Founders field a barrage of questions on a daily basis: from customers, investors, execs, employees, reporters and maybe even their parents who are still skeptical about how this whole entrepreneurship thing will work out. The ability to craft an elegant response to a hardball on the spot is practically part of the job description.
But perhaps equally essential is a founder’s willingness to apply the same level of scrutiny to themselves. Often, a founder’s most stirring revelation — and the change of opinion or action that follows — can come from the answers to their own questions.
To give you a taste of the kind of question that can prompt such a lightbulb moment, here’s what Clay CEO and co-founder Kareem Amin likes to ask himself regularly: “Are we taking real risks?”
This serves as a great period reminder to resist slipping into complacency. “We often say we’re taking risks, but if it's something you don't believe in, think you should do, or you know what the result will be, it's not a real risk,” says Amin. “A real risk is something you believe in even though you’re not sure what the result will be. You might be worried or afraid of the shame of failing if you make this decision. We should know which decisions are real risks, how many we’re taking and what the outcomes could be.”
As startups gear up to set their 2025 plans into motion, we figured we’d lean into the reflective mood of this time of year and round up questions like this one for more rigorous introspection. So we phoned in founders from all across the startup ecosystem and asked:
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?
We heard from some of the most thoughtful founders around, from seasoned repeat entrepreneurs to first-time founders eager to build intentionally their first go-around.
Below you’ll find their go-to questions — the thought-starters they return to again and again at every juncture of startup building. We’ve broken them down into four themes: questions to guide you as you make big decisions and shift your priorities, questions to figure out if you’re building the right product, questions to nurture your most important relationships at work and questions to help you recalibrate as your startup scales.
Some of these questions are worth jotting down on a Post-it for daily reminders, while others can help you get your bearings when you find yourself in choppy waters. We hope at least a few of them can bring you some clarity in the messy and meaningful journey ahead.
QUESTIONS TO REFOCUS YOUR PRIORITIES AND DECISION MAKING
The stakes of every single decision you make in the founder seat can feel extremely high. But it can be hard to parse out which problems are actually worth your extended consideration.
Use these questions to speed up (or slow down) your decision-making process and rejigger your ever-shifting ranking of priorities.
1. Did the work I do today actually move the needle on making the company successful?
A useful question to differentiate between urgent to-dos and distractions — particularly in the 0 to 1 stretch of a startup — comes from Colin Zima, CEO and co-founder of Omni. "When your startup is just five to 10 people, the company isn’t default moving forward like Google or even a late-stage startup,” says Zima.
“Whether or not you get a new customer or ship a feature or find a bunch of new prospects, that’s all on your very small team to execute. This question reminds me to spend time focusing on outputs rather than inputs — which may seem unpopular, but that’s ultimately the scoreboard. Trying is necessary but not sufficient for success. You have to tangibly create it and eliminate the efforts that don’t,” he says.
Ilana Borkenstein, CEO and co-founder of M7 Health, offers a twist on Zima’s question to quickly figure out which tasks are most pressing: “Can I describe how this activity contributes to our company’s OKRs in two sentences or less? If not, skip it,” she says.
2. If in a year we looked back on this decision, is this the decision that killed the company?
If you find yourself hand-wringing over a decision, stop and ask if this problem could pose an existential threat to the company. If not, you should be able to trust someone else to figure it out.
This is how Levels CEO and co-founder Sam Corcos safeguards his time to focus on the important stuff. “One of the most common issues I see related to a founder’s time management is that they have a set of important tasks that constantly get interrupted by seemingly urgent tasks that come into their inbox,” he says. “It’s important to keep a clear focus on what moves the ball forward for your company and not let shiny objects distract you.”
Often, scattered attention is a delegation problem. “If you find yourself constantly pulled in different directions, you should reflect on why that’s happening and make some changes. If it’s because you don’t have someone on your team that you can trust with solving these problems independently — like a Head of Operations — then you need to hire for that role immediately,” says Corcos.
“But if it’s because you have a hard time distinguishing between urgent and non-urgent problems, I’ve found that asking myself this question tends to clarify things. The answer is usually no,” he says. “Startups are default dead, so you have to ruthlessly prioritize the things that get you to default alive. That’s the CEO’s job.”
3. How can we shorten the time from hypothesis to insight?
Speed in a startup context isn’t just how fast you ship products — it’s how fast you can test your assumptions.
“The common wisdom is that startups are fast, but what does that actually mean? Big companies have far more employees, more capital and more technology. Often, big companies move with more velocity. But that velocity comes with a cost,” says Ravi Mehta, former co-founder of GPTcsv.ai.
“The faster a car is going, the slower it turns. The same is true for teams and companies. So when faced with a tough challenge, I return to this question. Often, startups can validate ideas in days and weeks while big companies take months and quarters,” he says.
Startups move fast not by increasing their velocity, but by decreasing their latency — the time from idea to impact.
4. What's the hard part — and am I working on it?
Wes Kao, former co-founder of Maven, likes to ask this question to keep herself honest about whether she’s avoiding the meatiest work on her plate.
“‘The hard part’ is the aspect of a project where if it doesn't work, the whole thing won't work. Everything else would be null,” says Kao.
“Many founders waste time on parts they already know how to do because it makes them feel productive. It feels like you’re making progress and getting quick wins. But if you delay thinking about the hard part, all that 'progress' could be for nothing because you thought too late about the most crucial piece that's necessary for the thing to work,” she says. (Astro Teller’s “monkeys and pedestals” concept is a helpful mental model here.)
5. Is there a way for me to make this a smaller decision than the one I’m considering?
To add some more efficiency to your decision-making process, former pro poker player and decision science expert Annie Duke encourages founders to ask how they can break big decisions down into smaller, reversible choices.
“Many founders feel that introducing process or adhering to a decision-making system slows you down. But knowing when it’s okay to save time is part of a good decision process. This is a question of assessing the impact and the reversibility of the decision if you get it really wrong,” she explains.
“It's the difference between hiring an intern and hiring a C-level exec. A good framing is to ask yourself, ‘If I pick this option, what’s the cost of quitting?’ The lower the cost of changing course, the faster you can go,” says Duke.
Founders should be continually asking: What's the smallest version of this that we can do at the least cost to us? Whether you have three, 30 or 3000 employees, you should always bring that mentality to your decision-making.
6. What’s the kill criteria for this project?
Just as important as deciding to do something is knowing when it’s time to quit. Annie Duke encourages you to name your “kill criteria” and observe your resolution to quit once you’ve hit them.
“There's all sorts of benchmarks that you can set for yourself of what you need to see happen within a quarter within two or three quarters. Those benchmarks become what I call kill criteria, literally criteria for killing a project or changing your mind or cutting your losses. If you miss them, it means you’re going to quit,” says Duke.
“Reviewing those criteria on a regular cadence with an outside advisor will help mitigate your tendency to say, ‘No, I know I can turn around. I can tweak the messaging or hire a new salesperson,’” she says. “This is the strategy that Ron Conway uses: ‘You're a brilliant person, I have no doubt you can turn around. But what does turning it around look like within what time?’”
“A simple way to develop kill criteria is with ‘states and dates,” she says. “‘If by (date), I have/haven’t (reached a particular state), I’ll quit.’”
7. Are we winning because we’re making good calls? Or are we doing well in spite of ourselves?
Wade Foster, CEO and co-founder of Zapier, uses this question to routinely assess whether he and his team are falsely correlating good outcomes with bad decisions. He’s also a big fan of Annie Duke’s — and applies her decision-making frameworks to his own evaluation of Zapier’s wins.
He points to Duke’s assertion in her book Thinking in Bets that good decisions can breed both good and bad outcomes. “Most people think because they make a good decision, they’ll definitely get a good outcome. But that’s not the case. A good decision could yield a good outcome, a bad one or a variety of outcomes,” says Foster.
“As you go along, if your opinions get so hardened on the wrong conclusions, that's going to weaken the ultimate outcome of what your company can become,” he says.
QUESTIONS TO SIZE UP YOUR PRODUCT STRATEGY
It’s easy to get wrapped up in the daily minutia of triaging customer complaints and shipping new features. But it’s just as important to pick your head up from sprint plans and lines of code and see if you’ve created the product you set out to build.
Here are some questions to return to as you draft up roadmaps, keep tabs on competition and launch new bets.
8. What is the customer actually trying to tell us with a feature request?
Colin Zima asks this question to unearth the real problem behind a feature request.
“When you build B2B software, you'll get requests for everything, and sometimes they'll be extremely specific. The actual request is the problem underneath the request,” he says.
To probe deeper into the customer’s needs, he suggests asking these sub-questions:
- Why do they need it that way?
- What are they trying to do?
- How are they doing it instead?
“There's almost more information in why a user is asking for a feature than the specific feature itself, and you have to keep asking why,” says Zima.
It's the customer’s sub-questions that help merge their requests with our vision of the future.
9. Are we pursuing this product direction due to inertia or because it’s right?
Gong CPO and co-founder Eilon Reshef asks this question to avoid making product decisions on autopilot.
“This question often reveals product directions that we may go with despite them clearly not being the ones we’d take today,” he says. “Technology may have changed or our customer mix may have changed. If we’re pushing forward on some antiquated product direction, we need to at the very least do this consciously.”
In a similar vein, he likes to ask: “What are we not doing because we’re fixated on some narrow definition?”
This helps Reshef and his team avoid becoming trapped in unnecessary confines. To illustrate his point, he looks at how railway companies lost out on a massive expansion opportunity by sticking to a rigid category. “Railway companies defined themselves as railway companies, not transportation companies, so they didn’t think they should offer air travel,” explains Reshef.
“If we work in a confined mindset, there are often pieces that we miss because we don’t think it’s our responsibility to solve — and not just radical pivots like rail to air travel,” he says.
10. Why won’t this work out?
Rick Song, CEO and co-founder of Persona, regularly writes up “pre-mortems.” He likes to identify the potential tripwires of every bet he makes before the decision is official — whether it’s a new hire, product or program.
“‘Why would a customer not want this?’ is often a far more interesting question than why they would,” explains Song. “When you're working on a product idea, there's a thesis for why you believe you’re right and it's really easy to constantly confirmation bias yourself into believing it’s the optimal decision,” he says.
“But once you can also find the counterpoint, the scenario where you’re wrong, you can start teasing out when it would start to make sense — the point at which it will work.”
11. How can we make the product more delightful?
There’s always room for an extra sprinkle of delight in your product.
“Most organizations — especially when mature — are driven by goals, deadlines, objectives, and key results. In such organizations, it can be difficult to create room for certain product qualities that are hard to measure or which do not directly impact growth,” says Rahul Vohra, CEO and founder of Superhuman (and the architect behind the wildly popular product-market fit framework).
So he creates room for those intangibles by constantly asking this question. “Your team likely has a dozen things they would do to make any experience more fun, joyous, and delightful. When you know what they are, pick one or two and insist that they happen.”
He also likes asking these two follow-ups:
- How can we make this so striking that people can't help but talk about it? “We talk a lot about making viral features, but true virality boils down to one thing: word of mouth,” says Vohra. “To get there, you need to create experiences that are so striking, so compelling, and so worthy of attention that your users can't help but talk about it.”
- How can we build this so that users don't have to remember to use it? “We use the RICE framework to score potential features: Reach, Impact, Confidence, and Effort. I find that the limiting factor is usually reach: most users will not use most new features. You can mitigate this by constantly pushing your teams to increase reach,” he says.
12. When we look at competitors who have failed, how do we avoid repeating their mistakes?
Kevin Caldwell, CEO and co-founder of Ossium Health, revisits this question to make sure he doesn’t just take stock of what competitors are doing well — but learn from what ultimately killed them.
“When deciding whether to embark on a risky plan, I also like to ask, ‘What did we learn and gain from previous failures of ourselves — and others?’”
13. 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?
Crossbeam CEO and co-founder Bob Moore holds tight to this reminder he learned from first startup, an analytics platform called RJMetrics, as it went head-to-head in the market with Looker.
“Later on in RJMetrics’ timeline, we started asking ourselves this simple question. Our answer was something that could connect the dots between all these new cloud data warehouses that were taking over the market and the emerging tools like Looker that provided a better user experience for analytics. That product would be the missing link in a value chain that would completely disintermediate RJMetrics,” says Moore.
The answer to this question eventually planted the seed for Moore’s second startup. “Rather than wait for it to show up and finish the job that Looker had started, a small team at RJMetrics built it as a hackathon project. That product ultimately became Stitch, which we successfully spun out and built into a substantial standalone company after RJMetrics was acquired.”
Kevin Caldwell also comes back to this spin on Moore’s question: “If a miracle product replaces our technology in five years, what will we have wished we had started developing today?”
14. If I was starting this business again today from scratch, what would I build to win the market?
Shippo CEO and co-founder Laura Behrens Wu poses this question to resist the sunk cost fallacy of product building.
“I try to not focus on baggage or tech debt or any other constraints when I answer that question,” says Behrens Wu.
QUESTIONS TO STRENGTHEN YOUR RELATIONSHIPS WITH YOUR CO-FOUNDERS AND TEAM
Whether your headcount is two or 200, the bar for communication is upheld by the founders. Revisit these questions when you find yourself in thorny situations with co-founders or are just reflecting on how to do better by your team.
15. What hurts me more? The fact that they did it in the first place — or that they did it without me?
Esther Perel is a renowned couples therapist, so she knows a thing or two about one-on-one conflict. If you’re hurt by something your co-founder did without your knowledge or prior agreement, she recommends asking this to get to the bottom of why you’re upset.
“I often ask co-founders this telling question: ‘What hurts you more? The fact that they did it in the first place — or that they did it without you?’ The former is an issue of power, the latter is an issue of care and closeness,” she explains.
“Conflicts rooted in care and closeness always come back to broken trust, the ‘I thought I could count on you’ kind of statements. When trust is broken, it shatters all of our assumptions about the relationship and our value in it.”
16. What’s the conversation I’m avoiding?
Raw Signal Group co-founder Johnathan Nightingale returns to this question again and again. He’d guess an answer has already popped into your head for this one.
“Every founder has an answer to this. They’re very tuned into the needs of their business, and it gives them a helpful drive to have hard conversations earlier and more directly than most other leaders do,” says Nightingale.
“But founders are still human, and many will still put off, or dodge around, the bits they know are going to be awful. Sometimes it's about a team that isn't working out, sometimes it's a toxic co-founder or board dynamic that everyone knows is lurking, but no one is eager to run toward,” he says.
Simply acknowledging the elephant in the room is a helpful first step. “That doesn't mean it's always as easy as ‘go have that conversation right now’ — that’s simple but sometimes disastrous advice,” he says. “For most founders, doing that moment of reflection, identifying it and naming it, is the kick needed to make progress.”
17. What’s one thing I’m afraid to ask my team but probably should?
Coa co-founder and clinical psychologist Emily Anhalt likes to ask this twist on Nightingale’s question to make sure she gets in the regular habit of having tough conversations.
“Fear often prevents us from uncovering the insights that could lead to growth. By leaning into discomfort and asking tough questions, you’ll create a culture of openness and innovation. Curiosity breaks down walls and invites honest dialogue,” says Anhalt.
18. Is my team missing any context to be able to make good decisions for the company?
Shensi Ding, CEO and co-founder of Merge, asks herself this question to make sure knowledge isn’t just trapped inside of her head.
A similar question is top of mind for Laura Behrens Wu as she heads into the new year: Where can I empower the teams more instead of making top-down decisions?
“I've been thinking about this one for 2025 and reflecting on where we did well and where we could have done better in 2024,” says Behrens Wu.
Puzzle CEO and co-founder Sasha Orloff takes this question even further to make sure he always verbalizes his expectations and vision to his team.
“My first time building a company I was obsessed with proving myself and making too many decisions,” says Orloff. “So now this is the question I ask myself most often: ‘How can I make sure my team knows what I’m thinking — and why?’ That way the team can combine the best of their experience and judgement, with our strategy and vision, and solve problems better than if I could do it myself.”
Orloff often comes back to this reminder that missing context tends to be the most probable cause of poor performance — not intentional sabotage. “It’s rare to have someone intentionally try and hurt the company and their career, so I try to bring my focus back to how I can best enable them to be successful. That’s true founder leverage,” he says.
19. How does our team now compare to the team last year?
Shensi Ding also finds it helpful to reflect on how the current team stacks up to previous iterations by routinely asking this question.
To get even more brutally honest about how the team shapes up as it grows, she asks this follow-up: “What percentage of the team do I think is mediocre or bad?”
20. Am I letting my team members operate in their respective zones of genius?
M7 CEO and co-founder Ilana Borkenstein asks this to reflect on whether she’s empowering her team members to execute within the domains they excel in.
She follows up by asking herself, “Am I giving them the combination of space, autonomy, and context that they need to do so?”
QUESTIONS TO CHECK IN AS YOU GROW
When your team no longer fits around a single table, all kinds of new problems can crop up. Refer back to these questions to recenter as you scale, both personally and as a company.
21. What’s the next glass ceiling?
Gong co-founder and CPO Eilon Reshef anchors around this question to spot impending constraints as the company scales.
“Even if we execute perfectly — which isn’t likely — where’s the point where we would hit a ceiling if we were to continue doing what we do now?” says Reshef.
He poses these additional questions:
- Do we have a limited market?
- Are some expansion areas blocked by strong incumbents?
- If we do see a ceiling, what can we do about it with enough time in advance so we can break it or go around it?
22. If we close 100 more deals that are just like this one, will we be happy or sad?
“So much of being a founder is about finding your first paying customers. Particularly in the early days, it can feel existential to show some traction. So founders build something for a market or a user where they know they can find traction. And then once they do, they find themselves in a successful but soul-sucking situation,” says Melissa Nightingale, co-founder of Raw Signal Group.
So she often returns to this reminder that not all growth is good growth — and the interest between you and your customers should be mutual.
“When talking to a prospective customer, particularly for a large piece of work or a long engagement, ask yourself this question,” she says.
She likes to pose these additional questions in tandem to figure out if these are the right types of customers and projects to pursue:
- Will this work bring out the best in our team?
- Will it feel like true partnership?
- Would I be excited if they talk about this project or post on social media about it?
- If we get known for this specific work, if we get a reputation for being great at it and that turns out to be a big part of our future growth, will that be a business I'm still excited to wake up every day and work on?
It's the worst to work as hard as you do as a founder on a problem or a solution you fundamentally cannot stand or do not give a shit about.
23. Where are we on the continuum of chaos and control?
“Companies and management teams default to control. You want to control outcomes, control the direction of the company, and understand your inputs and outputs. But doing this underestimates the cost of co-ordination and communication — and the value of chaos,” explains Kareem Amin, CEO and co-founder of Clay.
He compares the sweet spot to the controlled chaos of dancing with others. “If you go dancing, people can move around without bumping into each other and they can create a collective dance without the overhead of verbal communication. You want a healthy amount of that to create anything new or creative,” he says.
24. What am I doing that I feel constrained by? What could I relax that could make things much faster, better and more scalable?
Howard Morgan, longtime CEO and co-founder of First Round, advises founders to routinely question which constraints they can relax.
How? Start by writing them out. “Really explicitly take some time, 10 minutes to an hour, every month and ask, ‘What am I doing that I feel constrained by? What could I relax that could make things much faster, better and more scalable?’” he says.
“Look at it another way: we all write words — whether it’s a book, an email or a text. But don’t just flex your writing muscle. Tap into your ability to edit. How does a sentence — and a person, a company, an industry — change when you take away words? If no word is sacred, you start to serve the message rather than the author. Released from those constraints, the enduring idea emerges.”
25. What’s one area of growth I’ve been avoiding because it feels uncomfortable?
As the founder at a scaling startup, you graduate from leader of a rag-tag crew to head of a mature organization. You’ll need to grow alongside your company — which won’t always be comfortable.
Emily Anhalt suggests founders return to this question as a reminder that discomfort is necessary to grow. “Everything you want to accomplish as a leader lives on the other side of some discomfort. This question encourages you to confront resistance and invest in yourself, whether that means improving delegation, addressing insecurities, or developing healthier habits,” says Anhalt.