I recently met a founder whose approach to questioning has left an indelible impression on me. It wasn’t her polished pitch or her growth metrics that caught my attention, but rather the quality of the questions she asked. As an angel investor who’s navigated the tumultuous waters of both medicine and entrepreneurship, I’ve come to appreciate the power of a well-posed question. It’s a skill that can distinguish a thoughtful founder from one who merely reacts to the chaos of a startup.
This particular founder, let’s call her Riya, approached me with a question that was deceptively simple: “What’s the worst decision I could make right now?” It wasn’t just a rhetorical exercise; she genuinely wanted to explore the potential pitfalls that lay ahead. This kind of introspection is rare, yet invaluable. It aligns closely with what I often observe in my IVF practice, where patients continuously face life-altering decisions. The ability to step back and critically evaluate one’s choices is a skill that’s crucial both in fertility treatments and in startup journeys.
Riya’s question prompted me to reflect on how often founders overlook the importance of questioning. In my experience, many are obsessed with providing answers, whether to investors, customers, or their teams. They’re eager to assert confidence and control. But the truth is, the most transformative insights often come from the questions we ask ourselves. In the world of angel investing, as in medicine, there’s an inherent uncertainty. Navigating this uncertainty requires the courage to ask tough questions and the humility to accept that we may not always know the answers.
The notion of asking the “right” question isn’t just about risk mitigation; it’s about fostering innovation. In medicine, we constantly question our methods and assumptions. It’s a practice that has saved countless lives and improved outcomes. Similarly, in the startup world, questioning your assumptions can lead to breakthroughs. I’ve seen too many startups fail because the founders didn’t question their core assumptions until it was too late. They were too busy executing on a flawed premise to see that they were heading in the wrong direction.
Riya’s approach reminded me of what I wrote in a previous post, “The Silent Lessons My IVF Patients Taught Me About Startup Risks.” In both domains, the stakes are incredibly high, and the margin for error is slim. It’s the questions we ask — and the answers we’re willing to entertain — that can make the difference between success and failure.
I’m reminded of another founder I backed who, like Riya, was adept at asking questions. He once asked me, “Am I too comfortable?” It was a question that caught me off guard, as it’s not what you typically hear from a founder. But it was precisely this self-awareness that made him successful. He recognized that comfort could be a precursor to complacency, and complacency is the death knell for startups. This willingness to question his own status quo kept him agile and responsive to market shifts.
In the same way that I encourage my IVF patients to ask questions about their treatment plans, I urge founders to question their business strategies. It’s not enough to simply execute; you must execute thoughtfully. Ask yourself: Are you solving the right problem? Are you addressing a genuine market need? Are you taking real risks, or are you merely going through the motions?
A fascinating parallel exists between launching a startup and undergoing IVF treatment. Both involve a series of high-stakes decisions, often with uncertain outcomes. Both require resilience, a theme I explored in “Why Every Startup Founder Needs the Resilience of an IVF Patient.” In both scenarios, the ability to ask the right questions can guide you through the fog of uncertainty. It’s a compass that helps you navigate the unknown and make informed decisions.
I recall a pivotal moment during my own career transition from medicine to angel investing. I asked myself a question that was both terrifying and liberating: “What if I fail?” It was a question that forced me to confront my deepest fears and ultimately gave me the courage to pursue a new path. The answer wasn’t as important as the process of questioning itself. It was a reminder that failure isn’t the end; it’s an opportunity to learn and grow.
As I continue to work with founders, I find myself increasingly drawn to those who ask questions that challenge their own assumptions. These are the individuals who are not afraid to admit what they don’t know and are willing to seek out the answers. They understand that the journey is as much about exploration as it is about execution.
In closing, I urge all founders to cultivate the habit of questioning. It’s a practice that can lead to deeper insights and more effective decision-making. Don’t shy away from the hard questions, even if they make you uncomfortable. Embrace the uncertainty, for it is in the unknown that true innovation lies.
So, what question did you ask yourself today?