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November/December 2019

Leading in Legal IT

Leading the technology team in a law firm requires trust, clear objectives and a bit of magic.

Mark Gerow

Leadership in any setting is a tricky thing, a subtle and wonderful amalgam of vision and trust that is not to be confused with the management linked to it. In information technology (IT) leadership means convincing highly intelligent, creative and capable technology professionals to embrace shared objectives in support of the enterprise. In legal IT it also means convincing highly intelligent, busy and often skeptical legal professionals of the value of those shared objectives to the partnership or legal department. Leadership in legal IT is hard, and it’s essential.

As the saying goes, “Good artists copy, great artists steal.” In this article I share a few ideas that I have stolen from others along the way and which I have found particularly useful in my role as a manager and leader. I hope you will find some of them worth stealing in turn.

A few words about my journey may be helpful. I started at Intel in IT operations right around the time that personal computers were taking over the desktop, leaving five years later to follow my dream of running a database applications consultancy developing solutions for the who’s-who of Silicon Valley in the 1990s and early 2000s. After many career twists and turns, as well as hard-won and valuable business experience, I landed in legal IT, where I have been ever since. 

This journey has provided me some perspective on what is common to IT in all enterprises and what is unique to the legal realm. Of all the idiosyncrasies of law firms, the two that most necessitate effective leadership are (1) an aversion to risk and (2) decentralized decision making. The first because the benefits of technology come with inherent risks and unknowns. The second because obtaining approval for projects requires convincing many business owners, not just a few executives, as would be the case in a typical business.

Trust Is Everything

Years ago, I read that integrity could be distilled into the phrase, “Say what you do, and do what you say.” That is, your words and actions must be aligned. If I could only give one piece of leadership advice, it would be this. Trust is the foundation of any successful enterprise, but it’s fragile—it’s hard to earn and can be lost in an instant. A successful leader works every day to build a reservoir of trust through words and actions that are aligned.

To lead in technology, you must also demonstrate competence. Others must believe that you have a sufficient level of expertise to deserve their trust and are willing to admit what you don’t know so that others may lead in those areas. In my case I know software development. It’s what I’ve done my entire career. But ask me about a router, a server or a piece of telecommunications equipment and you’ll get a blank stare. My colleagues trust me both for my areas of competence and for my willingness to freely state my limitations.

Trust is also bidirectional. You must be willing to trust colleagues in their demonstrated areas of expertise. Too many would-be leaders underestimate the importance of trust—perhaps having attained a position of responsibility by being “the smartest person in the room”—so it may be hard to give up control. The key is to surround yourself with the smartest, most capable people you can and then build a “trust economy” that allows each to excel in their own way for their  benefit and for that of the firm.

Deliver Magic, Not Simply Innovation

“Innovation” is the term of the day. Every firm and legal department is striving to out-innovate the competition. Vendors stand ready to sell innovative solutions to you and to your competition. But, if any firm with sufficient financial resources can buy these products, what is it that will differentiate it from the others? Arthur C. Clarke wrote, “Any sufficiently advanced technology is indistinguishable from magic.” Competent technologists know that innovation is table stakes; to succeed you have to deliver magic. I define technical magic as that which delights and inspires.

The good news is that delivering such magic does not require the most expensive or even the latest technology. Rather, what is required is creativity and ingenuity. First, work to deeply understand the key processes of your firm. Then consider which process steps limit the end product, whether that product is delivered to clients or used internally. Don’t limit yourself to what seems achievable (that will take care of itself). Imagine what would delight your clients and then work backward to find the solutions necessary to achieve that effect.

Tell Stories, Don't Sell Features

The reason we technologists have jobs is that technology is hard. Busy legal and administrative professionals have other things to worry about. Our job, as technology leaders, is to identify where technology can enable and accelerate their objectives. To do that we need to tell stories about what that technology can do for them to build a conceptual bridge between technology and their world. By “stories,” I do not mean fiction, but rather painting a picture of what the technology will look like to them and their clients.

For example, don’t talk about how natural language artificial intelligence lets attorneys speak to their phone to get client data. Ask your attorneys to imagine a time when they were running late for a client meeting and forgot to print a copy of the client’s capitalization table. With our new voice-enabled knowledgebot, they can simply say “Send me the latest cap table for ABC Corp” while pulling into the parking lot. The document will be ready to open in their inbox by the time they sit down for the meeting.

Get Clear on Your Key Results

On my team we use objectives and key results (OKRs) to keep our focus on what is most important. Of course emergencies arise and priorities may shift, but OKRs help us avoid unnecessary “drift” because of unclear goals. OKRs also help to build trust by tying work back to measurable key results that generate clear business value. In addition well-written OKRs help us tell stories and avoid unnecessary technical jargon (although some key results do need to use technical terms in order to be sufficiently specific). An example of one of my team’s OKRs is:

“Deploy 100+ process automation solutions by 12/31/2019, as measured by:

  1. New robotic process automation (RPA) platform selected and licensed by Q1/2019.
  2. 3+ prototype RPA automations deployed by Q1/2019.
  3. 25+ non-RPA automations deployed Q1/2019.
  4. Firm-wide automation “hackathon” held to identify automation candidates Q2/2019.
  5. 50+ RPA & non-RPA automations deployed in each of Q2, Q3, Q4 2019.
  6. ROI for all automations reported by end of Q4/2019.”

These key results can then be split into more detailed individual OKRs and assigned to various team members.

While OKRs are a great management tool, their inherent clarity is also a powerful leadership aid by providing a road map for the entire team. They help peer departments and groups understand what your priorities are and what you expect to achieve. Moreover, by promoting transparency, OKRs help firm leadership provide appropriate guidance to ensure department OKRs are aligned with the firm’s goals.

When in Doubt, Overcommunicate

It has been said, “When you’re tired of saying something is when others are just starting to hear it.” While this may make you a bore at parties, in business it is right on the money! Busy professionals have a lot on their mind, and even those who report directly to you may not immediately understand the direction you are setting. Administrative and legal professionals have their own priorities and biases, so even more communication is required. The key is to continually adjust and refine that communication so that it is meaningful for the recipients (tell stories), is clear (OKRs) and engaging (magic). You must then deliver on those promises and clearly acknowledge any shortfalls (trust).

In a law firm, email is the clear medium of choice and is also the least expensive way to communicate. Regular progress updates about OKRs can be sent to any stakeholders One-on-one communication is the most powerful but can be harder to arrange with lawyers who are expected to spend their time billing. In any case communication should be tailored to the audience and connect any technology to its business benefit. My recommendation is to use all channels at your disposal so you can accommodate individual preferences for information consumption.

Multidimensional Leadership

Alas, we live and work in an interconnected, multidimensional world. It isn’t enough for IT leaders to manage and motivate their own teams in service to a monolithic end user. We work side-by-side with other administrative teams from finance, knowledge management, human resources, marketing and more. Each of these groups is simultaneously striving mightily to deliver on its promises to management and firm leadership. As new initiatives emerge and new ad hoc teams are formed, intra- and interteam dynamics follow a predictable evolution, as articulated in Bruce Tuckman’s stages of group development: forming, storming, norming and performing. Ironically, this is particularly evident during high-growth periods when the business is adding new head count and new initiatives—and when everyone is racing to keep up with growing demand.

All of the leadership principles described up to this point apply equally to cross-team leadership, and failure to take these principles into account will result in confused and unhappy teams, unnecessary and counterproductive internal competition, wasted effort and money, and degraded outcomes.

An example of alignment from my recent experience has been the creation of an operational data store at my firm. Our operational data store brings together key business data from all of our line-of-business systems into a single database that can be easily and securely queried to make faster and better-informed business decisions. This required—and continues to require—efforts to align IT, finance, human resources, knowledge management and marketing to decide which data to include, at what level of detail and to whom it will be made available. Only by slowly and carefully building a shared vision (story) for what the operational data store would deliver to business decision makers could we proceed effectively. Through many discussions (communication), we aligned our objectives (OKRs) and built trust. It would be dishonest to say that this team-building work is, or ever could be, fully done. Rather, the pressures on each department to deliver on its individual commitments are so great that, absent ongoing leadership, the interteam relationships would suffer and the operational data store could not have been built.


Leadership is an amalgam of many “soft” yet critical skills that may not come naturally to technologists. In our careers success came initially from a demonstrated ability to apply hard skills to solve well-defined problems. That is fine until you need others to share your journey, at which point “why” becomes as, or more important than, “what.” The legal IT leader must explain the “why this” with a story that will tie the “what” to business value. Then, answering “why together” requires trust from those involved that you are a worthy and honest companion. Finally, “why now” requires explaining the potential of the magic you propose to invoke. Combine these with plenty of persistence and patience, add regular and clear communication, and it’s amazing what can be accomplished together!

Mark Gerow

Mark Gerow directs Fenwick Labs at Fenwick & West LLP, where he is responsible for application development and business process automation at the firm. [email protected]