This week, we’ve crowdsourced a list of meaty self-reflection prompts from some of the most thoughtful founders we know.
25 Hard Questions Every Founder Should Ask Themselves
We’re hurtling toward the last stretch of the year. Even as the ink dries on 2025 plans and product roadmaps, many founders are taking on a less official, more solitary ritual: Self-reflection.
So if you’ve found yourself in an introspective mood this time of year, we’ve cooked up some food for your thought. We spent the past month reaching out to founders from all across the startup ecosystem with this question:
Which reflection prompts do you find most useful as a way to step back and think about your business, your team or your own leadership?
This turned out to be an easy ask from this naturally self-scrutinizing crowd. Founders generously offered up the questions they keep in their back pocket to return to as they navigate every juncture of startup building.
We heard from a mix of seasoned repeat entrepreneurs, plucky young founders, and long-time builders who’ve taken the leap to start up — folks like Superhuman founder Rahul Vohra, Clay co-founder Kareem Amin, Puzzle co-founder Sasha Orloff, and former Maven co-founder Wes Kao, just to name a few.
Some founders shared questions that serve as daily reminders to speed up their decision making and recalibrate their priorities. Some shared the questions they ask themselves to zoom out and take a hard look at their product strategy. Others put forward prompts for more periodic reflection on how things are going and where the company is headed.
Here’s a sneak peek:
- Did the work I do today actually move the needle on making the company successful?
- Are we pursuing this product direction due to inertia or because it’s right?
- If I was starting this business again today from scratch, what would I build to win the market?
- What’s the conversation I’m avoiding?
- If we close 100 more deals that are just like this one, will we be happy or sad?
- Where are we on the continuum of chaos and control?
Thanks, as always, for reading and sharing!
-The Review Editors
Recommended resources:
-A new interactive essay format from our friends at Every
-Why you need multiple leverage points to negotiate enterprise pricing
-A framework for understanding what makes a winning marketplace