Your Manager Isn’t Difficult. She’s Under Extra Scrutiny.

Part of my business is coaching engineering managers new to the job or struggling with a tricky situation or two.

Several times now, someone I’m coaching through it has come to me with problems managing up.

They say their manager is mistrusting, always wanting status updates.

Or they feel like they’re micro-managing.

Or they seem slightly paranoid or demanding or contradictory.

In each case, the manager was a woman, relatively new to the organization or in visible conflict with longer-tenured leadership.

This is about what’s likely actually happening.

I’m a boring-ass white guy in tech, and I can tell you that any woman who has risen the ranks of leadership at a tech company – especially in the product and engineering half of these companies – has been through some serious shit.

To get where they are, they’ve had to fight harder, prove themselves more thoroughly, and operate with less organizational trust than male peers in equivalent roles. What looks like “paranoid” or “demanding” behavior is often learned adaptive response to real organizational pressure.

If she’s been punished in the past for not knowing status (when a male peer wouldn’t have been questioned), she’s learned to confirm the status of everything. If she’s had her judgment questioned more often than predecessors, she’s learned to over-prepare. If she’s operating with less benefit of the doubt, she’s learned to be defensive.

This isn’t bad management. This is survival. And it means the playbook for working with her is different than what you’d use with a male manager who has inherent organizational trust and benefit of the doubt.

Now, regardless of gender, there are shitty managers out there.

But before we bucket any manager into that pointy-haired boss territory, it’s worth looking at what that behavior might be reflective of.

How to tell if this is what’s happening

Ask yourself:

• Is your manager relatively new to the company (especially compared to her boss)?

• Is she in visible conflict with longer-tenured leadership?

• Is her work getting unusual scrutiny from executives?

• Are other reports experiencing the same “anxious/demanding” behavior, or just you?

If you answered yes to 2+ of these, you’re probably dealing with a manager under structural pressure, not necessarily a bad manager.

What to do about it:

Over-communicate proactively. Don’t wait for her to ask for status updates. Send them before she needs to request them. Weekly written summaries of what’s shipping, what’s blocked, what risks you’re tracking.

Make her look good upward. When you talk to her boss or skip-levels, make sure she gets credit. She needs organizational capital more than male peers in the same role do.

Ask explicitly what she needs. “What level of detail do you need in status updates to feel confident when [VP/COO] asks about this project?” Get specific about her actual needs, not what you think she should need.

Build trust through consistency. Say what you’ll do, then do it. For 3-6 months straight. She might not believe you at first (because she’s been burned before), but consistency builds trust.

Don’t take defensiveness personally. If she gets defensive about a project, it’s probably not about you. It’s about the times before you when someone questioned her judgment and she had to defend herself.

A quick aside: The above are also handy practices for managing up, regardless of gender.

Important: This won’t fix itself overnight.

If you adjust your communication style and start over-communicating proactively, don’t expect immediate results. It might take 3-6 months of consistent behavior before she starts to trust that you’ve actually got things handled.

If you try this approach for 3 months and see NO improvement, then you have data that this might actually be a bad manager situation rather than a manager-under-pressure situation. At that point, different strategies apply.

The goal isn’t to fix structural inequality in tech (you can’t do that alone). The goal is to give you tools to navigate your current situation successfully while being aware of dynamics that many engineers miss.

Sometimes “managing up” means understanding the pressure your manager is under and adjusting your approach accordingly. Not because they’re difficult. Because they’re operating in a different reality than their male peers.

Chris Vannoy is the founder of Axiomatic, where he helps engineering leaders at B2B SaaS companies improve velocity, reduce deployment chaos, and keep engineering aligned with business priorities. He offers delivery transformation programs, fractional CTO services, and coaching for engineering managers. His approach focuses on practical systems that work without the ceremony of traditional agile frameworks. Connect with him at chris@getaxiomatic.com or learn more at getaxiomatic.com.