As a startup founder, questions provide the fuel to my work every day.
What happened with this email chain?
Did I respond to the request for more details?
Why is this feature not working on my site?
Is this all worth it?
Wait, why did I ask myself that question?
But questions don’t always need to be transactional, focused on moving ideas forward, or even philosophical to be considered valuable. Both in personal and professional life, I’ve found that thoughtful questions often give me time to pause and think about what I really hope to accomplish. I especially love questions that come from unexpected places.
Here are several questions I’ve heard in the past few months that have made me pause and think about my approach, my work, and my goals.
“If someone gave you money right now, what is the first thing you would spend it on?“
This fantastic question came from a friendly Uber driver in San Francisco. The 15-minute ride from downtown to Hayes Valley started the usual way most of these rides do, with a quick hello. But the question soon veered into Yahya’s backstory. He had just shut down his Italian restaurant after running it for 20 years. “It was a tough life, and I never saw my family, ever!” he said. When I talked to him about my company, he wanted to know if he could ask me a question. After a brief pause, Yahya asked, “What if someone gave you money right now? What part of the business would you spend it on?”
He went on to explain that in his work, he had to make quick decisions when his revenue flow changed. Should he use it to fix a lighting issue? Or to hire a part-time helper? The choice is never easy but knowing what your priority is at any point in time is essential, he said, stopping curbside to drop me with a friendly smile.
My takeaway? The answer to this question doesn’t always have to be consistent (nor should it be, if you are in the early stages), but knowing how to prioritize and move to action quickly is necessary. Asking yourself what you would do sets you free from analysis paralysis and prepares you better for when you have to make those decisions.
“What is the most delightful or meaningful aspect of your product for your user?“
Most investor conversations have prepped us to be ready with the numbers, and for a good reason. Traction, growth, and market sizes are all important, especially if you are trying to convince an investor that you are worthy of a bet.
The person asking this question was open-minded, friendly, but definitely not interested in my space or industry. IMO that’s a good thing. These types of people turn out to be the best ones to hit you with far out and unexpected questions, with little associated risk.
But this question was a thoughtful way to remind me why we were building our company in the first place. If you’re like me and are often self-critical of what you’re not able to do, this question reminds you of the real value you deliver. Whether it comes in the form of a testimonial or feedback, or a user’s comment, or the results from a survey or focus group, the response to this question is what keeps me firmly rooted in the impact of our work. It serves as a great reminder that ultimately, it’s what your users value that matters the most when building and growing your company.
“What’s the non-financial metric of success for your organization? “
I love this question that popped in my LinkedIn feed recently. Metrics are, in essence, financial or usage-based in our world. But if one were to remove the financial or utilization metrics, what’s a parameter of success? In other words, what is the impact we are looking to create?
Would enabling a million+ Gen Zers across the world to share their perspectives be a metric of success? In our case, definitely. Framing a “success” story in this way allows you to set your impact goals first and then work backward to see what usage metrics need to be achieved to get the goal.
“What is stopping you from getting what you want?“
The startup journey is hard, and the highs and lows can take a toll on anyone. But I love this question from another entrepreneur for how it frames a situation for me.
Frequently, circumstances go beyond your control. You can only wait so long after sending an email to follow up, and sometimes a contract coming through requires oodles of patience. But occasionally, what’s stopping you from getting what you want could ultimately be an indicator of approach or perceptions. For instance, when past experiences direct how you deal with future situations (“this particular negotiation will probably go the way the last one did!”) or when your perceptions cloud your judgment (“They will probably lowball our efforts.”)
Point is, you never know until you try. And just as importantly, you never know until you ask. And sometimes, it helps to dig into that inability. Honestly asking myself the question of what’s stopping me from getting my desired outcome can clarify if it’s something I can attempt to fix (or not!) so I can move ahead or move on.
