Dealing with Difficult Bosses: 3+3 Strategies
Navigating bad leadership starts with practical wellness and protective factors
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I have written previously about dealing with challenging staff and community members as a school leader and teacher.
This article was motivated by a reader reaching out to thank me for sharing hands-on, practical methods I offer. But she wanted one more: “What about difficult bosses? Aren’t they in a position of power, where I have little control over the outcome, even and especially if I disagree with them?”
I’ve written about a boss who missed the single biggest moments when leading. He never praised our accomplishments. It was remarkable; he was working harder not to acknowledge those of us that led our schools and needing support on the hardest of days.
Lack of worthy praise is one thing. How do we handle a boss who uses intimidation, blame displacement, and worse, steals credit for our work? I would love to tell you that they are far and few between, but I am writing this because that is untrue. Decades of research shows how we can lead successfully and help staff feel supported, acknowledged, and accessed in those important moments. The research keeps coming and I keep writing about it because the problem stubbornly persists.
We might think the issue is less pervasive in the education profession. After all, we are educators at heart. We came into this profession because we care about kids. In many instances, this is true, and we enjoy decent, ethical leaders. Too many times, educators became leaders because they possessed a greater desire for personal achievement and power. The first part is not the issue, however, power can change leaders. I have seen it happen.
I spent years riding out the kinds of leaders and leader-colleagues who made the organizational environment toxic, unproductive, and very, very CYA (cover your a--). We can all recall the days bosses such as this finally left the organization–there were parking lot parties while "Celebration" played as well as this easy-to-hum song as you waved them “good bye.” These are not environments in which children win, and that is the root of the problem. Secondary to that is our own wellness, which matters so we can lead learning environments, in spite of the incompetence above us.
Practical Ways to Survive Difficult Bosses
What do you do when you have to deal with difficult bosses day in and day out, knowing there is no end in sight? This can be a major stressor, let alone translating to obstacles they put up in our attempts to help students thrive.
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Here are practical steps to hang in there, manage your wellness so you can lead and teach well and interrupt their influence from behind.
1. The 80/20 Principle
Keeping my side of the street clean empowers me to focus on the aspects of a situation you can control (the 80%) while letting go of the uncontrollable (the 20%). Instead of wasting time and energy fighting insurmountable challenges such as bureaucracy, difficult colleagues, or uncooperative leaders, it is more productive to adjust my approach, sidestep obstacles, and focus on progress within my sphere of influence. This mindset helps save time, resources, and frustration while moving toward goals more effectively.
2. Mind Games
I am always surprised at how little is known about methods for tuning the brain for wellness that are rooted in decent science, such as binaural beats. These sound like sci-fi gimmickry yet there is strong evidence supporting the effectiveness for effectively reducing anxiety and modulating emotional states. These are easily accessible, if you have a pair of earphones (we all do!). So why not try it?
Here’s how these work: When the brain processes two different frequencies played simultaneously in either ear, it compensates for the discrepancy by perceiving a third, rhythmic "phantom" frequency known as a binaural beat. This audio hack works in calming the mind and reducing anxiety, and gives you a shot of what you need in those most stressful moments. Evidence shows 6-9 minutes of listening does the trick, so why not? Here’s a free online example.
Now that you’ve got your wellness honored, let’s take a look at practical strategies, with a well-mind you can use to approach the difficult boss…
3. Use AI (YES, AI!)
In my work, I have discovered that using AI can make my work more effective and efficient, which means I can offload unnecessary tasks to focus on qualitative experiences, interactions with staff, students, and parents, and yes, even that boss.
I have written about making use of AI as a school leader, and I characterize it as remarkably imperfect productivity. AI is remarkable for its ability to produce what appears to be high-quality work at immense speed, yet it remains imperfect because it acts as convincingly knowing while tricking users into accepting "workslop" that lacks substance or accuracy.
Employing AI wisely helps offload work that bogs me down, so I feel less stressed, and far more prepared to manage ineffective bosses. Be strategic, refer to “source grounded” materials and use it to make your work better quality and far more efficient, such as I did incorporating AI into writing better evaluations for teachers.
3 Other Strategies to Consider
In addition to what I’ve described above, consider these actions to help manage an unwieldy manager.
1. Document Everything (Build a Paper Trail)
- Confirm Conversations: After verbal instructions, send a follow-up email saying, "As we just discussed, I will do X by Y date.”
- Keep Records: Maintain a private log of projects, instructions, and outcomes to prove your actions if needed. Case notes, detailed and dated hold up well, if and when needed.
- Outline Responsibilities: Start projects with a written review of discussion, outlining who is responsible for what, signed off by everyone, suggests Robert Hosking via Fortune.
2. Manage the Interaction
- Stay Calm and Neutral: Do not react defensively immediately. Do not match their energy.
- Use Fact-Based Language: When blamed, focus on the facts. Ask questions like, "Can you walk me through the timeline so I can understand what happened?" (YouTube).
- Redirect to Solutions: Instead of defending yourself, focus on fixing the issue. Say, "You're upset, I'm upset. What do you think we should do?" suggests Quick and Dirty Tips.
- Don't Take it Personally: Understand that a blaming boss often behaves this way due to their own incompetence and insecurities.
3. Take Action
- Have a Direct Conversation: If the behavior continues, discuss it privately. Start with positive feedback, then use specific examples to show how the blame-shifting affects your work, recommends Dr. Pollack.
- Involve HR or Superiors: If the behavior is bullying or threatens your career, consider involving HR or a higher manager. However, warn your boss first to avoid being seen as "going behind their back."
- Find a New Job: If the environment is toxic, start looking for a new position. Do not feel compelled to stay in a situation that damages your mental health and career.
Our work as educators and school leaders is too important to let bad bosses funnel down from us to staff and kids. Too many people need us and stopping the cycle of bad leadership poisoning student growth starts with practical wellness and protective factors. Be strong and remember, our work is too significant to let bad management disrupt our control, and we have 80% control -- most is better than none!
Dr. Michael Gaskell is Principal at Central Elementary School in East Brunswick, NJ, has been published in 75 articles, and is author of three books: Radical Principals, Leading Schools Through Trauma (September, 2021) and Microstrategy Magic (October, 2020). Mike provides current guidance on AI, presents at national conferences, including ISTE (June 2023) The Learning and the Brain (November, 2021), and FETC (January 2025; 2024: 2023, and 2022); and works to find refreshing solutions to the persistent problems educators and families face. Read more at LinkedIn