The Hidden Psychology That Makes Good Founders Hard to Work For

By Giovanne Schachere

If you’ve ever had an employee tell you, “You’re a great leader… but…” — don’t ignore the “but.”

That “but” might be the most important leadership feedback you’ll ever receive.

For years, I couldn’t understand it.

Employees believed in my vision. They believed in the mission. Many thought I was brilliant, strategic, and relentless about building an organization that actually changes lives.

Yet some of those same employees didn’t always feel psychologically safe working with me.

How could both be true?

I wasn’t yelling. I wasn’t degrading people. I wasn’t trying to create fear.

So what was happening?

I realized I had been asking the wrong question.

The question wasn’t, “Am I a good person?”

The question was, “What does it feel like to work for me?”

Those are two completely different questions.

Lesson 1: Founders Often Lead From Survival

I didn’t start Mysti’s with investors. I didn’t inherit a company. I built it from nothing.

If you’ve ever built something from nothing, you know exactly what I’m talking about.

There were months where every dollar mattered. Moments where making payroll kept me awake at night. Seasons where it felt like I was robbing Peter to pay Paul just to keep the mission alive.

That changes your brain.

You stop seeing individual problems. You start seeing chain reactions.

A missed deadline isn’t just a missed deadline. It’s delayed billing. It’s delayed cash flow. It’s payroll. It’s client outcomes. It’s your reputation. It’s the future of the organization.

Employees often see the task. Founders see the consequences. Neither perspective is wrong — they’re simply different.

Put It Into Practice

The next time something frustrates you, stop and ask yourself:

“Am I reacting to today’s problem — or to everything this problem represents?”

You’ll be surprised how often you’re carrying yesterday’s survival into today’s conversation.

Lesson 2: I Brought My Previous Employers Into My Company

This realization was uncomfortable.

Before becoming a founder, I worked in organizations where I often felt unseen. Politics mattered. Recognition was inconsistent. Sometimes it felt like you had to outperform everyone else just to be noticed.

I thought I left those experiences behind when I became a founder.

I didn’t. I brought them with me.

Without realizing it, I was leading from years of believing that if I didn’t push harder than everyone else, everything would eventually fall apart.

Those weren’t leadership habits. They were survival habits.

Put It Into Practice

Ask yourself honestly:

“Is this how I truly want to lead — or is this how I learned to survive?”

There’s a difference. A big one.

Lesson 3: The Founder Is Usually the Least-Coached Person in the Company

Everyone talks about coaching employees. Who coaches the founder?

Case managers have supervisors. Supervisors have directors. Directors have executives. Executives have CEOs.

Founders? Most of us have nobody.

Nobody pulling us aside after a difficult week.

Nobody saying, “You’ve been carrying too much lately.” Instead, we’re expected to regulate ourselves while building the systems that don’t yet exist.

When you don’t yet have enough infrastructure, enough leadership layers, enough experienced managers — everything eventually lands on your desk. You’re building the airplane while flying it.

That’s exhausting. Not because you’re weak. Because you’re trying to build tomorrow’s organization while operating today’s.

Put It Into Practice

Find one person whose job is to challenge your leadership— not your business strategy.

Ask them one question every month:

“What’s becoming harder about working with me?”

Don’t defend yourself. Just listen.

Lesson 4: Remote Leadership Creates an Optical Illusion

Leading remotely taught me something I never expected.

I don’t see most of the great work happening. I see what reaches my inbox — the missed deadline, the compliance concern, the complaint, the resignation, the emergency.

If that’s all I consume every day, eventually I begin believing that’s all my organization is.

It isn’t. It’s simply all that’s reaching me.

Put It Into Practice

Every Friday, ask your leadership team one question:

“Tell me three things that went well this week that I probably never heard about.”

Train your brain to see success — not just exceptions.

Lesson 5: Psychological Safety Doesn’t Mean Lowering Standards

This was probably the biggest lesson of all.

I used to think psychological safety meant being softer. It doesn’t. It means being intentional.

People deserve accountability. They also deserve dignity. Those two things can exist together.

I still expect excellence. I still expect ownership. I still expect people to care deeply about the mission.

But I’ve learned that the way I communicate those expectations matters just as much as the expectations themselves.

Because people don’t experience your intentions.

They experience your patterns.

Put It Into Practice

The next time someone misses an expectation, replace this question:

“Why didn’t you do it?”

With this one:

“Help me understand what happened.”

One question creates defensiveness. The other creates information.

Information solves problems. Defensiveness hides them.

The Leadership Shift I’m Still Making

One of the biggest mistakes founders make is believing that because we carry the greatest responsibility, everyone should carry the same emotional weight.

They shouldn’t.

My employees aren’t responsible for keeping my family financially secure. They’re not personally guaranteeing contracts. They’re not carrying the same risks I am.

That’s my responsibility. And so is making sure the pressure I carry doesn’t become the culture everyone else experiences.

That’s leadership.

I don’t have this figured out. I’m still learning.

But if there’s one thing I’d leave with every founder, it’s this:

The company you’re building isn’t just shaped by your vision. It’s shaped by what your past taught you to fear. The more aware you become of that, the better leader you’ll become — not because you’ll care less, but because you’ll lead with greater intention.

That’s the kind of organization I’m trying to build.

And I think it’s the kind every person deserves to work in.

Giovanne Schachere is the founder and CEO of Mysti’s, a social services organization. He writes about leadership, organizational culture, and the real psychology of building something from nothing. Read more at Schachere.com.