The Leadership Question Most EdTech Founders Avoid

I ask every founder I work with a question that usually makes them uneasy.

"If you disappeared for 30 days starting tomorrow, what would happen to your company?"

Founders usually answer in three ways. Some quickly list all the problems that would get out of hand. Others hesitate and admit they don't know. A few say their team would manage just fine.

The last group may not have the biggest companies, but they're building something that lasts.

The Product Trap

Most EdTech founders I meet are great at solving educational problems. They notice where students struggle, where school staff need help managing classrooms, or where districts have data issues. They create solutions, improve them with feedback, and put all their energy into making their product better.

After 40 years in this industry, I've learned that your product is not your legacy.

I've seen companies with average products last longer than those with groundbreaking ones. Districts often stay with companies that have awkward interfaces but are always reliable. Founders succeed not just because of great technology, but because they build strong teams and trust.

Your product is just a tool. Your real legacy comes from what you build with your people.

The Team Test

When I ask the 30-day question, I'm really asking if your company relies on you or if you've built leaders.

You can see the difference in a few clear ways.

Can your sales team close deals without you on the call? Not just the small ones, but the big district contracts that usually need your founder story?

Does your customer success team solve problems the way you would, or do they always come to you because they lack the authority or confidence to decide?

When your product team faces a challenge, do they wait for your input, or do they understand your vision well enough to make good decisions on their own?

These aren't just about operations. They're about leadership. Your answers show if you're helping others grow or keeping all the responsibility for yourself.

What Actually Builds Legacy

Founders who build lasting companies, the ones districts remember, and people want to work for, do a few things differently.

They focus on developing people through daily actions, not just formal training. They include team members in customer talks, let them make decisions and take responsibility, explain why choices matter, and coach instead of just giving orders.

They build systems that work without them. It's not about paperwork that no one reads. It's about creating decision-making models that match your values, hiring people who truly understand the mission, and stepping back even if you could do the job faster yourself.

They stay steady even when it's tempting to react. The EdTech sales cycle is long and often unpredictable. Budgets change, key contacts leave, and pilots sometimes end without results.

Founders who last don't chase every new opportunity or change direction with every setback. They keep showing up, keep their promises, and build trust by being reliable.

The Real Cost

Every week, I meet founders who are worn out. They're working 70 hours a week, always the first to arrive and the last to leave. They're proud of their hard work and effort.

But when I ask the 30-day question, I see fear in their eyes. They've created a company that can't run without them.

That isn't something to be proud of. It's a warning sign.

The irony is that founders who focus on developing their teams and building systems and culture, instead of just solving problems, end up with more valuable companies. It's not only about money, though that often comes too. It's about developing something that keeps helping students and educators, no matter who is leading.

Where to Start

If you realize your company would have a hard time without you, that's actually a good thing. Being aware is the first step.

Start small. Pick one area where you're the bottleneck, like customer calls, product decisions, or district presentations. Choose one thing and help someone else take full ownership of it, not just handle the task, but truly own it.

They'll make different choices than you would. Some will be mistakes, and some will be even better than what you might have done. Both are valuable.

Give them real authority, not just tasks. Let them make mistakes safely. Guide them through the reasoning, not just the work. Share the background they need to make good choices. Then step back and let them lead.

Keep doing this for six months, then ask yourself the 30-day question again.

The Leadership You Leave Behind

Your product will eventually be replaced. Technology keeps changing, and someone will create something better, faster, or cheaper.

But the leaders you help grow, the culture you build, and the way you support districts during tough times—those things last.

Those are what people remember.

I've seen this happen many times. Founders who focus on people instead of just products, who build strong teams instead of making everyone depend on them, and who lead with steady effort instead of dramatic gestures—those are the ones districts remember. Their team members often go on to lead successful companies. They build something more valuable than just market share.

Legacy isn't flashy. It doesn't come from press releases or funding news. It's built quietly through many small choices to help others grow, create systems that work, and show up consistently even when no one is watching.

The real question isn't whether you can build a successful EdTech company.

It's about what kind of leader you want people to remember.

What kind of legacy are you building? If you want to talk about growing your team's leadership, send me a message.

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