I was just trying to help.

You can be compassionate and still be clear.

Jenny Allen writes The Bootleg Manager and the two of us have argued before: she works from the inside out, telling you how a hard situation felt as it landed on her, while I start from first principles.

This piece is one of those: she gave an employee flexibility she never defined, watched it stretch past anything she would have approved and felt the cost settle on herself, the employee and the team. Read it for the lived version of the problem.

In a week I will publish my own piece taking the same trap apart from first principles; the two belong together.

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A while back, I had an employee going through a complicated family situation.

What she told me was heartbreaking. I wanted to help.

I also didn’t want to pry, because the details were personal. So I asked the question that felt kind and reasonable at the time:

“How can I help?”

She needed flexibility – but given the uncertainty of the situation, she didn’t really know what that would look like.

I soon found out.

It started out with her needing to work exclusively from home.

This wasn’t really a problem – she could do her job remotely. It was mid-pandemic: everybody was working from home at least part-time.

But as time went on, I saw that she would cancel or decline meetings on short notice. She rarely kept her weekly 1:1s with me. And the emergency requests for days off became more frequent.

The flexibility she’d needed had expanded beyond what was reasonable.

Because I had agreed to flexibility without truly defining it, I didn’t feel like I could suddenly pull back from it. I thought it would be heartless to try to go back and hammer out a formal agreement given her stressful situation.

But I should have.

I should have sought to reset expectations and set clear boundaries.

Because the agreement we ended up with – unwritten and never discussed – is not one I ever would have approved.

I’d never defined any terms. I didn’t ask enough questions. I didn’t set a timeline. I didn’t specify what work she’d still need to complete, what we could postpone or reassign, or when we would revisit the arrangement.

Meanwhile, the rest of the team noticed.

I hadn’t told them anything beyond the fact that she needed some flexibility while she dealt with a family matter. They didn’t know the situation – but they did know how it affected them. The missed deadlines, the extra work they’d had to take on in her absence.

They responded with empathy. They jumped in to take things off her plate and worked around her absences. They were sympathetic.

At first.

But as time wore on, the situation started to wear on them. No one complained outright, but I caught a few side conversations and some increasingly pointed comments.

I had put them in a bad position, too. They were expected to absorb the impact of an arrangement they didn’t understand and couldn’t question. I shielded the employee from their frustration, but I also shielded myself from the conversation I should have had much earlier.

I had given her the grace I’d want someone to show me if I needed it.

But I knew even then that I would never have asked for THAT much grace. I would try to handle my situation and still produce. And if I couldn’t, I’d make a clean hand-off plan, then take leave to focus on my family.

I’d granted grace without guardrails – and THAT was the problem.

It was a spiral that any caring manager can fall into: support starts to mean protection from pressure, discomfort, and accountability instead of a clear path through a hard situation.

I learned that the hard way. But I learned.

That doesn’t mean I won’t offer flexibility to someone who needs it. Kids get hurt, parents get sick, marriages collapse. You can’t prevent life from getting in the way of work. And as managers, we want to respond like decent human beings.

But in the end, that support is still a work arrangement. You can be compassionate while still being a manager.

If I could go back, I would still offer support. I would still assume good intent. I would still try to help.

I would set terms that included what specifically the employee needed, for how long, and what specific work still had to be delivered. I’d lay out the need for communication if anything changed, and set a date to revisit the arrangement.

I would say:

“I’m sorry you’re dealing with this. Let’s talk through what support would help, what work still needs to be covered, and when we’ll checkback in.”

I’d balance care with pragmatism, leading to an agreement that considered the employee, the work, and the team.

I don’t regret caring about the employee. I regret blindly caring – and providing a blank check for support that the whole team had to cash.

Thanks for reading,

Jenny & Luca

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