Are you cut out for sales?

Some blunt truths about why so many lawyers fail when they pivot to "biz dev"

Last week I wrote a post on LinkedIn about the challenges that lawyers face when they pivot to a business development role. My basic point was that as a practicing lawyer, you’re rewarded for a certain set of skills but in sales, they actually might be counterproductive. Basically you want to have a bias for action, focus on outcomes, and try to be resilient.

There was a ton of discussion in the comments, which I always enjoy. A few common themes emerged, which inspired me to write this longer article today.

Note: I use biz dev and sales interchangeably throughout this article. To me they are both the same, but many lawyers just feel uncomfortable with the S-word and prefer “business development.”

Why I Wrote The LinkedIn Post

It’s because I think lawyers underestimate how difficult sales can be. Context: I’ve spent almost a decade working for legal vendors that sell technology or services to lawyers. Very often these vendors decide to bring on a former practicing attorney to handle sales, marketing or business development.

These ex-attorneys often end up underestimating the difficulty of sales. And most end up failing. I don’t know how else to say it without being so blunt.¹

Look I get that there are plenty of lawyers out there who can sell effectively. That’s what the highest paying rainmakers at firms are out there doing every single day. So yeah they definitely exist. But just because they’re out there doesn’t mean any lawyer who wants to pivot to a full time sales role will be successful.

Many companies have spent years, decades, even trying to figure out how to find lawyers who have the ability to sell. Large companies that provide products and services to legal (“BigVendors”) like Bloomberg, Thomson Reuters, Lexis, etc. seem to have cracked the nut, kind of. They’ve built infrastructure around their biz dev teams to enable ex-lawyers to step in seamlessly and produce revenue.

This is *not* easy to pull off by the way.

Countless legal tech startups have tried to mimic BigVendor’s processes, but fall flat. That’s because even if you build that infrastructure around your biz dev / sales team (which requires a huge investment in time and resources),² at the end of the day you still don’t know if you’ve hired the right people. Infrastructure is necessary, not sufficient to sales success.

At the end of the day your sellers—whether they have a law degree or not—have to be able to execute on the activities that lead to revenue.

By the way, sales veterans are professionally trained to do exactly this. Early on their careers they’ve learned that having as many conversations as possible with potential buyers gives you the best odds of success. So they instinctively run headfirst into calls and meetings, in an attempt to feel out objections. They recognize how important it is to ask for the business and constantly face the risk of rejection.

Lawyers, on the other hand, are not trained to do this. In fact, the legal career track seems to select for people who are the complete opposite.³ (more on this below)

So going back to my LinkedIn post—the purpose was to let any practicing lawyer know that if they want to switch to biz dev, it’s a completely different job. Candidly most lawyers I speak to who are interested in making the pivot do so because they’re unhappy at their job. Maybe they’re tired of billing hours. They’re often running away from something (vs. running towards something else.)

But lawyers are naturally good at sales, right?

There were a series of comments to my post all making a very similar point: Lawyers are already good at selling. Whether it’s rainmakers who bring in business, or advocates “selling” a closing argument to a jury—lawyers are ideally positioned and selected to make sales pitches.

I don’t have a response to this argument as much as I have perhaps a refinement of my main point. Because I actually agree! Plenty of lawyers are amazing sellers. Law firm rainmakers have been bringing new clients who spend millions (or tens, or even hundreds of millions) on the firm. So they definitely exist. I also agree that trial lawyers, or skilled appellate advocates excel at the art of persuasion.

However, these types make up only a tiny slice of the entire legal profession. The vast majority of lawyers are not good at selling. They are not good at bringing in business to their firms, and they are not good at persuading juries or judges to decide for their clients.⁴ That’s why those who *are* actually good at this stuff make so much money!

There are just so few of them out there.

The reality is that most legal work involves very little persuasion. Instead it requires attention to detail and conservatism. You are rewarded for identifying problems. Incidentally this is why many former law firm lawyers struggle when transitioning in-house. Their internal clients want quick solutions, not a laundry list of legal risks.

Doing good work automatically leads to sales, doesn’t it?

This is another commonly repeated myth. That somehow if I merely do good work and/or provide “excellent client service” it means I am great at sales. I can see the appeal of this belief. It makes you think that if I just do a good job at the pile of work in front of me, my clients will tell other potential clients, and soon I’ll be landing new business left and right.

Unfortunately, that’s not how it works.

Before I explain why, let me be clear. Excellent client service is something all providers—lawyers or not—should strive for. If you don’t do a good job for your clients, word will get out. When that happens, you can be certain that no amount of sales magic will enable you to get more clients.

Having said that, you need to do more than just a good job. Because there is no guarantee that your client will tell other people about the good work you’re doing.

There are plenty of reasons why that might be the case. Maybe your client is in a highly competitive field where they want to keep you a secret. Maybe they just don’t feel comfortable providing referrals. Or maybe they just don’t know anyone.

The responsibility of generating new business should *never* be delegated to your clients. You, as a sales or biz dev professional, have the responsibility to make sure it happens. Which means you have to constantly be engaging in conversations and meeting new contacts. You have to find creative ways to get people to talk about you and the work that you do.

I could keep going but I suspect most of you know what I’m talking about intuitively. Just look at law firm compensation. Service partners will always be paid less than the partners who bring in new business. If doing good legal work reliably led to more revenue, service partners would earn just as much as the rainmakers.⁵

Wait I thought anyone can be great at sales

It’s definitely true that if you’re bad at it, you can get better. And if you’ve never been trained, that getting coaching will make you more effective. That’s part of the reason why I write on biz dev / sales topics on this newsletter; my belief is that there’s an education gap that you can fill with examples, stories, and studies.

I’d even go along with the idea that given enough training, coaching, and practice—you can become really good at sales. As I mentioned earlier, in the right system and with the right corporate infrastructure, you can become an extraordinarily effective seller.

But can anyone become great at sales? I’m not so sure.

That’s because a huge part of sales success has to do with intangible aspects of your personality. That doesn’t mean you have to be an extrovert. But it does mean you have to be highly adaptable, willing to accept feedback from all kinds of people, and “go with the flow” when things aren’t working out your way.

The legal profession selects for people who do the opposite. We reward those who rigidly remain in a single career path for decades; believe in a strict hierarchy based on credentials; and embrace rules & tradition.

Those who make it through the lawyer training gauntlet—past the LSAT, past law school, past the bar exam, all the way to private practice—end up adopting these values. Which means if you want to pivot out of law to something like sales, you have to unlearn them. You have to abandon some of the things you used to believe.⁶

The most talented salespeople or business developers I’ve come across all have something about their personality that makes them extremely adaptable and flexible. They look forward, not backwards. Best way I can articulate it is, they’re fluid and pragmatic and find creatives ways to “flow” to a transaction/deal.

They’re not handcuffed by rules or tradition in the way that most experienced lawyers are.⁷

Which makes them incredible in uncertain, amorphous environments. They can receive and incorporate feedback from all kinds of sources—even if it’s someone “beneath” them. Taking all of that data and information into account, in real time, enables them to act decisively with incomplete information.

Which is exactly what you need in sales, when you’re juggling a million pieces of information from a range of stakeholders and internal influencers in the buying process.

Now is all that teachable? To me, the jury is still out.

Conclusion

One final word of warning to anyone who wants to pivot to sales or biz dev: Remember to look deep within yourself and try to understand what exactly is motivating you to make the pivot. Are you trying to become rich? Or are you trying to run away from tracking billable hours? If you don’t have some innate desire to persuade people to buy something from you—please consider taking another job.

Because right now, tech startups—especially the most hyped ones—will try to take advantage of your desire to escape the law. They often come venture backed, and will try to sell you a dream of doing meaningful work, wining and dining clients, and receiving company stock options that will let you retire early.

In reality you are walking into a chaotic situation where the product is all smoke and mirrors and no one there knows how to teach you to sell.

I say this because I have met plenty of ex lawyers who tried to go into sales and upon struggling—realized that they didn’t care for it in the first place. They just wanted to make a lot of money doing something cool, without really looking within to understand what it is they wanted out of a job.

And they never realize that kind of thinking is exactly how they ended up as an unhappy lawyer in the first place.

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1. Before you accuse me of being dramatic, let me just say that “failing” usually means finding another job (in law, or elsewhere) that’s a better fit

2. When I say infrastructure, I mean a combination of the following: an offering that customers are willing to pay money for, an established sales process where you know the number of activities (calls, emails, etc) you need to take to be successful; intel around how long a typical sales takes, marketing support, bite sized content (sales collateral) you can share with buyers; robust event marketing programs, a corporate brand that buyers are generally familiar with, etc.

3. This isn’t a slam on the lawyers either. Sales pros have their weaknesses. Very often they are too transactional, blunt about money, come across as unsophisticated and uneducated about buyer problems. Lawyers are often very good at … well, *not* being like that. Sometimes sales pros who are *too* salesy don’t work out either. The key is to be a sales pro in lawyers’ clothing so to speak.

4. In fact, some lawyers who *appear* to be great advocates are the opposite; they win because their client had a strong case. I remember when I was clerking at the Northern District of Illinois, watching countless trial lawyers utterly bomb in federal court. They made bad arguments, framed their positions poorly, and struggled to articulate basic points. And yet every single one of their websites positioned themselves as a “smooth talking trial lawyer.” It appears that many trial lawyers are better at marketing than they are at being trial lawyers.

5. There are some niche practice areas that are exceptions to this rule. But as a general matter, you can’t just rest on your legal skills; you have to know how to market, sell, and promote yourself.

6. A personal example: Before I went to law school I didn’t pay very much attention to where someone went to college. But after becoming a lawyer I definitely noticed it a lot more. I can’t explain how it happened or when it happened; all I knew was that education credentials were important and helped me size up people I’d just met. When I went into sales I had to unlearn all that and view everyone from the same baseline. Otherwise I would risk alienating key stakeholders / buyers just because they didn’t have the right credentials.

7. Incidentally this is what drives in house counsel crazy about their sales counterparts. Which I constantly joke about in my memes and Tik Toks.