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\u2019s first-ever CIO and its first female C-level executive. Those are just two of the many \u201cfirsts\u201d 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 \u2014 in just three weeks.\n\nA 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.\n\nDan Roberts: You\u2019re known for your grit. How do you define grit?\n\nMichelle 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\u2019s about knowing when it\u2019s time to go and conquer new things and give someone else a turn. That doesn\u2019t make you a quitter; that makes you smart and resilient so that you are built for the long haul.\n\nHow do you know when to keep charging down the field and when it\u2019s time to throw in the towel?\n\nA good example is my experience at Disney. I grew up thinking I wanted to work at Disney, and eventually, I got to work there \u2014 a dream come true \u2014 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. \n\nAt 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\u2019t get to go to Harvard, but something better came along \u2014 this amazing career shift that took me into technology.\n\nI 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 \u2014 and didn\u2019t 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 \u2014 and how to build resilience for yourself is a big part it \u2014 knowing when to stop pushing something that isn\u2019t 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\u2019s rarely a straight path.\n\nWhen we collaborated on the Leadership Development track of the CIO100 Awards event, you shared four pillars from your leadership playbook. No. 1 is \u2018Be Your Own Quarterback.\u2019 What does that mean?\n\nAny 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\u2019s being challenged, and they know how they\u2019re going to feel. How can you lead someone else if you don\u2019t hold yourself accountable and lead yourself? You won\u2019t always make the right decision, but if you are following and trust your gut and know yourself, if it\u2019s 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.\n\nThat naturally leads into No. 2: \u2018Know Your Team.\u2019\n\nThe working title of the leadership book I\u2019m working on is Beyond X\u2019s and O\u2019s, because the best coaches are those who go beyond the x\u2019s and o\u2019s 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\u2019re best at on a regular basis, they\u2019ll be so much more fulfilled, and they\u2019ll do some things that they\u2019re not great at because you\u2019ve given them enough time to do what they\u2019re best at. If you put someone in a job where they\u2019re constantly struggling, they\u2019re going to show up if they have to, but just for a paycheck. You don\u2019t win big if you\u2019re only showing up for a paycheck.\n\nIt\u2019s your responsibility as a leader to get to know them. If you\u2019re in tune with a person and you\u2019ve taken the time to build a relationship, you\u2019ll know when they need tough love or when they just need encouragement because they\u2019ve had a bad day. If you\u2019re 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.\n\nNo. 3 is \u2018Know the Whole Self.\u2019 What\u2019s the distinction there?\n\nPeople bring their whole self to work whether you see it or not. In every job I\u2019ve had, I am a mother, wife, daughter, sister, friend. Whatever\u2019s going on in all of those selves is happening at work too. It\u2019s 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, \u2018I\u2019m having a hard time right now.\u2019 I\u2019m sure we can all recall a coach, teacher, boss, or mentor you wanted to give your best effort for because they really saw you.\n\nThe pandemic shined a light on the whole self in a real way because we started seeing into people\u2019s physical spaces. We might have known they were a mom, but we didn\u2019t know they were a mom of three kids under five. We didn\u2019t 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.\n\nI 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\u2019s 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\u2019t accept anything less than that. Authentic real leadership is what I hope we take out of COVID.\n\nTell us about your fourth pillar, \u2018Make Sure You Always Have a \u201cHail Mary\u201d Play.\u2019\n\nIn football, Hail Mary is the last chance, last hope, when all is stacked against you and there\u2019s no time on the clock. If you\u2019re a great leader, not only do you have a play ready in those circumstances, but you\u2019ve 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\u2019ve prepared for those Hail Mary moments, you\u2019re 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.\n\nWhat\u2019s some of the best advice you\u2019ve given or received?\n\nI 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\u2019re 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\u2019t forget your roots. You\u2019re going to go and do all these great things, but don\u2019t forget where you came from.\n\nThat gets back to how you show up as a leader. It\u2019s 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\u2019t, know how to make use of self-care and take some time away until you can bring your best self back on the field.\n\nFor more from McKenna\u2019s leadership playbook, including how she galvanized her team to pull of the historic virtual 2020 NFL Draft, tune into the Tech Whisperers podcast.