As SVP and CTO for the Boston Red Sox, Brian Shield is responsible for the strategic direction of technology, fan engagement, day-to-day IT operations, and cybersecurity in support of the team, their fans, and Fenway Sports Management. With a career that has spanned multiple industries and bellwether companies, including FTD and The Weather Channel in addition to the Red Sox, Shield is known and respected nationally as a business-savvy industry innovator.
I sat down with Shield at the New England Sports Network Studios (NESN) for a recent episode of the Tech Whisperers podcast. In that wide-ranging conversation, we explored his leadership playbook, what a game-winning data strategy looks like, and the value of stepping outside your comfort zones as a leader, among other topics. Afterwards, Shield spent some more time talking about some of the attributes of great leaders and how to build a world-class IT team. What follows is that Q&A, edited for length and clarity.
Dan Roberts: What are some of the parallels between creating a World Series caliber baseball team and a world-class IT team?
Brian Shield: One of the most important elements of any successful CIO or CTO is building high-caliber teams. I’ve often thought that traditional businesses and IT organizations could learn a lot from how winning sports organizations construct their teams and develop their players. Any successful team starts with cultivating the right talent, whether that’s in baseball or in IT.
When you think about successful baseball teams, they have well-defined roles, highly capable leadership, and a thoughtful development process for their staff, much like the best IT teams. In baseball, you start with a farm system of young, capable talent. You have players with specialty skills — for example, relief pitcher, base stealer, defensive talent, etc. You have a starting lineup of your most talented players. Hopefully, you have a few All-Stars, together with a coaching staff, and a manager. To supplement your roster, you might bring in free agents to round out your team. Fundamental to each player’s success is a development plan that is unique to that individual player. Strengths, weaknesses, and areas of growth are identified with complete candor, backed by tangible findings. These methods are fundamental to a player’s ability to succeed but, more importantly, their ability to adapt as their competition evolves.
Successful IT teams are very much alike. Effective CIOs are always scouting out new talent — or should be. They have a plan to develop young talent by recruiting capable interns and early-career resources. They have a pipeline into colleges and universities, like baseball scouting organizations. These rookies are expected to learn the ropes from their coaches or managers, as well as from the veterans. IT teams staff for select domain skills and supplement with their own form of ‘free agents,’ aka consultants. You have your full-time lineup of veteran leaders. Your very best are your all-stars. At the top of the pyramid is your leadership team and CIO.
Where most IT teams fall short in comparison to successful ball clubs is their commitment to staff development. Too often, we treat professional development as an end-of-year assessment of strengths and weaknesses, with only limited candor about deficiencies and less commitment to a plan to evolve and grow. If development’s done right, you’ll have a high-performing team of diverse, complementary talent that can grow, evolve, and mature to allow the team to win well into the future.
What’s the lens you look through when you’re bringing on new team members?
This is a great question, particularly in today’s rapidly changing world. More than ever before, we look for good athletes. I don’t say that based on the business we are in, but rather, we look for resources who have the essential skills of the role, and, equally important, we look for resources who are hungry to learn and motivated to grow.
The best employees are energized by change, not threatened by it. We’ve changed our software development tools multiple times over the years. We’ve changed on-prem technologies to cloud-based technologies. There is a very real learning curve required to make these transitions successfully. Today, AI is likely to be the single greatest disruptor to the status quo we have ever experienced. As is often said, the pace of change will never be slower than it is today. Given the reality that rapid change is here to stay, these can either be opportunities for your organization and personal growth moments for you and your staff, or they can be debilitating. You have an opportunity when you bring on new team members to ensure they’ll not just meet your needs for today but also have the aptitude to evolve.
Great leaders are known for having strategic partners, not vendors. How do you build and invest in these relationships, and what are the benefits?
The question of the difference between vendors and strategic partners is a really important one. I think too often vendors might see themselves as providing a service only. We very much look for a strategic partner, and by that, I mean someone who’s not just selling a service or a product, but someone who’s thinking about our long-term requirements, someone who may be on another sales call for a totally different company and yet something pops in their brain and they’ll say, you know what, this would be really appropriate for the Red Sox. It’s someone who always has us top of mind.
In return, we invest in those strategic partners. We share our roadmaps, we give them an understanding of where we are and where we’re going so that they can best align with us and really maximize our benefits.
We’re blessed here at the Red Sox with some really great sponsors, and those sponsors are pivotal to our success on the technology side and, ultimately, the success of our business. And they really fuel a lot of our innovation as well. We’ve been very successful as a result of many of them and our ability to be able to cultivate these strategic relationships and move beyond just traditional one-and-done vendor relationships.
Building on that point, what’s your advice for technology leaders on how to think about and approach innovation?
You need to first understand your business strategy, your culture, your budget, and the skills of your team when assessing where and when to innovate. When is it appropriate to be an innovator versus a fast follower or a lagger? No organization is a leader in all areas of innovation, particularly with the rapid pace of change. You need to realistically assess areas where innovation can play a role. You need to understand when it is completely acceptable to be a 7 on a 10 scale. No one has the budget, nor the manpower, to be an innovative leader across all domains of technology, so you must choose: What select areas would realistically have the greatest impact on the success of your business with acceptable levels of risk?
Gone are the days of R&D where there was near exclusive focus on the R-research and little attention paid to the D-development. There needs to be an ROI associated with each innovative endeavor. Equally important, you don’t have to do this alone. When assessing your innovation strategy, leverage your peers and strategic partners. For example, while your organization may benefit from some specific use of AI, think about your peers, where this area of AI could mean the difference between success or failure. They will be infinitely more focused and committed to finding a solution than you would be, where you have limited risk or upside. Stay close to them and know when it may be time for you to innovate.
Place a portfolio bet on your innovation strategy. Make small bets across multiple forms of innovation if your budget allows, and more significant bets where the risk/reward makes sense. Leverage your partners in this assessment. Let them do some of the heavy lifting. Sometimes this is the best way to distinguish between who is a vendor and who is a strategic partner. Ultimately, build a portfolio of innovation where you honestly assess which technologies may make a difference, the criticality of this innovation to the success of your business and the risk of not doing anything, the ROI, and then determine whether you need to be a leader, a follower, or a lagger.
There is nothing wrong in choosing not to be a leader. The bigger mistake is to be attracted to shiny objects and squander time and resources on ill-conceived plans. I’ve kissed my share of frogs in search of game-changing technology. It’s learning from these endeavors that make us good CIOs.
Another hallmark of great leaders is their ability to adapt to change and continually evolve. Can you talk about that in context of technology’s role in the business?
One of the most important attributes of successful leaders is their ability to pivot — with new technologies, with business circumstances, understanding their culture, the business challenges that the company might be facing, competitive pressures, etc. Before anyone’s a successful CIO or technology leader, they need to be an effective business leader. And so, understanding what drives the business, what are the changes or concerns that the business might be facing, and then leveraging technology to drive revenue, improve productivity, reduce cost, address the competitive landscape, and future-proof the company as best you can, recognizing the world is changing at a dizzying pace — all of these are things that should be top of mind for any CIO and, really, are the hallmark of the most successful ones. It’s that ability to help set a vision and then drive alignment across their organization so that they can realize success and pivot as circumstances necessitate.
Let’s talk about the ‘f’ word: failure. How do great leaders find success through failure?
One of the most important things a CIO can realize is, you’re not always going to be successful, so you need to be able to respond to failures and be able to fail fast. Especially if you think about how quickly things are changing. With rapid change comes risk. You’ll be forced to make decisions with imperfect information; therefore, you will fail more often. That’s why it is so important to make small, manageable bets. Managing risk and responding and learning from failures will be one of the key differentiators between successful CIOs and unsuccessful ones.
Experienced CIOs recognize patterns of successful and unsuccessful projects. They recognize that whatever was driving the original enthusiasm is no longer there or risks have increased, and they know when to cut their losses. They pivot and they make their investments where it makes the most sense. They take a crawl-walk-run perspective in understanding risk/reward.
I think back in my own career at The Weather Channel, where I was responsible for a project representing more than a million-dollar investment in an innovative solution to solve an HD problem. Our partner failed, and our investment was lost. It wasn’t just our partner that failed; I failed to properly recognize the risks and pivot in a timely manner. Sometimes as leaders we place hope above realism when faced with potential failure. I was fortunate enough that our executive team and our board gave me a second shot. What we learned from our misfortune resulted in an award-winning industry solution. Just as important, the team and I learned from our mistake, which made us better leaders and better prepared for the future.
For a deeper dive on Brian Shield’s winning leadership playbook, tune in to the Tech Whisperers podcast.
