Relationship advice for overworked and underloved IT leaders

An IT leader’s on-the-job life expectancy directly depends on relationships with business executives. Here's how to cultivate those relationships (and common pitfalls to avoid).

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This article is part of a series highlighting key takeaways from my recently published book, Truth from the Trenches, A Practical Guide to the Art of IT Management. As a seven-time CIO, I’ve had an opportunity to observe the good, the bad and the ugly aspects of IT management up close and personal. Truth from the Trenches is my attempt to share my experiences with emerging IT leaders to help them avoid the chronic problems that afflict so many IT organizations.

Social scientists have become increasingly convinced that constructive, empathetic relationships with other human beings play a key role in increasing an individual’s life expectancy. That isn’t exactly news to IT leaders who realized a long time ago that their on-the-job life expectancy depends directly on the relationships they form with business executives. With the recent celebration of Valentine’s Day, it struck me to provide some relationship advice to overworked IT leaders who are seeking some love, or at least some respect, from their business counterparts.

There are so many things that can go wrong within an IT organization that shrewd IT leaders consciously or unconsciously build up a reservoir of trust and accomplishments that they can draw upon when IT fails to deliver on business expectations. To be perfectly blunt, if business leaders like and respect their IT counterparts, they’re willing to forgive a world of sins; if they dislike you, they can undermine your personal reputation and subvert your major initiatives. Here are a few suggestions for developing relationships that can weather adversity and actually make day-to-day business more enjoyable and more productive:

Invest in your relationships with executives

Successful relationships with business executives are two-dimensional in nature and have both a social and business component. The social dimension is actually the easiest to cultivate. Most individuals telegraph their outside-of-work interests rather openly and require very little urging to talk about their kids, favorite sports teams, alma maters, vacations, hobbies, etc. It’s actually quite difficult to fail to find some type of common outside-of-work interest that can form the basis of a social relationship with a business colleague. 

Quite unintentionally, I developed a close working relationship with the CFO at a former company that was triggered and sustained by our mutual love for the New York Yankees. The CFO and I were the first to arrive at work every morning and we would inevitably end up in the coffee bar. We exploited the opportunity to bemoan the Yankees’ failings — whether it was a failed at-bat, a dropped ball or bad call from the night before. Our shared pain over the Yankees’ failings paid off at budget time, when I was able to negotiate IT spending levels for the next fiscal year in a much more open and straightforward fashion.

In contrast, the business dimension of executive relationships is typically much more difficult to establish. 

A genuine curiosity about how a business works is one of the most important traits of successful IT leaders. Business executives cannot fail to be impressed when their IT counterparts proactively seek opportunities to learn about their problems and challenges. Just because IT leaders aren’t invited to participate in a business unit QBR, a sales pipeline review or a customer marketing presentation doesn’t mean that their participation would be unwelcome. Even if the leader’s ability to participate in such meetings is limited by a lack of domain knowledge, he or she will score points by exhibiting a personal interest in business operations and customer relationships.

Business travel is the perfect opportunity to cultivate relationships with business peers. There’s ample downtime during a business trip to casually talk about out-of-office interests, and there are multiple opportunities to participate in informal business discussions. Some of the most valuable lessons regarding the issues and opportunities facing a company can be learned in airline lounges or over business dinners, rather than in formal conference rooms. Invitations to travel with business peers or join them for lunch or dinner should never be casually declined.

Avoid common relationship mistakes

IT leaders make chronic mistakes in trying to build constructive relationships with their business counterparts. Several of the more prominent errors are:

  • Focusing on form over substance: Just because you attend a lot of regularly scheduled meetings with your business counterparts doesn’t necessarily mean you are developing effective working relationships with them! Familiarity sometimes breeds contempt instead of confidence.
  • Emphasizing analysis over intuition: Business executives frequently feel that IT leaders hide behind a lot of numbers, tables and viewgraphs. They would like their IT counterparts to speak from the heart and demonstrate more personal passion and commitment to specific projects and activities. Unfortunately, many IT leaders have been explicitly trained to refrain from emotional expressions of personal passion or intuition.
  • Failing to make regular deposits in the relationship bank: Relationships are not something you work on when things go wrong. They need to be nurtured and sustained even when everything is going along perfectly well. Leaders need to consciously devote time to checking in on and interacting with key business partners on a routine basis, even if they have no explicit agenda. That way, you don’t find yourself in a situation where you’re asking a business counterpart for forgiveness or funding after a long hiatus in face-to-face contact.
  • Being poisoned by your own team: A leader’s own organization may lobby against his or her relationship-building efforts. Business relationship managers, service managers or business systems analysts may feel that such relationships are their responsibility. Consequently, they may feel their roles are being co-opted or undermined when their leader starts devoting significant attention to their client group. On the other hand, they may be so frustrated by their inability to develop effective relationships with their clients that they advise their leader that business outreach efforts are doomed to fail.
  • Building relationships that are easy instead of those that count: Not all business units and functional teams are created equally. Whether we like to admit it or not, there’s an inevitable pecking order in the importance of a company’s business units and functions that usually corresponds to the financial results they deliver. Astute leaders will apportion their relationship-building time and attention accordingly.  More effort may be required to establish effective relationships with the leaders of dominant business units or influential functions but such efforts will yield disproportionate benefits when major decisions impacting IT are under consideration.

Chinese philosopher Lao Tzu said, “being deeply loved by someone gives you strength, while loving someone deeply gives you courage.” These same sentiments apply to the business relationships discussed above. The trust and respect of business partners will strengthen the role that an IT leader can play in re-engineering existing business processes or implementing longer term business strategies. Reciprocating that trust and respect will give IT leaders the courage they need to act on those impulses.

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