Managing Up and Across
What challenging professional relationships taught me about leadership
Last week, I was speaking with a client who was at her wit's end. "My Monday morning blues start on Fridays these days! I just can't deal with my boss anymore," she sighed. "He questions every decision I make, changes his mind constantly, and I'm walking on eggshells around him."
As she spoke, I couldn't help but wince. I had been there myself.
My Own "Difficult Boss" Story
In one of my previous roles, I had a manager, the SVP, who was the definition of overbearing. Every morning, I'd wake up to at least three emails and half a dozen Slack messages sent at odd hours, with feedback detailing minor changes to major initiatives I was handling. In meetings, I would be interrupted and offered opinions and directives, neither offering nor seeking context, some of which would contradict what he’d previously instructed me to do.
It drove me absolutely crazy. It all came to a head when he started to drop in on daily stand-ups with the engineering team that my reports were responsible for, and began to directly assign work to the engineers through DMs, sprint plan be damned. The flustered and overwhelmed engineers would reach out, asking how/why the priorities had changed since sprint planning and whether they should be worried that an SVP is attending their daily stand-ups. I'd go home frustrated, vent to my partner, and contemplate quitting. That is, until I had an aha moment.
The Day Everything Changed
It happened during one of our one-on-ones. As usual, my boss was nitpicking every detail of the presentation I had put together on the State of the Business when he said in a frustrated tone, “I just want to make sure everything is perfect. I am going to be presenting this at the board meeting and the last time I presented, they nitpicked every little thing and got hung up on the details. I can’t afford a repeat.”
That's when it hit me – his overbearing behavior wasn't about me at all. It was about his own fear and guilt from past experiences.
The Pattern I Gleaned
Once I had this realization, I started noticing similar patterns with other "difficult" people I worked with:
The colleague who played office politics? Deeply insecure about his position
The team member who could never make a decision? Paralyzed by anxiety about making the wrong choice
The peer who always had an opinion but never did the work? Struggling with impostor syndrome
These difficult personalities weren't being difficult for the sake of it. Their behavior was a mask for uncomfortable emotions they didn't know how to handle.
What I did about it
After my lightbulb moment, I changed my approach. Instead of getting defensive or frustrated, I started getting curious. When my boss would send those late-night emails, I'd respond the next day with questions seeking to understand the thought process.
I began to:
Get curious, not furious: When my boss would micromanage, I'd ask questions like, "What specific concerns do you have about this approach?" or paraphrase his note by responding with “Are you saying that …?”. The art of asking and answering questions is a critical executive leadership skill I will touch upon in a later post.
Name it to tame it: I started acknowledging the emotions in the room during meetings and seeking to understand the underlying emotions when terse DMs or emails landed in my inbox. "It seems like we're both feeling some pressure about this deadline. Is it caused by x/y/z?"
Be direct, with respect: Instead of bottling up my frustration, I learned to express my needs assertively. "I appreciate your thoroughness, but I think I could be more effective if we agreed on check-in points rather than daily revisions."
The Conversation That was a Game Changer
In the next meeting with that same boss, instead of my usual defensive stance, I tried something new. When he started his typical detailed critique, I said:
"I can see how much you care about getting this right. I care about that too. Could we talk about what success looks like for both of us?" We had a lengthy conversation about the goals, the assumptions we were making, the attendees, key focus areas, anticipated challenges, impacts and alternative approaches.
That conversation led to the best working relationship I'd ever had with a manager. This approach worked because my manager was willing to have an open conversation and engage in building trust.
What About You?
What "difficult" personalities are you dealing with at work? What masks do you think they might be wearing? I have assembled a list of 12 different difficult personas and coping strategies. Comment below if you would like to see more posts on this topic.
My colleague Divya Ramachandran and I are going to be hosting a workshop at the Grace Hopper conference next week on this topic. If you are a senior leader and attending GHC, we would love to see you there.
And hey, if you're struggling with a particularly challenging workplace relationship and want to talk it through, my inbox is open. Sometimes, an outside perspective is all we need to see the person behind the mask.
If this post resonated with you, there's more where that came from. Subscribe for regular stories and insights from my journey navigating workplace relationships. And if you're ready for one-on-one support, I'd love to explore how we could work together.
#RealTalk #WorkplaceDrama #LeadershipLessons #PersonalGrowth