Leadership Lessons: What We Can Learn from Bad Bosses

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Every leader has had a bad boss. Many have been one. The manager who fires off midnight emails, the constantly overwhelmed “everything is an emergency” type, the charismatic but totally unprepared leader, the boss who quietly manipulates through gossip. These aren’t fringe cases. They’re patterns. They show up in workplaces of every size. And in a world where hybrid work, burnout, and constant change are colliding, poor leadership behaviors hit harder than ever.

Research shows that managers shape more than performance. They’re responsible for up to 70% of the variance in employee engagement (Gallup). In other words, culture isn’t built by companies. It’s built by leaders — one action at a time.

In a recent episode of Tough Day’s podcast, host Katherine von Jan sat down with Mita Mallick, bestselling author, workplace culture expert, and creator of The Devil Emails at Midnight: What Good Leaders Can Learn from Bad Bosses. Rather than cataloging the villains of organizational life, Mallick reframes bad bosses as a leadership curriculum hiding in plain sight. Their behaviors teach us what to avoid, what to watch for, and how to lead better.

Here are the three archetypes from their conversation that every People Leader should understand — and what to do when you recognize them in yourself or your organization.

The Midnight Emailer and the Macro Manager: When Autonomy Turns Into Neglect

There’s a familiar workplace badge of honor: the 12:03 a.m. email. Mallick jokes about the boss who’s too busy for her team during the day but treats after-hours communication like a personality trait. The problem isn’t the timestamp. It’s the urgency without context or connection that leaves a team guessing what matters and what is truly most important.

However, one of Mallick’s most insightful archetypes is the macro manager which is the opposite of a micromanager, but not in a healthy way. A macro manager withdraws so far that employees lose access to guidance, air cover, and decisions only a leader can make.

As Mallick explains: “I’ll provide less guidance, less support. I won’t be there as a coach. I’ll just hover from above, afraid that I’ll dive into the details.”

This is not leadership. It’s absence.

In hybrid and distributed workplaces, this pattern is especially damaging. Research from MIT Sloan shows that unclear communication from managers is now one of the biggest predictors of burnout and disengagement. High autonomy works only when leaders stay connected enough to coach, unblock, and align.

What great leaders do instead:

• Hold consistent check-ins and never cancel them simply because tasks are “in motion”
• Set expectations for how decisions are made
• Clarify the first step, the last mile, and what “good” looks like
• Provide political and organizational support when employees need senior presence in the room

Think of it as active trust — not abandoning the team, but empowering them with scaffolding.

“The difference between trust and neglect is everything. A good leader knows when to step in and when to help.”
_{— Mita Mallick, Author & Workplace Culture Expert}

The Kind but Incompetent Leader: When Niceness Masks Serious Gaps

Every organization has one: the leader who is warm, beloved, endlessly positive, and utterly unprepared for the job. Mallick calls this the kind and incompetent boss.

“They’re so nice. They send pizza to your family on a Friday night. They remember your kids’ names. But they can’t lead a meeting or make a decision,” she says.

This archetype is one of the most dangerous because teams hesitate to name the problem. There’s no yelling, no bullying, no obvious toxicity. But incompetence creates quiet harm: employees cover for their manager, do parts of their job in the shadows, and eventually burn out. McKinsey’s recent research on capability gaps found that leaders often fail not from lack of effort but from lack of training, onboarding, and clarity.

What great leaders do instead:

• Identify skill gaps explicitly and support them with coaching and stretch assignments
• Build structured onboarding plans for new leaders
• Treat internal promotions with the same rigor as external hires
• Create psychological safety so teams can raise concerns early.

While we all appreciate kindness, it’s not really a leadership capability. Competence is.

The Gossip Boss: When Power Is Weaponized Through Information

Gossip exists in every workplace. Used well, it spreads stories and signals social norms. Used poorly, it becomes a weapon.

Mallick shared the story of a boss she nicknamed Gossip Girl who is someone who collected personal information and used it to manipulate, undermine, or divide her team. This isn’t harmless chatter. It’s politics, insecurity, and control disguised as connection.

During times of uncertainty like reorganizations, layoffs, leadership changes, gossip accelerates. MIT’s research on toxic workplace behaviors after 2020 found that gossip-driven cultures experience significantly higher turnover because people no longer trust the system around them.

What great leaders do instead:

• Shut down gossip by modeling transparency (“Let’s ask her directly”)
• Establish communication norms for the team: what’s shared, where, and how
• Redirect conversations back to the work (“We only have five minutes left. Let’s get back to the proposal”)
• Address harmful rumors directly when needed

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How People Leaders Can Build a Good Boss Culture

If bad bosses are everywhere, the solution isn’t to shame individuals. It’s to build systems that make good leadership inevitable. Here’s what Mallick recommends:

1. Protect time for real 1:1 connection. Canceled check-ins are a leading indicator of team drift.

2. Teach leaders how to coach, not micromanage. Coaching is collaborative. Micromanaging is corrective.

3. Create team agreements before conflict happens. Define accountability, escalation paths, and what urgency really means.

4. Write things down. Shared docs, action logs, and decision summaries reduce chaos.

5. Name the behavior, not the person. Whether it’s macro management or gossip, label the pattern so the team can discuss it and make it less personal.

6. Don’t tolerate harmful dynamics. Silence equals endorsement. Leaders must intervene early.

Better leadership is not the absence of bad behavior. It’s the active presence of clarity, coaching, and accountability.

Bad bosses don’t usually set out to cause harm. Most are overwhelmed, undertrained, insecure, or isolated. But their impact is real. Teams burn out, cultures fray, and companies lose talent they didn’t have to lose.

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Tuffy™ for working with “bad bosses”

Our AI Workplace Advisor, Tuffy, supports employees who are navigating the stress, confusion, or emotional toll of working with a challenging manager. When communication is inconsistent, expectations shift without warning, or a leader’s behavior creates uncertainty, Tuffy offers a confidential space to make sense of what’s happening, regulate your reactions, and map out next steps that protect both your well-being and your performance. 

Tuffy helps people pause before spiraling, clarify what they can control, and choose responses that bring more stability, structure, and agency to the situation even when their manager cannot. 

Here’s an example:

User prompt: “I'm having difficulty with my manager right now. She cancels most one-on-ones, disappears for days, then suddenly reappears in panic mode demanding an urgent update. No context. No clarity. Just urgency. I'm trying to be understanding as she's under a lot of pressure (we all are!). But I'm left guessing what actually matters and I need direction on some critical projects.”

Tuffy response: “That’s a tough spot to be in and it sounds like you’re carrying a lot of ambiguity while trying to stay supportive. When communication is inconsistent, setting some structure on your end can help regain clarity and reduce stress.

Have you considered sharing a proactive and structured weekly update via email to summarize progress on key projects, priorities, and where you need direction? This could give her something concrete to respond to, whether she’s available for a 1:1 or not. 

Alongside weekly updates, you can build strategies to navigate her unpredictability more effectively. Here’s what you could try:

• Prioritize What You Know: Focus on deliverables you’re confident matter most. If she hasn’t clarified priorities, use your judgment to ensure you’re moving the most important work forward.
• Ask for Quick Guidance: When she reappears, frame a question to get immediate focus, like, “Which project should take priority right now?” or “What’s the most urgent next step you need from me?”
• Create Alignment Briefs: If critical projects need direction, share a one-pager outlining options and ask her to indicate preferences. This minimizes back-and-forth and keeps things moving.

Need help refining these ideas into specific actions or talking points?”

When we study bad boss behaviors, and build systems to prevent them, we create workplaces where people thrive. As Mallick reminds us, every bad boss is a lesson. Every leadership gap is a chance to grow.

Learn more about Tuffy. Watch the demo.

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Want to dive deeper into how we can learn from bad bosses? Listen to our podcast with Mita Mallick.

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