What actually happens when you threaten to quit over another job offer: A former Microsoft HR VP explains why you already lost when you made the threat

• Chris Williams is a former Microsoft VP of HR and a podcaster, consultant, and TikTok creator.
• Williams writes that if the threat surprises your manager, it’s poor communication on your end.
• If you’re a frequent complainer, your manager may welcome your departure. 

In more than 40 years in business and leadership, including being the former vice president of human resources at Microsoft, I’ve seen a lot of employees threaten to leave. It rarely ends like they dreamed. Here’s why.

Being frustrated in your job is not unusual. There are minor irritations of technical issues or difficult colleagues. And there are longer-term, career-limiting frustrations. Maybe you get all the worst assignments. Or you never get the promotion you feel you deserve. Or you’re not paid what you want. Frustration seems to be a part of many jobs.

When that boils up to a head, you might feel you need to issue an ultimatum and threaten to leave unless changes are made. Maybe you’re demanding a new role or a better title, or maybe it’s more money.

But you’ve had it. “Do this or else,” you say. What happens now? Probably not what you thought.

It helps to look at this from your manager’s side of the fence to see what they might be thinking when you threaten to leave. Let’s look at three situations.

1. Surprise!

If your threat comes as a surprise to your manager, this is a huge red flag. They reel back, thinking, “Where did this come from?”

Their immediate reaction will almost certainly not be to grant your demand to try to save you. They’ll want to understand what’s really going on. Why are you so frustrated that leaving seems to be the only choice?

And more importantly, they’ll want to understand why you didn’t bring this up long before now. Why did this come to a boil without them knowing it was this bad?

If the threat to leave comes as a surprise, it’s not a reflection on the company or your manager. It’s a reflection on you. You’ve done a terrible job of communicating your issues. 

Your threat to leave seems rash and irrational. That’s not a good look. One that’s unlikely to work to your advantage.

2. You Again?

If you’re a frequent complainer, your threat is just more of the same. It feels like a Groundhog Day situation (see the Bill Murray movie of the same name). The manager is thinking, “Oh no, not you again.”

You’ve made your feelings known many times before. The company has made it clear they can’t do what you need. The money isn’t there, they don’t have the job you want, you are just not the right person, whatever. 

Threatening to leave just seems like the next step in your long, extended tantrum.

To be honest, most managers welcome your threat to leave. At least it puts an end to the chorus of woe you keep expressing.

Don’t be surprised if the manager accepts your offer and helps you pack up your things.

3. Bye!

Sometimes, your threat is seen as a resignation in disguise. You’ve been making all kinds of not-too-subtle noises about your frustration. Rumors are everywhere you’re looking for other jobs. You are often inexplicably absent, perhaps interviewing?

From the manager’s perspective, you’ve already decided to leave. This threat is just a last-ditch effort on your part to get… well, it’s unclear what you want.

If you threaten to leave with another job in hand, what’s a manager to do? They could perhaps match the pay and the title, but they can’t match the company, the role, or the situation. Each company is unique, and each team and role is as different as a snowflake.

If it’s all about the money, it’s only worse. You’re saying the only thing keeping you is money. What’s to stop the same conversation from coming up in a year or six months? Nothing.

If you’re seen as already gone and are now resorting to threats, your manager will often recognize the futility of any effort to rescue you.

The threat feels like blackmail 

In any of these cases, your threat to leave feels like blackmail — do this “or else.” Quite often, in the company’s eyes, “else” doesn’t seem so bad.

If you are vital to some effort — the only person with the keys to the finalization of some project — perhaps a counteroffer would be made to keep you around long enough to finish the task. 

But it’s only seen as a stopgap. As soon as the project is over, you can be sure that you’ll never be given such power in the future. The company won’t get into that situation again. Only a reckless manager would trap themselves repeatedly. They are reminded that the lingering cloud of blackmail is future threats.

In almost every case, when you make the threat, you’ve already lost.

Even if they meet your demands, it’s only temporary. All trust is gone, and your future at that company is limited. You’ll be forever seen as a risk to leave. Even if they grant your demands, they’ll be looking beyond you.

Learn to negotiate without threats

Again, I get it; you’re frustrated. The better solution is not to threaten but to negotiate. If you have another offer you’re willing to take, handle it very openly.

Spend time to clearly understand your value and impact on the company. Find a way to put that in terms that are meaningful to the company. Usually, that’s money, but it could be in customer impact, market presence, or internal efficiencies. Find a way to express those in money terms, too.

Have a good discussion with your manager about how you’d like to work something out. Let them know this isn’t a threat but that you’ve got to be realistic here. Outline what you consider to be reasonable compensation for that value. Clearly define why that role, that title, or that money is appropriate for the impact you provide.

Use this to work with your manager on a fair value exchange — one that works to both your and the company’s benefit — calmly, clearly, and with professional intent. This kind of clear, open, and straightforward negotiation is speaking in the language of business. It’s a reflection of your balanced and reasoned approach to the work.

The job market has changed 

Perhaps in years past, when tenures were longer and keeping employees was a vital concern, things were different. 

But today, with people moving between jobs all the time, tenure is lean. Replacing you is easier. The “else” side of “do this or else” seems like not a big deal to the company. 

It turns out that increasing fluidity in the job marketplace cuts both ways. And it limits your leverage when you threaten to leave.

So just don’t. To paraphrase Yoda: Leave or do not. There is no threat.