All Articles Education Educational Leadership A leader's guide to winning over the pessimists

A leader’s guide to winning over the pessimists

Educators can win over people who always see the glass as half-empty, writes Michael Gaskell.

6 min read

EducationEducational Leadership

A glass of water

(Pixabay)

One of the most sacred lessons I learned as a school leader was that by rewarding teachers with the gift of time, I can inspire loyalty, reduce burnout and show respect, making it an invaluable tool for improving teacher well-being and student excellence. You might assume that giving this level of respect to my team yields unconditional, unanimous faith in me as a leader. 

However, there are always a loud few who can poison the well when they look to undermine your authority, anyone’s authority. You know who they are. They generate negative energy at the store, the gas station and in the faculty lounge. And they’re adept at making everyone feel uncomfortable with your next move. It’s not personal, but it feels that way.  I don’t know why the glass-is-half-empty crew does this, and frankly, I don’t want to know. Instead, I focus on why it matters and how to navigate around it while maintaining my standards.

Imagine, as the school leader, you’re walking the talk on honesty, kindness, credit for time and the core values you’ve modeled. You’re transparent about mistakes, listen deeply in meetings, and maybe even share a personal story about life’s messiness to show vulnerability and encourage safety. It was honest, sincere and meant to connect. But then… crickets. 

There is that uncomfortable silence. You know the majority want to participate and wonder if they, too, are made uncomfortable by the few who inhibit our ability to thrive. I often push my team to “poke holes in my thinking” and generate ideas that can expand beyond my own. This multiplier effect offers creative value when people feel free to contribute, and that is my responsibility to encourage and stimulate. I do it constantly through modeling with the confidence and courage that this is the way to lead and to be led.

Model behavior you want to see

Staff gossip, skip feedback sessions, whisper or roll their eyes when you speak on values. It stings. So what do you do when your modeling doesn’t catch on? It can feel personal, like the time I had a doctor’s appointment at the end of a school day, approved by the boss, but at a liaison meeting with union representatives, I was questioned about my absence. 

Beyond the surprise that anyone noticed (or cared) that I was heading out for my doctor’s appointment, my mind slowed down, as it has to in moments like these. A younger, less experienced version of me would have snapped back. No matter how absurd the complaint was, I had a bigger job: model the way in my response. I was candid, describing my medical obligation. Then I was motivated to write this … and then move on. That’s the biggest step: move on. Do not dwell. I lose sight of a larger, much more important focus, which is always about student success, when I’m interrupted by others’ toxic motives or misinterpretations.

Keep your perspective when (not if) this happens. Because it will happen, and often in the most surprising times and places, when you least expect it. It happens to all leaders, and to the best of them. It’s not about your skill; it’s about others’ insecurities and anxieties with how they picture things should go. When we misunderstand something and are influenced by the more primal parts of our brain, it is human nature to fill in the blanks, and often our interpretations are wrong. That’s what we are facing. Reject this by responding in a way that counters their expectation (fight or flight). 

Don’t take it personally

Remember, don’t take it personally. People resist change for all sorts of reasons-habit, fear, or they just don’t see why it matters… yet. Step one: check your own mirror. Are you consistent? If you’re preaching openness but shutting down questions, no wonder they’re skeptical. True modeling means living it daily, flaws and all. Next, get curious. 

How? Set up low-pressure chats, one-on-one talks, and not more formal mechanisms like performance reviews. Ask, What’s concerning you? Do this with sincerity, then respond with respectful confidence, and then move on. I call less formal yet pivotal interactions “drive bys.” These are informal, walk-up moments where the casualness can reinforce authenticity. NEVER do this in email, which changes our perception from 3-dimensional human contact to 2-dimensional mechanics. A sincere effort by a leader to not only make the time to do this but to create more casual moments actually adds to the respect I gain in approaching this way.

Even when it seems like a disproportionate reaction, validate their concern. Empathy isn’t weakness; it’s glue sticking them to your willingness. Often, we can steer individuals back to logic and understanding if we are willing to hear them out.

Then, shift gears: make the abstract concrete. If openness is the vibe, try real-talk rounds in drive-bys and even in staff meetings – 2 minutes each, no judgment, just honest shares. Model it yourself. Someone says something tough? Respond with grace, not defensiveness. There may be a parcel of truth we can use to improve either our leadership or an issue within the school community.

Remember the value of praise

Public praise works wonders, too. When a teacher nails it – like owning a classroom slip-up  – call it out — loved how Ms. Jones owned that mix-up today. Takes guts. It’s contagious. But here’s the hard part: boundaries. If someone’s still undermining or spreading negativity despite your efforts, address it directly, privately, and kindly. I value your skills, but gossip hurts our culture. Can we find another way? Put the onus back on them. They may come up with a solution, but at the very least, you are demonstrating the standard you hold for those in the school, starting with you. Put your beliefs out in front of your faculty, every day, or they will create their own, and it’s very possible you won’t like their version.

Consequences might be needed, such as skipping them for leadership roles. Not to punish, but to protect the vision. And don’t forget the why. Remind everyone what these values do: build trust, make kids feel safe, and boost teacher morale. Tie it all to real wins: Last year’s parent feedback spiked because we listened better. Data sells. Finally, lean on allies. Get department heads or union reps to model too. It’s a team sport. If you’re feeling isolated, remember: change is slow. It takes ages to learn multiplication facts; adults aren’t any faster at it either. 

Keep showing authenticity, patience, and relentlessness. Not right at once, and there can be bad apples or people going through tough times that project out — stay the course. One day, you’ll look around and see mirrors everywhere, reflecting your leadership. And that? That’s when you know kids win.

Opinions expressed by SmartBrief contributors are their own.


 

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