Negotiate thoughtfully

#careertransition – #6 of 8 | I recently went through a process of career exploration and made a significant career switch. This series of 8 posts is a synthesis of the lessons I’ve learnt.


This applies on both sides – your current employer and your new one.

Let’s say you’ve run a process. You have a couple of offers. Or you’ve decided where you want to go and have gotten an offer. But your existing employer has also opened up an option or two that could be compelling.

The key here is to go back to that first principle of knowing what you want. Don’t negotiate if you know you’re not going to take it eventually. This is one of those things you really want to play well. If there is indeed something that would keep you, be upfront about it – but know that if it’s given to you, then you have to stay.

And on the flip side, if there’s nothing that’ll make you stay, don’t make asks. They’ll just end up wasting a bunch of people’s time and goodwill.

Your most helpful ally is being clear about what you want and what you’re solving for. And assuming that’s not something you’re going to get in your current place, you can just be upfront and treat any negotation or persuasion as a sign of love.

Some of these conversations can be hard – especially when you make an unexpected move. But it’s important to remember that you don’t need to justify it to anybody. It’s a call that makes sense to you, and that’s what matters. The key is having the conversation as respectfully as possible.

Similarly, at your new place – the best negotiations are simple and focused on one or two things that matter. Not attempting to throw the kitchen sink at the problem. Doing it respectfully matters because you want to start on a great foot.

And, in addition to speaking to friends who’ve been through similar situations, I can’t recommend using Claude or ChatGPT enough to prepare extensively for these conversations. It really goes a long way in preparing for sensitive conversations.