Every founder has stories that can become excellent thought leadership content. Unique, profound stories that will resonate with a wide audience. But getting those stories is, unfortunately, often easier said than done. That’s because many founders are hesitant to open up about the nitty-gritty of their day-to-day work, where the good stuff hides.
Your goal is to break beyond the founder’s canned answers to find a story worth telling. This will require doing things that feel uncomfortable, like interrupting the founder mid-answer and pressing on a previous point. If you just let the founder provide their go-to answers, even a great list of questions will yield mediocre content.
Read on to learn what good stories look like, how to ask questions like a pro, and when to interrupt answers. Acing these will earn you the raw material needed for excellent founder stories. A 30- or 60-minute interview, done right, can fuel weeks of high-quality content.
The four types of founder stories
Every founder story sits in one of four buckets: a pattern, a tension, a risk, or a belief. Each type of story can be interesting or uninteresting, depending on how it’s told.
Finding a pattern: The founder identifies a trend that is important for the reader to know. The trend needs to feel novel, or be presented with unique data, for this type of storytelling to work.
- A good story: “We noticed that token usage correlates with customer retention better than stated customer satisfaction. This suggests renewals are determined by how much the product is used, not whether users like the product.”
- A less-good story: “Everyone’s using AI these days, it seems. If you aren’t doing so, it’s time to make that change.”
Noticing a tension: The founder points out a conflict between two important things. Compelling stories in this “genre” will either describe a way to eliminate the tension or call on the industry to think about solutions.
- A good story: “Our Customer Success team let us know that our web copy set unreasonable expectations for time-to-launch, frustrating customers. While Marketing warned us that this could harm conversion, we haven’t seen a decrease. Moreover, customer satisfaction has improved meaningfully.”
- A less-good story: “Internally we don’t always agree on things, so it’s important to be able to hear both sides out and to make a judgement call and move forward together.”
Addressing a risk: The founder describes a risk they faced, whether they ultimately succeeded or failed. Compelling stories of this nature present an interesting scenario and provide a meaningful takeaway for the reader.
- A good story: “Our marketing team proposed a cartoon mascot for our conference booth. We knew buyers might find it off-putting, but we gave the go-ahead. Positive mentions on social media skyrocketed, suggesting novelty and whimsy stand out in a good way.”
- A less-good story: “We decided to swap out soda for water. I’m glad we did, because I feel a lot better and I’m sure others do too.”
Stating a belief: The founder articulates something they believe in. These stories work best when the belief is tied to either a current event or something happening in the founder’s life.
- A good story: “We believe that our employees should never put their safety at risk for business. If local schools declare a snow day, like today, we close the office so folks don’t have to drive in dangerous conditions.”
- A less-good story: “I agree strongly with a classic saying, namely ‘the squeaky wheel gets the grease.’”
Seven questions that get founders thinking
The following questions are great for getting founders to think beyond simple canned answers.
1. In the last few weeks, what has your ICP actually cared about?
Most founders can provide a few canned statements about their ICP, so ask a more granular question. “The last few weeks” should get the founder thinking about specific calls and current issues.
2. What do you think is going to be the next issue folks in your space care about?
If you ask a founder to talk about current trends, they will talk about the same things as everyone else. (Probably AI.) Request a prediction, instead, and the founder will start thinking about their own experiences and viewpoints. Don’t rush an answer; the interviewee should sit with this question for a minute.
3. What’s something in your current company stage you didn’t expect?
Get the founder thinking about what they’ve faced recently. Make clear that whatever surprised the founder does not need to be negative. If they were surprised by the sustained loyalty of their earliest customers, for example, that makes a great story.
4. Who is someone on your team that helped you overcome a big challenge?
Founders may worry about coming off as braggarts. You can sidestep this concern by focusing on someone else. If they don’t have a readily available answer, ask when they’ve historically relied on help from someone on their team.
5. If you could use a time machine and start the company again from square one, would you do anything differently?
Self-awareness is a rare commodity on forums like LinkedIn. If the founder is able to voice some kind of regret, it can lead to a vulnerable and compelling story. That said, it’s all right if the founder says they have no regrets. In that case, follow up by asking how the challenges they faced made them stronger.
6. What’s something you believe in (a principle, an idea, a quote) that’s different from others in your industry?
If you ask what competitors are doing wrong, or how they fall short, you will likely get a canned answer mirroring the sales team’s battlecards. Leverage a positive framing around personal belief instead to make the founder really think about the answer. (The founder may not have an answer readily available. Give them time to follow up, but do press for an eventual answer.)
7. Is there a specific approach you take to the company’s day-to-day operations?
Particularly in sensitive industries, competitors probably won’t make much of their workflows publicly known. Don’t ask a founder to compare their operations to a competitor, since the competitor is likely an unknown quantity. Focus on getting the raw details from the founder, and differentiate as needed while doing research later.
These questions map onto the four story types discussed earlier. Questions 1 and 2 evoke patterns; Question 3 evokes tensions; Questions 4 and 5 evoke risk; Questions 6 and 7 evoke beliefs. If you can address all of these questions on a call, you should have the foundation for a month of posts (or more).
The four signs you should hold up and zoom in
Founders often assume that their stories will go out into the world verbatim. Even if you assure them you’ll do editing, they may be overly cautious in what they say. If you can hear the founder self-censor in real time, you know what to push back against.
Listen for:
- Showing a half-second hesitation before starting a new thought, particularly if followed by a canned or vague answer. Odds are, the founder decided they shouldn’t say something out loud.
- Saying “anyway” rather than finishing a thought. The founder likely deemed their original thought too complicated or technical for the conversation.
- Qualifying any kind of process or discussion with “just.” The founder likely deems it unimportant, but that’s your judgement call to make, not theirs.
- Naming someone or something that doesn’t come up again in the story. The founder may have forgotten, or may think the full details aren’t relevant.
If you notice any of these, point it out, and be specific in what you want to hear about. Don’t just say “tell me more,” say “tell me more about the lost bid in March,” or “what role did Shreya play in this?” You can even say, “it seems like you skipped the full version of the story. Why was that?”
Of course, you’re not going to find a gem every time you ask the founder to go back. Sometimes a story truly is prohibitively technical or boring. But as the content expert, you should be the one making that call, not the founder.
Getting the real story
It’s not easy to dig for the real story, but you shouldn’t settle for anything less than authentic, unique, and compelling content. Over time, you’ll get a better sense of a founder’s background and interaction style and from there, it’s easy to create exciting content that builds the founder’s brand.
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Book a call →Questions people ask
What are the four types of founder stories?
Every founder story is a pattern, a tension, a risk, or a belief. A pattern is a trend the reader needs to know about. A tension is a conflict between two important things. A risk is a bet the founder made, win or lose. A belief is something the founder stands for, best tied to a current event or their own life. Any of the four can be interesting or dull depending on how it’s told.
What questions should you ask in a founder interview?
Ask granular questions that push past canned answers. What has your ICP actually cared about in the last few weeks? What’s the next issue your space will care about? What surprised you at this stage? Who on your team helped you through a big challenge? What would you do differently? What do you believe that others in your industry don’t? How do you approach day-to-day operations? Together they cover all four story types.
How do you know when a founder is holding back a story?
Listen for four signs. A half-second hesitation before a vague answer. The word “anyway” in place of a finished thought. The word “just” in front of a process or discussion, which means the founder thinks it’s unimportant. And a person or thing that gets named once and never comes back. Each one is a place to stop and ask them to go back.
How do you get a founder to tell the full version of a story?
Point out what you noticed and be specific. Don’t say “tell me more.” Say “tell me more about the lost bid in March” or “what role did Shreya play in this?” You can even ask why they skipped the full version. Not every story will be a gem, but the interviewer should decide what’s too technical or boring, not the founder.
