CIO legend Chris Hjelm on developing future-ready IT leaders

Legendary CIO Chris Hjelm built a career leading IT at large and innovative companies alike, and being intentional about developing future IT leaders has been a key part of his leadership playbook.

Chris Hjelm is a CIO legend with a career spanning Fortune 50 behemoths like Kroger and FedEx, innovative tech companies like Orbitz and eBay, and other high-growth e-commerce and startup businesses. The 2023 recipient of the Ohio CIO of the Year ORBIE Leadership Award is known for his track record of building and heading global technology strategy initiatives to drive innovation and transform legacy operations. Today, Hjelm serves on three boards of directors with a focus on strategy, cybersecurity, technology, talent, and operations.

On a recent episode of the Tech Whisperers podcast, Hjelm traced his career and experiences and opened up about his leadership philosophies and what he’s learned along the way. Four “mystery questioners” — Nick Kaufman, vice president of technology at Kroger; Annette Hater, vice president and global head of technology strategy and portfolio at Tapestry; CPO/CTO coach and mentor Leon Chism, former chief technology officer at Jellyvision; and Ryan Kean, CIO at Total Quality Logistics — joined us for the episode to probe specific aspects of Hjelm’s leadership playbook.

We spent some time after the show delving into what Kean highlighted as Hjelm’s intentionality around developing future-ready leaders. Hjelm also taught what he calls a “values-based leadership seminar” in each company where he worked. What follows is that conversation, edited for length and clarity.

Dan Roberts: One could argue that the most important role a CIO plays today is developing leaders. What are your concerns about the up-and-coming generation in terms of being both ‘today ready’ and future ready?

Chris Hjelm: I think about this a lot with my own kids, and I think we have a multidimensional problem to solve. One of the issues is that social media and smartphones have taken away from the necessity of building relationships through physical interaction. Another is that — and this is generalizing a bit — but this generation is often geared towards instant gratification: ‘It’s all about me.’ That’s really in conflict with the servant leadership model. It’s just about polar opposite.

What I’ve seen in some of those I’ve mentored who are right out of college is that, if they want something, they’ll network hard and reach out, but if they don’t get what they need or want, they stop investing in the relationship. What they don’t understand is that life is a longer journey. It’s not a single event, and they may want to have a relationship with me that pays dividends and gives them another opportunity down the road. If our business together today doesn’t work out for whatever reason, I’m okay with that. But I’m not okay with the lack of follow-through.

It also goes back to building those relationships face to face. I recently talked with a family member who was going through an interview process for a job, and it had all been done via videoconference. I said, you need to go there. Meet the senior leadership team, whoever your supervisor is going to be, ask good questions about the industry and the business, about what makes them tick and what’s important to them. Then decide if the team and culture is one you want to be a part of — because you’re going to be committing a big chunk of your life to this organization. To think that someone would be willing to make that call without getting to know the people makes me uncomfortable about the future.

I also think it’s one of the reasons why so many jobs are short-lived, because there’s just huge misalignment. There’s no emotional connection or depth, so when you hit a bump in the road or the next thing comes along, why stay?

What are some of the key learnings and takeaways from the values-based leadership seminar you teach that could help this next generation?

First is something we discussed in the podcast, which is this notion of leadership vs. management. It’s easier to create good managers — there’s a formula you can follow and get consistent results. Leadership’s a bit more abstract and highly dependent on life experiences. You have to get people to be critical thinkers, take risks, be innovators and to teach others. You have to build that muscle memory, which is why the military is so good at it. They’ve got a wide range of talent, they pick the ones who show potential, and they continue to grow them as leaders. Leadership development is a process. Just signing up for the job doesn’t make you a leader.

We also discuss things like being a great listener. I worked for a guy early in my career who said to me, ‘Don’t be afraid to weigh in, but I really like how you are a thoughtful listener. You don’t talk first; you listen first. Keep doing that. That’ll serve you well in your career.’

Manage your own career, and as part of that, sign up for tough jobs. The more screwed up something is, the higher you should raise your hand, because you’re going to learn a lot from it. You learn more from messes than you do pristine things.

Delegating is another super important piece of the equation. I delegate even when I am confident something’s not going to go well, because, again, it’s an opportunity to gain experience — with the caveat being that the shareholder cost isn’t too high. You have to let people take risks and fail. The important thing is that they learn from the experience and reinforce what they learned by sharing with others.

It’s also important to give your team all the credit. If something’s successful, it’s your team’s success. By the same token, if something fails, as a leader, it’s your responsibility.

Constant self-evaluation is important, too. I would do this even with my communications, for example, at a town hall meeting. I would reflect on my performance, and I’d ask the attendees, ‘How was that one? What was good? What could have been better?’ You’re not going to get better if you don’t solicit feedback. So if it’s good, I’ll do more of it. If it wasn’t so good, I won’t try that again. You have to seek feedback, and also give it to others, remembering that ‘feedback is a gift.’

We discuss about avoiding social media pitfalls. It’s a slippery slope and you just have to take the high ground and not get into these rabbit holes where there just isn’t a winning answer. I don’t care how strong you feel about something. The second you cross that line, you may be alienating half the world without a benefit to the company or shareholders.

In the seminar, we also spend time on expectations of management and what good managers do. We’re there to win; we’re not there to come in second. So set a high bar, hold people accountable, and put goals and objectives in place. I’m a big advocate of you can’t improve what you can’t measure, which helps align teams and makes success and failure clear.

I always say the best leaders are also teachers, and you’re certainly an example of that. How do you instill that in other leaders?

I can’t tell you how many leaders came to me over the years to tell me that they were applying for this job, that they were ready for it. And I would say, ‘Alright, who’s taking yours?’

I would explain, ‘Your opportunities are gated by the readiness of your successors.’ In one-on-ones with people and in mentoring sessions, I’d say, ‘I care about your development plan, but I care as much about the development plans of the people that are coming behind you, because you won’t go anywhere if your successor isn’t ready.’

Now, some jobs are harder to build successors for, but at least present options for finding good candidates. At least tell me, for example, who you met at a conference or know through your network who could do your job.

That’s also part of prioritizing talent as a key pillar of your strategy.

I always hammered home the importance of talent through an early Kroger experience. I remember someone who came in to me for an exit interview after I’d been at Kroger for about 18 months. He was really good — he’s someone who would have been on my future leader watch list — so when he came in and told me he was leaving, I wanted to know why. I thought things were good. He told me, ‘Well, I wasn’t seeing any opportunity and I wanted to get into management.’

I got the VPs and directors together, the top two levels of management, and I said this person is leaving and asked what they thought about him. They all said, ‘Oh, he’s great, we really love him.’ So I said, ‘How many of you would trade one of your existing managers for this guy?’ Every hand went up. So my next question was, ‘Why didn’t that happen?’

I said, ‘This is a deal I’m going to cut with all of you. If I do another exit interview for a high-performing person in your organization that’s leaving, I will do your exit interview next. High-performing talent doesn’t come along very often, and when they do, our job as a cross-functional team is to take care of them, to allow them to punch their tickets and be successful.’ We put in other processes to manage top talent, and I am confident that my leadership team didn’t forget that exchange.

You’re known for being a storyteller. How does that play a role in your leadership and your development of the next generation of leaders?

Developing leadership skills is a lifetime journey, and we all have stories of our respective journeys. As a leader, I would tell the stories because people remember them, and I expected the stories to cascade throughout the halls of the organization. I wanted to change the culture, and you change the culture by telling impactful stories that align with your mission.

I have a lot of storytelling examples I go through in the seminars, because there’s a theme to each of them and I want people to think about what leadership traits were exhibited in that story. I use stories to teach governance, to teach who you really work for — the shareholders. I use them to teach servant leadership.

I share stories from my own experience to show that it’s okay to take risks and to fail. To get leaders to understand that if there’s a misalignment in values, you need to go somewhere else. I try and give people the confidence to do the right thing, live their values, and if they’re ever in a situation where they shouldn’t be there, then don’t compromise who you are and what you value for a job. It’s not worth it personally nor does it create followership in an organization.

In the seminar, the stories are a way to reinforce what leadership is all about and to help give people confidence that, yeah, you can survive this issue — to stand in front of the board and tell them that management doesn’t really get technology, but they are learning. If you’re telling the truth and doing the right thing for the shareholders, nine times out of 10 things are going to go fine. But you have to take the risk that one out of 10 times you might be a casualty.

When I think about developing people and reflect on what’s worked and what hasn’t, I can’t stress enough how valuable telling the story is. When I talk about leadership, I say, ‘It’s tough but rewarding. It’s not a popularity contest. Trust me, if you’re doing the right things, you’re not always going to be popular, but you will be respected.’

The stories show them what that means. For example, firing people is no fun. It’s never easy. But I’ll give them some examples of when I’ve done it. We also talk about what’s good about being a leader. You broaden your impact. You get to see people like Annette and Ryan and Leon go off and be successful on their own. You get to make big decisions. You get to make more money. There are lots of positives. But make no mistake, it’s no walk in the park.