Chicago field notes
Last week I swapped Hounslow for Chicago and spent two days at the LSSO Rain Dance conference.
I came home with a notebook full of ideas, a mild case of jet lag and, most importantly, feeling genuinely re-energised.
There is something refreshing about spending time with legal sales professionals who are actively pushing the boundaries of what great business development looks like. Different market, different accents, but many of the same challenges we see every day in the UK.
As always, here are three things that stuck with me. Enjoy.
#1. Sales is psychology, not process
One of the standout sessions came from Graham Cox, a former MI6 negotiator (obviously I cannot find him on LinkedIn).
Whilst the session was framed around negotiation, the underlying message was much broader. Most decisions are driven by factors that sit beneath the surface.
People buy emotionally and then justify their decisions logically.
Trust matters. Perception matters. Motivation matters.
As AI continues to automate more of the process-heavy elements of business development, the human side of sales becomes even more valuable.
The best sales professionals are not simply good at asking questions. They are good at understanding why someone can say yes.
Who benefits from the decision? What risks are they worried about? How will success make them look internally? What happens if they do nothing?
Those answers are often far more valuable than understanding the technical requirements of the project.
Try this: The next time you’re discussing an opportunity, spend less time understanding what the client wants and more time understanding why they have the authority and motivation to make a decision. The real buying drivers are usually hidden in plain sight.
#2. The basics still matter
One of the best sessions featured a panel of General Counsel.
The format was brilliantly simple. Six rounds of quick fire questions. Thirty minutes. True or false answers. One-word responses. No lengthy presentations. No hiding place. Direct. Brutal. Honest.
One theme appeared repeatedly: no surprises.
Whether the news is good, bad or ugly, clients want to know what’s happening.
Early. Clearly. Consistently.
What frustrated the panel wasn’t difficult situations. It was finding out about those situations too late.
The second theme was equally important: understand my business.
Advice delivered in a vacuum has very little value. Advice delivered in the context of commercial objectives has enormous value.
Simple isn’t easy. But the basics remain remarkably consistent.
Try this: Pick one active client matter this week and ask yourself a simple question: if I was sitting in the client’s chair, what would I want to know right now that I haven’t been told?
#3. The biggest challenge isn’t technology
There was plenty of discussion around AI, automation of signals and the future of legal sales.
But three themes kept surfacing in conversations throughout the conference.
First, US firms appear far more comfortable involving dedicated sales professionals in client development activities. The relationship between lawyers and sales teams often feels more integrated than we typically see in the UK.
Second, both sides of the Atlantic are wrestling with exactly the same question: how do we train the next generation? If AI takes away some of the traditional learning opportunities, how do junior lawyers and business development professionals build the judgement, commercial awareness and experience they need?
And third, the biggest barrier to growth isn’t external. It isn’t the economy. It isn’t technology. It isn’t AI.
It’s trust. Specifically, the trust between partners and sales professionals.
The firms that seem to make the greatest progress are the ones where lawyers and sales teams operate as genuine partners, combining legal expertise, market insight and commercial thinking.
Technology can help. Process can help. Training can help.
But none of those things replace trust.
Try this: Ask yourself whether your lawyers and sales professionals are genuinely working as one team or simply operating alongside each other. The answer is often surprisingly revealing.
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