When the Leader’s Leader is the Real Problem

Ever been called in to fix a “leadership problem,” only to realize the real issue isn’t the leader you’re coaching, but the one above them?

Yeah. Us too. And let me tell you, nothing says "waste of time" like pouring hours into coaching someone while their boss vanishes faster than a dad who went out for milk in 1998.

The Case of the Vanishing Leader

Twice in the last year, we’ve been brought in because an organization had finally heard enough complaints about a leader that they decided to take action. Employees were frustrated, turnover was rising, and the company was hemorrhaging engagement. The solution? Leadership coaching and accountability.

So, we got to work.

Step one: Investigate. We dug in, gathered feedback, and built a plan. Step two: Coaching. We tailored strategies for the struggling leader. Step three: Accountability. We made it clear that lasting change required involvement from their boss.

And here’s where things went sideways.

The leader’s leader—who initially nodded along, agreed to timelines, and signed off on accountability measures—promptly disappeared like a bad Tinder date who suddenly "lost service."

No follow-ups. No engagement. Emails left on read. Deadlines missed. Zero ownership over their role in the transformation. Meanwhile, the struggling leader—who actually wanted to improve—was left flailing because their own boss wasn’t modeling the behavior they were supposed to be reinforcing.

Sound familiar?

It’s no wonder their direct report was a leadership disaster—they had no leadership. They were set up to fail because the person responsible for guiding them checked out like an intern at a Friday afternoon meeting.

And if there’s anything we know, it’s this:

🚨 No amount of coaching fixes a leader who is abandoned by their own boss. 🚨

So, what do you do when the real problem isn’t the leader you’re coaching, but the one who should be holding them accountable? Here’s what actually works:

How to Fix a Leadership Vacuum

✅ Expose the pattern.

If you’re seeing leaders consistently flounder under the same disengaged boss, make the pattern impossible to ignore. Get the data. Start tracking retention rates, engagement scores, and performance metrics. Present the numbers in a way that makes it clear: this isn’t a bad leader problem, it’s a bad leadership problem.

➡ Example Fix: We once had to present an entire PowerPoint titled “Leadership: The Great Disappearing Act” to an executive team. We laid out email response times (or lack thereof), ghosted check-ins, and team performance declines. The kicker? We included anonymous feedback straight from their employees. The room got so quiet you could hear a Gen Z employee closing Slack notifications.

✅ Redirect the intervention.

Sometimes, the struggling leader isn’t the one who needs the most help. If their boss is the common denominator in multiple leadership breakdowns, it’s time to make them the coaching focus.

➡ Example Fix: Instead of waiting for the boss to magically get involved, set up mandatory “coaching pairs.” We’ve done this by requiring both leaders to join the same training or performance review meetings. No escape routes. No “I’m too busy” emails. When senior leaders have to show up in the same room as their struggling direct reports, they suddenly care a lot more about follow-through. Because nothing makes a leader take accountability like being asked to explain their own mess in front of the C-suite.

✅ Force accountability.

Waiting for an absent leader to step up is like waiting for IT to fix your laptop—it’s not happening unless you escalate. If a boss won’t engage, make it public. Document, track, and share missed commitments with the broader leadership team.

➡ Example Fix: At one company, after weeks of ignored emails and missed leadership check-ins, we started CC’ing the executive team. Suddenly, the “too busy” boss had plenty of time for leadership meetings. Weird how schedules open up when their boss’s boss is watching.

✅ Get real about culture.

If leaders at the top aren’t engaged, then bad leadership isn’t a fluke—it’s the culture. One department struggling? That’s a leadership issue. Three departments? That’s a company-wide failure.

➡ Example Fix: We implemented an “Accountability Chain” at one company, requiring that any leadership coaching or performance improvement plan must have sign-off from two levels above the struggling leader. Why? Because if their boss wasn’t engaged, their boss’s boss sure as hell needed to be. It turns out, when senior executives know their name is attached to a struggling department, they suddenly start caring about leadership development.

The Real Takeaway?

If you’re seeing this dynamic play out in your own organization, take a step back. Is the real problem the leader… or the lack of leadership above them?

If it’s the latter, congratulations! You’ve just diagnosed why your leadership issues keep cycling through new faces but never really go away.

Time to fix the real problem.

Have you been stuck trying to coach someone whose boss won’t engage? Drop your experiences (or rants) in the comments. Let’s talk about what actually works when leadership fails from the top down.