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Jason Barnwell is an attorney in Microsoft’s Corporate, External, and Legal Affairs department. He leads Microsoft’s Legal Business, Operations, and Strategy team, with previous roles leading the Open Source Software practice group and counseling the Cloud and AI Platform Business. Prior to joining Microsoft, he was an associate in the Emerging Companies practice group at Cooley LLP. Before entering law school, he worked as a software engineer developing enterprise software. He earned his B.S. in Mechanical Engineering from MIT and his J.D. from the University of Southern California School of Law.

Florence Cathedral, Florence, Italy
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How do we become lawyers who can see, understand and solve the biggest picture issues? One lawyer’s mid-career reflection.


I came to law from engineering. My previous training and trade create an outsider’s inside perspective on how we solve problems with the practice of law. As lawyers, we often lay bricks to address the instant problem instead of looking at the bigger picture, spotting patterns, and architecting solutions that efficiently create more value.

An experience from the second month of my practice as a corporate associate at a big law firm exemplifies the pattern that I have seen again and again. I had to be naïve to spot the issue.

I was staffed as the junior most associate on an M&A deal advising our client as they sold their business. One afternoon we were assembling the shareholder consents necessary to approve the transaction for mailing. The process involved:

  1. printing out master documents;
  2. copying the master documents and placing the copies in stacks in the copy room;
  3. several paralegals and associates walking loops through the copy room picking up one document from each stack to manually collate a mailing packet; and
  4. adding a custom cover letter with share positions and nominal proceeds.

I was still an adequate software engineer back then. I told one of my colleagues that I could automate the process with some basic scripting. We could emit a document stack for each shareholder of crisply printed originals with the customized holdings statement using a little mail-merge. A six-person crew would have converged to one person pulling the collated stacks from the printer and inserting them into mailers. The rest of us could focus on other aspects of the transaction rather than walking laps in an ozone filled copy room.

My colleague declined my offer to automate our task without explanation. I pressed for a reason, and I was told that my process was not known, understood, or trusted. That was fair. And this work needed to be done right. I tried to explain that our automation would be wrong or right, but fully testable. I could run a small test for auditing before sending the whole job. Again, my offer was declined.

I planned to revisit this for the next M&A deal, but about six weeks later I realized why that would be pointless. I saw the itemized bill for the transaction. A small portion compared to the proceeds, but still a large number. There was a line item for my contribution. My hours worked multiplied by my billable rate. That client paid a lot for me to make copies. There was inadequate incentive for my firm to take advantage of the efficiencies I could offer. We respond to the incentives we are offered. Cf. Steven Kerr, “On the folly of hoping A, while rewarding B,” 9 Acad Mgmt Exec 7 (Feb 1995) (republishing “academic classic” because so many fail to heed its wisdom).

On a personal level, my intrinsic incentives were not aligned with the traditional and accepted law firm construct. I had to find a place to practice that rewarded efficiency. That saddened me because my firm was wonderful. I enjoyed our colleagues, our clients, and our work. Brilliant practitioners taught me. They showed me how to sharpen my lawyer knife. They turned me into a minimum viable lawyer. They cannot know my gratitude for their investment in me. But I could not un-see the value misalignment, and I saw no path to changing the system from within. I joined Microsoft’s legal department because I believed I could build my practice in a way that aligned with how I want to deliver value.

Microsoft rewards me for seeking efficiency through innovation and developing a future-ready practice. We have a candy store of opportunities to go after and a unique access to talented people and resources. Brad Smith keeps us focused on the most impactful opportunities. And he frequently emphasizes that if we innovate our way out of a job, he will find us another. I am a beneficiary of that ethos. My earliest lessons from the profession inform how I practice and how I seek to influence our practice. I hold on to my naïveté. It helps me ask questions that focus on the big picture. I have a metaphor that I now hold close: be the architect, not the bricklayer. I will try to offer an operationalizing framework for this concept after a brief explanation of the genesis.

The “architects and bricklayers” analogy evolved from a conversation at a meeting of the 2016 Fellows of the Leadership Council on Legal Diversity (LCLD) that centered on finding purpose in our practices. We discussed finding meaning in our work by contextualizing what we do as the process of building something valuable beyond completing a series of tasks. The sum or our work is building a cathedral, not just laying so many bricks. We started extending the analogy beyond “Why do we work?” to “How do we work, as leaders?” How does an expert technician (bricklayer) become a strategic advisor (architect)?

The Big Picture

We have the choice to build our practices by operating like strategic advisors who look at the big picture of client needs, or technicians who respond to narrower client needs with exceptional depth. We must find a practical balance between these approaches appropriate for our career stage and vision. Successful legal organization leaders often begin their careers as exceptional technicians and grow themselves into architects as they broaden their gaze. They typically push themselves to grow before being asked to prepare themselves for the future. My mentors and sponsors model this.

David Howard is our executive sponsor for law firm engagement. He is an exceptional technician who always sees the big picture. He is the architect who directs our law firm engagement strategy, and is intentional in pushing us to develop operational excellence that builds towards strategic differentiation. See David Howard, “Microsoft’s New Strategic Partner Program” (July 27, 2017); see also Michael E. Porter, “What Is Strategy?Harv. Bus. Rev. (Nov-Dec, 1996). An explanation of this duality may help.

We care about the price of the legal services we buy. We are market testing more work with comparative bidding to get more perspectives, from more diverse teams, with fair pricing. But we are less price sensitive and do not choose the lowest bid for much of our work. Strategic matters that yield poor outcomes because we did not invest enough in the right partner are not good value. This is why we focus on relationships and holistic value in our partnerships with our most trusted advisors who do our strategic work. Much of our work requires our outside counsel to see the big picture, and David asks us to advance that with culture and systems because be sees the bigger picture. It is hard to acquire his ability to see the bigger picture, but we can try.

Practically addressing the classic challenge that “What got you here will not get you there” and growing ourselves into architects is hard. We usually do not have time to put our practices on hold and take extensive business management and executive leadership training. We weave our growth plan into small gaps and seek efficient growth hacks.

My hacks started shortly after joining Microsoft. I began reading short form content from sources like the Harvard Business Review and started sharing excerpts and analyst notes. I cringe when I read my content, but creating a self-expectation reinforced by our colleagues that we will share our thoughts drives us to seek content and create mindshare. Documenting and sharing our observations also creates a content web that lets us remix our own content when we are asked to be an expert, even when we are not.

One approach to self-preparation is to actively shift our mindset and try to operate like we have our future role now. Consume information that person would consume. Start conversations with people and about topics that person would have. Develop a vision that person would use to lead others. Taking those demands upon ourselves can change our view and provoke our evolution. Acting like this before we are called can also help our mentors, our sponsors, and ourselves see relevant skill gaps and capabilities earlier when the stakes are lower and unlearning is easier. It can also help these people see our potential to do more.

My approach to this was risky. It was not always well received. According to a recent Deloitte report, 61% of workers across a wide range of industries acknowledge covering their true self while a work. See Dr. Christie Smith & Kenji Yoshino, Uncovering Talent: A New Model of Inclusion at 3 (2014); see also Clark & Smith, “Help Your Employees Be Themselves at Work“, Harv. Bus. Rev. (Nov. 3, 2014 (citing Deloitte report).  It may sound odd to some, but I had long been covering my curiosity.

However, to continue to grow at the pace demanded by my job, I had to learn to uncover.  I did that by asking a lot of questions.  Indeed, I would ask almost anyone in our department a question about almost anything in their area of expertise that was interesting. And I would try to give back anything I could that might help them accomplish something they cared about. I now have many teachers who invest in me. I am fortunate so many people welcomed me and helped me persevere through an uncovering process that was not comfortable because it was different. We are all different. And it is hard to differentiate yourself if you cannot or will not show people how you are different and why that helps you create value in a shared enterprise.

In hindsight, it is easy for me to see that curiosity is a core element of the legal counseling discipline.  I am an attorney, and the concept has special application for my practice. The architect mindset and trying to see the big picture of client service means understanding:

  • how our client’s business works;
  • how the work we do fits into their bigger picture;
  • how we can tailor our service delivery to map to their needs;
  • how we can offer solutions that go beyond their instant challenges and support their strategy and future direction; and
  • why our client values outcomes, how we can differentiate our offering, and how we can tell our value story in a way that resonates with our client.

This customer-obsessed approach to client service has been modelled for me in private practice and throughout my tenure at Microsoft. One of my Microsoft managers asked each member of his team to read The Reebok Rules and develop a client service plan that would help us strengthen the client relationship and turn ourselves into trusted advisors. That exercise was invaluable in creating a vision for each of us that steered our actions and investments to foster a trusted advisor relationship. Many legal technicians have internalized the responsiveness and substantive excellence that are the basis of becoming a trusted advisor, but how do we become strategic advisors?

Strategic Counselors Focus on Securing Outcomes and How They Are Delivered

Architects care about form and function. It is their role to understand the larger context of the client’s needs because design does not exist in a vacuum. Similarly, strategic advisors understand their counseling solutions are influenced by factors that go beyond laws. Design constraints can include politics, publicity, culture, and other factors that influence the client long after the matter’s outcome.

Our clients often want a specific outcome, e.g., winning a case or getting deal done. But for many clients the “how” matters too. They want a win with minimum publicity attached because the issue is politically sensitive. They want a deal done with counterparty goodwill left intact because there is an enduring partnership that must be preserved. They want a bill passed with bipartisan support because it must weather an unclear political landscape. Clients value solutions that uniquely address what they want.

Asking our client about the “aesthetics” of how she wants her matter handled can provoke a conversation about her bigger picture. We can strengthen our credibility with our clients when we can explain the options for how we can handle a matter, point to several other examples of similar work we have done that highlight multiple approaches, and then offer a recommended approach informed by what we already know about her business strategy, culture, and preferences.

One way to find out what our client likes is to ask her about other similar matters she has dealt with directly or observed. What did she like or dislike about those situations looking past the specific outcome? Was the resolution too slow? Did it consume too much of her time? Did the framing of the issue cut against her general policy agenda? There are many tactical choices that can help us align how we achieve an outcome with our client’s preferences. How we drive outcomes can differentiate us as more than a technician. Architecting tactical selections that advance the outcome and support our client’s larger goals marks us as strategic advisors.

My practice at Microsoft started in product counseling. I immersed myself in my clients’ products and services. I wanted to understand what we made, how we sold it, and how our customers derived value from what we offered. I changed my counsel to use the business’s jargon. My guidance was grounded in the context of our efforts and our competitors. I started my engagement by learning my new clients’ thoughts about how their previous counsel had served them and built upon that understanding. I always tried to focus our counseling team’s efforts on issues that were impactful for our clients. And I tried to look beyond the narrow questions I was asked and offered my predictions of where things may go.

Strategic Counselors See the Past, Look Around Corners, Bring Outside Perspectives, and Level the Playing Field

Architects design within the context of the past, present, and future. A common trait among our outside counsel who are strategic advisors is an understanding of our past. Microsoft’s legal department has substantial internal mobility for legal professionals. We often rely on outside counsel to be the memory that holds our institutional wisdom because our people move. Having a view on how and why we did something in the past and informing counseling with that context aids and adds credibility.

Bootstrapping historical context can be hard when we are supporting a new type of client work, but there are often sources of history. This includes the people who have previously served the client (both inside and outside of our organization), and any public information we can find (blog posts, reporting, position papers, testimony, etc.). Contextualizing why we are recommending a course of action within our client’s past actions and distinguishing why doing something the same or differently based on our client’s current strategy can be differentiating. Here is an example of the type of counsel an architect-lawyer might provide:

“I know you avoided these license risks in the past, but based upon your new approach to creating value from your intellectual property portfolio we think these risks are aligned with and complementary to the larger value story you are trying to tell your customers.”

Architects anticipate changes and design with the future in mind. We often use the sports analogy of “skating to where the puck is going” to indicate that we want solutions that will work within a future context. Paying attention to the direction of business competition, regulatory, and other constraints are trending and designing solutions that anticipate the future state of play is strategic advice. We value counsel that tells us not only where we are but helps us decide where we should go. Another architect-lawyer example:

“We expect that based on where the future visa cap is trending due to the policy agenda of the likely next election winners, you should develop more high-skilled technical employee carrying capacity outside of this territory.”

Great architects can influence the rules to enable their client’s vision. Sometimes the constraints that govern what is currently permissible are outmoded. Society, culture, and technology are ever changing. A strategic advisor considers not just working within what is, but what could be if we share our perspective with the right people. Many legal mechanisms (e.g., elected body regulations, administrative rule making, and judge made law) have a long development cycle that can require developing the right facts, framing the right story, and finding the right partner to advance the issue. Helping these partners understand our story often requires a long view on business needs and access to people who can influence the outcomes. Strategic advisors invest in understanding long-term business needs and developing relationships with the right people. They are indispensable precisely because, many years earlier, they started focusing on the long-term. These strategic advisors have no substitutes.

Architects seek broad perspectives and build upon designs that they see elsewhere. Indeed, that is one of the natural advantages of law firms. At Microsoft, we depend upon our outside counsel to be outside-insiders who operate on both sides of our bubble. Strategic advisors stay current on what the other participants in the ecosystem are doing, and how we should adjust our approach to benefit our outcomes. The architect-lawyer might share:

“We have observed that most of your competitors now offer a more conservative indemnity in their contracting. You are offering your customers coverage that is beyond market. Consider adjusting your default approach to be in-market or highlight this benefit more aggressively when telling your value proposition.”

My experience leading Microsoft’s Open Source Software counseling practice pushed me to look outside and look ahead to serve our business. We radically changed the products we made and how we made them. That required engaging with the open source community in different ways. Our counseling team had to bring perspectives to our clients and colleagues that helped them adapt to the opportunity that was coming. The biggest operational change was a focus on building the right relationships. Those relationships gave us the insights and influence we needed to be credible and deliver value. It also required a team effort.

Strategic Advisors Lead Teams of Diverse Experts and Make Them Better

Architects work with a team of expert technicians to advance their designs to the limits of the art. To be the architect, we do not need to be able to do everyone else’s job. Our highest contribution as a strategic advisor is often a combination of:

  • providing a clear design vision in consultation with our client;
  • effectively communicating that vision to our execution team;
  • delivering our depth expertise;
  • coaching other experts on the team so those people can meaningfully deliver their contributions into a larger work; and
  • synthesizing a coherent result for our client.

We need to help individuals on our team tailor their contributions and align to create the most impact for our clients. When we activate and harness our team in this way we catalyze value that is greater than the sum of the individual contributions.

Here is a hard truth:  The practice of law rewards our investment in being a good technician early on, but does not reward our investment in being a good leader until leadership is a primary part of our role.

The challenge for ambitious mid-career lawyers is that we need time and repetitious leadership opportunities to develop that skill. If we do not invest in our leadership skills before we are formally asked to take on a leadership role we may be unprepared.  Conversely, if we view ourselves as bricklayers and architects while people still think of us solely as bricklayers, we are more likely to seek training, relationships, and experiences that will prepare us. We may also start thinking about how to manufacture opportunities for our colleagues. If we act on creating those opportunities for others, we may hasten our own transition to strategic advisor. This is the secret to accelerating your career. Relentlessly invest in the success of other people.

The most interesting legal issues often need input from many types of experts, primarily because they cross disciplines. It is critical for us to be fluent in our client’s language, keenly focused on what our client wants and needs, and ensure that our client service team speaks coherently. Clients are often not experts in the sub-disciplines that impinge on their matters. We may not be experts either, but we must know enough to place the experts’ input into the client’s context, remove jargon that clouds the recommendations, and turn streams of expertise into clear, actionable guidance.

The architect-lawyer eventually views her clients as part of her team. We must invest in understanding the internal relationship graphs of our clients to be effective, especially when we deal with larger client organizations. Getting the information our team needs to do their work well, and landing our guidance in the right place, often requires us to navigate the organization without access to the org chart. When we engage with larger clients we may want to identify the super-nodes in their network early on. They can help us navigate not only the current shape of the organization, but what it used to look like, and why it changed. Strategic advisors who develop this level of organizational understanding can simultaneously share their relationships with their colleagues and keep them close.

The Growth Cycle

We are living this growth cycle now. Our Legal Business, Operations, and Strategy Team brings together incredibly committed and talented business, technical, and legal professionals with diverse perspectives and backgrounds. We exist to help our legal department build the future of the practice of law. Our individual success is built upon the success of our team. We are constructed to require collaboration among our team, within our department, and with our partners to succeed. We must acquire skills and effectiveness we don’t have yet to achieve our ambitions because our full definition of success lives in the future.

Microsoft Legal Business, Operations, and Strategy Team areas of responsibility and interaction pattern overview.
Microsoft Legal Business, Operations, and Strategy Team areas of responsibility and interaction pattern overview.

Be Skeptical, Intentional, Thoughtful, and Proactive

The observations above may not work for your practice. You should be skeptical. But I hope these reflections help you think through your approach and design the experiments you need to architect your practice.