I'm a Leadership Coach — Follow These 8 Conversation Tips If You're Dealing With a Toxic Boss

I believe managing up is a skill every successful woman needs to master, even when—or especially when—that’s hard. 

Difficult dynamics inevitably show up in long-established working relationships as much as new ones—which means managing up should be an ongoing part of your career. 

When bad boss behavior has someone reeling, speaking to them is often the last thing we want to do. We’re afraid of what might happen if we have that conversation and our fear erodes our confidence. We get caught in stories of what we risk if we did. We reassure ourselves we’re taking the higher moral ground, or have no choice so we feel justified in not instigating a conversation. 

But avoiding talking about any issue brings the risk of mutual mindreading: everyone imagines the worst of each other until those (mis)perceptions build a picture that works against us and our career. 

It’s important to say that sometimes when you’ve tried managing up or repairing difficult dynamics and know you are not valued, leaving is the right solution. 

But before it gets to that, also know you can choose to work better with the boss you have now. You can choose the perspective that their leadership tendencies are not set in stone. You can make room for the understanding that the boss is a work-in-progress themselves—not a bad person, but flawed because, well, they’re human. 

Your boss is senior, but not superior. As soon as you recognize there is a problem, it’s time to address it. You shouldn’t be impulsive—it’s too hard to stay in dialogue when we’re angered, scared or shocked. But with proper thought, a structured plan and a repertoire of responses at the ready, it’s time. 

Before you allow lack of confidence and fear to take over, ask yourself: What will happen if you don’t have this conversation with your boss? What do you stand to gain if you do and get everything you need?

Here are ten ways women manage up at work to deal with toxic bosses.

1. Understand why something feels wrong.

Inquire into your feelings more. What are you feeling? Fear? What are you afraid of specifically, and what is this based on? Rewind the narrative that is triggering. When you separate fact from the story, you will stop reeling and restore enough calm to be intentional instead. 

2. Consider what you will gain from a courageous conversation with your boss.

Understand the risks. What are the implications for your working relationship, your team and your future career if you do, and if you don’t? Top tip: be very honest about whether you’re guilty of mind-reading (guessing what you think they think) and if your instincts are to avoid confrontation.

3. Craft a courageous conversation starter.

You will want something that frames your partnership purpose. You should avoid being personal or getting defenses up at the outset. Here’s an example:

I asked for this time together because I’ve been thinking a lot about what happened (when…). What’s most worrying to me is that it feels like it has affected our working partnership. I wonder if we can talk about that. I’d like to understand better what’s happening for you and share what I found challenging. I hope by having this discussion we will draw a line, explore how you feel about working together and collaborate on ways we will work well together going forwards.

4. Rehearse. Rehearse. Rehearse.

Script your discussion three times: once from your point of view, once from their perspective and the third time, from outside both perspectives, as if you’re a narrator of the story. Why? By rehearsing three times, you can shift from truth to perception and from accusations to feelings. You will have the skill to keep reframing and keep communication open. Employing empathy will help you understand your boss and take the lead in improving the dynamics that aren’t working well.

5. Grade your third "outside" script. 

Does your courageous conversation clearly state what you want to express to the other person? Actively explore what you need to understand from them. Does it use open questions and avoid emotive language? Anticipate what they might say. Then adjust what you say and how you say it until you can genuinely imagine a flow to the dialogue. You are practicing staying open by doing this. 

6. Tackle your points of difference as a partnership. 

Have three points in mind that invite a partnership approach to move past your points of difference—notice, not “problems”—so you can both concentrate on succeeding again. 

7. Face your feelings, so you can respond, not react. 

As you rehearse, you will notice your feelings behind the arguments and accusations. Face them. You’re fine. With heightened awareness of your feelings, you will feel more in control. Understand and accept that what you’re reacting to may go back further than your boss and the current situation—this will give you a powerful perspective. 

8. Be the best at listening.

At this point, you’ve solved the big barrier to having courageous conversations—skill. All that’s left is to remember to actively listen when your boss shares their perspective. Keep your responses coming from a place of learning and mutual problem-solving.

9. Decide when and where.

Your confidence will be growing by now, so it’s time to lock in a time to talk while this thinking is still fresh. When and where is the right time to book time together? Consider when will be least pressured and most conducive for your boss as well as your preferences. 

10. Know that managing up isn’t over when this conversation ends.  

Follow up with a note of decisions taken together. It demonstrates your inner leadership, and gives you both an actionable framework to take forwards in your work together—something to circle back to if you need to course-correct again in the future.

--

This article reflects the views of the author and not necessarily those of Fairygodboss.

Helen is a Leadership Coach helping seasoned professionals who are at a career crossroads, needing to realign work they love with what matters most, but have got stuck in a cycle of trying. With Helens’ thought-partnership, they create a concrete plan to finally make aligned, confident transformation happen instead. 

If you would like help to rewind the stories that are holding you back and pivot to a new narrative where you act differently – and then get everything you want please click here to get the exact framework Helen uses with her 1:1 clients. Helen offers (complimentary) clarity conversations, and you can apply for a time to talk together here and she would love to connect on LinkedIn.

What's your no.1 piece of advice for dealing with a toxic boss? Share your answer in the comments to help other Fairygodboss members!