How Not to Bomb Your Offer Negotiation

So you know the first 6 rules. You’ve maneuvered through the initial offer conversation, you’ve lined up counteroffers from other companies, and now it’s time to move into the actual negotiating.

Naturally, this is the part where everything goes horribly wrong.

But worry not. Stick with me, and I’m going to make you into a superhuman negotiator. (Or at least an eccentric billionaire negotiator, which is sometimes better?)

Seriously though. In this article I’m going to deep dive on the whole negotiating process, and discuss the final 4 rules on how to negotiate a job offer.

Right. Let’s start from the top.

What does it take to be a good negotiator?

Most people think negotiating well is just looking the other person in the eye, appearing confident, and asking for tons of money. But being a good negotiator is a lot more subtle than that.


What Good Negotiators Sound Like

You probably have a friend or family member who’s infamous for refusing to take no for an answer. The kind of person who will march into a department store and bullheadedly argue with the management until they get a purchase refunded.

This person seems like they often get what they want. They make you cringe, but perhaps you should try to be more like them.

Rest assured, this person is actually a terrible negotiator. They’re good at being difficult and causing a scene, which can sometimes convince a waitress or shift manager to appease them. But this style of negotiating will get you nowhere when negotiating with a business partner (that is, an employer).

A good negotiator is empathetic and collaborative. They don’t try to control you or issue ultimatums. Rather, they try to think creatively about how to fulfill both your and their needs.

So when you think of negotiating a job offer, don’t imagine haggling over a used car. Think more like negotiating dinner plans with a group of friends, and you’ll fare much better.

Slicing up the cake

Another important difference between good and bad negotiators is that bad negotiators tend to think of a negotiation as a zero-sum game.

Imagine we’re negotiating over a cake. In a zero-sum negotiation if I get one more slice, you get one less. Any gain I make comes at your expense.

This seems obviously true with cake, right? So what makes a job negotiation any different?

Ah, but it’s not actually true for cake. What if I hate corner pieces and you love them? What if I really like the cherries? What if I prefer to scrape off some of the frosting, but you love extra frosting? What if I’m full and you’re starving, but you’ll agree to treat me to my favorite cake next time?

Of course, when I posed the question I didn’t mention anything about cherries or my feelings on corner pieces. It might seem like I just made shit up.

But this is exactly what good negotiators do. They bend the rules. They question assumptions and ask unexpected questions. They dig to find the core what everyone values and looks for creative ways to widen the terrain of negotiation.

While you were thinking about how to haggle over slices, I’m thinking about how to give both of us more than just half of a cake.

Different parties in a negotiation almost always have different value functions. We may value the same things—we both care about cake, after all. But we we don’t value them in exactly the same way, so there’s probably a way to give each of us more of what we want.

Most people go into a job negotiation thinking they need to stubbornly haggle over salary like slices of cake. They don’t ever stop to ask—hey, what do I actually value? Why do I value it? What does the company value? Why do they value that?

There are many dimensions in a job negotiation: salary, signing bonus, stock, a year-end or performance bonus, commuter benefits, relocation expenses, equipment, an educational stipend, a childcare stipend, extra vacation time, a later start date, getting a dedicated hour a day to work out or study or meditate or play solitaire. You could choose which team you’re assigned to, what your first project will be, what technologies you’ll be working with, and sometimes even choose your title.

Maybe you’re a frosting person, and the company is more into cherries. You never know if you don’t ask.

Hold onto this mindset.


Let’s pick up the negotiation where we left off. All the offers are in, and recruiters are eagerly awaiting for you to get the ball rolling.

Let’s start negotiating.

Phone vs Email

Your first decision is whether you’re going to negotiate over the phone or keep it over e-mail.

Talking on the phone not only signals confidence, but more importantly, it allows you to build a strong relationship with your recruiter.

Talking on the phone enables bantering, telling jokes, and building connection. You want your recruiter to like you, understand you, empathize with you, and want you to succeed. Likewise, you want to care about your recruiter and understand what’s motivating them.

The best deals get made between friends. It’s hard to make friends over e-mail.

However, if you don’t have confidence in your negotiation skills, you should try to push the negotiation to e-mail. Written, asynchronous communication will give you more time to strategize and make it easier to say uncomfortable things without being pressured by a recruiter.

That said, recruiters will always prefer to get you on the phone. It’s essentially their home turf. They’re also well aware that negotiating is easier over e-mail, and they have little interest in making it easier on you. They’ll often be vague about the offer over e-mail and only offer to discuss specific details on the phone.

If you want to stick to email, you have to push back against this. There’s no secret to it: just be honest and ask for what you want.

Tell them:

Hi recruiter, I hope your day is treating you well!

Re: your previous e-mail, I’d prefer to discuss the details of the offer over e-mail. I sometimes get nervous during important phone calls, so discussing the offer over e-mail helps me to keep a clear head and communicate more clearly. I hope this is okay with you. :)

No bullshit, no huff-puffery. Just telling the truth and asking for what you want.

There’s tremendous power in honesty and directness. Take advantage of it.

(Also, note how I wrote “discuss the details of the offer” rather than “negotiate.” Never describe what you’re doing as negotiating—that sounds immediately adversarial and haggley. Describe it instead as a discussion, and they’re less likely to recoil.)

Having Alternatives

I mentioned before how essential it is to have multiple offers. I’ll reiterate again—it’s very, very valuable to have multiple offers.

With other offers on the table, if your negotiation doesn’t work out, they know you’ll just accept another offer. Your negotiating position suddenly becomes a lot more credible because they know you’re willing to walk away.

This effect is strengthened if you get an offer from a prestigious company. And the effect goes through the roof if you have an offer from a company’s primary competitor (now they’ll really want to poach you from the big bad competitor-corp).

Some of this behavior is stupid tribalism. And some part of it is rational in trying to deprive competitors of talent. Either way, take advantage of it, and be tactical in which companies you aim for.

But what if you don’t manage to get any other offers? Does all the negotiating just go out the window?

Not at all. What’s important here is not actually having other offers. More specifically, it’s in having strong alternatives. Which is why Rule #6 of negotiating is: have alternatives.

A negotiation needs stakes. If there were no risk and you knew for sure the other side would sign a contract, what incentive would you have to offer them anything more?

Your alternatives are what give a negotiation its stakes. By signaling your alternatives, you allow your interlocutor to develop a mental model of when and why you’ll walk away from the negotiation. Your alternatives also have an anchoring effect on how much the other side thinks you’re objectively worth.

In negotiation literature, your best alternative is often referred to as your BATNA (Best Alternative To a Negotiated Agreement). Basically, it’s what you’d do if you walked away.

I like the term BATNA a lot, mostly because it sounds like a gadget Batman would lob at bad guys.

So what’s your BATNA if you don’t have other offers? Do you even have one?

Of course you do. Your best alternative might be “interview at more companies” or “go to grad school” or “stay at your current job” or “go on sabbatical in Morocco for a few months” (as it was for a friend of mine who was deliberating between joining a startup and gallivanting through North Africa).

The point is, you don’t need to have another offer to have a strong BATNA. Your BATNA’s strength comes from 1) how strong the other side perceives it to be, and 2) how strong you perceive it to be.

If your recruiter thinks that going to grad school is an awesome thing to do, then they’ll see you as having a very strong alternative, and the stakes of the negotiation will be raised.

But even if they think grad school is ridiculous, if you convince them that you’d be totally happy to go to grad school, then the burden is on them to make this deal more attractive to you than going to grad school.

Thus, you need to communicate your BATNA. This doesn’t need to be ham-fisted, but you need to make it a background to the negotiation. (Note: usually whenever you signal your BATNA, you should also re-emphasize your interest in reaching an agreement).


I’ve received another offer from [OTHER CORP] that’s very compelling on salary, but I really love the mission of [YOUR COMPANY] and think that it would overall be a better fit for me.

I’m also considering going back to grad school and getting a Master’s degree in Postmodern Haberdashery. I’m excited about [YOUR COMPANY] though and would love to join the team, but the package has to make sense if I’m going to forego a life of ironic hatmaking.

Note: one of the biggest mistakes I see here is from people who are currently working. If you already have a job, staying where you are is often your BATNA.

This means if you tell your interlocutor that you hate your job, then they know your BATNA sucks, and have no incentive to negotiate with you (on top of potentially thinking that you’re a negative person). Always emphasize the pros of your current company, your seniority, your impact, and whatever else you like about where you currently work.

You should make your decision seem genuinely close for it to be a strong BATNA.

What a Job Negotiation Means to an Employer

I’ve kept saying that to be an effective negotiator you need to understand the other side. So let’s take a look at what it’s like to negotiate as an employer. (I’m going to have to use the tech industry in my examples here; the details will differ by industry.)

First, we have to rewind and understand what brought us to this offer in the first place. What kind of resources have they spent so far in trying to fill this position?

  • Writing and posting a job description on all appropriate channels ($300)
  • Reviewing ~100 or more resumes ($1250)
  • About 15% of those resumes need to be phone screened, so roughly 15 phone screens ($2250)
  • Around 75% of those initial phone screens warrant a technical screen, so roughly 11 technical screens ($9000)
  • About 30% pass through to an on-site, so roughly 3 onsites. These onsites require the coordination of 6-7 employees ($10800)
  • Finally, they make one offer. The recruiter (and potentially the executive staff) need to spend time on the phone with the offeree convincing and negotiating. ($900)

Numbers nabbed from here.

All-in-all this process took about 45 days from start to finish.

Now say you end up turning down their offer. They’ve spent over $24,000 just extending this single offer to you (to say nothing of opportunity costs), and now they’ll essentially have to start over from scratch.

This is what a company faces if you turn them down.

Realize what a gauntlet they’ve been through!

Realize how important it is that you’re the one!

Out of the droves and droves who’ve shown up on their doorstep, you’re the one they want. They want to usher you into their tribe. They went through so much crap to get you here, and now they’ve found you.

And you’re worried that if you negotiate, they’ll take it away?

Further yet, understand that salary is only one part of the cost of employing you. An employer also has to pay for your benefits, your equipment, space, utilities, other random expenses, and employment taxes on top of all of that. All-in, your actual salary often comprises less than 50% of the total cost of employing you.

(Which means they expect that your value to the company, in terms of the revenue you’ll generate, to be more than 2x your salary. If they didn’t believe that, they wouldn’t be hiring you at all.)

So, this is all to say: everything is stacked in your favor. It doesn’t feel that way, but it absolutely is.

Realize that when you are agonizing over whether to ask for another few thousand dollars, what they’re doing is praying with bated breath that you’ll sign the offer.

If you don’t sign the offer, they lose. Losing a good candidate sucks. No one wants to believe that their company isn’t worth working for.

They want to win. They will pay to win.

And yet, you might worry: “but if end up negotiating more, won’t they have higher expectations? Won’t my boss end up hating me for negotiating?”

No, and no.

It’s your role that will determine your performance expectations, not how much you negotiated. Making 5k more or less in salary doesn’t matter at all. Your manager will literally just not care about this.

Remember how expensive it is to even employ you in the first place! Nobody’s going to fire you because you’re performing 5K worse than they expected you to; the cost of firing you and hiring someone else is a lot more than 5K to begin with.

And no, your boss won’t hate you now. And in fact, at most big companies the person you’re negotiating with won’t even be your boss. Recruiting and management are totally separate departments, completely abstracted from one another. And even if you’re at a startup, trust me that your boss is used to negotiating with candidates and doesn’t put nearly as much significance in it as you do.

In short: negotiating is easier and more normal than you think, and companies are completely willing to negotiate with you. If your intuition tells you otherwise, trust that your mental model is wrong.

How to Give the First Number

In part 1, I mentioned how valuable it is not to have to give the first number. But there are times when you can’t avoid it. In that case, there are ways to give the first number without giving the first number.

If a company asks you “what are your salary expectations?” you might say:

I don’t have any particular numbers in mind. I’m more interested in learning whether this will be a good mutual fit. If it is, I’m open to exploring any offer so long as it’s competitive.

Sounds good. But they push back,

I understand that, but we need to have a clear idea of what you think is competitive. I need to know whether it’s worth going through the interview process. We’re a young startup, so I need to make sure we’re on the same page as far as compensation.

That’s a strong push. But you can still push back.

I completely hear you, and I agree it’s important that we’re on the same page. I really have no particular numbers in my head, it all depends on the fit and the composition of the offer. Once we decide we want to work together, I think that’s the best time to figure out a compensation package that makes sense.

Most employers will relent here. But there’s a small chance they push further:

Okay, look, you’re being difficult. Let’s not waste each other’s time. What’s an offer that you’d be willing to take?

This is a decision point. They’re trying to take away your negotiating power and pin you to a premature decision.

That said, you probably will have to say a number at this point, or risk damaging the trust in this relationship. (They are making a valid point that startups can’t offer the same kind of cash as large companies, nor should you expect them to. They might be sensing that you’re not aware of this.)

But you can give a number here without actually giving a number.

Well, okay. I know that the average software engineer in Silicon Valley makes roughly 120K a year salary. So I think that’s a good place to start.

Notice what I did here. I didn’t actually answer the question “what’s an offer you’d be willing to take,” I merely anchored the conversation around the fulcrum of “the average software engineer salary.”

So if you’re forced to give a number, do so by appealing to an objective metric, such as an industry average (or your current salary). And make it clear that you’re merely starting the negotiation there, not ending it.

How to Ask for More

Say an offer is out there, and now you want to improve it. As always, be direct and ask for what you want. Here are generally the steps you should take.

First, reiterate your interest in the company. This is as simple as:

I’m really excited about the problems you guys are working on at Evil Corp…

Now frame why you’re asking for more. There are two choices here: you can say that you’re on the fence and that an improvement might convince you, or you can go stronger and say that you’re outright dissatisfied with the offer. Which approach you choose depends on how much leverage you have, how weak the offer is relative to your BATNA, and whether you have other offers (the weaker your negotiating position, generally the more tentative you should be).

Either way, be unfailingly polite.

If you’re dissatisfied with the offer, you might say something like:

I appreciate the work you guys put into constructing this offer. But there were a couple things I was unsatisfied with.

If you want to be more reserved, you can say something like:

The offer you guys extended was strong. Right now my decision is basically between you and [XYZ CORP]. It’s a genuinely difficult decision for me, but there are a couple of dimensions where, if this offer improved, it would be much more compelling.

Don’t just say something like:

Thanks for the offer. Here are some ways I think it could improve.

This makes you sound like an ass. Be polite, and if you want to strengthen the offer, tell them clearly how you feel about it. This builds trust and conveys seriousness.

Let’s say you want to raise the salary. Now that you have a specific ask, it’s time to employ rule #7: proclaim reasons for everything.

We all implicitly know the catch-22 of negotiation: if you say you want more salary, you’ll sound greedy. And no one likes greedy people, right? So why would they want to give more money to a greedy person?

I suspect this is the primary reason why so many candidates recoil from negotiating. They don’t want to feel greedy. It goes against all of their social conditioning. And yet, there are some situations in which most people would be totally fine negotiating.

Specifically, when they have to.

If you had to raise your salary or you wouldn’t be able to afford rent, or if you had to negotiate health insurance to cover a medical condition, you’d negotiate without a twinge of regret. The difference? That you have a reason for what you’re requesting.

It’s kind of a brain-hack, both for yourself and for your negotiating partner. Just stating a reason—any reason—makes your request feel human and important. It’s not you being greedy, it’s you trying to fulfill your goals.

The more unobjectionable and sympathetic your reason, the better. If it’s medical expenses, or paying off student loans, or taking care of family, you’ll bring tears to their eyes. I told employers that I was earning-to-give, so since I was donating 33% of my income to charity, I had negotiate aggressively to leave myself enough to live off.

But honestly, even if your reason is inane and unimpressive, it will still carry this effect.

Just saying “can you improve the salary?” sounds like you’re boringly motivated by money. But if you say “I really want to buy a house within the next year; what can we do to improve the salary?” this suddenly seems a lot more legitimate.

If they turn down your request now, they’re implicitly telling you “no Jennifer, you can’t buy your house. I guess you don’t deserve one.” No one wants to do that. They want to be the one who says “Alright Jennifer, I talked with the director and I made it happen. You’re getting that new house!”

Of course, it goes without saying that the reason you want money is so that you can spend it on things. What do they think you’re going to use it for, toilet paper?

I know. It’s stupid. It’s really stupid, but it works.

Just go with it, state a reason for everything, and you’ll find recruiters more willing to become your advocate.

Assert your Value

One effective move you can make in a negotiation, especially after an ask, is to emphasize the unique value you’ll be bringing to the company. Example:

Blah blah blah, I want X, Y, and Z.

I know that you guys are looking for someone to build out your Android team. I believe I bring a lot of experience leading a team of Android developers and I’m confident that I’ll be able to bring your mobile offerings up to parity with your competitors.

Let me know your thoughts.

Be confident without boasting or trying to hold yourself specific metrics (unless you’re supremely confident). Whatever you assert should be something you’ve touched on earlier in your discussions, but it’s okay to repeat it now as a gentle reminder. It reminds them of the carrot and shows that you’re still excited to add value.

This is not appropriate in every negotiation, especially for very junior positions, where it’s harder to differentiate yourself. But later in your career (or for more specialized/consulting roles) this can be a really valuable nudge.

What to Ask For

This brings me to rule #8: be motivated by more than just money. Note, this is not code for “if you seem like you’re motivated by more than just money, you’ll get more money.”

There is no bigger turn-off to a company than somebody who only cares about money. This is something you’re not going to be able to fake.

Actually be motivated by other things. You should be motivated by money too of course, but it should be one among many dimensions you’re optimizing for. How much training you get, what your first project will be, which team you join, or even who your mentor will be—these are all things you can and should negotiate.

Among these factors, salary is perhaps the least important.

What do you really value? Be creative. Don’t try to haggle over slices of cake when there’s so much more on the table.

Of course, to negotiate well you need to understand the other side’s preferences. You want to make the deal better for both of you. That’s why rule #9 is: understand what the company values.

How do you figure this out? Well, there are a few good rules of thumb.

First, salary is almost always the hardest thing to give, for a few reasons.

  1. It must be paid year after year, so it becomes part of a company’s long-term burn rate.
  2. It is almost always the thing that people gossip about, so paying someone significantly more salary can cause unrest.
  3. It tends to be the most tightly constrained by pay bands, especially at large companies.

So if you want more financial compensation, you should think about structuring as much of it as possible outside of salary. A signing bonus, for example, is easier to give than salary. A signing bonus has the advantage of only needing to be paid once, it gets the candidate excited about joining (because everyone likes wads of cash), and it’s generally not as public.

Remember that you can always get salary raises as you continue to work at the company, but there’s only one point at which you can get a signing bonus.

The easiest thing for a company to give though is stock (if the company offers stock). Companies like giving stock because it invests you in the company and aligns interests. It also shifts some of the risk from the company over to you and burns less cash.

If you are genuinely risk-neutral or early in your career, then you should generally try to assume as much stock as possible. If you aggressively trade cash for stock, you can end up with a higher expected value offer (albeit with higher risk).

A Brief Primer on Equity

You can skip this section if you’re already pretty familiar with how equity works. I’m going to speaking to the totally uninitiated here, because too many people get swindled when it comes to valuing stock.

First, understand there are two completely different classes of companies: public companies and private companies. If the company is public (i.e., it has IPOed and is listed on the stock market), then its stock is as good as cash. You will usually be granted RSUs (Restricted Stock Units), which are just shares like you can purchase on the stock market. Once these shares vest (that is, are released to you), you can turn around and sell them on the stock market. This is how they turn into money.

If the company is private, then things get a lot more complicated. For private companies, most of the time they will not actually issue you stock grants. Usually, they will issue you stock options. An option is a pre-agreed right to purchase shares of stock at a frozen price.

It’s important to note that when you want to leave a company, if you have options, your life becomes really complicated. You may have to pay a bunch of money to actually exercise your option (that is, buy your pre-agreed upon stock at the previous frozen price, or risk losing it), with no way to actually sell it yet. The only way to truly liquidate your options is when the company IPOs or is acquired. And many companies don’t ever do either.

Thus, options are very risky. It’s easier to get screwed by options, especially on tax implications. For a lot more information, see this post by Scott Kupor of a16z.

Equity Shenanigans

Many companies will try to play mindgames with you when it comes to equity. Several companies pulled these on me.

A common one is presenting the total value of the stock grant rather than the annualized value, despite the the stock not vesting evenly, or vesting over 5 years instead of the standard 4.

But the most egregious thing that companies will do is tell you absurd stories about the value of their stock. They’ll say: “okay, we’re worth this much now, but at the rate we’re growing we’re going to be worth 10X that in a year. So really, the value of your options is many millions of dollars!”

To not mince words: this is cynically dishonest bullshit. Don’t buy it even for a second. I got this a few times, and the only reason I didn’t walk away from the offer immediately was because it was always a recruiter pulling this crap. If it was a manager I would’ve turned down the offer outright.

Here’s why this is infuriatingly stuptags: [a company’s valuation is determined by investors. These investors see the financials and the growth rate of the company, and invest at a price that reflects the current growth rate of the company. In other words, they invested at a valuation that already took their 10x growth rate into account. Investors are not idiots. And unless you (or your recruiter) think you have privileged information or insight that the company’s investors don’t, you should probably take the investors’ word for it.

(Not to mention a company’s nominal valuation is almost always inflated due to preferred shares, debt, and survivorship bias, but let’s ignore that for now.)

So if a company gives you this hock of crap, fire back and tell them thank you, but you’ll be considering the stock at the same valuation their investors valued it at.

I mean, be nice. But don’t let them try to strong-arm you into accepting this garbage.

A job is not a suicide pact. Choose a company that is judicious and transparent, and you’ll be much more likely to find yourself respected and taken care of.

Other Things You Can Ask For

Because I’d be remiss if I didn’t point out a few other things.

Relocation expenses often come out of separate budgets at big companies, so this is generally very easy to get.

Look for creative benefits that would be particularly valuable to you. Maybe it’s covering your commuter expenses, asking for dedicated volunteer or learning time, getting sponsored for conferences, or even charity donation matching.

Don’t assume anything’s off the table until you’ve tried bringing it up.

That said, don’t throw the entire kitchen sink at them. A negotiation can quickly become cumbersome for an employer if you bring up a litany of changes. Keep the changeset as pithy as you can.

Negotiating Jiu Jitsu

Recruiters love trying to trick you into ending the negotiation early. They’re going to do this relentlessly. Don’t fault them for it—I suspect they can’t help themselves.

Just keep breaking out of their shenanigans, and don’t let yourself be pressured into ending a negotiation until you’re actually ready to make a final decision. This is especially grave if you have multiple offers, and you let one company pressure you into canceling the others. Companies succeed in doing this all the time, so I want to equip you with the skills to jiu jitsu out of these techniques.

Here are two situations you can break out of. (These are both real situations that happened to me during my negotiations, though the numbers and details are invented.)

Situation 1:

I ask for a 10K increase in signing bonus. The company gets back to me and says,

That’s really tough for us to do. I’m going to try, I think you’re worth it, but I can’t really go to my boss and fight for you unless she knows you’re going to sign. Are you going to sign if I get you that 10K?

You should be thinking: ah, this person is trying to force me to a decision point and take away my negotiating power.

I respond:

Okay, so what I’m hearing is that you’ll have to expend some personal reputation to get me a 10K bonus. If you end up going to bat for me, are you confident you’ll be able to get that 10K?

They respond:

I think I can, it just comes down to you Haseeb. If you’re serious about joining us, then I’ll go fight for you. But I need to know for sure you’ll sign.

Great. Time to Jiu Jitsu.

That makes sense. Unfortunately I can’t commit to signing yet; I’m not yet at the stage where I can make a final decision. Like I told you before, this weekend I’m going to sit down with my family and talk things over with them. Choosing the company I’m going to spend the next few years at is a commitment I take really seriously, and so I want to be sure I’m making a well-considered decision.

But since you’re confident that you can get an extra 10K, let’s do this instead: in my mind, I’ll pretend this offer is [X + 10K] and as I’m considering my final decision, that’s where I’ll value it. I know it’s tough for you to go and get that from your boss, so I don’t want you to do that until I’m certain I’m going to sign.

They then vaguely recant and promptly get approval for the 10K bonus.

Situation 2:

I ask for a 20% increase in stock package. The hiring manager, knowing that I’m negotiating with other companies, then fires back:

I want to get this stock package for you. And I know I can, we’ve got the budget. But before I do that, I need your word on something.

What’s that?

I need you to give me your word that if I improve your offer, you’re not going to just turn around and take our counter-offer to [COMPETITOR_COMPANY] to improve your offer with them.

You should be thinking: so basically they’re asking me not to negotiate. Cute.

Let me see if I understand what you’re saying. You are willing to improve my offer, but only if I agree that I won’t tell [COMPETITOR] what you’re offering me. Is that correct?

Well no, I can’t legally do that. What I mean is…what I mean is, look. I like you. But if I improve your offer and you just take our offer to [COMPETITOR], you’ll be violating my trust.

Okay, let me be sure I understand you here. If you give me this offer and I tell [COMPETITOR], I will be violating the trust under which you’re granting me this improved offer. Is that correct?

Uhh…Look. How about this. In my mind, I’m going to go get you this stock package okay? And in my head, I’m going to do it with the assumption that you’re the kind of person I think you are, and you’re going to consider our offer in its own right and not just shop it around. Fair enough?

I nod. He gets the improved offer. I continue to negotiate. Antics averted.

(In case you’re wondering, if he had said “yes,” I would have turned down the proposal.)

The Path to Signing

It’s not enough to just continually ask for stuff. Companies need to sense that you’re actually moving toward a final decision, and not just playing games with them.

Your goal in a negotiation is not to be difficult or elusive. True, you should assert your value and carefully consider your options, but you can do so in a way that’s respectful and considerate toward the companies you’re talking to.

Don’t go dark on people. Be open and communicative. I keep saying be honest and I mean it—be honest.

Aside: I keep talking about honesty, and you might protest that this is antithetical to my earlier rule of “protect information.” It’s not. True, you should protect information that might weaken your negotiating position, but you should be as communicative as possible about everything else (which is most things).

Negotiating is all about relationship, and communication is the bedrock of any relationship.

This brings me to the the final rule: be winnable. This is more than just giving the company the impression that you like them (which you continually should). But more so that you must give any company you’re talking to a clear path on how to win you. Don’t bullshit them or play stupid games. Be clear and unequivocal with your preferences and timeline.

If there is nothing that a company could do to sign you, or you don’t actually want to work for them, then don’t negotiate with them. Period.

Don’t waste their time or play games for your own purposes. Even if the company isn’t your dream company, you must be able to imagine at least some package they could offer you that would make you sign. If not, politely turn them down.

It costs each company money to interview you and to negotiate with you. I didn’t negotiate with every company I received an offer from, but if there was one key mistake I made in my job search, it was that I still negotiated with too many (in large part because I didn’t think my job search would be successful).

Making the Final Decision

Okay, it’s decision time.

(Yes, you do have to make one.)

Three things to keep in mind here:

  1. Be clear about your deadline.
  2. Assert your deadline continually.
  3. Use your final decision as your trump card.

When you start negotiating you don’t have to be clear about your timeline because you probably don’t have one yet. But once you get into intermediary stages, you should set for yourself a deadline on which you’ll sign. It can be for an arbitrary reason (or no reason at all), but just pre-committing to a deadline will allow you to negotiate more clearly and powerfully.

“A weekend with the family.” I found works nicely, as it has the added benefit of roping other decision makers in. Then when companies push you to end negotiations early, you can re-assert this deadline.

Companies should all be totally aware of when you’re going to make your decision. This will raise the stakes and galvanize negotiations as the deadline approaches.

This deadline also lets you defer your decision while still improving offers. Your narrative should basically be “I want to see the strongest offer your company can muster. Then I will go into my cave, meditate for 10 days, and when I emerge I will have decided in my heart which company to join.” This gives you enormous power to avoid any on-the-spot decision points or premature promises.

Eventually, deadline day will come. Try to make this a business day (say, a Friday or a Monday) so that you can communicate with recruiters during this day. If a hail mary is going to happen, it’ll happen here.

Even if there’s only one company in the running, you should always always wait until the last day to sign your offer. Yes, even if you’re certain you’re going to sign and even if it’s your dream job. I’ve seen many scenarios in which offers spontaneously improved as deadlines approached, or a fallen player gets up and presents you the holy grail in the 11th hour. Either way, there’s no harm.

Finally, your trump card. Save this for the very end. Your trump card is these words: “If you can do X, I will sign.” Note, this is NOT “If you give me X, the offer will be more compelling blah blah blah.” Fuck that. It’s time to make a promise.

Every company that’s still on the table, let them know what it would take to sign you (unless there’s nothing they could do). And when you make the final ask, don’t forget reason-giving, even if it’s the same reason as before!

Hi Joel, I’ve been thinking it over and it’s genuinely a really tough decision for me. I loved everyone at [COMPANY] but the one thing that makes it hard for me is the salary. As you know I’m trying to pay off my student loans so salary is really important to me right now. If you can improve the salary by 10K a year, then I’ll be totally ready to sign.

With luck, they meet you half-way. Or, with a little more luck, they’ll meet you all the way.

And just because I know someone will ask—yes, once say you’re going to sign, you should always sign. Never go back on your word. It’s a small world, people talk, and these kind of things will come back to haunt you. (More importantly, never go back on your word because you’re the kind of person who never goes back on their word.)

Tell all of the other parties that you’ve made your final decision. Thank them for the negotiation. If you did it well, they’ll usually thank you back, tell you to keep in touch, and to reach out again in a couple years next time you’re on the market.

And that’s it. You did it! Congratulations! You’re still alive, right?

…You’re not moving.

Well, that’s fine. It’s time to celebrate your new job, you beautiful fool! (Drinks are on you.)

If you got some value out of this article, share it with a friend who’d benefit from it. Or better yet, follow me on Twitter and I can be your friend.

There’s a lot more in the works.

Until next time,

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Managing Partner at Dragonfly. Effective Altruist. Airbnb, (acquired by Coinbase) alum. Writer. Former poker pro. Donate 33% of my income to charity.

San Francisco
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