OEI Day 3: What If We're Solving the Wrong Problem?

Day 3 at the Okoboji Entrepreneurial Institute was the final coaching day. One last chance to perfect their pitches before these brilliant students present to the judges today. After two days of watching patterns emerge, I knew exactly what I needed to do: be the person willing to ask the uncomfortable questions that everyone else was dancing around.

Because here's what I'd learned: these students could identify problems all day long.

They just weren't identifying the right problems.

The Engineer Who Almost Solved the Wrong Problem

I sat down with an engineering student who volunteers his weekends teaching kids at a local-to-him facility. He came to me with a clear problem: the educational software they use is buggy, crashes constantly and makes his volunteer sessions frustrating for everyone involved.

His pitch was technically perfect.

He could identify every glitch, every user interface flaw, every system inefficiency. The organization had even asked him to create a new, tailored software solution. So naturally, that's exactly what he was proposing.

"Walk me through these problems," I said.

As he described them in detail, something started nagging at me. These volunteers show up, excited to work with kids, and spend half their time troubleshooting software instead of actually teaching.

"Tell me about the other volunteers," I pushed. "What's their relationship with technology?"

That's when it clicked. Most of the volunteers aren't engineers like him. They're parents, retirees, college students from various majors. They don't want to become software experts. They want to inspire kids about education without becoming IT support specialists themselves.

"So what's the real problem here?" I asked.

Long pause.

"They don't have time or capacity to learn any system, no matter how good it is."

Bingo.

Suddenly his entire mood shifted. Yes, they needed better software. But the real solution wasn't just debugging the current system or creating a more elegant interface. It was designing something so intuitive that volunteers could walk in and start teaching immediately, without training, without technical expertise, without eating into the precious time they'd carved out to work with kids.

Same technical skills. Same software solution. Completely different problem statement.

The Pattern Everyone Was Avoiding

This wasn't isolated. Session after session, I watched students present surface-level problems while the real issues lurked underneath, unspoken.

The sustainable home goods student from yesterday? She kept talking about consumer education and environmental awareness. But when we dug deeper, the real barrier wasn't that customers didn't care about sustainability. It was that they didn't have time for complicated refill processes that took longer than just grabbing a new bottle off the shelf.

Then there was the serial pitch competition winner who built a customizable 3D memorial lamp business - this was his second time at OEI. He's in the black, making solid money, is building solid contracts with funeral homes. He came to me worried about scaling too quickly, wondering how fast production should ramp up as his retail product gains traction in a notoriously saturated market.

But as we talked, he kept lighting up when he mentioned all the pitch competitions he'd won, all the awards, all the recognition. So I pushed deeper.

"What gets you most excited about those competitions?"

That's when the real conversation started. Turns out, he doesn't want to just scale a memorial lamp business, though he still has great passion in that endeavor. He wants to be on the other side of the judging table. He wants to teach other students how to perfect their pitches and launch truly successful products and services.

This vision was so much bigger than the memorial lamp - and he knew it.

Here's the kicker: this guy was my own competition during the Big Idea Challenge a few months ago. He was gracious enough to tell me he thought my idea should have won.

Looking back on that conversation now, I think he told me that because he knew his real solution was bigger than the original memorial lamp idea. He knew in his gut he had bigger potential and was holding himself back.

The pattern: Everyone could identify what was broken. No one wanted to ask why it mattered.

Time: The Ultimate Truth Revealer

Here's what I discovered about time in these conversations: when you ask people what's eating up their time, or what they wish they had more time for, that's when they tell you what they actually value.

The volunteers didn't value becoming software experts. They valued connecting with kids.

The sustainability customers didn't value environmental complexity. They valued convenience that happened to be sustainable.

Time isn't just a constraint - it's a revealer of priorities. And most of these students were solving for what people said they wanted instead of what people were actually willing to spend time on.

The Elephant We're All Avoiding

Here's the uncomfortable truth that hung over every coaching session: most of us are too polite to challenge the initial problem statement.

We're afraid that asking "But is that really the problem?" sounds like we're not listening, or we're being difficult, or - worse - that we might discover we've been barking up the wrong tree entirely.

It's a kind of codependent fear. We don't want to risk rejection by pushing back on what someone says they need. So we solve the surface problem and wonder why our brilliant solutions don't stick.

But here's what I reminded these students: the judges today aren't going to invest in polite and perfect. They're going to invest in useful.

Connecting the Dots

If Day 1 was about showing up, and Day 2 was about having real conversations with real humans, then Day 3 was about having the courage to ask the hard questions within those conversations.

Because it's not enough to talk to your potential customers. You have to be brave enough to challenge what they tell you. To dig past the surface complaints and find the time-and-energy problems that actually drive decisions.

The best solutions don't just solve problems - they solve the right problems.

What I Told Them Before Today's Pitches

As these students prepared for their presentations today, I reminded them of something crucial: those judges have seen a thousand pitches that solve the obvious problems.

What they haven't seen is someone brave enough to stand up and say, "Everyone thinks the problem is X, but I discovered it's actually Y."

That's the pitch that gets remembered. Not because it has the most data or the slickest presentation, but because it demonstrates the kind of thinking that uncovers real market opportunities.

The students who will succeed aren't just the ones with the best technical skills or the most thorough research. They're the ones willing to be uncomfortable long enough to find the uncomfortable truths.

The Question That Changes Everything

As I packed up after the final coaching session, I thought about the one question that consistently broke through to the real issues:

"What do you wish you had more time for?"

Not "What's your biggest problem?" or "What frustrates you most?" Those questions get you surface complaints.

But when you ask what someone wishes they had more time for, they tell you what they value. And when you know what people actually value, you can build solutions that align with their priorities instead of their complaints.

Taking My Own Medicine

After three intense days of coaching, I found myself lying upside down in the grass, grounding myself and reclaiming the time and mental space these conversations had filled.

Because here's the thing about asking hard questions all week: they don't just apply to the students. They apply to me, too.

What problems am I solving for my own clients that might be surface-level? What do my clients wish they had more time for that I'm not even asking about? How can I apply these same uncomfortable questions to grow my own business?

The best part about mentoring isn't just helping others see clearly - it's having your own assumptions challenged in the process. These students didn't just get coached; they coached me right back by making me examine my own work through fresh eyes.

Sometimes you need to lie upside down in the grass to let all those insights settle into place.

Today: Watching Them Fly

Today, these students pitch to the judges. I won't be there to see them, but some will present the surface solutions they came in with. Others will present the deeper problems they discovered by being brave enough to ask uncomfortable questions.

I know which ones I'd invest in.

Because at the end of the day, the world doesn't need more people solving obvious problems obviously. It needs people willing to say what everyone's thinking but no one wants to mention:

"What if we're solving the wrong problem?"

Sometimes the most valuable thing you can do is be the person brave enough to ask that question - of others, and of yourself.

Disclosure: Iowa Lakes Corridor is a client of Vertical Marketing and Design.