The Importance of Questioning for Founders

After two decades in the startup ecosystem, I've noticed one glaring issue that consistently leads to failure: Founders not asking the right questions. I had an aha moment when I read 'The Book of Beautiful Questions' by Warren Berger, which outlines thought-provoking questions for success. Here are 5 such questions founders need to ask themselves to build impactful products: ▶ 1. If this problem didn't exist, what would you lose? This helps you evaluate if a problem is truly worth solving. If there's no significant value in addressing it, you're wasting resources. ▶ 2. What if we did the exact opposite? It helps you see things from a different perspective. So you can open doors to unconventional ideas and solutions by asking this question. ▶ 3. What's the hidden assumption here? Assumptions lead to blind spots. Engage with your target group to uncover insights and build a product they'll love. ▶ 4. If this were a game, what would the rules be? Think of your product challenges as a game. Add things like rewards or levels to make it more engaging. This can help you find creative solutions to improve user interaction with your product. ▶ 5. How can we make this problem desirable? Transform problems into opportunities. Start with possible solutions, test them, and adjust based on feedback. This will improve the solution and keep stakeholders involved in the process. Remember, groundbreaking solutions often start with asking the right questions. Implement these in your approach, and watch your products resonate with your target group. What’s a question you would add to this list? #productdevelopment #innovation #creativity

Questions, especially the uncomfortable kind, are what truly unsettle the status quo, disrupt the assumptions and help us reimagine. They uncover blind spots, challenge ingrained beliefs, and spur the sort of breakthrough thinking that mere incremental improvements can’t reach. A disciplined questioning uncovers flawed assumptions before they derail the strategy. It reveals unseen opportunities by challenging conventional wisdom.  It ignites curiosity within teams, spurring innovation not through command but through inquiry. This is a skill, and it requires cultivating a mindset of perpetual skepticism - consistently doubting the convenient narratives that we become comfortable believing. It's recognizing that deeply held organizational beliefs, if left unquestioned, can quietly sabotage progress. Here are three ways that helped me develop my questioning practice: 1. Interrogate your successes, not just your failures. We instinctively scrutinize setbacks but rarely question successes. Yet, today's success often creates tomorrow's blind spot. 2. Question the questions themselves. I consistently reflect on whether I’m asking the right questions—not just good questions, but strategically valuable ones. 3. Prioritize questions that expand perspective rather than confirm bias. Confirmation bias is seductive because it simplifies decisions, aligning neatly with existing views. I intentionally seek out questions that provoke debate and discomfort. Our role is not to arrive swiftly at reassuring answers, but rather to keep our intellectual discomfort alive and productive. It's within this state of persistent inquiry—uncomfortable, challenging, yet ultimately clarifying—that breakthrough thinking emerges and transformative leadership truly takes shape.

It’s not about the answers. It never was. In fact, answers have become cheap. The best sales leaders and startup founders I have worked with aren’t the ones with the flashiest pitches or fastest answers and solutions. They are the ones who pause… listen and ask the right questions like What’s holding us back ? or what's the cost of not taking action right now? and the list goes on. Anything that will help shift the mindset. When I was in enterprise sales and consulting, I understood the value of questioning but I only discovered its real power after becoming a coach because as a coach, I have seen how one well-timed powerful question can shift a mindset, unlock a breakthrough, or enable someone to move into a growth and success lane. And in today’s world filled with dashboards, and AI-generated insights, answers have become cheap. But the right questions? are still rare, human and powerful. So if you are leading a team, closing a deal, or scaling a company, remember: You don’t need all the answers. What you need is the courage to ask better questions to your team, clients and partners. Because clarity , momentum and credibility don’t always come from knowing more. They come from thinking deeper, asking the right questions, and listening. #SalesLeadership #StartupFounders #CoachingMindset #StrategicQuestions #SalesTransformation #storytriggering

You don't have to have all the answers if you can ask the right questions. I’m often asked about books that have been helpful to me over the course of my career. I often refer to a book I read much earlier in my career that focuses on the value of questions. It’s tempting to think the job of a leader is to solve every problem, but I’ve learned that growth happens when we resist that urge. Instead, by asking questions, we can empower others to think critically and find their own solutions. In "Leading with Questions," Michael J. Marquardt explains that great leaders ask questions not to test knowledge, but to inspire reflection and action. They understand that well-placed questions can encourage creativity, foster ownership, and build trust. One key takeaway from the book is this: the best questions are open-ended, focused on possibilities, and designed to encourage exploration. When you prioritize questions over answers, you demonstrate trust in your teams and create space for learning. For example, instead of providing a solution, asking, “What options have you considered?” or “What do you think will happen if we try this?” invites others to think critically and take ownership of their decisions. #leadership #LeadingWithQuestions #communication

What if the most powerful way to lead or solve problems isn’t by having the answer, but by knowing which question to ask? I built a career by starting with questions. Asking the right questions—not just any questions—was the most powerful way to create clarity, build alignment, and unlock momentum. It wasn’t just a habit; it became a strategy for navigating complex challenges, transforming teams, and driving growth in some of the world’s most iconic companies. We transformed McDonald's by introducing digital ordering through kiosks to elevate the customer experience. At Volvo Cars, we shifted the model of car ownership through subscriptions. These weren’t just product ideas; they were complex problem spaces requiring an entirely new way of thinking inside the organization. Surfacing the right questions is the unlock. It shifts us from judgement to actually understanding what matters. The result?  Smarter thinking, tighter alignment, and more confident decisions. In an age of thinking machines, we’re living through a “raising of the bar” on human contribution. But this isn’t something to fear provided we accept the old notion of contribution is dead. It’s that simple. 💡 In a world accelerating with AI, learning to ask better questions may be the most valuable skill we build.

“I’m looking for an accountant.” That’s all I said at a networking event. Before I could finish explaining why, a founder jumped in: “Have you thought about building an AI agent to do the work instead?” And just like that, I was reminded why so many promising products fail to gain traction. 🙉 The founder wasn’t listening. 🙊 He didn’t ask a single question about what I needed. 🔨 He had a hammer—and I was just another nail. In 15+ years working with startups, I’ve seen this mistake over and over again: Founders pitch solutions before they understand the problem. It’s why I often recommend the book 𝙏𝙝𝙚 𝙈𝙤𝙢 𝙏𝙚𝙨𝙩 by Rob Fitzpatrick or, more recently, 𝙃𝙪𝙢𝙗𝙡𝙚 𝙄𝙣𝙦𝙪𝙞𝙧𝙮 by Edgar Schein. The message is simple but powerful: Ask more, tell less. Especially early on. Because when you lead with your pitch instead of curiosity, you lose people. You miss what really matters. And you make it all about you. That moment at the event? It could’ve been a relationship starter. Instead, it was just another awkward sales pitch I couldn’t wait to escape. Here’s the shift that builds relationships: ✅ Ask open-ended questions. ✅ Be curious about the other person’s reality. ✅ Don’t try to win the conversation—try to learn from it. Great founders don’t dominate rooms. They unlock them—with the right question, at the right time. #HumbleInquiry #entrepreneurialjourney #customerdiscovery

One of the things I've learned (the hard way!) about being a leader and a founder is: The right question is more important than the right answer. In First Round Capital's latest article, 25 Hard Questions Every Founder Should Ask Themselves, founders share the questions they ask at pivotal moments. Wes Kao asks, "What's the hard part — and am I working on it?". This one hit home for me - its so easy to stay busy working on the easier activities while the real progress requires pushing through the headwinds. Colin Zima asks, "What is the customer actually trying to tell us with a feature request?" This is so key -- customers are really busy. The last thing they want to do is stop what their doing and make a feature request. There is usually a much bigger problem (and much bigger opportunity) underneath the request. Finally, I love this one from Bob Moore: "What's the new product that would terrify us the most if it were launched tomorrow? And if it doesn’t exist, why aren’t we building it?" We're not building in a static universe -- even more so now that AI is accelerating product development. This fives teams permission to take a step back from what's in flight and consider a) what is the real opportunity and b) how might competitors change the landscape. What question do you ask to spark a new way of thinking? https://lnkd.in/gEBTqSXJ