Bullish: How To Ask For More Money, Part I

There’s a lot of advice out there about negotiating for raises. Do it, and do it often; keep records of your accomplishments so you can make your case. Please, dear god, make sure your sentences don’t come out sounding like questions. (I need a raise? I am a valuable member of the team?)

Here’s the Harvard Business Review on How to Negotiate Your Next Salary. From HBR, among other suggestions: Do your research on what the company pays others and what other companies pay for your role. (I have long advocated salary openness – see Bullish: How Talking About Money Can Make You More of It.)

But I think that a lot of the decisions and communications that determine how much money you make just don’t always happen in a formal negotiating meeting, in which you know in advance that you will be discussing your salary and that you should come prepared.

I think a lot of the difficulty of negotiating is even knowing when the negotiating part starts. (If you’re wondering, maybe it already has! Or maybe it never starts unless you start it!) Sometimes, “negotiating” is spending an hour writing a three-sentence email spelling out your requests.

I also think that there are a lot of ways to get more money without having to think as though you’re going into combat. Sometimes, companies are doing well, and asking for money isn’t that big a deal, and also wins you respect from the people around you who were making more than you the whole time. Asking for more shows self-awareness. It’s not a fight; it’s a way to become a peer.

Other times, wherever the battle over money takes place may not be where you think. Better to have people on your team than have to persuade enemies.

Here are a few ideas.

Try drafting the decisionmaker to your team.

If you are negotiating a fee for a freelance gig or a salary for a full-time position, there are a few postures you can take.

You can make a negotiation sound like a polite argument if you want. Sometimes that’s just how it goes. You can give ultimatums! Awkward.

But sometimes the person doling out the money doesn’t have that much personal stake in it. If she screws you over, she’ll get a pat on the back from a higher-up for saving the company a few thousand dollars. Or, if she helps you out, she’ll get a pat on the back from you, and a mere shrug from those higher-up. The money’s not coming out of her pocket. Her motivations are shifting and unclear.

Sometimes you can draft her onto your team.

Assume that the person is on your side, fighting with some kind of “bad cop” who controls the money. So, instead of, “I need you to give me more money,” it’s like, “I trust you to get me as much as you can from the big guys.”

In actual practice, I’ve often had success with, “Look, I really want to work with you – I trust you to get me as much as you can.”

This has worked well when working with professors trying to bring my educational comedy shows to their university. Of course we’re on the same team! We want to share the love of punctuation with young people! So, “My fee is $2,500, but you know the ins and outs of the administration – I trust you to get what you can for me.” It has also worked well in a variety of other situations.

In one case, this strategy got me an extra $7,000 on a freelance contract that had already been negotiated, but turned out to be a lot more work than I thought. I said, “I know the contract’s already signed, but if you have a way for you to pull some strings the company…” As it turned out, that guy did have a way to pull some strings with the company. And when I got paid, he (I assume) felt like he had done a good deed – standing up for someone who needed it – rather than like he’d been strongarmed into doing something he didn’t want to do.

Even in cases in which the person paying you really is the decisionmaker, a bit of feigned naivete can work here. “It’s been great meeting you! I know you’ll talk to whoever you need to to make my case, and I hope it works out!”

In a full-time job situation (things are looser in small businesses and startups), you can sometimes spin this as, “I like the top people here so much that I would like to join your club now. The club where we are all awesome together and get paid accordingly. I respect the fuck out of you. Let me into your Borg cube!”

It’s kind of like pledging a fraternity. But still: this is a presumptive sales attempt to get yourself and the decisionmaker on the same team.

Imagine an adult life drastically different from the one you have now.

In The Princess Problem, Laura Vanderkam wrote that young women do not plan and negotiate based on the very real likelihood that they will have to be breadwinners for their future families:

There are many reasons women earn less than men. Discrimination is one, but expectations matter, too. Young men are four times more likely to negotiate their first salary than young women, according to Linda Babcock and Sara Laschever’s 2003 book Women Don’t Ask, resulting in $500,000 more in earnings by age 60. Sure, it’s tough to ask for things, but as Claire Shipman and Katty Kay’s best-seller Womenomics documents, professional women increasingly negotiate for flexibility and part-time positions. Money appears to be the exception. Since women will do things for their children that they’d never do for themselves, the likely explanation is that young women do not see supporting their future children financially as a crucial part of mothering.

When negotiating, please assume that your future self – a gentlewomanly 35 or 45 year old – will want to own property, will be funding her own retirement, and will at some point need to support people other than herself.


(See Bullish: Breaking Free From Terrible Situations for more on the idea of your future self.)

Even if you don’t plan to have kids, it is likely that any partner you may have will get sick or be unemployed for awhile, and/or that your parents will get sick and stay sick for a long time.

If you are a twenty-five year old woman for whom financial independence itself seems like quite an accomplishment, you simply cannot think like that when you are negotiating. If needed, imagine you are your 45-year-old self. Imagine you are Helen Mirren dressed as the Queen. Imagine you have someone else’s nursing home bills to pay.

You might also come prepared with a Very Serious Adult Reason like the above to the question, “Why do you need all that money?” For instance, “My parents are getting older, and as the oldest/only/most responsible one in the family, I need to be prepared to step up.” It’s nice to have that in the back of your mind – except that no one will ever ask you that.

I think that every time I’ve ever half-expected someone to ask me, “What do you need that kind of money for?”, instead, someone has been pretty impressed that, obviously, other people must be paying me that kind of money.

In so many areas of life, the rich get richer and the poor get poorer. Asking for more money often gets you both money and respect (especially from men), whereas being “nice” or taking one for the team gets you neither money nor respect.

(See Bullish: Extreme Advance Planning for Very Smart Women.)


I think it’s morally acceptable to lie when you are asked for personal information that’s none of anyone’s business.

In life, if the man at the deli asks whether you’d ever sleep with someone on a first date, a good response would be, “Excuse you.”

But in a job interview, if someone asks you whether you have a boyfriend, saying “I don’t think that question is appropriate” is fine but of course puts the chill on things; I think it would also be acceptable to say whatever answer you think the interviewer wants. So, “No, I’ll worry about that in a few years when I’ve reached management level,” or, “Yes, I live a pretty settled lifestyle.”

I also think it would be fine to tell the man at the deli that you always sleep with men on the first date, but only attend first dates that take place on private jets. Or that you’re married to God.

People who ask you inappropriate questions deserve your deflection.

A friend of mine – let’s call her Francesca – was working at a company where she knew she was underpaid by a considerable margin; her manager said openly, “You could get $20,000 more if you went somewhere else.”

Soon, an old college friend put Francesca in the running for a new position. Even for a high-level job, she was asked to fill out a boilerplate application. (In pen! “Have you ever been arrested for a felony?” Etc.)

The form asked for “Current Salary,” which is when she called me. “This is just a blatant attempt to pay me less!”, she opined.



I debated with her the merits of lying. Sure, it could backfire. Theoretically, if you lie anywhere in the hiring process, then if the company found out and wanted to fire you, they could take you to court. Theoretically. (If you’re a freelancer, the chance of repercussions from lying about what other clients pay you is basically nil.)

But if Francesca was making $70,000 when her current manager and the friend who referred her for the new position both agreed she should be making at least $90,000, putting $70,000 on the form was going to keep her earning less than she was worth … forever.

She put $90,000 as her current salary, and asked for $95,000. She received $95,000.

I think that if a company is willing to pay you $95,000 for your work, your work is therefore worth $95,000. No need to give some HR person an excuse to exploit you based on the dick moves of the previous person who exploited you.

And trust me: If a recruiter or HR person has a limited budget for hiring and needs to bargain someone down, young women are Walking … Fucking … Targets. We’ve found the three candidates we want to hire, but we don’t have the $250,000 in the budget that it would take to make all of them happy. Who can I get to work here for $7,000 less than they requested? Um, the girl.

Don’t let that happen.

I am reminded of an anecdote about actor Jerry Doyle, now a talk radio host, and most famous for playing Chief of Security Michael Garibaldi (a tough Bronx cop, out in space!) on the science fiction show Babylon 5. Doyle had little to no acting experience and lied on his resume to get the role. Of course, he must have also nailed the auditions, which is kind of the important part.

As legend has it, when the writer/producer of the show discovered the deception – after Doyle had been playing Garibaldi for some time – he shrugged and said, “Yep, that’s what Garibaldi would do.” It was cool.

(See also Bullish: Are You Thinking Too Small?)

When things get really bad…

One woman wrote to me in a pretty bleak situation – she was moving to a more prestigious role, but it turned out she would actually be taking a pay cut. She was in the middle of negotiating, via email, for a salary I would characterize as, “similar to the free packet of peanuts they give you on the plane.”

Yet, when you are in that kind of situation, every extra thousand dollars a year matters. It matters a lot. It’s the difference between packing regular sandwiches for work or “sandwiches” that are mostly filled with the free condiments in the office fridge (mmn, ketchup and pepper on white bread!)

A few bits of advice for making the best of a bad situation:

Don’t agree to a range. If you agree to “$30,000 to $35,000,” you’re getting $30,000.

If you’re taking a pay cut, don’t say so. No pity parties. Just negotiate for the most you can. Some people will not respect you if they find out you’ve taken a pay cut. If anyone does find out, shrug it off and say, “It was worth it – this place is obviously a better way to build a career.”

When asked for your minimum, don’t give a real minimum. Imagine the minimum of the person asking the question. That person eats real sandwiches, takes vacations, and gets decent haircuts. Also, your minimum must account for emergencies (laptops break all the time, and that’s hardly the worst “emergency” you can imagine) and savings. Don’t give a girl-minimum.

Again, try to draft the person to your side. Not, “I think I can eke by on $30,000 per year,” but, “You know what the cost of living is in Chicago these days.”

In sum…

There’s a little bit of subtext here, in that a lot of women do hew to stereotype: We don’t like conflict and we’re pushovers.

Studies have repeatedly shown that women ask for less money and ask less often. One bad negotiation can put you thousands of dollars behind, per year. Plus compound interest and shit. An entry-level negotiating mistake can easily mean hundreds of thousands of dollars over a lifetime.

Your future self may want all kinds of weird stuff that you cannot possibly imagine now. (I didn’t like beaches or beer until I was 30! In a decade, I went from living in squalor to pressing creases into my hand towels!) But whatever she desires in future decades, she’ll want options and resources.

I guarantee you that your future self is not going to complain when you set her up with money in the bank and a cushy career where people treat her with respect and pay her accordingly.

Originally published on The Grindstone. Next: See Bullish: How to Ask for More Money, Part II.

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