Leadership playbook: Michelle McKenna’s winning formula for CIOs

A transformer, teambuilder, and trailblazer, Michelle McKenna founded her executive advisory firm, The Michelle McKenna Collaborative, after spending 10 seasons as the National Football League’s first-ever CIO and its first female C-level executive. Those are just two of the many “firsts” McKenna has accomplished over the course of her career, which has also included executive leadership roles at Disney and Universal Orlando Resort. While at the NFL, she drove digital transformation, launched new businesses, and, among other feats, pulled off the virtual 2020 NFL Draft at the height of the COVID pandemic — in just three weeks.

A 2022 CIO Hall of Fame inductee, McKenna knows what it takes to think differently about the possibilities of technology and how to forge a powerful legacy of digital leadership. On a recent episode of the Tech Whisperers podcast, we unpacked some of the unique moments from her career, the challenges and lessons learned, and why she believes CIOs need to focus on developing the human side of technology to accomplish big, bold things. Afterwards, we spent some time talking about a few keys to her success. What follows is that conversation, edited for clarity and length.

Dan Roberts: You’re known for your grit. How do you define grit?

Michelle McKenna: I have heard grit described many ways. When I apply it to myself, I think about how hard I am willing to work. No job is too small or beneath me. I also never forget where I came from, a small town in Alabama. It takes a certain amount of grit to get from where I started. But I also think it’s about knowing when it’s time to go and conquer new things and give someone else a turn. That doesn’t make you a quitter; that makes you smart and resilient so that you are built for the long haul.

How do you know when to keep charging down the field and when it’s time to throw in the towel?

A good example is my experience at Disney. I grew up thinking I wanted to work at Disney, and eventually, I got to work there — a dream come true — and I was blessed to be one of the top talent who were given the opportunity to work in many different roles in the company. When I joined, I had just begun to think about my MBA and was seriously considering leaving the workforce and taking on the debt to go to Harvard Business School.   

At the time, a very influential person in my life, Al Weiss, the former president of worldwide operations for Disney Parks and Resorts, told me that staying at Disney and being a part of this management rotation would be better than a Harvard MBA. I will never know if he was right, but I do know I have managed to have a successful career, beyond my wildest hopes and dreams. The Disney alum crew looks out for each other, and I am so happy to have had that experience.  In the end, Disney paid for my MBA at Crummer Graduate School of Business in Orlando. So I didn’t get to go to Harvard, but something better came along — this amazing career shift that took me into technology.

I steadily grew at Disney and was put in charge of many new things, including, at the time, the largest technology transformation the company had ever done. I wanted to continue growing and applied for the top role — and didn’t get it.  It went to an external hire, someone who had been a CIO for many years. I understood their rationale, but I knew that was my cue to go where someone would give me a shot at the top job. So I think grit is also knowing when to go. Resilience — and how to build resilience for yourself is a big part it — knowing when to stop pushing something that isn’t moving and accept that this is how it is and then pivot or maneuver to get what you want another way. There are so many ways to go up the corporate ladder and it’s rarely a straight path.

When we collaborated on the Leadership Development track of the CIO100 Awards event, you shared four pillars from your leadership playbook. No. 1 is ‘Be Your Own Quarterback.’ What does that mean?

Any book I write will be full of football analogies, as I have learned so much from the game.  Being your own quarterback means knowing yourself well. I think the best leaders in the world have strong self-awareness. They know themselves and what motivates them. They know their value system and when it’s being challenged, and they know how they’re going to feel. How can you lead someone else if you don’t hold yourself accountable and lead yourself? You won’t always make the right decision, but if you are following and trust your gut and know yourself, if it’s an informed decision from deep inside you, how could that be wrong? This takes a lot of internal work, including being vulnerable enough to hear things you may not like hearing.

That naturally leads into No. 2: ‘Know Your Team.’

The working title of the leadership book I’m working on is Beyond X’s and O’s, because the best coaches are those who go beyond the x’s and o’s and really know the players and how to put together a winning team. So this is about knowing what your people enjoy doing, what gets them excited about work every day, and what they are best at. If you give a person the chance to do what they’re best at on a regular basis, they’ll be so much more fulfilled, and they’ll do some things that they’re not great at because you’ve given them enough time to do what they’re best at. If you put someone in a job where they’re constantly struggling, they’re going to show up if they have to, but just for a paycheck. You don’t win big if you’re only showing up for a paycheck.

It’s your responsibility as a leader to get to know them. If you’re in tune with a person and you’ve taken the time to build a relationship, you’ll know when they need tough love or when they just need encouragement because they’ve had a bad day. If you’re the CIO of a large team, it can be impossible for you to know this for everyone, but by being vulnerable yourself and showing your true self at work, you will learn what people care about.

No. 3 is ‘Know the Whole Self.’ What’s the distinction there?

People bring their whole self to work whether you see it or not. In every job I’ve had, I am a mother, wife, daughter, sister, friend. Whatever’s going on in all of those selves is happening at work too. It’s just a matter of, can I compartmentalize it enough to get my work done? We all need a leader who will let you bring those other selves to work and give you permission to say, ‘I’m having a hard time right now.’ I’m sure we can all recall a coach, teacher, boss, or mentor you wanted to give your best effort for because they really saw you.

The pandemic shined a light on the whole self in a real way because we started seeing into people’s physical spaces. We might have known they were a mom, but we didn’t know they were a mom of three kids under five. We didn’t know they were caring for an elderly parent until you saw them walk by in the background. I think we have a real moment in time to change the way we approach people at work and take those lessons with us as people return to the office. Let them bring their whole self to work and acknowledge that. It will help you retention-wise and recruitment-wise.

I think the younger generation has lost a lot of institutional trust, but what they can still have is individual trust. If you build individual trust, it’s actually stronger than institutional trust, because if you can get them to trust you as their leader, they will stay with you. And this generation just won’t accept anything less than that. Authentic real leadership is what I hope we take out of COVID.

Tell us about your fourth pillar, ‘Make Sure You Always Have a “Hail Mary” Play.’

In football, Hail Mary is the last chance, last hope, when all is stacked against you and there’s no time on the clock. If you’re a great leader, not only do you have a play ready in those circumstances, but you’ve practiced it. I use that metaphor because Hail Mary plays work. Some of the best sports highlights in the world are Hail Mary plays, and some of the most significant personal triumphs end up being Hail Mary moments. If you’ve prepared for those Hail Mary moments, you’re not scared when they arrive. For me, doing the [NFL] virtual draft was scary because no one had done anything like it before. But my team had been through a lot of Hail Marys. We knew that we had laid the foundation for the Hail Mary play to work. Being a leader is about laying a foundation where a last-second effort can help you win.

What’s some of the best advice you’ve given or received?

I tell people when storms are in their way and they feel themselves wavering to imagine yourself as a tree. Stand tall like a tree with deep roots, but let your branches flow in the wind. You may even lose a branch or two, but if you’re firmly rooted in yourself, you will get through whatever storms may come. I remember my dad telling me that, but more in the context of, don’t forget your roots. You’re going to go and do all these great things, but don’t forget where you came from.

That gets back to how you show up as a leader. It’s always mattered, but never have we had a generation like this one holding us accountable to it. What you say and do matters, and you need to be conscious about bringing your best self every day. And when you can’t, know how to make use of self-care and take some time away until you can bring your best self back on the field.

For more from McKenna’s leadership playbook, including how she galvanized her team to pull of the historic virtual 2020 NFL Draft, tune into the Tech Whisperers podcast.

IT Leadership