A majority of the CEOs, board members and business executives I speak with say they’re frustrated with both their IT leadership and their digital progress. Maybe it’s a side effect of COVID or a skewed sampling of executives I encounter, but even before COVID, I was hearing more and more exasperation with IT leadership.

As part of my interviews, I ask every executive to name which companies they admire for having built a credible digital and information technology (D&IT) capability that has proved sustainable over a significant period of time. Without realizing it, the vast majority point to organizations that share a common CIO characteristic: longevity. But in my experience, these same executives don’t always exhibit enough patience to let their own IT leadership succeed. Instead, I see unbridled CIO churn.

As IT becomes even more complex and critical to the business, I see more cases than not where enterprise leadership fails to understand the basics of what it takes to succeed – and what enables success. Even as COVID forces changes in business models and shifts priorities from long-term programs to short-range, tactical IT adjustments, there are at least three basic CIO-related factors for D&IT success:

  • Digital and IT are long-term games, not a series of two-year efforts or projects.
  • CIO longevity is a key factor because time is needed to tie together many moving parts.
  • The required credibility, relationships and trust can only be built through experience over time.

For half a century, I’ve watched frustrated enterprises time and again ignore and violate two or three of these factors. As the results of doing so eventually catch up with them, especially during the COVID era, many companies have been thrown into whirlpools of churn.

Three Requirements for Digital Enablement Success

Let’s take a closer look at these three basic requirements for success:

  • Digital and information technology are long-term games. It takes years to build a healthy, integrated portfolio of applications. It takes years to adjust systems, processes, IT governance and skills to fit a business that is changing. It takes years for the business, customer and partner communities to properly utilize systems. Yet, some enterprises shift the IT leadership or IT organization every few years from one reporting relationship or strategy to another.

    They bring in a wunderkind CIO who does a bit of clean-up and applies some spit and polish, but ultimately leaves the organization with a cesspool of technical debt. Instead of the healthy, user-owned foundation of master data management (MDM) needed in today’s data-intensive era, they instead leave behind a different kind of MDM: a major data mess. Digital and IT must be led, understood and managed for the long term. This is compounded by having to constantly evolve.

  • CIO success must be viewed as a longevity play. With few exceptions, every successful CIO has told me it took five to seven years to be in a position to aggressively contribute to the business beyond a clean-up in aisle four. The pattern they describe is:
    • 6 to 12 months: Understand the inherited IT landscape, players and real challenges.
    • 3 to 12 months: Set initial priorities, fix what is immediately broken, fight the incessant fires, lay out a plan for years two and three.
    • 12 to 24 months: Start executing on an initial plan, select processes and practices, begin to assemble the team of winners and leaders, gain initial confidence of the staff and business, select partners.
    • 24 to 48 months: Do their best to institutionalize common messages, processes, practices and plans, while initiating programs to really reduce technical debt and learn to work with the business and partners.
    • 36 to 60 months: Adjust processes and learn that the great athletes hired as leaders may have all come from different sports. Refine the team to focus on a common purpose, develop the CIO team and business-meaningful agenda, and institutionalize governance and processes to minimize issues such as technical debt.
    • 48 to 72 months: Understand how D&IT can significantly work with the business and make long-term vs. just quick-fix contributions, while fully institutionalizing the CIO team/business agenda as much as possible.
    • 60 to 84 months: Step-by-step, broadly execute the CIO team/business agenda of big hits.

Frustrated enterprises repeatedly change jockeys and horses every two to three years and never get a CIO who can perform in full. Others tell me they don’t have time for this slow approach, but fail to see their pattern of failure over many years.

  • The required credibility, relationships and trust can only be built through experiences over time. Just because the executive recruiter said the new CIO will be terrific and the CEO likes her, it doesn’t mean she has instant credibility or the trust of her staff and the business. Yet I talk to so many superego “celebrity” or “drive-by-shooter” CIOs who regale me with how well-respected they are, how quickly they built relationships and how trusted they were from day one. Forgive me for being cynical.

    Business executives, IT staffs and partners have instinctively learned to be cautious about bestowing credibility and trust. These must be built over time: one event at a time, one person at a time, one department at a time and reinforced, over and over.

It Takes Upfront Understanding and Commitment 

Successful D&IT requires the enterprise to realize it’s in a long-term relationship with a CIO – not a fling. True, all parties will have frustrations. Mistakes will be made. There will be mismatches of a new IT leader and the enterprise where hard decisions must be made. However, the commitment to a multi-year relationship must be at the enterprise’s core and the newly onboarded CIO. All too often, I talk to CIOs or CEOs who tell me, “Well, I’ll give it a two-year shot, but …”. Wrong attitude.

To work long-term, the CEO, board and senior business executives need to internalize and demand dialog related to the three aforementioned requirements. They need to hear the incoming CIO’s vision of how to tackle these challenges and understand their roles – before they make an offer.

A Parting Thought

One additional observation: Since March, I have encountered over 30 enterprises that are simultaneously changing IT leadership, bringing in a new CEO and/or CIO, re-adjusting for COVID, changing nearly all IT-business reporting relationships, reacting to the new CEO’s direction, diverting to accommodate a major merger/demerger, trying to re-skill and increase citizen development, all while changing all IT development, delivery and hosting approaches.

I’ve watched a distribution company, two financial institutions and an energy enterprise now enter their third iteration of massive change in the past three years alone. All have expressed a deep desire to transform their D&IT, but I fear they are more likely to be churning butter. Am I the only one who sees these patterns as a problem?

If not, as one highly experienced executive recruiter serving the IT leadership space once told me, “Those folks have been my sugar daddy. It’s turnover city. Then again, I guess they’ve gotten the IT they deserve.”

Bruce J. Rogow

Bruce J. Rogow is a Principal at IT Odyssey and Advisory in Marblehead, Mass. Known as the counselor to CIOs and CEOs... Read more