The Sales-Legal Divide (And How To Repair It)

Sales runs on speed. Legal runs on caution.

In most growing B2B companies, these two functions are bound together by necessity but separated by mindset. Sales is rewarded for closing new business. Legal is rewarded for preventing costly mistakes. Both are essential, yet their incentives and instincts couldn’t be more different.

It’s no surprise, then, that—due to differences both cultural and structural—the partnership between sales and legal is often strained. But it doesn’t have to be. With a clearer understanding of what drives each department, the relationship can shift from friction to flow, improving the customer experience as a result.

Before we talk about how to fix it, let’s look at why the tension exists in the first place.

“Show Me The Incentives, and I’ll Show You The Behavior”

The first problem is mismatched incentives. Salespeople have time and revenue pressure in the form of quarterly or annual quotas. Legal not only has no sales quota, but also has an extra duty to mitigate risk, even if that might sometimes mean slowing down or stopping a sale.

The result is that sales and legal serve as a check on each other. Without a strong and attentive legal partner, I’ve observed that sales reps will absolutely push the boundaries of what constitutes a “good deal” for the company, to an uncomfortable place. After all, why not? Their commission check is not based on the dollar value the company can collect from the contract, not on the level of risk in the redlines they accepted.

This is not a bad thing. Without the cleverness, ambition, and entrepreneurial spirit of salespeople, the typical organization’s growth would drag. Yet introducing potentially ruinous risk into customer contracts is not a price worth paying.

Humanity Is Scarce In The Sales-Legal Relationship

Clearly, the relationship between sales and legal is there for a very good reason. Even just recognizing this can go a long way. In short, this tension is more so a balance to be thoughtfully managed, not a problem to be fixed.

But what often happens is that attorneys tend to view salespeople as thoughtless and commission-hungry, and salespeople view their company’s counsel as someone they must avoid (or even manipulate) to do their job. Each has a hard time viewing the other’s humanity.

This is worsened by the games of status inherent to each profession. Salespeople are taught to avoid putting prospects on a pedestal, to preserve the value of their time, and in general to reaffirm their own professional self-worth—overall, a good thing to do. This is because the natural tendency of someone whose job it is to ask for money is to do the opposite: to see themselves as of lower status than the executives to whom they sell. Sales often sees in-house counsel as of higher importance than themselves, too: after all, the lawyer has the power to veto the terms of a deal that sales would otherwise like to do, if push comes to shove.

Counsel often comes from the opposite perspective. A full 60% of United States presidents were previously in the legal profession: it wouldn’t be unreasonable to say that our society puts attorneys just as high on the status spectrum as it puts salespeople toward the bottom of it. Legal sometimes reinforces this pedestal because it aligns with the tradition and professional culture of law, and because it’s easy to partake in the societal revilement of salespeople overall, even unconsciously.

And so the divide between these two departments can seem wide. But sales and legal teams can add much more value to companies when they cooperate effectively, so it behooves us to try to close this gap.

What Can Sales Do Better?

First, sales should stop putting legal on a pedestal. When I used to lead sales teams in a past life, I coached reps to bring self-awareness to these status dynamics. When unspoken dynamics become spoken, they often lose their subconscious power to cause damage.

Mindfulness exercises as simple as visualizing the person (who you perceive to be of higher status) feeling their full range of human emotions, one after the other, can help remind us that no matter what job we do, we’re all still people, and that differences in status are all social constructions.

I encourage salespeople to treat their company’s legal team as their partner, not as an untouchable authority. The right balance lies somewhere between two inhumane extremes: on the meek end, avoiding or trying to manipulate legal into helping close a particular deal; and on the other, domineering side, trying to overly delegate the sales process to counsel to outsource sales work to them.

Next, practice empathy for the perspective of someone who does not have a quota and is nevertheless both busy and critical. Legal does not want to sabotage deals—but at the same time, they have a uniquely important duty to protect the company in ways that salespeople do not.

It’s helpful to keep in mind the higher-order priority: delivering a smooth, respectful, trustworthy experience to the client, who—like both sales and legal teams—is made up of humans that are just trying to do their job well, without unnecessary friction.

Sales, Brush Up On Legal 101

Avoid asking your in-house counsel basic legal questions, and you’ll help nurture these relationships. As a rule of thumb, if you can watch a short YouTube video covering a particular topic to get a foundational understanding of a business concept, you’ll be able to ask much better questions and get fewer rolled eyes. Instead of asking, “The customer asked to remove the liability cap, can we redline it out?”, research it first!

Remember that customers, and especially your prospective customers’ legal counsel, will often ask for maximalist redlines, testing if the sales rep they’re working with understands the business context or not. When you relay these demands wholesale to your own counsel, it’s not helpful, and legal might feel annoyed at having to be your Law 101 teacher.

A more nuanced version of a customer request to take to your counsel might sound like this: “The customer accepted the large majority of our redlines, but they also asked to strike the cap on our liability as the vendor; while I know that’s not feasible, what might be a reasonable give in this situation, considering the several years this customer has been with us already across our other product lines?” Whatever the details are, consider the basic implications of what you’re asking before making the request; if you don’t understand them, then try to self-educate before you fire off that email to legal.

Besides, it’s good practice as a salesperson to make sure you’re not trying to negotiate legal terms too early. When I asked a friend of mine, who is a high-performing enterprise seller at Oracle, for his take on this, he wrote:

“There’s an inherent understanding that a large organization, say $1B+, is going to be less likely to budge on terms when it comes to master agreements. But the biggest sticking points are always indemnity and liability. As a seller, I save it all for the final 3rd of the sales process. I want the buyers bought-in on what they’re buying so that, if needed, they can support me with legal.”

Joe Barhoum, Professor of Sales @ University of Portland

Here, Joe shows us his mastery of both sales and customer experience: he doesn’t involve legal until he’s agreed on terms with his customer, which allows him to both save legal’s time as well as to take responsibility for his own sales strategy, from start to finish.

To concisely summarize my advice to sellers—from mindfulness, to self-education, to saving anything related to legal terms and structure till the end of your sales process—it’s that you’ll serve everyone best if your instinct is to take matters into your own hands, not to deflect responsibility for thinking through thorny issues. The best salespeople are great businesspeople first and foremost, which, not coincidentally, is similar praise I give to the best lawyers I know.

What Can Legal Do Better?

Of course, this dynamic is far from one-sided. Just as salespeople should put themselves in the shoes of attorneys (and their clients), educate themselves on the responsibilities of other departments, and take deep responsibility for their own sales process, so should GCs make more of an effort to understand and respect the unique mindset of salespeople. Even recognizing the financial and mental pressures of being in a quota-carrying role, at a deep level, can go a long way.

If you’ve never owned your own legal practice or had to “eat what you kill”, ask yourself: how would it feel—in your bones—if your compensation was 50-80% based on what you closed, and thus on factors ultimately out of your control? It should become clear that the culture of urgency entrenched in the sales profession is there because it is a feature, not a bug.

Next, be honest about the tendency to overplay your authority internally in your organization. How do you feel when you say “No” versus when you say “Yes”—which one feels better in your body? How might that tendency be playing out in your relationship with sales or sales leadership? You can be an expert and also be approachable and solution-oriented (and I argue that your commercial success will be greater if you possess both of these traits together).

Practice this same collaborative empathy in customer conversations, even if the client's lawyer and procurement leader haven’t also chosen to practice mindfulness in this interaction. Likewise, don’t assume that non-lawyers (including sales and procurement but also your own company’s CEO) know how to fully consider the legal impacts of their suggestions.

Help Your Sales Reps Progress As Businesspeople

From a knowledge perspective, we’ve already covered how it’s the responsibility of the sales department to gain 101-level legal knowledge without coming to you. But the converse is also true: if they are coming to you for help and they’ve done as much homework as can be expected of a non-lawyer, how else can you enable them?

First, consider that they may or may not have received risk management training from the CRO or CEO. If they haven’t, could you run a webinar and record it for training purposes, on the company’s risk management profile and key legal priorities? In this or other training you produce, going over the most common situations you deal with—likely relating to indemnification and liability, as we quoted above—and any standard guidance you might give in those situations, can help provide a “legal cheat sheet” to salespeople to ensure they only bring you the trickier questions.

Next, assuming you’ve made some headway towards enabling your sales team to be better businesspeople with some basic legal training, there are some specific things you can do to maximize the value you add in your interactions both with your own sales team internally, as well as with external customers and their counsel. Take a very short period to ask sales for the business context of the deal in progress, what the customer seems to most care about, and context around any sensitive issues.

Hopefully, sales has done a good job of building consensus among their buying committee, and can equip you with much-needed context—on everything from the customer’s politics and internal relationships, to the drivers of urgency that are helping this deal get done. Contracts aren’t negotiated in a vacuum: if you’re feeling apprehensive about not having enough context, ask for it before you allow yourself to be looped in with a customer.

If your spidey sense tells you you’re being asked to help the seller with what really should be sales process work, you can point back to the training you’ve created to preserve your time. In these instances, instead of the canned response, “This is a business issue not a legal issue”, can you find more nuance? What about, “Have you tried the standard response we discussed to these kinds of indemnification-related questions, back in the December legal training? If so, what did they say?”

Your job isn’t to be their sales manager. But if you approach questions about whether something is a business term or a legal term from a coaching perspective, eventually the sales team will be in a much better position to bring you into sales processes wisely, rather than indiscriminately.

Away From Status Games, Toward Customer Experience

Thus far, I’ve asked the sales and legal teams to each be more self-aware, to behave differently, to lightly coach each other in some specific ways, and to strike a balance that’s inherently difficult to strike. That’s always going to be difficult to do! But my intent is not to preach: rather, I’ll help to point to an overarching goal that we all share, to help everyone in the GTM organization, including the deal desk, operate from a joint principle. What might that be?

I suggest that Customer Experience is the principle that can arbitrate many of these fine-grained questions, such as: Should legal be the one to take over at this point in the Acme deal, or should sales take the lead on that meeting? If there are good reasons for either sales or legal to handle that by themselves, let’s say, then could we tiebreak these kinds of issues by instead asking what would make more sense for the customer?

When a sales rep, for example, loses an argument internally and is tasked with having a conversation that really is a legal one, or vice versa, it feels genuinely strange to the buyer who is simply trying to do their job. People evaluating expensive new solutions to their business problems want to do so without excessive drama from the team that sells them the solution. Even with high-quality internal sales and legal training, any games of status being played in the selling organization will still ultimately be felt by the customer.

The C-Suite Sets The Tone

Let’s say you are now convinced that sales and legal are not opposing forces, and should strive to be strong complements to each other, and you agree with me on some of what sales and legal can each do better.

It’s still worth asking whether all of this is even addressing the true root cause of the problem. Whose priority really is it to improve alignment, reduce internal friction, and improve the customer journey? Ultimately, it rests neither with sales nor with legal. It must be the executive team's priority as a whole.

While sales and legal both can do a lot to improve their relationship, and therefore to close more high-quality revenue with less risk, the entire executive team is who sets the tone for how this relationship should go. When the C-suite genuinely cares about growing revenue predictably, which means presenting a unified front to customers, they will make clear what sort of behavior is and isn't tolerated and lead by example.

After all, sales and legal don’t report to one another, so that relationship can’t always be improved in isolation. It truly takes a village.

So while we can ask both salespeople and attorneys to be mindful of status games and to be the best possible versions of themselves when teaming up to bring in revenue, it’s really our partners in the C-suite who must maintain a human-oriented culture that inspires customer trust—and wins deals. And that is ultimately who must pay attention to the subtle team dynamics on which great organizations are made.

About the author

Alex Boyd is the co-founder and head of commercial operations at ViewExport, a Slack eDiscovery tool startup. Having led sales teams, as well as multiple acquisitions and company sales that involved cross-functional sales and legal efforts, Alex has a deep appreciation for the dynamics of operating revenue teams. Based in Portland, Oregon, Alex is a proponent of conscious capitalism and mindfulness in business.