Here's how to deal with difficult counterparties — according to lawyers who have been doing this for 20+ years

Dealing with difficult counterparties can be nerve-racking and drain all of your energy. Yet, there is a way to make it more pleasant, help you preserve your energy, and help your client better.

We’ve asked three lawyers with over 20 years of experience in the industry to share their tips as part of our How I Contract interview series. 

Here are their recipes for success.

Take the high road, engage other teams

“Take the high road, and stay calm and rational. And include more people on the call.  

Have your sales or procurement rep join you and ask for their counterparts from the negotiating counterparty to join as well.  

Discuss the clause in question at a high level in the context of the real business relationship and likely outcomes rather than a word-by-word negotiation. 

Plan with your sales/procurement rep how to bring the business parties around to your point of view and leverage them to calm the difficult person on the call.  

Make sure you have a reasonable compromise to present (are you the difficult one?).  

And know when to walk away — and agree that beforehand with the rest of your sales/procurement team.”

Sally Whitehead, former Global Senior Director, Commercial Contracts & Legal Operations at Sophos

Give in on points that you really don’t care about

“Sometimes you have to give in on points that you really don’t care about solely for the purpose of showing good faith, willingness to negotiate, and making progress. No sense in explaining that the counterparty is not making sense.”

Lucy Bassli, founder of InnoLaw Group, ex-Assistant General Counsel at Microsoft

Remember that it is never about you

“Remember that it is never about you. If someone is being difficult, realize that they may be having a bad day. I try to be extra gentle in my tone and words if the counterparty is being unpleasant.”

Hebe Doneski, the founder at 108 Legal

Understand what that reason is and see if you can work through it together

"I like connecting on a personal level with other people. By doing that, most of the time, I find out they’re not being difficult per se. They’re reacting how they are for a reason.

I just need to see if I can understand what that reason is and see if we can work through it together.

Sometimes it’s as simple as a misunderstanding of why we’re asking for a certain change. Sometimes they have a lot of contracts to get through that day and they’re frustrated with having to review more revisions from me. Sometimes they have serious things going on in their lives that have nothing to do with me and I just need to be understanding about it (while of course making sure the language is the best possible for my employer!).

We’re all just people trying to do our best."

Michelle Fleming, General Counsel for Bell Techlogix and a How to Contract member

Call it out

"99 times out of 100 you have more leverage than you think. 

If someone is being difficult then just end the meeting or call. Say something like: “This isn’t productive.  I am going to meet with my team and see if we can move forward or not”. 

It’ll often bring the temperature down. 

Sometimes you need to signal that the lawyer’s difficulty is threatening the deal - call it out."

Andy Dale, General Counsel & Chief Privacy Officer at OpenAP

Wishing you success!