You got where you are by working hard.

You set a goal, and then you followed through. You put in the extra effort. You pushed through resistance. You figured things out when they weren’t clear.

And it worked.

It worked so well that “try harder” became your default strategy.

If something wasn’t going the way you wanted, you didn’t question your approach. You just added more effort.

Except—now it doesn’t always work.

When to stop trying harder

Now your goals are more ambitious. You are leading a team, not just leading yourself, and suddenly the relationship between effort and impact is much more complex.

Effort is still required, but where you focus matters more than how hard you push.

As you grow as a leader, you have to learn to identify when direct effort will work and when it’s time to shift your focus from the obvious problem to the systematic issue that caused it.

To help you get started, here are three common leadership situations that require systems-level problem-solving.

1. When the team is working hard, but progress has stalled

If you have a team where each member routinely produces good work on their own, but you still aren’t meeting your goals, the problem is unlikely to be effort. To get unstuck, you have to identify and address what is holding the blocker in place rather than expecting the team to just push through it.

2. When people stop following well-documented procedures

The procedures most likely to be ignored are administrative: submitting timesheets, writing weekly updates, updating documentation, or submitting bug reports. The kind of work that is tedious and unglamorous but has a big enough impact that you can’t do away with it altogether.

If you spend a significant part of your week reminding people to do this type of work, more forceful reminders aren’t likely to solve the problem long-term.

3. When you hate everyone

This one is the worst.

It starts with low-key resentment of your team members. Then questions and ideas from other people start to feel like personal attacks. Eventually it feels like you have to carry the whole team on your own.

In this situation, trying harder not only doesn’t work—it makes the problem worse. Left unaddressed, this is the fast track to burnout—or a 1:1 about your “toxic leadership style.”

Introducing the Leadership Stack

Knowing you have a systems problem and figuring out how to fix it are separate things.  The Leadership Stack can help.

The Leadership Stack is a tool for reframing squishy human problems as human system bugs.  It mirrors a framework tech leaders know well: the tech stack. 

Here is how it works:

Find the Bug

First, use the leadership stack to identify which layer or layers your issue originates from. 

For example:

• It might be an interface issue if individual work is strong, but work falls through the cracks (or gets duplicated) during collaboration.
• It might be a data issue if your team delivers work that misses expectations.
• It might be a security issue if feedback or disagreement triggers defensiveness, withdrawal, or emotional outbursts.
• It might be a permissions issue if you lack the information or authority needed to make progress.
• It might be an operating system issue if your team’s work gets derailed or redirected even when you are meeting stated objectives.

Fix the bug

Once you know what kind of bug you have, you can use the stack to redirect your effort toward system adjustments.

• Interface: Instead of asking your team to communicate better, identify what makes communication difficult and fix that.
• Data: Instead of fixing or micromanaging work that doesn’t meet expectations, identify what you know that they don’t and close the gap.
• Security: Instead of trying to control or repress reactions to feedback or disagreement, treat them as signals and address the concern they highlight.
• Permissions: Instead of working around missing information or authority, get access to what you need—or make the gap visible to someone who can address it.
• Operating system: Instead of pushing against the system, identify the (probably unspoken) organizational expectation your approach violated, and look for an alternate path to your objective.

Easy for you to say. . .

This is all much easier said than done because real organizational systems are much too complex to fully explore in an article like this.

Sometimes you will get stuck on a problem that is actually a compound issue—it has roots in multiple layers, and you have to address more than one to move forward. 

Sometimes, especially when problems are rooted in the permissions or OS layers, you can’t fix the bug. In that case you have to get support from someone who can fix it, work around it, or exit the system. 

Additionally, since you are part of the system, it’s difficult to get enough distance to see the whole system clearly—especially when you are contributing to the problem you are trying to solve.If you’d like some help putting these ideas into practice, please let me know. I offer a leadership debugging session to help you work through a specific issue currently blocking your team as well as customized options for longer-term engagements or work that includes you and your team members.