Two massive barriers to good value storytelling (series recap):

  1. It requires hard work, taking time we don’t have
  2. Even if we have the time and do the work, our current chapter might prove unflattering

Herein, I focus on #2. Ego is often the enemy and, thus, we must frequently first edit the stories we tell ourselves.

I give short shrift to #1 only because it lends itself better to books, coursework and practice than a brief blog post (or even a long blog post).

In the beginning, there was the current state. We start by mapping existing processes, capturing meaningful data, and (eventually) using that data to craft a story (last post) that resonates with our business stakeholders.

Per usual, easier said than done. The rigor and effort required to overcome inertia consume finite resources (almost no one has strategic reserves of time and attention). Mapping and measuring is often labor intensive because we don’t just need to know who does what and how, but why. And not the superficial why but the root-cause why.

It is astounding how often we dig into long-established processes and the reasoning behind a particular step turns out to be ¯\_(ツ)_/¯. Vestigial activities are endemic, as are kludges and compromises born from expediency (the need for speed). We are awash in technical, process, and cultural debt.

The status quo, however, rarely bears any evidentiary burden whereas proposals to improve on the status quo are often subject to strictest levels of scrutiny. We need to get our story straight, including being prepared for one troubling angle of inquiry: how did you let it get so bad? Identifying an opportunity for improvement can be flipped on its head as an indictment that persists whether or not we secure the resources required to remedy the issue. Volunteering for additional accountability is not an appealing option.

Early on, our story is rarely a happy one (and that’s ok). As discussed last post, we often default to vague stories because we have no other choice. We lack the details, data, and insights to paint a compelling picture. Resource constraints are, as always, a primary culprit—which is why we must be selective in the stories we aim to tell well. But another blocker is the forgivable fear of what we might uncover.

The excusable ambition is to tell a story in which everything legal does is awesome—with even more awesomeness bound to result from earmarking additional resources for legal. But this narrative will usually ring false. Because it is not true. Which creates a conundrum. Maximizing throughput at current resourcing levels would, at first glance, seem foundational to a persuasive story of how incremental resources will be deployed to benefit the business—i.e., use what’ve you got wisely before asking for more.

Unfortunately, there is likely considerable waste embedded in our current operating model. Even if we prefer to believe our initial design decisions were impeccable (no) and our execution thereof flawless (also no), we are confronted with the harsh reality of entropy as the world moves faster than our department ever could. The endless pursuit of optimal requires regular recalibration. True transformation requires much, much more. But telling a story in which a pivot results in a positive outcome is almost invariably an admission that, at some point, our choices and behaviors were suboptimal.

We do not like to look bad. But we probably need to look bad before we can get good.

The first step is admitting imperfection. Take, for example, this fabulous case study from my friend Alex Hamilton’s must-read book on contracting, Sign Here (reprinted with permission, of course):

That’s four very different stories.

The common Why is “because the government said so.” This Why is not fun—money spent to preserve, rather than create, value in response to increased legal complexity. But, as Whys go, sufficiently clear and compelling. More intriguing are the divergent Hows.

The companies resemble one another, from a distance. Each company is partnering with the same New Law company to tackle the same problem. Each has sufficient rigor around process and metrics to the point of being able to identify specific bottlenecks. Yet, despite superficially similar levels of sophistication, there are material differences in outcomes.

The Department of Slow. By attempting to insert a provision, not required by the new legislation, to materially increase their counterparties’ potential liability, Dept B moved 4.5x slower than Dept D. This delay cuts right to the heart of the relationship between legal work and business outcomes and why divorcing legal considerations from business value can diminish the legal function’s standing with business stakeholders.

(h/t Alex Su)

According to Gartner, when legal guidance is too conservative, business decision makers are:

  • 2.5 times more likely to forgo business opportunities that legal recommendations have made less attractive
  • 2.5 times more likely to suffer delays in capturing opportunities as they work through legal guidance and requirements
  • 4.25 times more likely to scale down the scope of opportunities

What lawyers consider “conservative” can put a company into an “aggressive” posture vis-à-vis counterparties with whom they are trying to do actual business. Consider this entire thread  about a lawyer costing an individual client millions of dollars by taking maximalist negotiating positions in a genuine effort to protect the client’s interests.

With the thread in mind, the questions prompted by the case study include: was the attempt to contractually increase the other side’s overall liability a net positive to the business? Did it merit the increase in cycle times, and the attention costs associated therewith? Was the resulting friction in the commercial relationship worth it?

I don’t know.

I can’t know. The answers are context dependent. Maybe an inciting incident or leadership change altered the business’s risk tolerance and this repapering exercise presented an opportunity to redress their risk profile. Not my circus, not my elephants.

Facts are annoying that way. So in a display of internet courage, I will hazard a guess that this business’s raison d’etre is not to maximize its counterparty’s potential liability. Just as I am fairly confident the business’s primary objective is not to minimize its own liability (winding down operations would be the surest route to unlock this dubious achievement).

From personal experience, telling a businessperson “well, there’s a risk” is essentially a content-free statement. Every business decision, every action and inaction, balances a variety of enterprise risks, only some of which are legal in nature. Attempting to eliminate risk, or minimize risk in a way that ignores net business impact, is one way the legal function becomes labeled the Department of No and the Department of Slow, with the primary complaint among our stakeholders being that in-house lawyers “don’t understand my business.”

It remains incumbent on the legal function to identify legal risks and characterize those risks properly. We need to intelligibly translate legal risk into potential business impact (probability, frequency, severity). Indeed, the dream is to price risk properly and integrate it directly into the business calculus. Which is another way of saying, our role includes helping to advise the business on taking smart risks.

Inevitably, we will still have to tell the business that which they would rather not hear—like new privacy legislation requires us to update many existing contracts. But we will find a much more receptive audience if we have consistently demonstrated we are allies invested in helping the business make money.

A credible (rather than incredible) bearer of bad news. The legal department needing more resources will be among the unpalatable truths that almost no one will be eager to accept.

Informing the business that legal has been wasting money for years will not endear us to our audience in the right way—savings-centric narratives are a dead-end path of least resistance that reinforce the attractive fiction that the company should be spending less on legal. On the other end of the spectrum, pretending like legal is eternally perched at the apex of resource optimization and operational excellence is (likely) transparently laughable.

The middle road is to do the best we can to optimize the resources we have while also asking for the resources we need. Pick the low-hanging fruit (i.e., patent, preventable waste) identified in the process mapping/measurement exercise and present the resulting improvements to support the case for more resources to move beyond incrementalism. In the case-study example, reform the delay-inducing contract language and then cite the already improved cycle times in the petition for (i) the resources and (ii) cross-functional collaboration necessary to address the delays caused by slow approvals and signatures, the topic to which we will return next post.

I know. I remain a citizen of good standing in Obvioustown. But the middle path is rarely chosen because it requires being bold (asking for more money) while also being prepared (putting in the work to get the story straight), including being prepared to recognize where we are falling short (looking less than perfect). Most departments are situated near one of the extremes—too shy to ask for the resources we need (no value stories to tell) or too quick to do so without any meaningful effort to get our house in order (our stories are vague and incredible).

Some level of humility is an important part of credibility. But not too much. Technical, process, and cultural debt are not unique to legal. The law department’s ways of working are unlikely to be the most inexplicable part of the collective goat rodeo. It often seems like the business makes money in spite of itself. Humility paired with competence and tangible progress towards improved business outcomes should be enough to convince persuadable stakeholders that additional resources will be put to good use.

Likewise, we should not apologize that increasing legal complexity drives up the costs of doing business. That’s the problem we’re responsible for addressing, not responsible for creating. Instead, we need to clearly articulate the business value at stake in a manner that reflects our roles as allies in driving superior business outcomes, including advising the business on taking smart risks. This does not guarantee we will secure the requisite resources (expect legal to still be chronically underfunded) but it does improve our chances substantially as we change perceptions about being the Department of Slow/No.

Photo of Casey Flaherty Casey Flaherty

I am the co-founder and chief strategy officer at LexFusion, the go-to-market collective of legal innovation companies (tech and services). I am also the co-founder of Procertas (competency-based tech training). I was a BigLaw litigator and then in-house counsel who went into…

I am the co-founder and chief strategy officer at LexFusion, the go-to-market collective of legal innovation companies (tech and services). I am also the co-founder of Procertas (competency-based tech training). I was a BigLaw litigator and then in-house counsel who went into legal operations consulting before one of my BigLaw consulting clients hired me full-time to help them build the biggest and best legal project management team in world. A Lean Six Sigma black belt, I tend to think in terms of scalable systems that properly leverage people through process and technology. I am deeply experienced in legal operations, legal tech, strategic sourcing, process improvement, systems re-engineering, and value storytelling, in addition to spending over a decade in the legal trenches as a practitioner. I’ve long served  as a mesh point between law departments and law firms to promote structured dialogue that fosters deep supplier relationships (read about that here). I am a regular writer and speaker on practical legal innovation.