Managing Up

Understanding Your Boss's True Motivations

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Everyone you work with has what I call ‘shallow motivations’ and ‘deep motivations’.

The shallow motivations are the things you can come up with if you know where a person lies in the company org chart. So, for instance, if you see that Jane is in sales, you can probably conclude that she’s motivated by landing deals and hitting milestones and winning performance bonuses.

Deep motivations are what you get when you look past the role to consider who they are. This includes how they see their life, who they wanted to be when they were younger, what they desire today, and what they want to achieve in the long arc of their career.

Normally, as a manager, you’ll build a model in your head for each of your subordinates. Knowing how your team functions and what motivates each of them makes it easier for you to do your job. You know which buttons to press. You know the types of task assignments that make their eyes light up. You know who’s at risk of leaving, and who isn’t.

But that’s not what this essay is about. This essay is about doing all of that … to your boss.

Understanding Your Boss

Your boss, like everyone else, has deep motivations. Knowing what these ‘true’ motivations are will be incredibly useful given that you’re working under her, in the same way that understanding ‘true’ motivations for each person on your team makes it easier for you to work with each of them.

But let’s use a concrete example to illustrate this point.

Say that you want to pitch a proposal to your boss. You’ve got a small team of software engineers and designers, and they’re all busy working on a release that’s due in a couple of months. Your proposal is that you want to take two software engineers and a designer and have them work on a smaller project, one that would make it easier to do future releases — that is, all the releases after this one. This would mean dropping one or two minor features from the upcoming release — a small sacrifice, you think, for higher future velocity.

There’s only one hitch: your boss says no. She says that the next release should be your topmost priority, and you should focus on that to the exclusion of all else.

Now comes our question. Would your assessment of this situation change if you found out:

  • Your boss’s impending promotion is pegged to the delivery of this release. This makes it super important to her, and she is rightly antsy about your request, or
  • Your boss’s daughter was recently diagnosed with a chronic illness, and she’s been thinking of leaving the company, or
  • There’s been rumours of the company getting acquired soon, and your boss just wants to cash out.

It’s highly likely that any of these three pieces of information would significantly affect your assessment of the situation. It’s also likely that your actions would differ greatly if you knew these facts beforehand.

The point I’m making here is that if you know of your boss’s true motivations — really know, the same way you know your best friend like the back of your hand — if you know your boss as well as that, then you’re likely to be way more effective when working for her.

This effectiveness presents itself in three ways.

The Benefits of Understanding True Motivations

The first major benefit of understanding your boss’s true motivations is that you’ve now unlocked access to the simplest, safest method to present criticism to her.

Granted, presenting criticism is a big topic, one that’s far larger than just ‘understanding motivations’. We’ll cover the intricacies of that in some later post. For now, though, understanding your boss’s motivation unlocks the most basic form: people are more receptive if you frame criticism in terms of what motivates them. You’ll be surprised at how effective it is to say: “I know you’re interested in accomplishing X, but Y is getting in the way of achieving that. Wouldn’t Z be better at helping us achieve X?”

Concrete example: let’s say that your boss is motivated by an upcoming promotion, and in your company, promotions are tied to the quality of releases. Saying “the way we’re packing our releases now is just slowing us down” is probably going to be a lot less well received compared to “I understand that delivering releases are your highest priority, and that it’s super important that we deliver on time and on target. But the way we’re packing our releases now is just slowing us down in the long run. Shouldn’t we take some time to work on our release process?”

Sufficiently rational bosses should be able to work out the implications of your criticism regardless of how you present it, and see that addressing the core of your complaint would help them with their goals. But bosses are — sadly — humans, not rational calculating machines. Because criticism is a touchy thing, you should do whatever it takes to make the link explicit between your critique and your boss’s true motivations.

This leads us to our second benefit: if you have an accurate model of your boss, you’re going to have a higher probability of success when pitching proposals.

I got this idea from Phillip Guo, currently Assistant Professor of Cognitive Science at UC San Diego. When he was a fairly new assistant professor, Guo wrote a blog post titled Whose Critical Path Are You On? which hugely influenced my thinking on organisational behaviour. Guo wrote:

I just had such a tremendous moment of clarity that captures the essence of all of the interactions I've had with all of my mentors throughout the past 13 years as a student, summer intern, and junior employee in the software industry:

If I was on my mentor's critical path, then they would fight hard to make sure I got the help that I needed to succeed. Conversely, if I wasn't on my mentor's critical path, then I was usually left to fend for myself.

By critical path, I mean the path of work that is critical for their career advancement or fulfillment at the given moment in time. (…) If you get on someone's critical path, then you force them to tie your success to theirs, which will motivate them to lift you up as hard as they can.

When Guo wrote this in 2014, he was thinking of his past experience as PhD student and tech industry intern. He noticed how — if he placed himself in his boss’s critical path — he would have a massive organisational tailwind behind his back. He also noticed how he would have to work a lot harder if he chose to carve a path of his own.

The trite version of this advice seems to be “please your boss and good things will happen” — but it’s not that simple, of course. Your boss might still be a terrible mentor. The key insight here is that if you so choose to get on someone’s critical path, you are essentially staking your success to theirs, which motivates them to help you regardless of their capabilities.

Understanding your boss’s true motivations is my way of saying “know where their critical path lies.” Of course, I don’t mean to argue that you have to get on their path — that decision depends on your personal goals and the context of the organisation you’re in. But it’s always good to know that the option exists, and it’s helpful to know where the space of potential critical-path-proposals lie. This, in turn, means that you get to choose proposals with a higher chance of success.

The third and final benefit to knowing your boss’s true motivations is that you are better able to serve as the shit shield for your team. Why? This is intuitive: if you understand your boss’s true motivations, you’ll be better able to predict her reactions to events within the company. This, in turn, helps you protect your team’s output from the vagaries of organisational life. This is more important than you think: I believe that the bulk of events that you need to handle for your team are directly related to your immediate boss. Learning to work with her is key to your performance as manager; in some situations, you can’t increase the output of your team without first taking your boss’s true motivations into account.

I hope these three benefits are sufficiently compelling to you. And so now we turn to the final question that emerges: how, exactly, are you supposed to divine your boss’s true motivations?

Properly Calibrated Observations

The first thing that we need to address is the fact that most of us naturally create mental models of our bosses in our heads. It is a universal human instinct to generate narratives in order to explain the actions of the people around us. If you ever observe children playing, for instance, you’ll notice that even two year olds would attempt to tell stories to each other.

As human beings, we have a generalised storytelling component in our brains. You observe your boss’s actions and come up with a story to explain her behaviour. If, on multiple occasions, you observe her rejecting proposals, it’s easy for you to conclude “Ah, my boss is quite risk averse.” It’s equally easy for someone else to conclude “Ah, my boss is authoritarian.” The tricky thing is to properly calibrate the narratives you come up with, because it’s too easy to stick to the first compelling narrative that pops into your head.

What I do to prevent this from happening is that I try as much as possible to stick to a three step process.

The first step is to generate multiple competing explanations for some set of observed behaviour. It’s not enough to think “my boss is risk averse” — that’s just one explanation. It’s important to also consider “my boss doesn’t like people challenging her authority” and “my boss has high standards for proposals and I should figure out what they are” and “my boss is clearly bored by badly presented ideas” all at once.

This first step prevents you from sticking to the first story that your brain generates that happen to fit all the facts you observe. If you understand that your brain is a story generation machine, then you’d understand that it’s able to generate other equally compelling stories as well. You should let it run for a bit to see what else it comes up with.

The second step is to assign confidence ratings to each of these stories. For illustrative purposes, I’ll use percentages, but it’s ok to keep this at the level of intuition and feeling — for instance, one of my friends say that he has a ‘feeling of confidence’ and he adds and subtracts from that feeling as he goes.

Say that I’m quite confident my boss is risk averse, since that matches up with other observations I’ve noticed while working with her. However, I’ve also observed her snapping at overly-ambitious subordinates, which lends credence to the idea that she doesn't like to have her authority challenged. I will rate the following stories like so:

  • My boss is risk averse — 40%
  • My boss doesn’t like people challenging her authority — 30%
  • My boss has high standards for proposals — 15%
  • My boss is clearly bored by badly presented ideas — 15%

My current explanation for her behaviour is that she is risk averse, which is why she’s rejecting all these proposals put before her. If, in the near future, I observe her doing something else, that new observation should strengthen one story and weaken the others, causing me to re-evaluate my notion of her true motivations.

This seems really trite and obvious, but we should remember this is not how our brains normally work! My habit of generating multiple competing stories and updating the likelihood of each is a trained behaviour. It is as unnatural as riding a bicycle, or using chopsticks.

What most people do is the exact opposite: they generate the first plausible story (e.g. “she hates me!”) and then proceed to ignore all disconfirming evidence from that point forward.

This leads us to the third step: actively seek out disconfirming evidence. It’s important to remember that as subordinates, we are not passive observers. It’s one thing to sit around waiting for events to strengthen or weaken specific explanatory narratives, and quite another to take action to test our various hypotheses.

As an example here, I could go to my boss and ask her why she rejected most of the proposals she saw in our last meeting. I could frame this as a desire to “better understand her thinking … in order to present better proposals to her in the future”. Of course, I don’t have to take what she tells me at face value — she could very well be lying. But the very action of asking produces more evidence that I can factor into my judgment of her person.


Failing to understand your boss’s ‘true’ motivations is one of the ways I've seen highly intelligent managers stumble in the early years of their careers. This was surprising to me, until I realised that they weren't taking the time to build accurate intuitions about the people around them.

It's probably worth reiterating here that seeking a deeper understanding of your boss doesn't imply that you have to get on your boss’s critical path ... unless you want to. Nor does this imply that you should become a sycophant.

What it does mean is that it’s always a good idea to build an accurate model of your boss in your head. A more accurate model is built by understanding your boss’s ‘true’ motivations — which will in turn help you when you offer criticism, when you’re making proposals to her, and when you need to protect your team from her actions (though ideally, of course, you won't have to!)

Of course, if we step back and squint our eyes at this entire argument, what I'm saying is functionally equivalent to “take time to understand your boss — the same way you should take time to understand everyone else around you. Do this because being good with people is how you win at organisational life.”

Sometimes complex techniques have simple roots. Understanding ‘true’ motivations is a stellar example of this; it's simply how you get good at emotional intelligence.

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