Letters to a Young Tech Attorney: Don’t Be an Asshole

Credit: Josue Bieri

If any of your relatives ever told you that you should go to law school because you like to argue, it didn’t mean that they thought you should go to law school. It was just a polite way of letting you know that you’re an asshole.

We’ll get back to this point later because I want to move on to telling you how to be a better technology attorney.

I’m an attorney, and I’m mostly not an asshole (at least, not while I’m being an attorney). Specifically, I’m an in-house attorney. I’ve been in technology law since the 1990’s. That was before the cloud. That was even before “SaaS.” I’ve been in this space this whole time because I really really really like technology and love working with innovative products and the brilliant teams that develop them.

Now, technology companies tend to need other technology companies as vendors — that’s the nature of the industry. If you’re running a platform, your team is going to want to use various widgets, APIs, analytic whoseywhatsits, and a load of things that suddenly exist and will make your product even that much better. And for each vendor, a company has to execute a contract (except for the guy that delivers fruit every week — it’s not clear who pays him or if we even asked for the fruit). This is where the legal team comes in.

You know who enjoys negotiating vendor agreements? Nobody. Not the attorney at the customer of the vendor. Not the attorney at the vendor. Even the mother of an attorney on either side would say, “Meh. Vendor agreement. I’ll pass.” Exactly zero people enjoy negotiating vendor agreements. Possibly fewer than zero.

I’m not saying that negotiating a vendor contract is among the least enjoyable ways I could spend a workday. I can think of a few worse things that could happen at work: showing up naked to a meeting like in that dream I always have but this time it’s not a dream; getting stuck in the elevator with someone using nail clippers for a few hours; or swallowing a shard of glass that was embedded in a pear in this week’s fruit delivery. What I am saying, though, is that there are many other more interesting, fun, and strategic things an in-house technology attorney can be doing.

I’m at the stage in my career when negotiating a vendor agreement usually requires a couple emails and maybe a phone call to work out an issue or two. This generally goes smoothly because most the other attorneys I deal are reasonable people who understand that in the agreement, we’re trying to patch up any major differences between our business risk frameworks. I usually don’t farm out vendor agreements to outside counsel because (i) I want to understand first-hand what we’re getting into and (ii) they only represent about 5% of my time.

There’s an implicit shorthand to vendor agreement risk management. And it works.

One of the few things at work that can sour my normal laid-back demeanor is when one of these vendor negotiations goes off the rails due to another attorney that has what I’ll politely call outlier negotiation methods. Their style is often confrontational, intentionally obtuse, or just unreasonable.

It’s on calls with these folks that things go off: My sense of humor can turn caustic; I’ll move from brevity to verbosity just to see if they really don’t understand or are just trolling; and I can become as impatient as my 4-year-old after that one time he mistook my cup of coffee for his hot chocolate. In short, despite years of being professional and steadfast in the face of almost everything, I can turn into an asshole right back.

I’ve noticed these outlier vendor negotiation methods cropping up more recently among younger attorneys in technology. If it helps, here are five thoughts I have that will help you not only be a better attorney to work within a vendor negotiation, but also provide more value to your company, provided out of purely selfish reasons.

It’s OK to be Wrong

If someone on a conference call or in a meeting points out an error in your document — typo, factual, or legal — own it. Don’t double down on it.

This can be incredibly hard to do when you’re the only attorney from your company on a call and you’ve got a few of your business people with all eyes on you across the Polycom, waiting for your reaction. Everyone makes mistakes. If you’re working with a group of people who don’t understand that, consider alternative employment.

If you’re not there yet with yourself or your colleagues — or if time doesn’t permit — confirm that you’ll check it out after the call and move on to the next issue. Don’t let your ego get in the way.

This comes up a lot because that form contract you negotiate day-in/day-out has become so familiar to you that you might just see past some of its flaws at this point. Let someone with a new perspective help you out. Nobody is trying to trick you.

Not-admitting-to-fault usually goes like this on a conference call with the other side (I’ve reduced the legal issue to a math problem, for clarity):

Me: Alright, just a heads-up that it looks like you have a typo in Section 12. It says that 1 + 1 = 3. 
Other Attorney: [pause] No. That’s not a typo.
Me: Are you sure? 
Other Attorney: Yes. That is not a mistake. 
Me: Hmm. So you’re saying that 1 + 1 = 3?
Other Attorney: Yes.

It can go on like that for awhile. Granted, it’s not a simple math problem, but it’s usually a fundamental legal concept on the same level. So much that as the conversation continues to run in circles, it’s hard not to feel like you’re being gaslighted as the other attorney doubles down on a clear mistake. Last time this happened, I called a few attorneys afterward to make sure I wasn’t going crazy, including an attorney I didn’t actually like very much but who happened to be an expert in this specific area. The consensus was that I was not crazy.

This also happened recently in a situation where the proposed language from a vendor specifically was against the vendor’s business interests without impacting us. I conveyed this to the other attorney, who immediately became suspicious and shut me down. He insisted that I was wrong and he was right. Here’s a pro-tip, when another business attorney starts a sentence with “As a professional courtesy, just want to let you know that…” about your MSA, you’re probably not being hoodwinked. You’re most likely being extended an actual professional courtesy and you at least might want to consider looking into it.

Everything Happens for a Reason

You know when someone dies and someone still alive says “Everything happens for a reason?” You know how that’s bullshit? (Well, everything does happen for a reason from a causal perspective, but not really from an intent perspective.) Anyway, know where that cliche isn’t bullshit? In a contract. Everything in a contract should be there for a reason. A contract is the nexus of a million business points, all nestled safely in their own sections. And you should know — or be able to find someone at your company who knows — those reasons.

The point here is that there absolutely needs to be a rationale for why something is in your contract in the first place and how that syncs up with the rationale I’ve given you for why our company needs to change it. You need to tell me why something can or can’t be done, not just a superficial brushing off. The following responses are not things that tell me why:

  • Your proposed change isn’t “market”: I don’t even know that that means. If anything, when I hear “that’s not ‘market,’” I’m on the phone immediately afterward to at least a few outside attorneys and some in-house friends to see what their view of “market” is. Beyond that, I don’t care what’s “market” — as mentioned above, I’m looking to bridge your risk framework and my risk framework, so let’s talk about the issue in that context, not some vague concept of “market.” If it doesn’t work, it doesn’t work — but let’s at least have a real discussion about it.
  • We can’t make that change because the section needs to be reciprocal: Blind reciprocity is just that: Blind. Rarely are — for example — reps & warranties reciprocal because two parties are by definition responsible for doing different things under the agreement subject to different risks at different exposure levels. Same same but different.
  • My CEO/CFO/GC says no: I don’t care. If you’re going to appeal to this type of authority, either get that authority on the phone or get me a rationale. Don’t tell me that Mom-and-Dad-say-no.
  • The Board of Directors requires this: No. I know what boards formally approve. It’s most likely not the thing you’re talking about. Maybe your CEO, CFO, or GC mentioned to the BOD or audit committee in an over-wordy dry deck that such-and-such was going to be addressed in a certain way, but that’s a far cry from the BOD requiring something.
  • We can’t make that change unless the annual contract value is $X dollars: Really? You said that you wouldn’t negotiate at all unless the value was $X dollars, and, yet, here we are. Have you really quantified the potential risk-to-revenue scenario of that specific provision? I’ll bet you $X dollars that you haven’t and that this is just an arbitrary threshold that makes some risk-averse person in your company feel better.
  • We’ve already made more changes than we normally do: Tell me more about your contextless bubble world. We’re working on a relationship here. And paint me like one of your French girls. Also, tell your biz dev guy to stop giving you negotiation tips.

It’s OK to Not Know Something

Kind of related to the points above: If you don’t know the answer to a question or don’t know the rationale for something, just say you’ll look into it.

Company forms can evolve in weird ways, the reasons for some provisions — whether driven by your finance team, marketing team, engineering team, or outside counsel — long forgotten. Don’t be pressured into making something up on the spot or — even worse — setting a false standard. It’s going to catch up to you, either from the other party’s side or from within your own company.

And if you see your business team on a call look at each other and shrug before they go ahead and answer a questionable business question — follow up with them afterward to check on how confident their answer was.

Don’t Be an Asshole

Let’s get back to the first paragraph of this post. It goes both ways.

Don’t be an asshole. What does that mean? Use common sense, from an intellectual perspective and a social perspective.

There’s an endless universe of this, but here are my top four:

  • Contract Cramdown. Don’t send a new draft of a contract minutes before a call. It’s discourteous. And if you send a draft of a new contract after the call has started, it’s a red flag that not just you, but your entire company isn’t to be trusted.
  • Mid-Level Manager Ambush. If you’re going to have other people on the call, list them on the meeting invite and call out what they do. This not only gives me a sense of what issues are going to be important to you, but it also lets me know which of my business people I need to have on the call. While I’m pretty familiar with my company’s operations, I’m not going to be a substitute for my CTO, product manager, or whoever. This especially applies to finance people. Trust me, you do not want me to be running numbers on a call, as several amendments filed with the SEC can demonstrate.
  • Redline Mayhem. When I send a redline of a contract, I hit the issues that matter to me, draft a brief bullet list of explanations for each one, and then invite a call to discuss. Please — please — don’t just send a redline back without comment. I’ve opened an invitation to discuss. If you don’t want to discuss, just say that’s your final final and we can end everyone’s misery much sooner by moving on to another vendor.
  • Deal-Breaker. Don’t ask if something is a deal-breaker. This is the third worst hyphenated business jargon behind no-brainer and back-of-the-envelope.

Final point on this: Use empathy. Don’t take adversarial positions because you’re sitting on the other side of a metaphorical table. Try to understand what the other party’s concerns are and understand what it’s like to be in their position. Seriously. Try it. This is going to put you you in a better position to offer solutions that make everyone happy.

Reminder: Use Your Powers for Good

Every single in-house attorney I know has somewhere on their resume or LinkedIn profile or body art a statement along the lines of the following: “Enjoy working closely with the business side” or “I believe the legal function is an integral part of the business team.” But I don’t see this happening in reality sometimes.

To put it another way, I see a lot of missed opportunities for attorneys to effect change within their business organizations and cultures, which is a large part of what being part of the business team is.

I’ve been stunned at the amount of bureaucracy abound at relatively small companies — the need for attorneys to get approval from the most unlikely of people. A couple of attorneys who I dealt with in situations like this told me (after negotiations were over) that each approval that was required was pretty much independently implemented from the others, meaning that the only person who had any idea that all of this was required was that attorney. This was also in the face of sales teams complaining that the legal team was holding up contracts.

If this is happening at your company: You have the ability to change it. Even if an existing process is in place, and it’s not working, take action to change it — it’ll make life easier for you and build your credibility. Even if the person who put it in place is still there and wields enormous power, if you can make this better, you will prevail.

Also remember that the legal function has a perspective into pieces of the business that most people in your company don’t have — a kaleidoscopic view that can enable you to see situations where the right hand is doing one thing and the left hand another, among other things. Take action when you see this. But know how to read your organization’s culture to make change welcome — it’s easy to hamfist this type of thing and be forever known as the meddling attorney who wanted to wear all the hats. (Deep apologies for the wearing-all-hats buzzspeak.)

Look for Guidance

This one has nothing to do with negotiations directly, but it’s probably the most important: You should be receiving ongoing guidance and mentorship from your GC or someone in your legal department. If you’re not, that’s not OK, and you should (i) consider other pastures to move onto and/or (ii) look to your network to find someone that may be a mentor or at least a person you look up to that you can check in with.

Where that Leaves Us

Alright, that opening bit about being an asshole shouldn’t apply both ways, but it does.

Of course I shouldn’t lose my affable avuncular composure in the face of all the things I mentioned above. By tech industry age standards, I’m practically ossified, anyway. But given the increasing frequency I’ve been seeing these things, it’s an issue, especially noticeable among product-focused technology attorneys I’ve dealt with since returning to California (we’ll get to finance attorneys another day — that’s another level).

But remember that the technology space is small on the business side and even smaller on the legal side. Most decisions are eventually made on credibility, whatever the metrics are for that, and you want to make sure you put the most credible foot forward for both your company and yourself.

Does this whole rundown apply to most tech attorneys? Probably not.

But, as the saying goes: Run into an asshole in the morning, you ran into an asshole. Run into assholes all day long, then you’re the asshole. I’m not running into them all day long. But I bet I’ve negotiated with a few tech attorneys who are.

Then you’ll know.


I occasionally write things here on Medium. You can listen to my sometimes dark but generally funny and useful Ask a Lawyer podcast, Unwonk, here. You are also welcome to read my Ask a Lawyer column in Deadspin here . I’m on Twitter here and here but still don’t understand why.