David Cunningham came to the role of CIO as an interim position initially but came to like it so much he moved on from his life as a private consultant for firms. Now a CIO at law firm Winston & Strawn LLP, Cunningham spoke with Pulse Q&A founder about IT in the legal sector, transitioning into the role of the CIO and why lawyers shouldn’t work exclusively from iPads.
*This interview has been edited and condensed for clarity.”
Mayank Mehta: How do you and your team make the decisions you do today be it leadership strategy or even some of the product and technical choices you’re making?
David Cunningham: There’s a lot to it, of course. I’m not sure if you’re familiar with the law firm and the type of people that we have and the services that we provide. Is it better to back up a step and provide you some of the context?
Mehta: Yeah, that’d be great actually. Especially as I think it would help a lot in understanding what you do.
Cunningham: We’ve got about a thousand lawyers, about ,2000 people in total and as a CIO, IT is part of my organization, and I also have an even larger group that focuses on analysis of discovery and litigation data. So we’re doing a lot of the data analysis and workflow and providing services directly to the clients as a paid service.
We have a very big research and intelligence unit as well. And we have the risk management aspects as you would expect. And then we have a change management and a learning aspect all around technology. In addition to all the things you’d expect on the IT side, infrastructure, services, monitoring. So to answer your question about how we make decisions; some of them can be a range because we do so many different things.
We’re making security and risk decisions and we’re deciding what services to provide to our clients in some areas. So of course there’s not just one answer to that. But one advantage that I’ve enjoyed for my tenure here is that I’ve been able to speak to our clients a lot of the time. Rather than only staying within our walls, we’re asking people what they would like to change, cause lawyers in general prefer things to be rather settled and not to change quickly.
Traditionally, I’ve been able to spend a lot of time with clients as well as legal departments that are considered the most progressive in the industry and ask them what they’re doing. And over the last six or seven years is really where the faster change has been coming from. That gives me a luxury of being able to ask a lawyer what they think their client wants.
If I’m speaking to the client directly then I’m able to come back to our firm and say “here’s what they’re doing, or here’s what they aspire to do in three to five years. Why don’t we get there even faster?” That way by the time they’re ready, we’re able to work with them or we’re able to help get there faster. And what we’re finding is–Winston’s been very good about this– that it’s advantageous to not only change with the client but actually help them change faster. And so that allows me not only a direct line with our customers–and to be very accurate about what it is we want to accomplish–but a better way to engage our lawyers and our leadership and specific objectives.
This is what the client expects. We want to help them get there. And the nice thing that actually helps, the more change that we’re able to accomplish, it actually helps our business. In the law firm world, that may seem like an obvious response in some industries. In the legal sector, it’s been a bit counterintuitive because you may think a law firm wants to only bill by the hour and stay very traditional and not change in order to maximize its profitability.
What we have learned early on and enjoyed is that if we’re finding alternative ways to work with our clients and to be more in line with the things that they consider a value, it not only helps the client, but it actually helps our business as well. And that’s a long way of saying that the decisions we make are generally by listening to the client and just aiming for what they’re trying to achieve.
Mehta: Makes sense. Is that unusual for the legal world or is that happening more and more? Where traditionally you’d say “Hey, let me talk to the lawyers and actually understand what they’re looking to do,” and go through their eyes rather than directly converse with the clients.
Cunningham: Yeah, it has traditionally been a huge obstacle because going directly to the client was very uncomfortable for the lawyer. If anybody from IT or any other departments said “Hey, can I talk to your client?” They may say yes, but it’s also uncomfortable. They might be concerned about what you’re going to say to them. There was a group that formed about six years ago now that’s called CLOC (the corporate legal operations consortium).
I was fortunate to be there on the ground floor when they were just a few people in a room.They were basically our clients–or the people who run the business of our clients– and they were looking at ways to change the legal industry. It was already becoming more of a buyer’s market than it was. So I had the luxury of being able to sit down with them in the early days and that gave you that first opportunity and now that the organization has grown from a dozen people to 3,000 people. So now it’s becoming more of the norm. But it is still the exception, but quickly becoming the norm. I’ve been kind of riding that for the last six years and felt like that really gave me a headstart.
Mehta: And then in terms of the actual technology decisions that you guys are making, how much do you think about using traditional sources versus perhaps a peer group that you trust versus a new form of research or R&D that you guys are able to take advantage of as part of making your platform decisions?
Cunningham: I’ve talked to the people that want to sell us advice and that sounded helpful in concept, but it never really was. This was partially because professional services are a niche and then legal is a niche within that. And so I didn’t find myself turning to any professional paid provider of advice. I know many do. To me it’s talking with my peers, it’s talking with the clients as I mentioned. Then it’s about really sitting down and talking about business process life cycles, as boring as it sounds with our business leaders and then with the software vendors.
What we’ve tried to do is evolve firstly from custom software where we started and secondly to what I would call “beautiful silos”. In other words software that was really great at what it did but it only had part of a complete beginning to end process. And we’re continually working with fewer vendors that provide a wider part of an entire end to end process. We focused on seven processes that are the core of running our firm. We’re asking ourselves, “What’s the best we can do to automate those, provide a visualization of everything happening within those and then provide that information right to the fingertips of the lawyers on their mobile device.”
Mehta: Let’s transition from there into your journey and where you are today. What does that look like? How did you distinguish yourself amongst your peers to get to where you are as part of the leadership?
Cunningham: I probably had a quite a different journey than most because I was a consultant to law firms for 20 years and so, instead of being the CIO, my job was to be the technology and risk auditor of large law firms. I was generally with a consulting firm that grew from a small group to the biggest in the industry. And I was generally hired by the managing partner or the COO of the law firm.
My job, along with my team, was to take a look at everything. We’d look at 45 different aspects of the firm and understand how they’re actually applying technology. Some cases were very technical if your disaster recovery covered by your systems running in the proper way. But often times looking at it more from the effectiveness standpoint. Are they actually affecting the business and how are they helping your lawyers do their job? And so my job was to come in and be very critical of those areas. Write a report that highlighted and rated the capabilities on a 1-5 scale in each of these areas.
And I did variations of that for a long time and I did that for over 200 law firms, in the US and across Europe. To some degree, I never wanted to be a CIO. As I’ve said many times, it was because I saw the challenges CIOs face. Sometimes they were underfunded or they were doing their job in a way that wasn’t really mitigating the risks as necessary. And so I saw a lot of the negative side. Winston was a first for me. It was the first time I stepped out of the consulting role to be employed by a single firm. But it’s in large way the same role because now I’m still consulting but to this one firm, asking “How do we do all that better?”
I’ve got a lot of relationships as a result. I know a lot of people across the industry because I’ve worked with them and helped them or guided them (or not helped them in some cases!). ButI had an understanding of how different firms have done things and I can, in combination with the CLOC, take the client’s perspective. I was fortunate to step into this role, not as a technical expert to say, “Let me tell you how to design” but really from the business perspective to say, “Here’s what we need to accomplish.”
I was fortunate in the consulting firm, we merged with a business consulting firm in the midst of that. And so they were not technical, they were focused completely on the psychology, the leadership, the metrics, the long range planning of the same firms. And so that allowed me to really absorb that and ask, “How does our technology help?” It has helped me quite a bit to bring that perspective to Winston.
Mehta: Obviously it was a planned transition given what sort of opportunity that you saw, but how was that transition for you and what were some of the challenges that you didn’t anticipate coming in spite of having done this for so long?
Cunningham: It was interesting because I’d been a consultant for so long. It was funny how it was different in some ways because one. The first 90 days were almost exactly like consulting projects. I’m coming in and meeting the people, basically assessing our status today and mentally, if not literally, rating the firm on how it was doing and looking for areas of improvement. And so I felt like it was just one more; my 201st consulting project.
But I also realized that sometimes I might deliver a report in a consulting context and the firm would say, “No, we don’t want to change at all. We acknowledge your report. We still don’t want to improve.” And I realized, wow, if that happens here, I’m kind of stuck. But obviously they hired because they, they wanted to improve. So that didn’t happen.
But it was the first time I had authority because I had always influenced people without authority. Yes, I was hired by the managing partner as a consultant. So I had that implied authority, but I would work with the IT departments of firms and say, “Hey, here’s some ways that you should change.” And I would need to convince them of that change and work with them over a period of time to make the improvements. And here people were sitting at a table waiting for me to make a decision to tell them exactly what to do. And that was an oddity for me, that they would actually consider me the authority they had to listen to. But you know, fortunately that’s not the way I like to run things anyways.
And so we’ve got a great team where they don’t need me to be in authority. They don’t need me to tell them what to do. We work a lot together as a team. And so I would say for a while I had to be the authority as we were growing our team, but now I’m very much back into a consultative role because we built up a very strong team that doesn’t need me there every day. And so it’s, we really come together around design workshops and focusing on prioritizing how we solve problems together. And so it’s almost like it’s evolved away from an org chart more into a design team that meets on a weekly basis, which I really enjoy.
Mehta: And the transition, is that something that sort of came to you as an opportunity or were you seeking it when it came about?
Cunningham: I wasn’t really seeking it. I was helping another firm hire a CIO position and therefore I was being their interim CIO for a while and I started to enjoy it. I didn’t quite expect that. And so the recruiting firm that we had hired to help that firm who’s in a different city said, “Hey, you know, we’ve got this other opportunity.” So it was just interesting timing that I became a little more open to it. I started to see the benefits and then Winston themselves had just hired an auditor to come in and really say what they should do to take advantage of technology. And as part of that program, they decided to create a strategic CIO role and it was just good timing.
Mehta: Let’s transition to some of the questions from the community. We hear more and more that IT is no longer sort of thought about as a traditional cost center that it needs to be now involved in the business and to do that you need to think about running IT as a business more and more. What does it mean to do that and what does it mean within the legal sector?
Cunningham: I don’t think about running IT as a business. Maybe this is because law firms are profitable but still immature from a business standpoint, but I really shine the spotlight on the business and say, “How do we use technology to run the law firm like a business and in a new way?” Is that relevant to your question?
Mehta: Yeah, I think so. Especially as we think about every business as a tech business. And I would imagine this is also true within the legal world. What are some of the changes that you’ve seen in the legal world and what are some things that you’re excited about as well?
Cunningham: Law firms, like accounting firms and engineering firms, are what I would call a “people business”. It’s professional services with highly educated people. It’s all about their expertise and about their relationships. So I would argue it doesn’t start as a tech business. The traditional challenge has been how do you introduce technology into that “people business” in order to improve it? What’s the right balance?
That’s a 15 year journey we’ve been on. So it’s not a new question. We’ve made huge strides around areas like electronic discovery and a big focus on data analytics. Now everybody talks about machine learning and data-driven insights. I would say, if you call it the practice of law, how do you help lawyers do their job more effectively and more efficiently? That has been a very traditional focus of technology in the law firm business for a long time.
What is emerging now is a complement to that is the application of technology to the business itself. How do I run the firm in a more advanced way? I’m very active in this area and I actually interviewed about a dozen people that have either operations or innovation in their title and I would ask them, “What is your firm’s business model?” And no one had an answer to that question, which I thought was interesting because these are mature companies–not startups–that make a lot of money and do very well for themselves and have a lot of smart people.
And so I give them all credit, but there isn’t really a defined business model at the core of that. That’s an opportunity. Obviously the firm is successful and we’re all growing even in these tough challenging times. I would say that’s the new focus. The focus for leadership and technology in the legal market is focusing on what we generally call legal operations.
And so I don’t spend any time thinking about how I run the business of IT with technology. We do that all the time. I spend all my time thinking about how we can better run the firm with technology.
Mehta: Has Apptio’s equivalent of the world come into your world as well? Where you’re able to measure the costs and see the returns like a sales and marketing leader would be able to see the impact of technology in real time through these dashboards. And after that companies like that have become increasingly popular. Is that the case with you guys as well?
Cunningham: I’ve spent a little bit of time with Apptio and so I understand your point. It’s certainly not a product that’s used in legal. But to me it’s a little bit the wrong question. It’s not what we focus on. We do not say, “How much does this product improve sales?” We have to look at the people, the process and the technology and–we’re very focused right now in talent management, on the human capital management–if we can better match the demand of work we have coming with the supply of expertise we have, whether it’s recruits or lateral lawyers we bring from other firms, or the learning, coaching and career development we do. If we can better match that supply and demand, how does that affect our business? So it’s not about buying a product and asking how much money I can make. It’s about saying what are the metrics that define this business process and then how will that affect employee engagement, client satisfaction, and profitability?
I’m not an expert on Apptios but I think it’s more focused on measuring the technology.
Mehta: Are there any exciting new technologies that are particularly exciting to you that you’ve either come across or done POCs or pilots with, or even implemented specifically within the sort of legal realm?
Cunningham: For us I would say most of the products we use are the same products that other firms use. And so it’s not like there is one killer product that only we own or that we’ve custom created.
Where we spend a lot of our energy is blending together the user experience across different products. One is like I mentioned before. I have seven key business processes we’re focused on. So we’re automating those, providing a visual understanding of what’s happening in each area.
We have dashboards that the lawyers can interact with in those areas. We started by looking at how many products does it take to solve all of those to get those processes optimized. The answer was over 20 and so it’s not that we were after one killer product.
It was really saying, “How do we minimize it so we invest in the fewest number of really great products. Second, address these areas with fewer interfaces, fewer systems and workflows.” So we’ve been doing that. And then we spent time designing our own–and I hate to call it intranet–but service delivery platform, whatever you want to call it, to bring those systems together. Therefore we wanted to make sure that on mobile devices or on your monitor that a lawyer could interact with those systems without having to go to six different places to understand everything we know about a client. So getting that 360 degree view of any asset, whether it’s a client or a project or an expert or a peer firm. How do we bring all that information together in one place and make it so you can see that information at kind of a click of a button?
Law firms may be a bit different to other organizations. We don’t have a headquarters that does everything. We’re pretty distributed. You’ve got a thousand lawyers. You’ve got 400 partners and all those partners are doing leadership activities themselves. And so one of our greater challenges is we’re not trying to get a great system in the hands of six people. We have to get into the hands of hundreds of people everyday doing their job. And that means that has to be really simple so that people actually use it and they’re getting a lot of information visually from it, as well.
Mehta: I would imagine given that your team is so distributed, you guys have a mobile first mentality or at least are thinking about the idea of business on-the-go continually. Are there new technologies or products or applications that you guys have deployed that would be interesting there? And secondly, do you guys have a traditional deployment for hardware or do you guys think about your new workforce, especially on the sales and the consultants in the field as iPad-enabled? And if so, does that sort of take away any productivity from the traditional devices that people have had?”
Cunningham: On the deployment side, I mean we provide everybody with a very nice, very light Windows-based laptop. So that’s kind of the starting spot. And then they are welcome to bring the phone or pad of their choice to the equation as well. And we’re increasingly seeing that iPad pros–Surfaces to a lesser degree–are a great mobile solution. And so our job is to make it so it doesn’t really matter what the end point is and they all have to be brought into our secure environment. So we have to know about them and we have to integrate with them. But the iPads are great because a lot of people have a train ride. So they need to review documents and be able to red-line a document on the train. We’ve tried very hard to secure a document management system.
For most organizations that’s a smaller aspect of what people do, but for a law firm it’s the core. It’s the record of everything that happens with the clients. And so our greater challenge perhaps is that we need to provide this completely mobile environment where documents are flying back and forth, but we need to keep things in this secure encrypted document management system that makes sure that we handle the compliance and the records management aspects, but also the collaboration and for sharing. You can imagine how important version control is, for example, to a lawyer. So we want you to red line on your iPad, but we also have to make sure the version control is perfect. And so, yeah, so it’s very core to us as a law firm.
Mehta: The question that came from the community that’s related to this is you see the sort of duality of devices now. One of the questions that came in from Kerry Bray at Reservoir Group–and he’s done a lot of work with document management. He’s grappling with reducing the IT costs in running the company more efficiently. They’re going through the idea of being an iPad first or iPad only type organization and actually doing away with some of the Windows based PCs or the traditional sort of MacBooks et cetera. Are you guys thinking in a direction like this? And if so, what are the reservations in rolling that out or is this a planning process and if not, then why not?
Cunningham: What kind of business are you referring to?
Mehta: So in his case it’s called Reservoir Group. It is in the oil and gas business. They actually have a ton of people that are distributed across the board. They have a ton of document management that needs to happen both to protect IP, but also in enabling people to get access and get processes done really quickly to be able to move forward in the field. So there’s some similarities across both. How would you think about that?
Cunningham: I wouldn’t at all. It just a completely different use case. Lawyers, no, maybe not. Lawyers is a general term, but if you imagine you’ve got a real estate transaction where you have hundreds of leases and some 80 page contracts going through different revisions and the people reviewing these are very document intensive people. So I think other industries are probably viewing a lot more and checking and doing some workflow. And so I completely get why that would be relevant. But to a law firm, I would be lynched the next day if a keyboard disappeared.
Mehta: But even the keyboard enabled iPads wouldn’t necessarily be something that’s sort of top of mind in reducing costs while maintaining productivity?
Cunningham: That is an excellent complement to the workhorse of a real keyboard and machine.
Mehta: Alright, so we have just one final question. What are some of the top questions that you and your team are grappling with this year that either the community can help with or at least know what are the right questions to ask and think through?
Cunningham: I don’t know if it’s something a non-law firm community can help but maybe other professional service firms. I think we’re fine at doing our jobs. We are trying to take it up a level and define the metrics and getting back to your Apptio-type question. Then defining the actions we can take and how they change some key metrics for us. And so we’re taking a balanced scorecard approach to the business which says, “Hey, yes gotta look at financial information or financial objectives, but you also look from the client’s perspective and you’re looking at it from the employee’s perspective.” Then you’ve got the firm’s business processes. Those four elements have to be in balance in order to be a long-term success. And so we are charting out how the processes that we’re improving actually affect certain metrics and how those metrics are then noticed by the client.
If we actually achieved these changes, does a client feel them? Do they notice them? Do they have an impact? And then how does that affect the clients value and satisfaction? When the client is feeling satisfied and getting value, how did that then circle back and help us do more? And so we’re defining the business model of the firm basically.
Using that as a way to justify significant IT investments so that we can keep improving the business. We’re inventing it. And so if anybody has any perspective or case studies or even thoughts in the area, that’s certainly something that is useful to us.