by acrooks | 2025-06-22 19:40:27+00:00
There are two fundamental ways to win a negotiation. By "win", I mean achieve an outcome outside the norm, such as an above market rate salary.

1. Negotiate from a position of strength

You pointed out a couple of these, like when you have a strong personal brand (like Patrick) or when the market dynamics favour employees. The former is not something you can control so, when the market is in this place, you should take advantage of it to propel yourself. However, the former is completely within your control. You can spend some time and effort building a personal brand. Many people discount the value of a brand and the effort spent building one, but it totally works. I have marketing-savvy friends who, since early in their career as juniors, spent a lot of time on LinkedIn thought leadership & brand building. And it totally works. In fact, I have one such friend who was recently part of a restructuring layoff (i.e., not related to performance). Because of the brand they built, once they posted about the layoff on LinkedIn, they had 12 offers within a week all higher than their previous salary.

Another area where you can gain leverage is when you already work at a company that wants to retain you. The only time a business will bend over backwards for an employee is when the conversation is about retention. To make the conversation about retention you need to be completely willing to walk, and your negotiating position is strengthened if you have counter offers. To maintain your political capital (which will be important if you stay) you need to be careful about how you play this game. I've worked with people in the past who approached the business confrontationally, saying "if you don't give me $X, I quit" - that strategy only works once. But there are ways to structure this conversation where you don't leave a bad taste in anybody's mouth.

2. Care about something different than your counterpart

Often the person you're negotiating with cares the most about optimising certain metrics. You should try to spend some time figuring out what those metrics are and see if there is something different that makes a difference in your life.

e.g., your employer might be really under the gun about managing fixed salaries. This is very common in a lot of businesses to try to manage their headcount. So they might be more willing to give you a $50k cash bonus compared to a $25k salary increase. Or maybe they're more open to an extra week or two of vacation vs. salary.

This phenomenon has been really helpful for me in the last year. I run my own business, but my business is fully bootstrapped, so I don't have a board or any investors to please. As a result, I'm not as motivated by ARR as other SaaS companies. Sometimes I encounter customers who would rather pay me a 3-4x one-time fee instead of ARR. By making these deals I immediately guarantee what would have otherwise been four years of cash (potentially with a cancellation risk during the term). A VC-funded SaaS business would almost never make a deal like this, because such a deal would not have a material impact on valuation.

Another example - I was moving recently and sold some furniture. I was chatting with somebody who was an optometrist who wanted to buy a few things, which I listed at $200. They offered $100. I countered, asking for the right to use their employee discount, and ended up getting $500 in value.

So you should also spend some time trying to figure out what your negotiation counterpart cares about. Maybe there is an arbitrage where you can both get exactly what you want, instead of needing to find an outcome where one person wins and the other one loses.