Finding the Resistance

At Stackify, I was doing what startup founders do best: sprinting through the office, juggling strategy, product, sales, marketing, and engineering all before lunch. I had a dozen ideas a day. Half of them were good.

I was trying to do everything myself. Everyone was moving fast. But under the surface, something was wrong. The team was overwhelmed. Deadlines slipped. And the more I pushed, the more everything stalled.

Then one day, my COO, Craig, asked to talk. My stomach dropped. First thought? “Crap. Is he quitting?”

He wasn’t. But the conversation hit harder than a resignation.

He told me I was the problem. Not our competitors. Not our team. Me.

Recognizing the Pattern

I had my hands in too many things. Ideas were flying faster than anyone could keep up. Craig handed me a book: Rocket Fuel, by Gino Wickman. The book explains how successful companies need both a Visionary and an Integrator. One to see the future, the other to make it happen.

The message was clear: I needed to understand the kind of leader I was, and the kind I wasn’t.

I was a visionary: the big idea guy who could see where we needed to go, but not how to get there. I realized I needed Craig to help filter my ideas and turn them into reality.

This later dawned on me: That same visionary-operator split shows up across engineering leadership, too.

Many small companies have a visionary CTO, but they’re missing the other half: a VP of Engineering. Someone who knows how to build the systems and teams that make scale possible.

That imbalance blocks the growth and success you're working so hard to build. Until you see that clearly, you’ll keep pushing harder, wondering why nothing is working.

Start With the Mirror

It’s easy to spot resistance in other people. The PM who won’t give up control. The engineer who rolls their eyes when you talk about user feedback.

But the hardest form of resistance to recognize is your own.

You may not realize you’re the bottleneck until someone has the courage to tell you the truth. As an engineering or startup leader, you're juggling strategy, product, technical, and operational responsibilities.

Sometimes that truth comes from a Craig. Other times, it comes from burnout, failure, or patterns you can’t ignore anymore.

But let’s not wait for that moment to break you.

Ask yourself:

Do I invite team ownership or cling to control?

Am I delegating real responsibility or holding onto roles I’ve already outgrown?

If you’re burned out and everything feels stuck, it’s worth asking if you’re the common denominator.

That doesn’t make you a bad leader. It makes you human.

But if you want things to change, you have to go first.

Spot the Resistance

Once you’ve looked in the mirror, look around you. Even the best teams wrestle with organizational friction and dysfunction. Once you identify them, you can start figuring out how to fix them.

These are some of the most common types of resistance your company might be fighting against.

The Leadership Void: When the System Fails the Team

Sometimes the resistance isn’t coming from people. It’s coming from the org chart. You might have a CTO, but no one is actually thinking strategically.

People feel like they’re building in the dark. Priorities shift weekly. Decisions bounce around. When no one owns the work, no one really owns anything.

It’s a lack of organizational structure and culture.

What to Do:

Write out the four key leadership jobs: Strategic, Product, Technical, and Operational. Name who owns each one. Ask whether they have the authority, skill, and capacity to lead.

If you’re covering more than two yourself, it’s a gap. If you’ve filled a role with someone who’s stretched thin or not built for it, it’s still a gap.

Don’t fill leadership roles based on who’s available. Fill them based on what the team needs to thrive.

The Tiny General: When One Person Can’t Let Go

They say they want to delegate. But nothing moves without their signoff. They become the tiny general, convinced every decision still depends on them.

This isn’t arrogance. Its identity. They’re used to being the hero. Letting go feels like losing relevance, and the longer they hold on, the less anyone else steps up. Team ownership and courage can’t flourish.

What to Do:

Some micromanage because they don’t trust their team. Others have never seen another way.

Scaling requires shared responsibility. But it only works when people are trusted to lead and supported when they do.

If you're in this environment, you can’t always fix the person. But you can name the impact. You can work on rebuilding trust and model the leadership you want to see.

Individual Resistance: When People Don’t Want to Change

Some people just want to stay in their comfort zone, whether it’s coding what they’re told, avoiding user conversations, or keeping decisions to themselves.

That’s not always defiance. It’s comfort.

But when the expectations change, that comfort becomes resistance. And sometimes, people quietly opt out.

What to Do:

Show what good ownership looks like. Set clear expectations for how the role is evolving. Give people room to try, and back them when it’s hard.

If someone’s struggling, don’t isolate them. Pair them with someone who’s already embraced the change. Make the goal progress, not perfection.

Not everyone on your team will adopt product thinking, and that’s okay. But if you want to grow shared ownership, someone has to lead the way.

The Machine: When Process Becomes the Problem

Sometimes the problem isn’t people. It’s the system around them. Bloated workflows. Endless approvals. Six tools to ship a bug fix.

No one owns the friction. Everyone just accepts it. It’s “how things are done here.”

The Machine slows everything down until your team gives up trying.

What to Do:

If your process is blocking progress, fix the process. Cancel meetings that don’t matter. Cut approvals that don’t add value. Simplify your tools until they serve the team, not the other way around.

Even in a big org, you have more influence than it feels like. Start with what you can change. Control the controllables.

Start asking “What if we don’t do this?” about everything.

Cultural Drag: When the Old Beliefs Won’t Let Go

Even when the process has changed, culture pulls things back.

You say you value outcomes, but praise whoever ships the fastest. You say ownership matters, but you only promote people who stay in their lane.

That’s cultural drag. The quiet gravity of old habits is reinforced by what gets noticed. People don’t believe what leaders say. They believe what leaders celebrate.

Culture is what gets repeated. Your goals and behaviors have to match.

What to Do:

Align what you say with what you do. Praise clarity. Reward ownership. Celebrate courage, even when it’s messy.

Your team watches what gets recognized. Make sure it reflects the culture you actually want to build.

Find Your Craig

Looking back at all these forms of resistance, from leadership voids to cultural drag, I realize they're all symptoms of the same thing: systems and people protecting what they know, even when it's not working.

Resistance is the price of real change.

But it’s not a sign you’re doing it wrong. It’s a sign you’re trying to do something real.

If no one’s resisting, you’re probably not changing much. If resistance is everywhere, the environment is trying to protect itself.

Sometimes it’s telling you there’s a leadership gap or that the culture hasn’t caught up yet. And sometimes it’s telling you you’re the bottleneck.

Resistance is never just noise. It's your environment telling you what it's ready for, and what it's not. It’s always feedback. The real question is whether you’re willing to hear it and act on it.

You can’t lead through resistance alone.

That’s what I learned in that meeting with Craig. I didn’t need to try harder. I needed someone to help me lead differently. Someone who saw what I missed, told me the truth, and stayed long enough to help me change.

I also had to listen. Self-awareness is hard.

So find your Craig. Then go be that person for someone else. That’s how we lead through resistance. Together.

In the next Part, you’ll build the system that helps them thrive.