Winston & Strawn’s CIO Dishes on Choosing and Using Practice Management Technology

Winston & Strawn’s CIO Dishes on Choosing and Using Practice Management Technology

Winston & Strawn CIO David Cunningham discusses his firm’s experience with practice management tools.

Ian Lopez, LegalTech News, February 17, 2017


Major law firms are being asked to do more with fewer personnel, and with lawyers taking a lot of the work previously given to administrators, practice management technology has become a more ubiquitous component of the workflow.

As found in the American Bar Association’s 2016 Technology Report, practice management technology use at large firms (500+ personnel) has jumped in the last year alone by about 40 percent. Among the major firms using this technology is Winston & Strawn, an international firm that touts a team of 850-plus attorneys and expertise with technology around issues facing law firms worldwide.

The man behind the gadgets is chief information officer David Cunningham. In choosing, implementing and overseeing the use of technology for one of the U.S.’s largest firms, he’s learned some lessons from his experience with practice management software.

Here’s Cunningham’s breakdown of and advice for using practice management:

What do you take into account for choosing and using firm technology? Thinking long-term and benchmarking against Big 4 consulting firms has a huge influence on us. Instead of simply replacing one system for another, we asked why law firms are 10 years behind how other professional service firms manage their resources. We knew we had an opportunity to fundamentally change the efficiency and effectiveness of the business.

Practice Management tool of choice and why? We spent four years analyzing our needs and assessing every product on the market. We custom developed a few solutions along the way to address important gaps, like an early matter budgeting and dashboard system and our app store-like intranet. However, we’re now in the midst of implementing a dozen aspects of Prosperoware’s Umbria platform, in conjunction with a natural language query system and a few data analytics and visualization tools.

Is this the first PM tech you guys have used and if so, why the switch? We’ve been using our custom Budget Manager tool for four years, but we will kill it this year. It allowed us to understand our historical matter data when developing a matter budget, but the Umbria system will replace it with more sophisticated analysis and better integration with experience management.

Pros of using this tool: Umbria moved beyond “legal project management” and is executing on our ambition for an end-to-end ERP/business/client Intelligence platform. It doesn’t replace our accounting, HR, library, or CRM systems, but it provides the core data model across these systems and, combined with our WinstonWay intranet, the lawyer interface to most of our information.

What can be better? PM Systems, Umbria included, are still in their infancy. Each capability takes a lot of design and workflow time to get in production. But, it’s an opportunity to shape the future.

Greatest struggle in implementing technology and how you overcame it? Even more than budget or time, our bottleneck has been having great tools. We’re finally at a place where we have all of our key vendors in place, so this year and next year are completely focused on the quality of our execution. Our challenge is to blend together the key systems so they provide a seamless (and mobile) experience so our lawyers see them as simply “the way you work at Winston.” Getting the data and design that good is a challenge for our entire firm; it’s not just an IS issue.

Key things law firms need to look for in choosing practice management technology and why? If the practice/project management system expects a lawyer to do more work than before or to stop what they are doing to go to a separate PM system, you will lose the battle. A great system will reduce work, lower the number of places a person has to find information, and give a lawyer more real-time insight when they are doing the work they already do.

Almost every system we considered expected us to replicate firm-wide capabilities in their PM system (e.g., financial/profitability analysis), didn’t adequately replace silo capabilities (e.g., time entry), and/or left key gaps (e.g., sophisticated experience/talent management).

Advice for other law firm CIOs getting staff onboard with using PM tech? Our staff is actually eager. We have 400 active projects just in IS, which is a bit crazy. We use tools like Microsoft Planner, Visual Studio, and Slack to track teams and tasks, but we’ll also experiment with using Umbria for our staff so we’re on the same page as our lawyers.

A firm without your PM Tech would look like… Without a broad “ERP” mindset to PM systems, I think it’s likely that “legal project management” will be adopted by only a minority of lawyers, with particular practices, clients, or personalities. That’s a more comfortable change, but not one that fundamentally kicks a firm into the world in which we now live.

What are some insights made possible with this technology that weren’t available before? These insights are still evolving, but this is what gets us excited. Some examples:

  • Case Strategy: Learning from past cases to identify the strategy, team, timeline, and risks of a new matter.
  • Client Intelligence: Identifying issues and patterns in industries and companies to understand how better to help clients and potential clients.
  • Talent Management: Building the ‘best fit / best value’ team for each matter, based on experience, results, relationships, costs, etc. And driving recruiting, retention, and career development plans based on our pipeline.

How has PM changed the way you practice? We’re still early to claim big wins. But firm and practice management knows that practice management systems, data, and processes are key to our objectives to strengthen our culture, be a destination firm for top lawyers, increase predictability of costs and results, etc. It’s not about “practice management;” it’s about running a business well in a highly competitive environment.

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