Having been both outside legal counsel at a law firm and in-house legal counsel at a global software company, I often try to take advantage of having sat in the shoes of both outside advisor and client.
The inspiration for that, and what drives Parkwyn's values, is the message from one of my favorite books, The Trusted Advisor by David Maister, Charles Green, and Robert Galford.

The book’s basic premise is this - As an advisor, your (prospective) clients do not need to hear about your long list of credentials or the long list of cases you’ve handled before. If they are taking the meeting with you, they've done enough homework to believe you are qualified. Instead its about personal fit. And personal fit often comes down to the ability to show empathy to understand and relate to the problems of your client.
(1) Being a Great Listener
Lawyers are great listeners when it comes to getting the facts down from a client, but sometimes at the expense of seeing the bigger picture, or understanding what the client wants to do with those facts. The Trusted Advisor preaches that clients are looking for empathy more than the ability to take dictation or assurance of technical competence. Perhaps this is out of fear that a busy lawyer will not have the time to sufficiently invest mindshare in their case (despite the high hourly rates!), or because of just a basic human desire to feel like someone understands the challenges they are facing.

This kind of empathy is not unique to an advisor role, it applies to so many other relationships as well. But against many a lawyer’s instincts, it applies to lawyers and their clients too. Don’t get me wrong, its not necessary for all professionals. If I was going to have a complicated surgery, I might want a doctor who was cold and focused, no empathy and like a robot. Never makes a mistake.
When I talk with a client, I like to visually imagine I’m in my client’s office on the other end of the phone sitting and talking to this Art Dicker lawyer guy. When I give a client an explanation of the law, I try to think if I wasn’t a lawyer for 20 years, would I have understood what I just said? What details could my client be easily mixing up? What assumptions am I making that I shouldn’t assume the client already knows? As lawyers, we often forget that we have 3 years of law school and a lifetime of practice to master legal minutiae. If we don’t filter and emphasize the more important concepts over others, and explain things in linear, non-legal terms, our clients will often get lost. I find explaining the "why" behind the rules also helps a lot as well.
(2) Avoiding Technical Overload
Sometimes its not just about how we as lawyers communicate verbally or non-verbal communication, but rather in writing. When I was in-house counsel, we had a firm we used whose writing style was far too technical both in substance and especially in style. For example, a simple email explaining what documents we needed to provide and steps we needed to take was littered with unnecessarily complicated vocabulary and new defined terms in almost every sentence. The email read like a contract. If the email was intended for Art Dicker (“Art” or “me”) and only me as the in-house counsel for Asia Pacific (the “AsiaPac GC”), it might be okay. As AsiaPac GC, I can get through complicated vocabulary (the “Big Words”) in English and stomach a lot of terms with specific definitions (the “Defined Terms”) using other Big Words.

But the primary audience was our Finance team, people used to working with big numbers not Big Words. You send me an email like this, you make my life more difficult because I cannot simply send it on to the Finance team without having them coming into my office 10 minutes later and asking me to “interpret” the email for them. Or knowing they will come, me preemptively having to actually sit down and summarize it in a second email for them before they read the law firm’s original email. If you are my outside counsel and I’ve told you at least two times this is who the email is for, and you still write like this, I’m sorry, you’ve failed. You didn’t understand or appreciate what my pain point was.
(3) Delivering Advice with Value
There is no easier way to anticipate someone’s pain point and show compassion than if you’ve been in your client’s shoes before. For example, having tried to start a business before, I can completely relate to the lonely journey you have to make as a founder (it does help to have co-founders!). Founders as clients of mine may ask questions from time-to-time which an arrogant lawyer might think are amateurish compared to the questions you get from big company clients. But what I always find remarkable is what incredibly fast learners founders are (they have to, to be founders) as well as how extremely appreciative they are for the advice they get (because their business is their baby).
Provided you leave your arrogance at the door, a lawyer especially with prior in-house experience can share what you’ve seen work with other early stage companies, and also best practices of bigger companies. Time and separation from the in-house role will also give you enough context to judge what processes seemed helpful at a big company and those which could be done without. Especially when you’re dealing with a much smaller employee, customer, or vendor population and a more cost-sensitive client. This kind of honest and relatable advice builds trust.
Of course, the in-house experience helps most working with other in-house lawyers as clients. Big companies are often in a difficult spot. They generally have more at stake as far as corporate reputation and regulatory risk. So their instinct is to be cautious, especially having heard stories (real or exaggerated) about other companies which ran into trouble. But at the same time, they have incredible pressure from the business teams which (purportedly) hear and relay back that competitor XYZ is doing this or that, and that there is not as much risk in reality as Legal is fretting about. “We can’t let this business opportunity go or our competitor will surely snap it up” is a common refrain.
In these situations, as outside counsel, you have to be true to your principles as always, but also be keen to which way the client is leaning and where the pressure is likely coming from internally. You're trying to craft an answer for the in-house counsel as your client that gives her the tools she needs to manage the business side. In fact, there can sometimes be ample ambiguity in many rules, and often times there is no clear right or wrong answer. The risks we are talking about at times are quite hypothetical. In these situations, the client is often looking for a rationale that is both intellectually honest but let’s the company proceed with a way forward.
Sometimes this is best handled with a detailed memo or email where a follow-up call lets the in-house and outside counsel speak more freely to tell the client what we really think. When I’m writing a memo for a client, I often leave certain points leading in a direction and deliberately open to give a chance to explain more on a call. Despite common belief, most in-house counsel do not necessarily need to have everything clearly fit into the four corners of tightly constructed memo.
Unless the memo clearly states exactly what they’re looking to see, no in-house counsel is going to take the memo alone without a follow-up call. That follow-up call is where a lot of the value is “off-the-record.” An experienced in-house lawyer is going to give their outside counsel more leeway to say what they really think, and convey that they’re not expecting to hold them to every last word. Otherwise you get a memo so caveated it has little value left at the end. These kind of offline conversations are also one of the biggest chances where outside advisors and in-house counsel build trust.
Whether its with founders, company executives, in-house counsel, or otherwise, walking in the shoes of your client, anticipating their pain points, and delivering advice they can actually use is what makes a lawyer a Trusted Advisor.