CIO Mark Settle on what makes a winning IT battle plan

Mark Settle is a seven-time CIO and three-time CIO100 Award winner who wrote two must-read books during his CIO journey, Truth From the Valley: A Practical Primer on IT Management for the Next Decade and Truth From the Trenches: A Practical Guide to the Art of IT Management. Today Settle serves on the advisory boards of several venture capital firms and personally advises multiple startups. He also continues to publish truth-telling thought leadership across multiple channels, including his newsletter, “The Modern CIO.”

On a recent episode of the Tech Whisperers podcast, Settle discussed the leadership principles and philosophies that have guided his successes, while also unpacking some of the teachings from his various writings. Afterwards, we spent time exploring how his interest in the American Civil War has influenced his leadership approach, how today’s digital leaders can apply lessons from the battlefield to the battles they’re facing in the workplace, and other advice for current and aspiring CIOs. What follows is that conversation, edited for length and clarity.

Dan Roberts: In addition to your storied work as a CIO, you’ve also developed historical knowledge of the American Civil War that Freddy Kerrest, your former boss at Okta, describes as ‘off the charts.’ What about the Civil War draws your interest?

Mark Settle: Everything that goes wrong in a military campaign is a near perfect mirroring of what goes wrong in IT initiatives. You see poor or inconsistent communication between all these groups involved. There’s a lack of proper coordination. A lot of times, people are doing good things, but they’re doing it at the wrong time and not informing the other people what they’re doing. There are petty jealousies and rivalries among leaders, which influence their responsiveness to taking direction or what they’re going to do next. There’s a mismanagement of resource and logistics. Sometimes the wrong people get to the right place and the right people get to the wrong place.

I just finished The Chickamauga Campaign, by David Powell, which is a 700-page, hour-by-hour depiction of a two-day battle that occurred just outside of Chattanooga. In the first day, the Union forces were completely overwhelmed by an early morning surprise attack by the Confederates and were driven back to the shore of the Cumberland River.

When you think about an IT organization trying to pull something off that has strategic impact, poor communication, inconsistent coordination, rivalries among not only you and the business but within your own team, not having the right resources at the right place at the right time — the whole thing can just go completely sideways in almost exactly the same way.

Which Civil War leader would you say had the leadership traits to be a successful CIO today?  

I really admire Grant’s persistence. No matter what happened, he kept grinding ahead, and let’s face it, you have to have persistence to be a successful CIO. There’s an epic story about Grant at the Battle of Shiloh. It was a two-day battle, and the Union army was overwhelmed by a surprise dawn attack on the first day. That evening, Grant was sitting under a tree in the rain and one of his lieutenants came up to him and said, ‘It’s been the devil’s own day,’ to which Grant replied, ‘Lick ’em tomorrow, though.’ 

That’s Grant in a nutshell, and I think that kind of persistence is a key trait of successful CIOs in many dimensions.

What are some of the areas where digital leaders can take a page from Grant’s book when it comes to persistence?

As a CIO, you’re always being asked to do more with less in terms of budget and staffing. So you have to be persistently resourceful. A great example are cloud costs. Nobody ever says, ‘Oh, yeah, Mark showed up, put in the solution, we’re all good now. We’re very satisfied and happy with what we’re spending on the cloud.’ No, it’s an ongoing saga. And in all those cases you have to be persistent.

In terms of staffing, you have to persistently manage performance, and people will respect you for that. You might think IT is in a walled-off fort, not visible to other people in the company. Nothing could be further from the truth. A large cross-section of your IT team is living in a glass house, and whatever dysfunctionality is occurring within your organization is far more obvious to people outside of IT than you can imagine. Even if your IT group is in a warehouse away from every other corporate facility, there are just too many interactions that go on with your business partners, and if you’re not persistently managing that performance, it will come back to bite you, and undermine the proactive things you want to do in the future in terms of budget and staffing. 

Another dimension of persistence lies in the fact that all IT organizations are service organizations. To one degree or another, they’re delivering services to every employee, from executives all the way down to the lowest-paid person in the organization. Because everyone relies on those services, expectations go up all the time. At a minimum, you’ve got to be persistent in maintaining service levels. Ideally, you persistently find ways to raise your service levels to avoid mistakes and exceed expectations.

I’ve been blessed because I’ve had some great people in my organization that had a real customer-first service mentality about their internal customers. There are others that just get worn down after a while by all the negative blowback that you can get sometimes from customers. So you have to persistently guard against that.

A third dimension of persistence is around relationship cultivation and nurturing. If six months have gone by and you haven’t talked to the head of procurement or supply chain or manufacturing, when you show up, it’s almost like you’re starting from scratch with the relationship. It doesn’t take a whole lot to send signals that you’re aware of their problems, their interests. That persistence applies not just to internal relationships but external ones as well. It doesn’t hurt to drop an email when you see somebody had a great earnings report and say congratulations.

Those three dimensions — resource management, service delivery, and internal and external relationship building ­— all require conscious persistence. If you’re not persistent, I don’t know how you could really pull the job off.

The US military is the best leadership development organization in the world. What leadership insights did you take away from your experience as an Air Force officer?

I was in the ROTC program at MIT, and when I came out, I was assigned to a research lab on the outskirts of Boston, Air Force Cambridge Research Lab. When you think of leadership, you normally think about managing and leading people and running projects involving people. That wasn’t really the case at the lab. In some ways, the work was a continuation of the type of activities I’d been involved in in school. But what was different was that academia is a pretty unstructured environment, and the military is very structured. There are ways things get done, and there are a lot of trip wires. It’s a completely different organizational model that you have to adapt to.

That’s not so different than someone coming from a master’s program and going into a large corporation. They operate in fundamentally different ways. So a big part of what I learned from the Air Force was navigating the bureaucracy. An interesting follow-on is that a couple of years later, I applied for a job at NASA, and the guy that hired me said, ‘Normally, I wouldn’t hire somebody right out of school for a job like this. But if you could live with the bureaucracy in the Air Force, I think you’re going to be able to do okay here at NASA.’

What’s your advice to IT leaders who get stuck climbing the career ladder and can’t break into the executive level? What are some of the reasons people get stuck?

I think people still have tech blinders on, especially at the early stage. So one reason you get stuck is you think you’re supposed to be the ‘technical brain’ of the company, and all technical innovation will flow from you and through your team. What the business is looking for is somebody who understands and can navigate organizational politics and build alliances and get stuff done and work with other people. The business knowledge and experience you have and your ability to work constructively with other people are the things that advance your career.

Another issue is micromanagement. You’re not going to advance if you’re trying to solve every technical problem and control everything that goes on all by yourself. If you don’t have people you can rely on to get stuff done, you’re going to fail. It’s that classic saying: Hire people who can replace you. Or there’s the Steve Jobs quote: ‘It doesn’t make sense to hire smart people and tell them what to do; we hire smart people so they can tell us what to do.’

The last piece is, if you’re promoted — say, from senior manager to director  — relationships with your former coworkers have to change. You can’t show favoritism. It undermines the organization and makes the organization political.

People will say, ‘Oh, I’m not biased,’ but then every Tuesday you have lunch with Tom because you worked together for five years prior to your promotion, and you don’t have lunch on a weekly basis with anyone else on the team. People tell themselves they’re above that, but they’re not subconsciously above it. They’re going to be influenced more by those previous connections, so you have to consciously work against it and maybe have some sit-downs with people and say we’re going to have to redefine this relationship.

Are there any books on the Civil War you would recommend CIOs read to help prepare for the next round of battles they will face?

I have done a lot of reading, but you really don’t get a visceral sense of the management and leadership issues involved until you visit the battlefield. So my advice would be to identify a major Civil War battlefield close to you or easy to get to on your next business or family trip. Find a book about that battle that is of sufficient length but not overwhelming. Read the book, then walk the ground they fought on. I think many if not most CIOs would find that to be an inspiring experience in preparing to fight their next rounds of professional battles. 

For more leadership insights and advice from CIO legend Mark Settle, tune in to the Tech Whisperers podcast.