Birth of a Salesman

Last year, I left the law world and joined a legal technology startup as a sales rep. My original hypothesis was that it’d be a great fit for me because I enjoyed sales (when I ran my own law practice) and because there was a great opportunity at the bleeding edge of an industry I was familiar with. (I never wrote about this specifically but alluded to it in my post Get Lucky By Knowing Your Industry and Knowing Yourself).

It’s now been eight months since I’ve entered the world of tech sales. Things haven’t gone exactly as I planned, but for the most part, things have gone well. Last month, I was promoted from being a Sales Development Rep (SDR) to Account Executive (AE) position on an accelerated timeline in part due to my performance. Sales has come to me much more naturally than law ever did.

Before I move on, a quick explanation: In software sales, you frequently see specialization in roles of sales reps. It’s like an assembly line for sales. SDRs are responsible for cold calling and setting appointments for AEs, who are then responsible for closing the deal. I joined my company as a SDR (a position typically held by someone with little to no experience right out of college).

My experience as a SDR (and in sales generally) has been pretty good. Cold calling may seem like a nightmare to most people, but I find it kind of fun. Certainly it’s no worse than doc review or cite checking. When I talk to my friends, they’re often incredulous that I enjoy calling strangers and getting rejected again and again. But it’s true. I don’t mind the rejection, and I love it when I’m successful and able to set that appointment.

My conversations with my law friends also got me thinking. The skills and talents that make for a great lawyer are often very different than those required to be a successful salesperson. I’ve done well because I have some natural competitive advantages in my role, such as having legal industry knowledge. But more importantly, the sales industry has certain values that mesh well with my personality. A few that come to mind:

Mistakes are encouraged. Sales skill development requires that you go out there and make lots of mistakes. You grow by having bad conversations, pitching people the wrong way, and just messing up in general. It’s very much a trial and error process. In law, mistakes aren’t just discouraged, they’re not even tolerated. Perfection is expected. In my former life, I was always criticized for making careless mistakes. Now I’m praised for thinking quickly and acting decisively. They’re really just flip sides of the same coin.

Your credentials and past matter less. Law is very pedigree-conscious. You’re assumed to be a good lawyer if you went to School X or Firm Y. We live in the past. (That’s also why litigators always worked off old forms and briefs; “precedents”). Not so in sales. As long as you have a college degree, you don’t really have an advantage if you went to a good school or previously worked for a big company. Sales pitches are also constantly evolving.

Asking open ended questions. As a SDR, I was constantly told to make sure I ask open ended questions that allow my prospect to talk about themselves and their processes. You never know what they might bring up, and if they raise an unexpected but important point, you have to run with that. On the flip side, in law you’re always trying to build a record. So you’re trying to get people to say certain things by framing your questions in a specific way. The most obvious example is through the use of leading questions during cross examinations. I’m not gonna lie-there were times I found myself doing a mini cross X when I was trying to pitch someone on the phone. It usually did not turn out well.

Results matter more than hours worked. As a lawyer, I’m rewarded more if I spend 100 hours on a matter but lose the case, than I am if I spend 50 hours and win a case. This creates all sorts of perverse incentives and just feels wrong. In sales, you are measured by what you generate. Whether that’s appointments or closed business, nobody really cares how long it takes you to get it done. As long as you produce results, you are rewarded.

Optimists win, pessimists lose. Being a great lawyer requires you to be prepared for all possibilities, so it’s super helpful to imagine everything going wrong. If you have a knack for this, you’re probably a pessimist. Being a great salesperson requires enormous persistence and resilience which means it helps if you can be sustained by a tiny glimmer of hope. If you’re good at this, you’re probably an optimist.

It hasn’t been all that long but so far sales has been a great fit for me. Hopefully things continue to go well. Stay tuned for more!

Biographies Can Mislead Us About the Path to Success

I published an article on LinkedIn about John Quinn and his winding path to creating the Quinn Emanuel firm:

During law school, I was a voracious reader of biographies. I saw them as road maps to success. My takeaway from reading the hundreds of detailed profiles of successful people was that if you were smart and worked hard, massive success would directly follow.

I had no idea how completely wrong I was.

Feel free to read the rest of the article here.

Get Lucky By Knowing Your Industry and Knowing Yourself

Over the past few weeks I’ve had a several conversations with my friends about risk, finding the right place for your personality, and how to get in early on emerging trends. I thought I’d share some of my thoughts in this post.

Continue reading “Get Lucky By Knowing Your Industry and Knowing Yourself”

My Business Has Failed. Here’s What I Learned.

My business has failed.

It feels weird to type that out. It took a really long time for me to admit that simple fact to myself. And even longer for me to write about it.

A year ago, I launched my law firm and publicized the good news with great fanfare. I suppose it’s only fair that I also share the bad news publicly too.

I have absolutely no regrets about starting my own firm. I made many mistakes, and learned a lot of difficult lessons. But I also received some huge unexpected benefits. For my next move, I’ll be joining a tech startup in San Francisco. I’ll give you more details at the end of this post.

Continue reading “My Business Has Failed. Here’s What I Learned.”

Tough Times Will Lead to Personal Growth

When you’re going through difficult times while you’re in your 20s or 30s, it’s easy to fall into a downward spiral and end up depressed. It’s difficult to see past your own challenging circumstances. You might think: Maybe if I didn’t encounter this setback, my life would be so much better. It doesn’t really matter what realm your setback is in. It could be your career, your romantic life, your personal relationships, or something else.

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It’s not easy to recognize this but usually your difficult challenge comes with silver linings. For example, you may discover that you’re stronger than you thought you were. (See Grit: The Power of Passion and Perseverance by Angela Duckworth) You may realize what you really, actually want out of life. You may learn that your friends/family are there for you. Or you may find out who’s not there for you–which is incredibly valuable information.

It’s really hard to take the long view when you’re going through tough times. But if you make it through you’ll become a stronger and wiser person. A lot of success in your life involves knowing what your weaknesses are and being aware of your limitations. Someone who has never encountered failure, disappointment, or despair won’t have the necessary strength to get through difficult times when the stakes are higher.

When you’re young–say, in your 20s or 30s–you can bounce back from the worst failures. But when you’re much older, it’s a lot harder to overcome your mistakes. Although not impossible–some continue to experience personal growth well into their 80s and 90s. (See Triumphs of Experience: The Men of the Harvard Grant Study by George Valliant)

I try to tell myself all this whenever I encounter obstacles. It’s hard to really see when you’re going through difficult times, and feel that there’s no end in sight. So it’s always good to keep reminding myself that no matter how bad things get, there’s always a silver lining.