Veteran CIOs on leading IT today

We live in a world where volatility, uncertainty, complexity, and ambiguity (VUCA) can either paralyze you with fear or energize you with unlimited opportunities. Because of this, leadership matters more than ever. And no organization develops leaders, at scale, better than the military.

For a recent episode of the Tech Whisperers podcast, I sat down with three transformational leaders who started their careers in the military: Mike Goodwin, CIO of PetSmart and a former Army officer; DiAnna Thimjon, a strategic advisor to CxOs, four-time CIO/CTO and former Army officer; and Woody Groton, CIO of Draper and a former Army officer who is currently a Brigade Commander for the Army National Guard.

During our wide-ranging conversation, we explored the foundation of leadership practices and philosophies they gained from their military experience and how those lessons have continued to serve them well in their civilian careers. Afterwards, we spent some time focusing on key tenets today’s emerging leaders can apply to develop and grow in their careers. What follows is that conversation, edited for length and clarity. 

Dan Roberts: DiAnna, what would you say is the biggest or hardest shift to make as you are rising up the ladder from manager to director?

DiAnna Thimjon: It’s a different role as you shift from manager to director. It’s realizing your entire organization is essentially run by someone else tactically, so really backing off and letting them fail or succeed on their own. And then you have to figure out how to focus very differently on alignment, making sure all the leaders are on the same page, because now you have really good leaders and they’re all running in different paths.

In IT especially, managers tend to want to hang on to some of the hands-on work after they become directors, and that’s often because they’re promoted due to skill, not leadership. So suddenly they find themselves at a director level and they’re just a really good engineer. They don’t have any other tool in their toolkit except doing it themselves. So it’s hard for them to let others own things completely.

It’s really important to get a good mentor or someone in place to help them. Usually what you hear is the horror stories, where someone fails miserably and then they learn and pick themselves up and go again. We’ve got to find a way to prevent that.

Mike, you’ve referred to middle management as the key pivot point in leadership. What do you mean by that, and what causes people to get stuck in the middle?

Mike Goodwin: This is really a transition point when you go from directly leading the team that’s doing the work to leading leaders. It can be challenging to work through that, because you’re kind of the glue in the organization, when you really think about it. You’re holding the senior team as well as the first line. You’re translating back and forth between those two, so you have to effectively be able to coach up and coach down. You have to tailor your communication from first line to senior management. You have to tailor your communication for the type of audience, the type of content.

You also have to figure out how to escalate issues and how to put frameworks in place that give you visibility to what’s going on. Because you’re not going to be meeting with the direct team on a day-to-day or weekly basis in a lot of cases. So you have to put in place scorecards or ways to get the visibility to make sure that things are on track and try to determine where your attention has to occur and be able to focus on that.

If you can do that effectively, that’s the point that can launch your career, and you’ll continue to go forward because you’re going to constantly hone those skills. If you can’t effectively do that, then that’s where this ‘stuck in the middle’ comes in and you aren’t able to elevate out of that point and you really are performing more as a micromanager of the leaders.

As DiAnna mentioned, we have to do more to prepare and develop middle managers. What you’re doing with The TechLX is a good example, because a lot of leadership development is targeted for that first time manager or for that senior-level person, and yet there is a unique set of leadership skills that needs to be honed in training for that middle manager.

Drawing on what we can learn from the military, what are some of the specific leadership tenets IT organizations need to be focusing on? Woody, you’ve mentioned speak truth to power, lead upward, tolerate honest mistakes but don’t tolerate integrity violations.

Woody Groton: To expand on Mike’s point, in the military, you have leadership training at every step of your career, from the basic course up to senior service college and even beyond for general officers. That next-generation leader training is so important, and it’s something we’ve used with great success at Draper.

When it comes to specific leadership tenets, the four Cs of military leadership are candor, commitment, courage, and competence. So speaking truth to power: You have to have that, you have to have that candor, both up and down, and the commitment and the courage to be able to do that, because it’s not easy to tell the boss that this isn’t right, or this is something that I’m seeing that there’s an issue. But the best leaders will take that advice and try to impact change on it.

That’s leading upward as well. Organizational-level leaders don’t have all the answers. They’re providing that vision, that commander’s intent, what the desired end state is, and it’s really up to the subordinate leaders to then figure out how are you going to make that happen. And the more that we can do that in the civilian world, the better. Don’t micromanage. Our new CEO has been really great on that: You’re the CIO. I’m not going to tell you how to do your job. You recommend to me what technology can do to help transform our business.

As for tolerating honest mistakes, people are going to make mistakes and you can’t punish them because they made a human honest mistake. The thing that’s important is to learn from that mistake and move forward. And learn from your peers’ mistakes. Now, if you continue to make those same mistakes, that’s when it’s going to become an issue.

The integrity piece — in the military, it’s life or death. But even in the civilian world, if you don’t have integrity, you can’t be trusted. You lose trust, whether that’s with your leadership or your subordinates. They’re going to see right through that. Another part of it is taking action for the good of the organization when someone doesn’t have integrity.

In today’s world, do you think we need people to be more “versatilists” than specialists?

Goodwin: I don’t think it’s an either/or. I think we need both. You do want some specialists for those deep areas where you are going to have to rely on that to get you out of trouble or get things done. But those are probably not the lion’s share. You definitely want more versatilists, because you need to be able to have breadth, and things are so interconnected nowadays. You can’t do anything in isolation anymore, especially in the IT field.

Groton: David Epstein’s book Range: Why Generalists Triumph in a Specialized World talks about the value of this. One example he uses is Roger Federer and how he played a lot of different sports before he focused on tennis, and that made him a better tennis player.

In the military, you were always given new jobs based on your potential. You might not have ever had any experience with that, but they know you’re a good leader, you have the potential and you can go in. And of course, you’ve got technical staff and others that can support you.

DiAnna, that’s something I see reflected in your career path. You didn’t seek out certain industries — you sought out problems to solve.

Thimjon: I don’t think I did it with the intention of being disruptive in a career pattern, but to your point, I sought out opportunities that interested me. When I was in the Army, I did all kinds of jobs and worked in such different roles, and I really liked that. I like the idea that I don’t get surfaced the same problem tomorrow that I got today.

When I started at my first company, I was out in a distribution facility managing a group of people who selected cards and put them in boxes. I got an opportunity to go into sales in a technologist role, and I remember a very senior leader pulling me aside and saying, ‘You really need to pick a pillar. You should stay here.’ But I thought, I’m kind of bored with this particular thing. I’d really like to see what else there is in this company.

In that process, I got a chance to do some really hard, wonderful jobs. I learned how a retail CPG company runs. Eventually I ended up in Mike’s organization in IT. I went from there to a number of places, from federal contracting to a law firm. I was in a mutual fund company. My last job, I was the CIO for a company that stood up humanitarian centers for Afghanis and unaccompanied minors at the border. We stood up IT on the spot in that moment.

I offer that to say that there’s a lot of greatness in diversity. Each one of those, though, needed almost the same kind of leader. They needed someone who could come in and put some structure in place. They needed someone who was interested in hard problems. They needed someone who could be a leader. I kept hearing over and over, ‘We don’t really need a technologist. We really need leadership. The team needs leadership.’

Woody, I love your statement that perpetual optimism is a force multiplier. What does that mean when it comes to leading others?

Groton: Force multiplier is kind of a military term. If you have an infantry unit, the force multipliers might be air support or the engineers that are going to get you across the river. In the corporate world, I think that, as leaders, we want to do that. It’s kind of a compliment I’ll use on some of the staff: You’re a force multiplier. You’re really getting in there and being that catalyst to make things better. Managers can get a 100% out of their team, but leaders can get 125%.

Being a leader is a lot like being a coach. It’s getting them to get out there and to be the best player they can be and to win games, have that enthusiasm. If you’re dwelling on the negative, you’re not going to be as successful. Always look on the bright side. Be positive. Give your staff what they need to get the job done so they can build the confidence, you have trust in them, and they trust you.

That creates that perpetual optimism, and it is a force multiplier. It means your team is going to be better than they ever could have been without that enthusiasm. Knowing that they have your support, that you’re going to be with them and they’re going to have your back. It’s just going to make you a better, more successful organization.

Tune in to the Tech Whisperers podcast for a deeper dive on the foundation of leadership practices and philosophies these executives gained from their military experience and how those lessons have continued to serve them well in their civilian careers.