Confronting Your Boss - When and How To Do It

Confronting your boss - when and how to do it

A few years ago, Gallup did a survey and found that only 13% of employees felt engaged by their jobs. And almost a quarter of us were “actively disengaged”, which means we pretty much hate going to work every day. That’s pretty bleak isn’t it? When I try to calibrate these numbers with my own experience, a couple things jump off the page for me. First, the lion’s share of people I meet and mentor have a few critical, unresolved issues with their boss. Touchy things that are hard to deal with. But issues, that if removed, would make all the difference in the world to their happiness (and engagement) at work. Second, most of us are so uncomfortable or unsure of how to confront our managers with these issues, we choose to suffer in silence indefinitely. The impact seems to be reflected in those sad statistics. 

One of the areas I find myself coaching on most frequently is the question of when and how to confront a manager with critical issues about relationship, working conditions, salary and other fundamental drivers of job satisfaction. It never seems like the right time. There are always other priorities. The mood is never quite right. What if it goes badly? Is it really that bad in the first place? Maybe I’m just being oversensitive … it’s easy to talk yourself out of having the tough conversation with your boss. And so, we suffer on.

This week I’m going to offer advice on how and when to confront your boss about the big issues … salary, temper, relationship, trust. I hope it’s helpful to you.

Not surprisingly, the issues that cause us the most pain at work are the hardest ones to talk about. How do you approach your boss about this stuff?

I haven’t had a raise in three years and I deserve more.

My boss doesn’t seem to trust me and micromanages everything I do.

My manager yells and is aggressive and it’s starting to affect my confidence.

I got passed over for a promotion but I’m too afraid to ask why.

What I was hired to do and what I’m being asked to do are wildly different.

These are big problems. They affect the most basic tenets of motivation – purpose, autonomy, fairness. They are critical to get right but so often they are not. It’s hard to know how to broach these subjects because they are so loaded with consequence. To bring them up seems tantamount to accusation. Sure, you might be able to improve things by talking about them, but they could just as easily get worse. It’s easy to see why so many of us choose to grin and bear it instead of confronting our managers. I get it.

Today I’m going to share a few thoughts on when and how to approach these issues with your boss. I don’t have all the answers – it’s a hard one. I also don’t know the specifics of your situation. We’d need to do a coaching session for that. My hope is that by sharing my perspective, at a high level, you can have some of the tools you need to start building your own strategy for dealing with these tough issues.

When should you confront your boss?

For most of us, the answer to this question <when to confront your boss?> is, “Never”. It always seems easier to defer, delay, turn the other cheek. For others of us, confrontation inevitably comes when we’ve reached the breaking point. A series of incidents boil up until we can’t take it anymore, and finally we blow up in spectacular fashion and try to pick up the pieces later. Neither is the right approach. Even though these are highly charged, emotional issues, we need to be smarter in how we resolve them.

When people ask me when they should confront their boss with a contentious issue, my advice is almost always, “once you’ve built some leverage”. The problem is, too many of us wait until we’re at our weakest to confront our bosses with the hard issues. After a huge mistake, after a big fight, when we just can’t take it anymore. That is the opposite of leverage. When we’re upset or damaged or struggling, we have everything working against us.

When my coaching clients ask me when to talk to their boss about a big issue, I recommend they start by creating leverage. Get a win, do something and get recognized for it … anything. Wait for a moment when things seem positive – from your boss’s perspective at least. That is the moment to have the tough conversation. Next time you feel like you’re boiling over, like the straw has broken the camel’s back, take a breath, make a plan, get some leverage back, and then confront your boss from a position of strength.

How should you confront your boss?

Most of us get these big conversations wrong. We approach them with emotion, without a plan. We don’t end up getting our points across. We come off as flaky and selfish and hypersensitive. Then we regret doing it in the first place. Before you have a hard conversation with your boss, consider the following:

What is the outcome you’re trying to achieve? Are you just venting or are you pursuing a specific result?

Are you considering all perspectives? Are you coming across as self-centered or are you thoughtfully acknowledging your boss’s position?

Are you presenting in a personal context or a business context? Do you know why?

Will you start by reaffirming your desire for a positive outcome or will you just launch into your complaints?

Do you plan on presenting ultimatums? Are you sure you want to do that? Can you live with the result? Are you bluffing? Do you have a backup plan if it goes badly?

My goal in posing these questions is not to dissuade you from having a tough conversation with your boss. You need to have them from time to time. Rather, I want to make sure you’ve thought your plan all the way through. In general, I try to avoid ultimatums unless I’m prepared to leave the company and torpedo the relationship. Ultimatums are rarely necessary in my experience. Knowing what outcome you’re pursuing is also critical to a positive result. If you haven’t visualized what a positive end to the conversation looks like, it’s very difficult to make it happen. If there is no positive end possible, ask yourself why you’re having the conversation in the first place.

My advice for these types of confrontational conversations is to start with a clear idea of the outcome you want, be sure to provide context and acknowledge your boss’ perspective, explicitly state your desire for a positive outcome, avoid ultimatums, and know what your back up plan is. Once you have a clear sense for these things, and you have leverage on your side, you can be confident in having the tough conversation.

I’d love to hear about your experiences with these types of confrontations – good and bad. They’re extremely hard which is why so many of us avoid them. I hope my perspective has been helpful to you.

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