I will be negotiating salary soon, and I THINK the salary range will be a nice increase for me, but I will lose some strong benefits.

Is it impolite to be specific and compare benefits during the negotiation? Examples if the company offered $60K:

"$60K is close, but since I currently commute only 1 day per week, and here I would be expected to commute 5 days per week, I was hoping to get $70K"

or

"$60K is close, but since my current company sends me to paid training 2 weeks a year, and here I would be expected to self-study at home on my own time, I was hoping to get $65K"

Does comparing benefits like that carry any weight, or should I just do the standard negotiating of specific numbers and vacation days I am trying to get? Could comparing specifics come off as rude, or as if I am devaluing what the new company offers?

No, it's not rude. It's not only the paycheck amount that matters, there are other things, like the health insurance, vacation days, remote work ability, flexi timing etc. and lot other things to be considered when you discuss the offer.

So, previously, if something was part of your employment package, or you company paid for it, it's fair to ask whether you can get the same benefits in the new company also.

Remember, paycheck in one part of it, you'll still need to follow and comply with the company policies to do your work and ensure you keep getting that paycheck. If you're not OK with the overall perks, you're going to be not happy very soon.

Does comparing benefits like that carry any weight, or should I just
do the standard negotiating of specific numbers and vacation days I am
trying to get? Could comparing specifics come off as rude, or as if I
am devaluing what the new company offers?

It's not rude, but it may not be effective.

Just because you had a particularly appealing benefit or two in your previous company - that doesn't make you worth any more to your new employer.

In addition, you can easily fall into a "well what about" back-and-forth discussion about every little aspect of both jobs.

You would be better served coming up with an amount that you feel is a fair salary for the job and ask for that. Leave out all the hundreds of little factors that caused you to come up with this amount.

It is not rude, but it is also not likely that this path will get you anything useful in negotiation. Like, your instincts here are killer, you might even have a natural talent for negotiation, but you are pointing those instincts in an ineffective direction.

Here is a partial list of what negotiation and sales involve.

Understanding interests

Do you remember the last time someone convinced you to do something that you otherwise weren’t likely to do? Did they use threats? Did they tell you that it was in your best interest to do as they say? Was it like a soda/beer ad where they just showed you a vision of people who have their lives together who happened to do the thing they wanted you to do?

Salesfolk have a maxim, “tellin’ ain’t sellin’.” People somehow do not agree with you if you tell them what you think is true. Instead, good salespeople ask a lot of questions. They ask questions about the other party’s problems. They ask questions about the other party’s interests. They ask friendly questions about the other party’s family. They ask the ‘exactly’ questions—the ones like “so you’re saying ...?” and “am I understanding you right that ...?”—questions that in the ideal case the other person says, “Yes, exactly!”

Good salespeople want to figure out your interests, so that they can create options—tradeoffs that one or the other side could offer that could make it into the final sale. They absolutely do not want to be stuck negotiating over just one number like price. If they are there then that creates discomfort: “I want the price higher, they want the price lower, we cannot simultaneously both be happy.”

They will also, by the way, try to do as much research as they can in advance to determine these interests and options. They may come to the meeting with a notepad that contains a dozen such options or more, tailored specifically to their target.

Our commonalities can breed connection but also create competition. In the face of that competition, differences drive the deal. That is the fundamental fact of trade. If we are characters in a post-apocalyptic zombie film, and we are in exactly the same situation, I cannot trade you my weapons for your food. It does not matter how hard I try. Because we are in the same situation—we both have too many weapons and not enough food—we must compete over the scarce food with our weapons. But if we are in the same film but have different situations—if you have more weapons than you need and I have more food than I need—that difference leads to us making a deal and trading food for weapons and both being better off.

This is where you show the most talent. You are able to creatively come up with other options and trade-offs, “paid training,” or “commute less,” or, yes, “higher salary.” You can be even more creative if you would like. “I would like it in my contract that once per year I get to have a performance review with my immediate supervisor in a company-paid helicopter ride costing no more than $500.” It does not mean that they have to say yes just because it is an option—it is just one of the possible trade-offs that you could have in this discussion. The more options you can have, the better.

Do not under any circumstances then shoot yourself in the foot by trying to say “Let me tell you about all of the options that we are not doing, and let us focus only on money!”

You are cutting down the field of interests to just one and you are going to lose.

Common interests and the simple choice

“Now, I have gained a significant edge over my ancient adversary, for the first time in ages… Stay with me, and I will guarantee the Golden Age of which I spoke, and you a part in it. Leave, and you will be snatched away by the other. Darkness and disorder will follow. Which would you have?”

Luke smiled.

“I know a good sales pitch when I hear it,” he said. “Narrow it down to
a simple choice. Make them think it’s their own.”

Coral squeezed my shoulder. “We’re going,” I said.

— Roger Zelazny, Prince of Chaos

I wish I still had a copy of the best sales pitch I have ever seen. It would be so nice for reference. It was buried in one of those “this easy trick…” or “you won’t believe…” cheesy ads, so that part sucked. In addition they used a trick which I find somewhat dishonest, “we will spend an hour talking about how your digestive health impacts your brain health before we talk about what we are trying to do to solve it”—the gambit involves the sunk-cost fallacy, the idea is that you have already poured an hour into this presentation so you had better get something out of it. But if you push those aside the pitch that followed was absolutely glorious, and had the form “So let’s assume that you want to solve this problem, you want a probiotic supplement to start replenishing these good bacteria and promote good digestive health so that you can have good brain health. Here are the things that I want to recommend that you get absolutely right, or else you are just wasting your money.” And he gave a nice 5 or 10 minute tutorial about all of the trade-offs different supplements have, and which was better, and then he said, “As you can tell, I am a bit of a geek about this stuff. If you want you can do all of this work yourself and you can potentially get a good deal and that is totally up to you. But I have also started a company which just makes these pills, with all of those trade-offs done right, and if you don’t want to do all of that work, we would love to sell you some pills.” Heck, if he had not done the two other bad things, I might have likely bought from him rather than feeling exhausted.

A negotiation is about a problem, often a problem of conflicting interests. But you also have common interests, and a bigger problem that you both want to solve. Especially in employment contracts, after the above asking and listening you might be in a position to say, “okay, given what you have told me that your company needs, I can tell you that you need __ . You will kind of have two options. One is to hire someone with a subset of __ and try to train them in the other stuff. That is fine and it is cheaper and if you want me to come on as a consultant to train them on whatever they are not as good at, I would be very happy to help, but it is not absolutely necessary if you give them good direction and hire someone really willing to learn. Or you can look for someone like me who has all of __ already, but that can be a little pricier as we already have jobs so you have to pay a little extra to poach us, especially if your benefits are not quite what we are used to.”

A lot of negotiation and sales is just being on the same page about your common interests. Sometimes the best thing to say is “hey, we are both on the same side, we both want to see __ , and if we work together, I am sure we can find something that fixes the problem.”

You must never choose something for someone else. They will hate and resent you. But you do have some freedom to narrow down the choices and to massage their phrasing a little bit and to simplify, simplify, simplify. And that comes from your common interests, the fact that you are on the same side.

Now here is why I am telling you this, your examples do not point to a common interest and do not talk to this other person as if they have a real choice. Their choice is to give you more money or not, and you are not clearly articulating what they get for the extra money. You are not putting yourself “on their side” and so you are just trying to weasel a little more money out of them. It does not communicate common interests at all; you have narrowed it down to a simple choice, more or less money, but were not skillful in the “make them think it’s their own.” The excuse of “here is what I am giving up and what I expect in compensation for it” does not help, and might even hurt, since it seems to focus attention on the money and make it seem like all you care about is the money.

Rapport

There is a ton I can say about this but I think I will leave this side mostly blank. Above all else, you want someone to like you, and you want to like them. You can do this in many ways; one is to indicate your openness to feedback by actively soliciting it, “wow, as I said that sentence it felt very convoluted to me, was any of that unclear to you? if not, how could I say it better?” Also to just remember names and roles and to not make assumptions and to be deeply respectful and to avoid anger and blame. If you cannot make a deal then you want them to still think of you in glowing terms so that you can lay out the big thing, “hey, it looks like we cannot reach a contract here that works for the both of us, which is totally OK—like I said, you have a choice between these two ways to go and I think you are just better served right now by going down the other route. But, I want to schedule another interview a month from now, see whether you have found the person you are looking for. And if so, is there any one-on-one training that I might be able to offer them; and if not, I don‘t know, maybe the whole cash-flow situation that seems to be binding you is more relaxed and the buy-up option is preferable.” You want them to say “yeah this conversation was such a joy that I would love to talk to you again in a month.”

Finding what’s fair

Nobody wants to get a bad deal. Part of your research should be that you should know what is a good deal given your experience and skill-set. Actually, you should know what an aggressively high target is for you, and you should back down a little from that, so that you can get a good deal and leave your counterpart saying “yeah they drove a hard bargain but they didn’t squeeze me for every cent.”

Part of that good deal is knowing that at a big company there is generally a human resources department which does a bunch of market research and sets certain salary boundaries for a role, and then your salary might have to fall within that bracket as part of the rules of that company. You can potentially ask about such things. Can you negotiate a signing bonus? Or other bonuses? Maybe a bonus conditional on a good performance review in 6 months. Those sorts of things may still be on the table. But you really want to know what those salary boundaries are. If you are really slick you might be able to build up so much rapport that you can just ask, “so which one of these options is right for you depends on how much money your HR department is willing to go towards, I don’t know if you’re allowed to share the salary brackets for this job title with me but if you did I could tell you which way I think is best for you.”

This is also why you never want to reveal a number first. If you tell someone “here is what I make” you anchor them to that number rather than what it could be, what is fair for that responsibility and position. If they push and push and insist, that is where you need to say something like “look I am prepared to share this with you but I will ask that you share your salary brackets for this position first so that all cards are on the table” or else “I am prepared to share this but I really would like us to agree up-front that this is not going to be any sort of starting point for discussing compensation, but rather that we will agree to look up what salary range is fair for this sort of position.”

Swaying those brackets, or swaying informal brackets in someone’s head at a smaller company or start-up, is also possible: but you have to make it really easy for your counterpart to convince the bracket-holder. This is where an independent standard becomes really handy. If you can say “hey, let’s feed these into the Stack Overflow salary calculator for this region and see what’s fair,” you can actually create a situation where they have everything they need to go back to their HR department and say “hey I know you were just looking at this at an introductory level but I am looking for someone with this sort of experience and I am told by this calculator that it goes a bit above our brackets and is there any flexibility to adjust these so that we can hire the right person at the right price?”

If you can focus on a deal that gets you options that you really want (and they don't mind) in exchange for options that they really want (and you don’t mind) and can serve your common interests and build rapport, you are like 90% of the way there: if both parties also believe that the deal is fair by independent criteria, then I do not see why they should not both be ecstatic about the deal.