Two Managers, Two Lessons

How Opposite Leadership Styles Taught Me to Stop People Pleasing

From the “Corporate Crossover” series

A monthly collaboration exploring corporate life from both sides of the divide.

Each month, I write first from the post-corporate perspective, then my writing-partner-in-crime, Imelda Wistey, responds from inside corporate walls through her post. Make sure to subscribe to her newsletter The Corporate Collateral!. We cover everything - identity, money, relationships, time, authenticity, all the complex realities of corporate life that rarely get honest conversations.

Later this week, we’ll go live to discuss our different viewpoints and take questions from both our communities.

This is the real talk about corporate life you’ve been waiting for.

I had two managers in my corporate life who couldn’t have been more different. Between them, they taught me everything about people pleasing, external validation, and eventually, after I left, how to validate my own work.

Neither of them set out to teach me these lessons. But the contrast between their management styles became the unexpected education that shaped how I work today.

Manager One: The Freedom That Nearly Broke Me

My first manager didn’t believe in KPIs or stats. He gave me the freedom to give updates as I saw fit, without pressure, without pushing me to do more than I could handle.

He encouraged me to follow whatever projects I needed and only requested updates when leadership meetings required them. He trusted me completely.

The pros were many. I got to explore areas of our department that no other operations person touched: the processes, the workflows, the automations. This was the beginning of everything I do now. He gave me space to discover what I was actually good at, beyond my job description.

But there were cons I didn’t see coming.

Sometimes he had no idea what my workload actually looked like. And my eager twenty-something-year-old mind, desperate to prove I belonged, interpreted every new project as confirmation that this must be normal. That I just needed better time management. That I needed to be more efficient.

He gave me a chance when I was still a student with no diploma. So when he assigned me work, I thought: “This is what showing up perfectly looks like. This is how I earn my place here.”

I was people pleasing from gratitude.

From the belief that external validation, his trust, his continued assignments, meant I was doing it right.

Enter: my first burnout.

I never told him I was drowning. I just kept saying yes, kept taking on more, kept trying to prove I deserved the opportunity he’d given me.

Looking back, I realize his hands-off management style wasn’t the problem. My inability to set boundaries was the problem. But I didn’t know that yet. I thought the problem was that I wasn’t working hard enough or smart enough.

Manager Two: The Micromanager Who Taught Me Boundaries

My second manager was the complete opposite.

He came from a highly structured company and wanted to apply that mentality immediately. He didn’t observe first, he restructured. He requested yearly goals, tracking methods, daily updates on projects that sometimes didn’t have much movement.

He didn’t listen to my years of experience in the role. He told me I had “too many ideas” and needed to pause.

The cons felt overwhelming at the time. His micromanaging energy was exhausting. Every Teams message from him, “Hey, what’s the status?”, made me want to scream, “Just leave me alone!”

My mind felt anxious about needing to deliver work on his timeline, even though I knew what was actually needed and when it needed to be done.

Performance reviews became nerve-wracking. Even though I did amazing work based on the results we achieved, I still felt like he could have a completely different perception. I couldn’t tell if my work was actually good or if his constant check-ins meant I was failing somehow.

But here’s the strange gift: I didn’t want to please him.

With my first manager, I people-pleased out of gratitude and eagerness. With this manager, I was just annoyed. I wanted him off my back.

And that annoyance? It forced me to do something I’d never done before.

I started setting boundaries.

Because of his high micromanaging energy, I learned the boundaries I NEVER added or enforced before. I negotiated my energy levels. I refined my idea creation process. I learned how to showcase my ideas so they wouldn’t be seen as “too much.”

I learned to say: “This project doesn’t need daily updates because there’s no daily movement. I’ll update you when there’s something to report.”

I learned to say: “This is my workload, and this is what’s realistic this quarter.”

I learned to say: “I need space to think through this before we implement it.”

I wasn’t people pleasing anymore, at least not in the same way. I was learning to cater to my own fulfillment and joy in the work I did. I was learning to protect my energy levels. I was learning how not to allow someone’s stressful management style to take over my nervous system.

The Unexpected Integration

Here’s what I didn’t expect: both managers taught me something essential about validation and boundaries.

The first manager taught me what I was capable of when given freedom and trust. He showed me I could explore, create, and innovate beyond my job description. But he also inadvertently taught me that without boundaries, freedom becomes overwhelm.

The second manager taught me that I could survive, and even thrive, in environments that felt restrictive and controlling. He showed me that boundaries aren’t just about protecting yourself from bad management; they’re about honoring yourself in any management situation.

Between them, I learned:

External validation feels good, but it’s not a reliable compass. My first manager’s trust felt amazing, until it didn’t. Until I was burnt out and resentful because I kept chasing his approval by taking on more than I could handle.

Internal fulfillment requires clear boundaries. My second manager’s micromanaging forced me to define what I needed to do my best work. I had to get clear on my own standards, my own timelines, my own creative process, because his standards didn’t match mine.

People pleasing comes from different motivations, but the result is always the same. Whether you’re pleasing out of gratitude or pleasing to get someone off your back, you’re still giving away your power. You’re still looking outside yourself for validation about what’s good enough.

What Changed After I Left Corporate

Leaving corporate didn’t immediately fix my relationship with validation. I still caught myself:

• Checking the numbers to see if my work “performed well”

• Seeking approval through comments, shares, and subscriber counts

• Feeling anxious when I didn’t get immediate feedback on something I created

• Questioning whether my work was valuable if it didn’t get external recognition or if I need to pivot once again to connect more

But here’s what’s different now: I have the boundaries those two managers helped me develop.

When I notice myself slipping into people-pleasing mode, creating for approval rather than purpose, I can catch it. I can ask myself:

“Am I doing this because it feels true, or because I think it will get validation?”

“Am I honoring my energy levels, or am I overextending to prove something?”

“Am I creating from joy, or from the anxiety of needing external approval?”

Most days now, I choose purpose over praise. Not because I don’t care about feedback or recognition, I do (being human and all of that). But because I’ve learned that the work that matters most to me often unfolds quietly, without an audience, without immediate applause.

And I’m okay with that.

Because those two extremely different managers, one who gave me too much freedom without structure, and one who gave me too much structure without freedom, taught me how to create my own structure. How to honor my own freedom. How to validate my own work.

Even though my corporate world involved very different management styles and varying levels of performance pressure, I’m grateful for both experiences.

I left corporate with boundaries I can set everywhere - not only in my career and business, but also in my personal life.

And that’s a gift no performance review could ever measure.

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What’s Next in Corporate Crossover

If this resonated, keep an eye out for Imelda Wistey's from The Content Collateral response from inside the walls of corporate tomorrow. I’m curious how validation and boundaries show up when you’re still navigating daily corporate dynamics.

We’ll go live later this week to dive deeper into both perspectives and take your questions about people pleasing, boundaries, and finding fulfillment.

See you in the comments, and see you live. ✨

Kelly 🖤