Arguing with your boss: How to do it and still have a job
One of the first (and best) bosses I ever had was a retired very senior officer from one of the beardier parts of the British Army. He never talked about what he’d done in his military career. In any room he always sat with his back to a wall, facing the door. He was an unstoppable force who actively sought out immovable objects (and usually ended up moving them). I loved him and I loved working for him.
He taught me bundles about leadership. The two years I worked under his direction, despite coming so early in my career, were some of the most fruitful I had from a leadership and learning perspective. Inevitably, when he moved on, he disappeared, never to be heard from again, and I realised I needed to hold on to the lessons I had learned working for him . My hunch was that it had been an experience unlikely ever to be repeated (as has indeed proved to be the case even 20 years later).
Occasionally, as a cocky 22-year-old, I was bold enough to tell him I disagreed with him, and most of the time, this went very badly indeed. On one occasion, he grabbed the office return address stamp, gripped me by the shoulders, and imprinted it onto my forehead, such that my face was emblazoned with the message IF FOUND PLEASE RETURN TO LONDON SW1A 1AA (you can look that address up if you feel like it).
After a few similar experiences, he finally took me into his office and said something to the effect of: “I need you to tell me when you disagree with me, that’s what you’re paid for. But you need to learn how to do it better unless you want me to lock you in the filing cupboard and throw away the key”.
(Side note: you had to be there to understand why this was ok. I can’t imagine it happening now. But I can honestly say I look back on these exchanges with great affection).
Anyway, the lesson he then gave me was this: if you’re going to disagree with someone, force yourself to agree with them first.
Then, try your argument again.
Me, R, and the unstoppable force, L, pixellated because I don’t want him to hunt me down. I’m imitating the moustache he was growing at the time.
Now I would love to say I had applied this lesson faultlessly throughout my career, but I would be lying. However, the times I have managed to do so, it has worked every. single. time.
The thing is, the idea isn’t new. It has the hallmarks of classic Stoic philosophy: focus on what you can control; accept external events with phlegmatism; and understand that human suffering comes from the stories we tell ourselves about events, not the events themselves. As Marcus Aurelius said:
“Everything we hear is an opinion, not a fact. Everything we see is a perspective, not the truth.”
Marcus Aurelius, stoic philosopher. Picture credit: National Geographic
In the past couple of weeks I have been reminded again of the effectiveness of this approach as a sort of mental trick you can play on yourself to get off your high horse, climb down from your soapbox, and check yourself before you do something you’ll later regret. Of course it’s not surprising how much the topic of “disagreeing with your boss” comes up in coaching conversations with my clients. These are some of the most challenging moments you can face as an ambitious young leader (or an ambitious old one for that matter). But three recent examples gave some great case studies for how to navigate them.
Names have been changed but these stories are (as they always are here) 100% real.
Case Study 1: Sarah.
Sarah’s story is the classic “victim of your own success” scenario. In her early roles she had attracted a lot of attention for having some of the happiest clients in the business and for getting seriously good results with her team. She then spent the following two years trying to come to terms with a workload that had steadily (or not so steadily) expanded beyond capacity.
Unsurprisingly, she found herself increasingly anxious and frustrated. When we met she saw two options:
Say nothing and keep suffering, or
Give her boss an ultimatum she didn’t actually want to follow through on.
But as we talked it through, we found a third way. Sarah had to force herself to agree with her boss’s perspective on the situation first. This was painful but ultimately created a huge amount of creative energy.
During the session she finally landed on the thing she’d been avoiding: “I want to thrive, not just survive.” Guided by this, she crafted a clear, simple message to prepare her next one-on-one: here’s what used to work; here’s what’s not working now. Here’s what I need to do my job well, and a reasonable timeline. And - crucially - I’m committed, but not at the cost of my health or identity.
Ultimatums don’t generally work. Not with your spouse, not with your kids, not with your physician…and definitely not with your boss.
As soon as she had understood her boss’s perspective, recalibrated her own view, and created a framework for the conversation, her confidence shot up. And she had a new leadership skill in her repertoire: healthy disagreement.
Case Study 2: Claire
Claire was preparing to meet her boss to discuss a proposed team restructure.
Her version of the plan and his version looked very different, and she was all too aware how important this conversation was. She’s only recently been promoted, so is definitely under a certain amount of scrutiny.
Her instinct when we started talking it through was to defend her ground. Why? Because she was afraid that “caving” would make her look weak in front of her team (more scrutiny).
So we started by thinking about it from a different perspective: what if the goal of this meeting isn’t to win an argument, but to demonstrate leadership? If the focus changes to “how do we serve the business better?”
She’s a super smart person, so it didn’t take much more than that to work out what to do. And, spoiler alert, she had to start by forcing herself to agree with her boss’s opinion. Not permanently, but for long enough to find the middle ground. BEFORE the meeting (this is the crucial part).
She went away not with a script for the meeting (seriously cringe), but with a structure for how to navigate it:
- Start by naming the shared goal (better service for the business)
- Position herself as a partner, not an opponent (“this is how you + I will collaborate now and in the future”)
- Consider that despite her strongest convictions, the other person may have a point too.
Case Study 3: Josh
When Josh got left out of a client meeting he felt would have been a great development opportunity for him, he knew he had to raise it with his boss. The problem was, he knew his boss saw it differently from him, and that she was not exactly famous for being approachable with feedback.
At the beginning of our conversation, Josh was understandably upset and not a little bit wound up. He admitted as much himself: “I know I’m right about this, but I also know she’s just not going to listen”.
We talked it through. As we dug a little deeper, Josh admitted that he realised this wasn’t personal. Travel budgets were also a factor, as was the profile of the client in question, who always preferred small, informal meetings. What did he do? He began to force himself to see his boss’s perspective.
“Let’s assume you’re right, and you should be in that meeting. What will be the result if you stick to your guns?” I asked him. “Nothing good”, he admitted. The opportunity had already been and gone. So throwing a tantrum to try to get his way wouldn’t get him anywhere.
What we worked on instead was a way for Josh to frame the discussion in a way that allowed him to feel he was getting his point-of-view across, but also that he understood the constraints and the reasons behind the decision. But it was understanding his boss’s perspective that was required FIRST, in order to unlock Josh’s new perspective on the situation.
So there it is. The magic recipe. If you want to disagree with someone, you must first force yourself to agree with them.
if you want a practical way to play this trick on yourself, well here are two:
A simple T chart. The left column, my argument, the right column, your argument. Stack ‘em up.
Write two pages of letter paper arguing vehemently as if your life depended on it against your opinion. See if you can’t convince yourself that you’re wrong, or at least, that the other person may have a point.
One final thing. If you’re reading this and thinking “What? So I just have to fold? Do whatever my boss says and agree with them on all things?”, well, that’s not my point at all. My point is that by trying on their argument for size, seeing how well it actually fits, you will, without doubt, learn something new about the situation. You will realise what parts of it you were wrong about. And you will show those around you that you can put the most important things (the business as a whole, and the relationships and social equity you hold within it) first. Ahead of your ego. Ahead of your need to be right.
That’s leadership.