The Ordinary Story of Trevor: The Guy Who Became Known for His Questions
A case study on how a Techstars program director learned to help founders by asking, not telling. Read time: 6 mins
Happy Friday y’all!
Quick reminder about the *new* Ordinary Genius sending schedule and layout:
Every Tuesday = playbook. Every Friday = real case study 👇
This week’s case study highlights how Trevor Boehm, a Techstars program director, learned to help founders by asking, not telling. Let’s dive in :)
1. Here’s the thing he wanted:
Trevor wanted to actually help founders.
Not just give them advice that sounded smart. Not dispense wisdom from on high. Not tell them what to do and send them on their way.
OKAY PAUSE… some quick context… if you are unfamiliar, Techstars is an accelerator program Trevor and I worked at together.
Every 3 months, 10 startups (and roughly 30-50 founders) would go through our startup “bootcamp” (for lack of a better word). All with the goal of growing their business, raising more funding, and beyond…
okay back to my story…
Trevor wanted founders to leave Techstars having figured something out… something real, something they could act on, something that felt true to them.
The problem was, everyone who came to him wanted answers.
They wanted to be told what to do next.
“Should I raise now or wait?” “Should I pivot or push through?” “Should I hire this person?”
Trevor had been a founder himself. He’d built Frame Agency, a learning design company. He’d co-founded Penny, an Instagram commerce startup. At one point he even sent a bunch of koozies to space. (I’m not joking, I have a koozie from him that says “this koozie went to space”)
He knew what it was like to be in the arena (lol), making decisions with incomplete information and just wanting to know what to do next.
He could have just given advice. He had opinions. He had experience.
But he realized something: when you tell people what to do, they might follow your advice… but they don’t own the decision. And if (or when) it doesn’t work out, they blame you. Or worse, they never build the muscle to figure things out themselves.
He wanted something different. He wanted founders to leave knowing what they thought, not what he thought.
So he stopped giving advice… and he started asking questions… good questions.
2. Here’s how he did it:
Trevor’s approach was deceptively simple: he just repeated back what founders said to him, in a different way.
A founder would come in: “I don’t know if I should focus on growth or product right now.”
Most mentors would say: “You should focus on growth” or “Product has to come first.”
Trevor would say: “What are you really trying to solve right now?”
And then he’d shut up.
The founder would pause. Think. Then start talking through it themselves.
“Well, we have users, but they’re not sticking around...”
Trevor: “What happens if they don’t stick around?”
“We lose them and have to keep acquiring more, which gets expensive...”
Trevor: “So what does that tell you about where to focus?”
“...I guess we need to fix retention before we scale.”
and just like that, the founder just solved their own problem.
Trevor didn’t tell them what to do. He asked clarifying questions until they surfaced what they already knew.
The Questions He Actually Used:
“What are you really trying to solve?”
“What happens if you don’t do this?”
“What’s the version of this that feels true to you?”
“What are you optimizing for?”
“What would this look like if it were easy?”
Simple questions. No tricks. No clever frameworks.
Just genuine curiosity and the discipline to not jump in with answers or absolutes.
The Move That Made It Work:
The key was what he did after asking the question: he waited.
Most people ask a question and then fill the silence with their own thoughts, or another question, or a story about themselves.
Trevor just sat there. Comfortable with the discomfort.
That silence forced founders to think. To process. To articulate what they actually believed instead of just reacting.
Founders would look at him like, “Aren’t you going to tell me what to do?” but eventually they’d start talking. And once they started, they’d figure it out.
3. Here’s what it cost him:
Time.
Asking questions instead of giving answers takes longer. You can’t just tell someone what to do and move on. You have to sit with them. Wait for them to process. Ask follow-ups.
Trevor spent hours in office hours with founders. Not because he was slow but because he was doing the harder, more helpful thing.
Risking being seen as “not helpful” at first.
Some founders left his sessions thinking, “He didn’t even tell me what to do.”
They wanted a “guru”. They wanted someone to hand them the answer.
Trevor didn’t do that. And early on, some people interpreted that as him not knowing the answer, or not wanting to help.
It took time for founders to realize: the ones who worked with Trevor ended up making better short AND long term decisions than the ones who just collected advice from everyone else.
The discipline to shut up.
This is harder than it sounds. When someone asks you a question, the instinct is to answer it. Especially when you have an answer.
Trevor had to constantly fight the urge to jump in with “Here’s what I would do.”
He had to trust that founders were capable of figuring it out themselves even when it would have been faster to just tell them.
4. Here’s why it worked:
Psychological ownership.
When you tell someone what to do, it’s your idea. When they figure it out themselves (with your questions guiding them), it’s their idea.
People execute on their own ideas way harder than they execute on someone else’s advice.
It built the muscle.
Founders who worked with Trevor didn’t just solve one problem… they learned how to think through problems.
So the next time they got stuck, they didn’t need Trevor. They could ask themselves the same questions, walk themselves through the same process. Whether they realized it or not, Trevor gave them a framework for long term success.
It was actually more honest.
Trevor didn’t pretend to have all the answers. He wasn’t performing expertise.
He was genuinely curious about what the founder was trying to do, and he helped them surface their own thinking.
Founders trusted him because he wasn’t trying to be the smartest guy in the room. He was trying to help them be smarter, and he was trying to understand their thought further in the process.
It separated the serious founders from the advice collectors.
A lot of people just want to be told what to do. Either they are overwhelmed, or they aren’t confident in what they are building, or they want to try and alleviate some stress or responsibility from making mistakes.
Trevor’s approach filtered those people out. The founders who stuck with him were the ones willing to do the hard thinking themselves and those were the founders who actually built something.
5. Here’s what he avoided:
He didn’t give advice just to sound smart.
Plenty of mentors want to show off how much they know. They jump in with war stories and frameworks and tactical advice… not because the founder needs it, but because it makes them feel useful.
Trevor avoided that trap.
He wasn’t there to perform. He was there to help.
He didn’t ask leading questions.
A leading question is when you’ve already decided what someone should do, and you’re trying to guide them to your answer.
“Don’t you think you should focus on growth right now?”
That’s not a real question. That’s just advice disguised as a question.
Trevor asked clarifying questions… genuine curiosity about what the founder was thinking, not steering them toward a predetermined conclusion.
He didn’t fill the silence.
Most people can’t handle the awkward pause after asking a question. They jump in with more explanation, or a story, or another question.
Trevor just waited and sometimes when you wait long enough magic happens.
He didn’t try to be everyone’s guru.
Some mentors want to be the go-to person for every decision. Trevor built founders who could think for themselves.
Which meant they needed him less over time and that was the point.
6. Now go:
This week, try this:
Pick one conversation… could be with a friend, a colleague, someone on your team… where you’d normally give advice.
Instead, ask: “What are you trying to solve?”
Then shut up. Let them think. Don’t fill the silence.
See what happens.
Bonus: Here’s what you can steal from Trevor
Replace “Here’s what I would do” with “What are you optimizing for?”
Get comfortable with silence… let people at least try to figure it out
Ask clarifying questions, not leading ones
Trust that people are capable of finding their own answers
Your job isn’t to be the smartest person in the room… it’s to help others think clearly
Next week: The Genius Guide to Not Taking Things Personally
P.S. Trevor now works as an Operating Partner at Saturn Five, he also wrote a book called Levers: The Framework for Building Repeatability into Your Business. If this story resonated, hit reply and tell me what topics you want to see us cover next. I read every response.
Writing from Austin and very full still from Thanksgiving,
Your question master, Alex
This is such a valuable approach. As a founder, people are constantly talking at you - offering opinions, suggestions, etc. through the lens of what worked for them. They want to be helpful, but this often misses the mark. What's really useful is helping you think through what's relevant from all of the different options for your specific context. Filtering and prioritization are often the biggest levers and effective questions help surface those insights.