Microsoft’s ex-VP of HR says your boss is your most important ally at work. Here’s how to win them over.

• Chris Williams is a former VP of HR at Microsoft and podcaster, consultant, and TikTok creator.
• He writes that your boss is your most important ally.
• Williams explains that you don’t need to be a suck-up, but you need to be visible and supportive.

If you want to get a raise, be promoted, or avoid the layoff, you need allies. Allies in the room where the decisions are made. And the best ally to have is your boss.

I’m the former VP of HR at Microsoft, and I’ve been in that “room where it happens” more times than I can count. When it comes down to it, your best assurance for success is to have a supporter in the room.

It’s simple math: The company has only so much money allocated for raises, or so many slots available for promotion. Or they need to cut a certain number of people. But there are many more people vying for those perks or trying to avoid those cuts. Choices must be made.

Choices must be made

Those choices are made in discussions. Of course, spreadsheets are made with all the available candidates. They are filled with columns describing the various metrics and merits upon which an objective decision can be made. 

Leaders pore over those sheets sorting them this way and that. Trying to decide which metrics matter more. Which way of sorting yields the clearest answers. Which objective measures they can use to make these incredibly hard choices.

But the final choices are not made simply from the spreadsheet. The edge cases are too close — the choices too hard. 

Sometimes that’s a roundtable discussion with all the managers together. Sometimes it’s one-on-one with the leader and each team manager.

In any case, the tough decisions are made based on all the objective factors and, by necessity, some subjective ones too.

That’s why you need an ally. Someone in the room where it happens. Someone arguing your case. Someone explaining why you, and not that other person, should get that raise. Or deserve that promotion. Or need to stay.

Edge cases are the issue

The difficulty is not at the top. The people who sort right to the top of the objective lists are almost never in question. They are clearly the ones to get the raise or the promotion. Or those who sort right to the bottom are the clear choices to let go.

In fact, the vast majority of the cases are handled with objectivity based on metrics and merit.

The problem is at the margins. When there are just a couple of slots left and still a number of candidates. This is where arguments are had. Where the strength of your ally is tested.

You need someone on your side, making your case. Who is willing to advocate you? Because you are most definitely not in the room where it happens.

Your best ally is your boss

They know you, your work, and your value. Having them on your side is the difference between their saying, “Wait, they are great, they deserve it,” and their simply shrugging it off. And letting another manager take that slot.

People often misunderstand the need for allyship. They think they need to be a sycophant, or a suck-up, to win their boss as an ally. Some worry they need to be their boss’ best friend for them to be their ally.

But most bosses aren’t like that. They want to reward, promote, and keep the best people. Because doing that helps them succeed.

How to win an ally 

So how do you get your boss to be your ally?

There are several keys to winning them over.

1. Be visible

The first key is to be seen. Toiling away in darkness does little to gain support. So you need to be visible. Make sure you and your work are noticed.

You can do that privately in your one-on-one meetings, highlighting the work you do.

But more effective is making a bit of a show of your accomplishments. Speak up about them in meetings. Make sure they are on the published reports. Offer to speak about them at the next large meeting.

This not only gets on your boss’ radar but also makes it hard to deny when it’s clear everyone knows what you’ve done.

This is hard for many people who hate to “toot their own horn.” But it’s essential to gaining support.

2. Be useful

You need to be sure you’re working on the right things. Offer to help on the tough challenges. Work on the things that make a difference for the organization.

Those are the things that will impact your boss’ success and therefore be key to gaining them as a supporter.

If you can’t get assigned to those things, don’t despair. Find some small ways to have impact.

Look at the many things on your boss’ or your team’s plate. There are undoubtedly small items that are off to the side. Hard to gain traction on. Hard to find volunteers for. But still things that would be great to have done.

Find one of those and just knock it off. Find the time to make progress. I like to do them even without asking. Just nail it, and then announce it.

Of course, when you get it done, people have to know. See above about visibility.

Do two or three of those things, and you’ll certainly be seen as a valuable asset. Someone worth that raise or worth keeping around.

3. Be supportive

Lastly, you need to be someone of value. Someone the boss can count on to simply handle things. Someone who is part of the solution.

This means being part of the team. Not being a whiner. Being willing to raise your hand when others are busy trying not to be noticed. Tamping down the discontent. Seeing the light at the end of the tunnel when things get dark.

In short, be an ally for your boss and your team. Be someone who is trying to help move the entire team toward the goal. Someone your boss wants to reward and to have around.

The best way to earn allyship and respect is to give it

In my experience, these decisions are made using all the best criteria, with all the best intentions. It’s when it gets down to those last few slots when it helps to have an ally. 

If you make your boss your ally, they will represent you well in that room where it happens. And that’s all you can ask.