I Coached 6 Clients Through Working With Difficult Leaders This Quarter. Here's the System That Actually Works

3 strategies for managing "impossible" personalities (without sacrificing your mental health or your reputation).

The biggest mistake is thinking “If I just explain it better, give them feedback, or show them they’re wrong...then they’ll change.” Here’s what to do instead.

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Occasionally, I think back to the times I reported into difficult leaders. The managers that were sometimes volatile or impossible to please.

I remember the disagreements. The feedback that stung in all the wrong ways…vague, indirect, or avoidant.

When I reported into a manger like this, I struggled to cope. My coping mechanism was maxing out on self care just to get by. I needed yoga, a monthly unlimited membership to SolidCore, monthly massages, monthly facials, and a meditation practice. I lived for the solace that the weekends brought me because I didn’t have to deal with them. But every Monday morning sent a chill down my spine. No amount of self care took that feeling away.

Why Working With a Difficult Leader Is So Taxing For High Achievers

I am wired to succeed.

The situation with my manager felt so dire because I was in a position where I felt like no matter how hard I tried, I was going to fail. My manager and I didn’t click and I didn’t understand how to deliver what they wanted consistently.

It was a recipe for disaster for a high achiever like me.

What I wish I knew when I was trying to navigate working with a difficult manager was to parse good and relevant advice from unhelpful advice in the heat of the moment. Advice that was unhelpful kept me fixated on my manager’s flaws. For example, when I got feedback that stung, I would go and find an article on bad feedback or “bad managers”. And when I found an article that was topical, it made me feel seen by highlighting exactly all the ways my manager delivered the feedback the wrong way and why that was bad.

Ultimately, that was a waste of my time.

Eventually, I learned that their flaws are the thing that you actually don’t have power to change. In my case, I stopped searching for advice kept me angry and disempowered. I wanted solutions.

According to research from CIPD, the gap between good and bad management is staggering, here’s two takeaways that stood out to me:

• Workers with bad managers experience high levels of stress and negative impacts to their mental health. According to the CIPD study, 50% of employees with bottom-quartile managers reported that work negatively impacted their mental health, compared to just 14% of those with top-quartile managers

• They cultivate malaise and overall dissatisfaction. In that same study, only 38% of employees with poor managers indicated that they were willing to go above and beyond their job requirements, compared to 74% of those with excellent managers

The last point hit home, specifically within the context of my work with high achievers. High achievers are exactly the folks that are wired for going above and beyond and when stuck under a difficult manager without the right coping mechanisms, that innate desire to exceed expectations can go away.

When you think about it, the time lost to burnout, to increased stress, and to career stagnation cannibalizes the time you actually need to invest in getting to where you want to be.

It stalls your trajectory.

If you’re in survival mode, you’re not building the strategic relationships, visibility, or a portfolio of wins that actually advances your career.

Most people never learn how to win in a scenario like this.

When my clients say some version of “I need help navigating my relationship with my manager”. I’ve come to learn that what they actually need is a system for operating successfully with a manager that’s difficult (and likely won’t change).

Let’s talk about how to solve this.

How to Work With A Difficult Boss, Successfully. Three Simple Tips.

The thing most people get wrong about managing a difficult boss is that it’s not a person problem, it’s a systems problem.

My highest-performing clients didn’t actually fix the leaders who were constantly frustrating them. They built systems. Systems are important because they allow you to limit your emotional investment in these interactions. Every time you get “stung” by a negative interaction with a difficult leader, you’re forced to spend time recovering. These 3 tips will help minimize the sting so that you can focus more of your time on what matters.

1. Pick Your Battles Using This Framework (Not Emotions)

If you work with someone difficult, it might be tempting to change your default setting at work to disagreement.

When someone triggers us, we associate them with negative feelings. We start to notice all their flaws and missteps (whether those missteps matter in the moment or not!). When things are tense, everything eventually becomes a landmine.

But if you’re defaulting to “no” on most things, you’re actively making your life harder.

If this is you, try this filter before you push back. I want you to ask yourself two questions:

1. Will this disagreement materially improve the outcome or am I disagreeing on principle?

   1. High achievers are wired to focus on what’s right. Instead, shift your focus to impact. This question helps you unpack the effects of disagreeing with them, instead of immediately submitting to the knee jerk reaction of how their words or actions made you feel or whether they’re right or wrong.

2. What’s the opportunity cost of spending my political capital here vs. saving it for something that matters more?

   • We’ve all heard about opportunity costs. When our emotions are high, it can be hard to think through how our responses can damage our political capital. There are times when the hit is worth it and times when it’s not.

Reflecting on these two questions gives you choices, even when it feels like you don’t have them. You’re consciously choosing when it’s strategic to push back vs. when it’s not based on what serves your bigger objectives.

2. Leverage Choice Architecture. Your Secret Weapon for Constraining the Chaos

Sometimes a difficult manager is someone who has trouble with clear decision making.

Maybe you send them a presentation deck for feedback and it leads to a 2 week delay and 20 rounds of revisions. And with each round, you were both getting increasingly frustrated with each other.

In these situations, instead of asking open-ended questions like “What do you think of this deck?” Try presenting a limited set of options (2 or 3 MAX).

This approach is grounded in choice architecture. My mom is a natural choice architect and very wisely gave me two options for dinner each night as a kid. I had no idea what she was doing — I always felt empowered and in control. Little did I know that she was using a concept popularized by behavioral economists Richard Thaler and Cass Sunstein.

When decision-makers are erratic or indecisive, giving them a constrained set of options (rather than a blank canvas) reduces decision fatigue and accelerates clarity.

Here’s 3 ways you can use choice architecture to wrangle an indecisive leader:

1. Instead of asking: “What do you think of the Q4 strategy deck?”, try: “Should we lead with the revenue projections or customer success stories in slide 3?’”

2. Don’t send a long document or presentation and wait for feedback. Send it and explicitly point them to/tag them on the slides where a specific question or piece of feedback is required of them.

   1. Previously you may have asked “what do you think?” and now you’re going to say “We can present the data like this (using raw data) or like this (using percentages). Which one do you think tells a better story?”

3. Frame their choices in terms of outcomes: “Do you prefer we go the fast and scrappy route or take the more polished route and delay this by a week?”

   1. Maybe they want to go with multiple rounds more feedback, but they need to know that it will cause a delay.

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WORK WITH ME

Want help navigating an impossible leader at work?

Here’s what a recent client had to say:

My husband was just remarking on how much my mindset has changed in the past few months, to which I replied, “That was all Ashley!”. After years of not being truly seen/appreciated by the leadership team at my work, I just felt really small, invisible, and unconfident. You gave me the confidence to level-up. You also helped me to stand up for myself and be more visible at my current job.

She landed a Director promotion. Priceless.

Let’s chat about coaching and see if we’re a fit.

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3. Look For Patterns. Their Behavior May Not Be As Erratic As You Think

When we work with someone difficult, we feel the direct impact of their behavior. That makes it difficult to take a step back and do a root cause analysis (RCA) of the situation. It’s personal. Frankly, most people think about RCA in relation to solving technical/scientific problems or finding solutions to business problems, but the relationship you have with your manager IS data and you can deconstruct it to understand their behaviors.

Sometimes managers have patterns hiding in plain sight.

I recently talked a new client through this. She was convinced her executive was just “moody”. She’d watch him be perfectly reasonable with her, then turn around and absolutely eviscerate a colleague in the same meeting. It felt random and terrifying. And while his wrath hadn’t hit her yet, she was anxious that it might.

I asked her to think about the moments he blew up and whether there were any patterns she could identify. And after a few minutes, something clicked. She realized that every single time someone was delivering bad news he hadn’t heard before, he had a bad reaction.

He hated being surprised.

Her next steps were clear. Communicate clearly, early, and transparently.

My point with this tip isn’t that all difficult managers are secretly reasonable. Some really are just volatile. But some just have triggers you can learn to navigate if you zoom out.

I hope these were helpful reframes, now I want to share a few strategies that are not effective.

How Not To Work With A Difficult Leader

I don’t want to minimize the impact of working with a difficult leader, manager, or colleague. I struggled to work with the leader I talked about in the beginning of this newsletter. But now that I’m on the other side, I can say with confidence that I have a more productive set of strategies. Ones that actually work for myself and others!

Here’s what doesn’t work:

1. Hoping They’ll Change

I remember the times when I thought, if I just explain it better, if I just give them feedback, or if I just show them they’re wrong...then they’ll change.*

I was wrong.

There’s a time and place for feedback. Particularly with folks who are open to it. But feedback is not a great use of your time if you know your boss isn’t open to it or worse, could take it poorly.

I recently explained this to a client with an analogy I’ll call “The Seattle Effect”.

You don’t move to Seattle and expect LA weather year-round. That’s not going to be your reality. You can’t change the weather. You have to make peace with the fact that it will rain a lot. If that’s not your jam, maybe you decide you no longer want to live there. If you decide to stick it out because there are other things about living in Seattle that you really enjoy, then you deal with the weather by buying rain gear.

Sometimes dealing with a difficult manager requires the same mindset shift.

You need to change your perspective from “how do I fix this person?” which is essentially the same as saying “how do I change the weather?”. Your new perspective should be “how do I create the right conditions for success for myself given that this is my reality?”.

2. Fighting Fire With Fire

Sometimes you just can’t help yourself and you give into the temptation of waging your own all out war. It usually happens after the relationship takes one too many hits. There’s not a lot of trust, it’s damaged. Your passive aggressive tone turns combative and maybe even condescending. While it might feel cathartic to “win” a spat with your manager, if you intend to stay at the company - you’re essentially putting a target on your own back.

Fighting fire with fire = destruction.

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CLOSING THOUGHTS

My highest-performing clients figured out that You can’t control a difficult leader. But you can control the systems you build to work with them.

The people who wait for the difficult boss to change stay stuck. The people who build systems around the difficult boss move forward.

Good luck. See you next week!

Ashley

P.S.

If all else fails, remember this.

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