead?”  

See the rest of tweets below:

21 questions by Jason Cohen:

  1. If you had a magic wand, what would you change? Can be a small thing.

  2. What could kill the company? Of those 30+ things, are there any worth being a little proactive about? (E.g. Monitor for early signs)

  3. Brand exercise. What qualities, feelings, attributes do we want? Which amplify what we are, versus aspire to be? How could we come that?

  4. What’s one thing you are going to start doing over the next three months to materially help someone else with their priorities?

  5. In the past 12 months, where have we wasted a lot of time and energy due to poor or missing internal communication? What can we do instead?

  6. If we had to halve the number of support tickets per customer in six months, but all of us 100% focused, how could we pull it off?

  7. What are the top problems/worries/fears/opportunities facing our customers? How could we address those with features or marketing?

  8. What should the single most important metric the consort be moving for the next 6-12 months? How could we all impact that metric?

  9. What are our customers telling us, that we’re not listening to? (Prepare /w/ data from support, social, survey, etc). What should we do?

  10. Suppose that between now and revenue doubling (any time frame) no new hires are allowed. How would we accomplish that?

  11. If all our source code were stolen, would it matter? What should we do differently such that it wouldn’t matter?

  12. What are 3-5 important things about us that our customers / the market don’t know? How could we institutionalize communicating it?

  13. What’s something curious about you that not many people know? (Better: collect ahead of time and everyone guesses who’s is who’s)

  14. What did you wish you were told in the first week of employment?  (Use the result to start an orientation presentation.)

  15. What would you say to convince someone to work here for 30% less money? Those things should be on “about us” and work to keep constant.

  16. What are the top reasons customers love us? Leave us? (Maybe do NPs survey ahead of time). What should we do about that?

  17. Premortem. A year from now, things are bad. What could have happened to us and why? What should we do soon to prevent some of that?

  18. When we have our next retreat in one year, what do you want to say you’ve accomplished? Personal and professional. Can we help each other?

  19. Describe a time you really had to struggle, whether or not you persevered, at work or home.

  20. What role could we hire to make the maximum difference to the success of the company overall? Requires knowing strategic lever. Then, hire!

  21. What qualities in each other do we admire? What do we dislike? Can we distil that into a core set of values? Then we’ve codified culture.

So, as you can see from the above questions, any question is worth asking as long as it triggers some ideas you can implement to grow your startup SaaS business.

Since today’s post is about questions, let me ask you this:

How are you tracking your purchase processes? If your business doesn’t have any automated PO system whatsoever, you should consider test driving for free today!


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