Learnings on Negotiation with Catherine Stewart

I did a quick interview with my colleague at Automattic today on the topic of “negotiation.” Catherine’s an ace negotiator, and you can learn some simple tips on how to negotiate better in this quick 4-minute recording.


Key Tips on Negotiation via Catherine Stewart/

  1. Listen carefully.
  2. Bring relevant questions.
  3. Meet in-person.
  4. Take notes.

Transcript of the Audio/

John Maeda/ Tell me about negotiating. I know that’s when I negotiate, it’s hard for me. It’s not a science for me, but I know that you’re really good at negotiating. Any tips for how to negotiate better?

Catherine Stewart/ I love negotiation, and one of the things I love about it is it’s a way to come together with another person, another company, and find a solution that together creates a better world for the people at the table.

This is often not what people expect when I say that I like negotiations — because they think of it as something that’s confrontational or combative, or that it’s fighting a zero sum game where one person loses and another wins. The best negotiations are when both parties leave feeling that they’ve won.

I like to keep the other person’s interest very much in mind, and to not lose sight of what’s important to me; and instead come to the negotiation with a very strong sense of what is important to them. And if I don’t have that sense to start, then listening is what the first meeting needs to be almost entirely about.

JM/ That sounds like Design — you mean like understanding your customer?

CS/ Exactly. If I don’t already feel I understand their business, I come with questions in my mind that will help me get to know what’s important to them better so I understand it. Sometimes with a really complex negotiation, I have already taken the time to model out what’s important to them better so I understand it, and what their business looks like. And to understand the P&L — or at least the P&L of the business unit I am working with – so that I understand the financials of their and what drives their business. By talking with them, I can learn more even about them — and I learn if I guessed right. It’s more than the metrics; it’s often about things that don’t have anything to do with money.

For example, when negotiating to purchase a company, it has a lot to do with the vision. It may not actually be as important to them what the purchase price is, so much as that the vision for how they want their company to evolve over time is realized.

JM/ So, knowing that it’s about the money — but not that it’s all about the money.

CS/ It’s usually about the money at least in part, but there’s so much more to any business deal than the money. That’s why listening is so incredibly important. Because there are things that I care about more than the other person, and there are things they’ll care more about than what I care about. In a great negotiation, we can make trades on those things that each of us cares less about — and in the end we’re happier than when we started.

JM/ For a younger business thinker out there about to head out to a negotiation, do you have a few tips for them, other than listening and being careful to have the right questions?

CS/ There are a lot of tactical things I like to do — like meeting in person when possible. You learn so much about how a person feels about what they are describing when you can see their face and hear their tone of voice. I think that you lose a lot of information that is impossible to get when you are doing it over the phone.

JM/ So don’t negotiate over the phone or Slack!

CS/ If it’s important to you, then it’s important to do so in person. Also, taking notes is really important because you think you’re on the same page as somebody, and it’s when you exchange your thoughts at the end you confirm them. “Hey, here are the things I think we talked about and this is where I think we landed.” So that after the smile and handshake at the end ,you know that you’re almost all the way there, but not 100% there. And for you’ll need your notes as there will still be some things to iron out.

JM/ So make sure you bring a pen or pencil! Thanks, Catherine.

CS/ Thanks, John!