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Are You Playing Checkers Or Chess With Your IT Organization?

Strategic IT leaders are adept at playing chess with their organizations


Every year in IT is an ordeal. Budget cutbacks, conflicting priorities, uncooperative business partners, contentious contractors, vendor disputes, skill gaps, disgruntled employees, quarreling teams, unwanted attrition, personnel issues, sagging engagement scores, customer complaints, failing projects, new regulatory requirements, unresolved audit findings, growing technical debt and new tools that create as many problems as they solve. It’s a veritable minefield.

Navigating that minefield becomes a game, a little bit like playing checkers or chess.

The differences between checkers and chess

Checkers and chess have some obvious similarities. They’re played on the same board. Both games require patience, analytical thinking and problem-solving skills. Chess pieces move in a more complex and somewhat erratic fashion. Consequently, chess players are forced to develop longer term strategies, typically planning actions they intend to take 4-6 steps beyond their current move.

Checker pieces, in contrast, move across the playing board in a somewhat simpler and more linear fashion. Most checker players are only thinking 2-3 steps beyond their next move.

Although both games require similar skills, chess is widely considered to be more complex and harder to master. I think it’s fair to say that navigating the minefield described above bears more similarities to a game of chess than checkers.

Are you playing checkers or chess?

IT leaders need to ask themselves if they’re thinking 4-6 steps ahead of the tactical crises within their 2023 minefields. Are they developing longer term plans to improve the performance and business impact of their organizations in 2025 or simply reacting to the crises of 2023? If you’re prepared to personally take that test, I’d challenge you to answer the following questions.

Do you spend time with critical business partners on a periodic basis to gain insight into their understanding of industry trends, review the current performance of your company (good or bad) and determine how their teams are contributing to that performance (also good or bad)? Or are your one-on-one conversations with business partners perpetually focused on current projects and pending action items?

Do you have a vision of what the staffing and structure of your organization should look like in 2025 or are you awarding headcount vacancies to members of your team that scream the loudest for additional support? Do you have a sufficient understanding of the challenges and opportunities facing your company over the next 2-3 years to develop a strategic staffing plan? (If your answer to the second question is ‘no’, you’re not spending enough one-on-one time with your business partners or you’re in the wrong job.)

Are you focusing conversations about new technologies within your organization on tools or products that could clearly have a positive business impact or are you giving your team free rein to evaluate any technology they find intriguing, assuming you’ll be able to find a business use for whatever strikes their fancy?

Are you proactively finding ways of maximizing the benefits of the new hybrid workplace and minimizing aspects of hybrid work that are fueling employee discontent and burnout? Or are you simply letting nature take its course and assuming that the members of your team will instinctively optimize the ways they choose to interact and collaborate in the future? Is it time to re-evaluate, reconfigure, replace or augment your collaboration tech stack or perhaps establish guidelines for the use of individual collaboration tools?

Are you consistently sending the right signals to your organization about the importance of information security? Do they understand that security is everybody’s job and not simply the responsibility of individuals assigned to the infosec team? IT should serve as a model of security awareness and policy compliance for your entire company. If security isn’t part of the intrinsic DNA of IT’s culture, how can you possibly expect the rest of the company to appreciate security vulnerabilities and comply with the safeguards you have put in place?

Have you clearly identified high potential individuals within your organization who can serve as future leaders and are you providing them with periodic attention, guidance and mentoring? Are you actively seeking opportunities to assign these individuals to activities that will test and develop their capabilities? Or are you willing to play Russian roulette with the external job market every time you need to fill a leadership vacancy on your team?

Do you continually display a visceral intolerance for creeping bureaucratic practices within your own organization that waste time, frustrate team members and distract attention from true business priorities? Do you visibly foster continual improvements in current work practices or are you subtly sending signals that you’re largely satisfied with the status quo?

Are you striving to become a Grandmaster at the game of IT?

You can’t succeed at chess simply by becoming a master manipulator of rooks or knights or bishops. You need to become a master manipulator of all the pieces on the board to ultimately become a chess Grandmaster. In a similar fashion, individuals seeking to become Grandmasters at the game of IT need to maintain their focus on all of the challenges posed above while managing the inevitable tactical crises of 2023. Those who succeed will find themselves leading organizations that are more relevant, more impactful and more widely respected by their business partners in 2025.

Success at navigating the 2023 IT minefield (i.e. playing checkers) may provide some transient emotional rewards but strategic success in building a high performance, high impact IT organization (i.e. playing chess) is much more satisfying and ultimately more beneficial for your team and your career.