5 hard questions every IT leader must answer

Leadership is not something that just happens. Leadership must be measured, managed, and invested in. After all, how IT leaders are selected, trained, evaluated, and compensated materially impacts the future performance of the enterprise.

So, again, when was the last time you had a substantive conversation about leadership with your direct reports? How frequently do you critically examine whether your IT/digital organization is well led? What set of metrics does your organization employ to evaluate IT/digital leaders?

The IT industry is undergoing a crisis of confidence. This is due in no small part to the erroneous presumption that IT and digital organizations have their leadership game in order. Quality leadership is not something that can be taken for granted. It’s time to turn an analytical eye to the state of leadership in our industry — and here are five key questions IT leaders must ask themselves to truly know whether they are successfully leading IT.

Is your focus on point?

Daniel Barchi, Naval Academy grad and award-winning CIO at CommonSpirit Health, explained to me that there are three areas IT leaders can allocate their time: People, process, and technology. Barchi suggests the optimal allocation for IT leaders is 80% people, 15% process, and 5% technology. Unfortunately, many IT leaders — especially those of the order-taker type — invert that triumvirate, placing the lion’s share of their focus on technology.

Are you and your direct reports allocating enough time to leading people?

Are your people primed for success?

In Good to Great, Jim Collins suggests that decisions about people — who is on the bus — have to precede decisions about objectives — i.e., where the bus is going. Several CIOs have shared with me the anecdote regarding how Apple design icon Jonathan Ives typically responds to the question, “What’s the secret to your design success?” Ives reportedly responded, “We fire the A- people.” The point being that a group of passionate high performers is what is necessary to deliver the sought-for end state.

Talent is a differentiator. Are your IT leaders doing everything it takes to attract, nurture, grow, and retain the kind of talent necessary to succeed?

Are you helping your organization ‘see the future’?

Barbara Cooper was the beloved and now retired CIO at Toyota Motors North America. Having served as an IT leader in five industries, she is one of the top CIO “coaches” in North America. Barbara counseled me that it is not enough just to have a vision of the future. Our industry is too full of sic “transformational” CIOs being airlifted into enterprises only to slink away 18 to 24 months later having abjectly failed to create digital value.

Creating IT value requires a team effort. One has to get the organization to internalize and unite behind a collective vision of the future. Barbara jokingly quipped that “as a child of the ’60s” she learned that while you “can’t share the trip” — i.e., one person’s vision is not enough — you can get everyone moving in a common direction. To do this she set her direct reports down one day in the conference room:

“Ok, I want you to think out three years. ’Cuz five is a little much. I want you to pretend that you are driving into the parking lot. You are walking into your office. You are going to go through your day. You are going to have your first meeting of the day. You are talking to somebody in the door. You go and get your coffee. You have a series of hallway conversations. You are thinking about some of the things and the problems you have. I want you to play that out — almost like a storyboard in your head — what is going to be different three years from now?”

These individual visions were shared, consolidated, amplified, and linked to enterprise objectives.

Is that kind of collective vision-making part of your company culture?

Are you emphasizing the value of relationships?

Most of the voluminous academic literature on leadership focuses on the traits/idiosyncrasies of the individual leader and not on their relationships with key associates. As an IT leader, do you have a track record of helping or hindering colleagues in fulfilling their career objectives?

Vince Kellen, a digital force of nature and CIO at University of California San Diego, borrows insights from NHL scouts. He is looking for IT “skaters” who, when they step onto the ice, make the other four teammates better hockey players.

How leaders view themselves and others and how they are viewed by others is a critical causal driver of leadership success or failure. Tony Blair was able to reverse a multi-decade decline in Labour Party electoral success when he realized, “People judge us on their instincts about what they believe our instincts to be. And that man polishing his car was clear: His instincts were to get on in life, and he thought our instincts were to stop him.”

Leadership success requires connectedness to the community. How connected are your IT leaders throughout the ranks?

Are you effective at making a positive impact?

Franklin Pierce, America’s 14th president, is viewed by most historians as being one of the very worst presidents. Every action he took “made things worse,” as was discussed on “The First 15,” Episode 93 of the American POTUS podcast.

Have your actions made things better or worse?