Four Courageous Conversations For Every IT Leader

By Charles Araujo
business meeting

Four Courageous Conversations For Every IT Leader

By Charles Araujo

Over the last month, a single word has repeatedly risen in my consciousness. I started the month delivering the opening keynote at the LEADit conference in Canberra, Australia. I returned home and immediately left for the Pink Elephant Leadership Forum in Scottsdale, Ariz., where I delivered a morning keynote. As I spoke and then talked with people afterward, I found myself repeating the same word again and again: courage. 

While in Australia, I also participated in a "hypothetical." Originating in the U.K., a hypothetical is a simple panel construct, but one in which the participants play a fictional role in a hypothetical situation put forward by the session moderator; in our case, the moderator was the indefatigable Rob England, better known as the IT Skeptic. During the hypothetical, I played the role of CIO and, because of the challenging hypothetical situation, I kept having some difficult conversations with the rest of the panel. As we wrapped it up, I said, "The issue we haven’t addressed is there is a good chance that if I acted like this in a real career environment, I'd be looking for a job soon. These are tough conversations to have. They take a lot of courage. But the best, most successful IT leaders I know are having these conversations every day."

The incident made me realize that "courage" is the one thing that we don't discuss enough when it comes to what it takes to be a great IT leader—the kind of leader we need to take us into the future. But as I contemplated it further, I realized there are four specific, courageous conversations that every IT leader must be prepared to have if you are going to lead your organization into the future. 

Conversation #1: With Your Boss

“What are we capable of accomplishing?”

One of the consistent themes during the hypothetical was the balance needed between IT's current commitments and new projects in the pipeline. Rob England deftly played the "minister" (we were a government ministry in the hypothetical) and kept putting ever-new demands on the organization, driven by the political crisis of the moment. I found myself constantly saying, "If this is your new top priority, then we will need to discuss what things we are not going to be able to accomplish so that we can get this done." It was a constant struggle of prioritization. True to form, England pushed back, saying that he needed it all done, which forced me to stand my ground and insist that he prioritize the demands or put our entire delivery model at risk.

Telling your boss "no" is never easy and will often put you on the fast track to a new position "outside the organization." Therefore, many IT leaders understandably never go there. They put up a mild protest, but then take on the new responsibility and do their best to manage. This is why most IT executives (and their teams) are under such strain. We have rampant demand that far exceeds supply. IT leaders may be reticent to say "no," but, clearly, saying "yes" unconditionally isn't the answer either. Instead, a more courageous conversation is required.

I believe the right response in this all-too-common situation is, "Yes, we will need..." The key is to not refute or deny the new demand, but simply state to the requestor what it will take to deliver it. This is fundamentally a question of capabilities. Every system has a finite production capability based upon design and capacity. In no case, can any system either produce something that it is not designed to produce nor produce in excess of its available capacity. It is a simple fact, but one that we often ignore during these exchanges with our boss. We believe that somehow "we can get it done" and so pretend that we have the capability of accepting unlimited demand. But the hard reality is that our capacity is, in fact, a constraint, and without this kind of control, we will run the risk of delivering only a small percentage of what we have committed to accomplish.

Four Courageous Conversations For Every IT Leader

It is much more honest and respectful to be upfront about our organizational capabilities, limitations and options. That is what the phrase, "Yes, we will need…" does. Typically, you will end that sentence with either a description of the prioritization that you need to take place ("…to deprioritize…") or the resources that you will require to expand your capabilities (either people or money). It postures us in a positive position of saying "yes," but we are also honestly acknowledging our limitations. That takes courage. But it is required if we are to effectively execute our roles and fulfill our duties to our customers.

Conversation #2: With Your Customer

“What should we not do?”

During my keynote in Australia, I identified what I call the "four new rules of the new era." One of these rules is that we will be defined in the future by what we do not do. As technology becomes truly ubiquitous and finds its way into even the most pedestrian applications, it will simply become impossible for IT organizations to reasonably maintain control over all of it. Nor should we want to. The days of IT being the sole source provider and sole manager of technology are over. We need a new approach.

We need to begin having a courageous conversation with our customers. One in which we discuss candidly which businesses we should be in and which we should not be in. As IT professionals, we need to stop seeing ourselves as managers of technology. Instead, we must see ourselves as providers of strategic technologies that produce a competitive advantage. As we move into this future, our value will not be defined by our ability to manage and deliver this vast array of technologies that could just as easily be delivered by other organizations. Our value will be derived from the strategic technologies that we co-develop and deliver and that provide some form of unique advantage or differentiation to the organization.

This revelation also brings realization. We will be unable to deliver that kind of strategic innovation unless we shed all of those non-strategic technology platforms. It will demand that we be brutally honest about which elements of the technology stack, while perhaps important, do not provide the type of competitive and differentiating value that warrant our involvement. Those elements of the technology stack are the "lines of business" that we must exit. We must simply select an appropriate delivery partner and then get out of the business of providing those services.

The challenging part is that we have spent the better part of the last four decades "training" our customers on how to interact with us. And the linchpin of those conversations was that "everything technology-related comes through us." So, to acknowledge that this is simply no longer the case will take courage. The immediate reaction will understandably be one of, "Well, if I don't need IT for this any longer, do I need them for anything?" It is a fair and honest question—and one that we need to be prepared to answer. Having this conversation will be scary. It will be inviting our customer to challenge everything for which we have historically stood. You will have to make this transition rapidly and deliver on your promise that an increased focus on the most strategic organizational initiatives will yield a competitive advantage and differentiation.

That's a courageous promise, but it's one that every IT leader must be prepared to make.

Conversation #3: With Your Team

“What delivers strategic value?”

Humans are creatures of habit. Technical people take that age-old idiom to another level. Despite the rapid state of technological change, IT organizations and the IT professionals that comprise them have remained largely unchanged for the last 45 years. Structurally, organizationally and procedurally, we have largely done the same things, the same ways, for years. The problem is that many of those things that we have done for years have now become commoditized. They provide little discriminate value. Yet we continue to cling to them.

Four Courageous Conversations For Every IT Leader

The hard truth is that the vast majority of the work that today's IT organization performs does not provide any form of business value that is truly strategic or differentiating. It may be important and even crucial to day-to-day business operations, but it is also something that can often be provided just as easily by outside organizations. As long as those services are not truly strategic, the moment they can be acquired less expensively than the internal organization can provide them, a conflict will exist. Fear will lead IT professionals to try to "protect their turf" and attempt to justify why they must continue providing this service. It does nothing but erode the trust with our customers and delay the inevitable.

Just as we need to be courageous in our conversations with our customers about what services provide meaningful business value, we need to have the same conversation with members of our team. As an IT leader, you must be brutally honest with yourself and your team. Of all of the things you do on a daily basis, which of them provide true strategic value to the organization? The real answer is that there are probably a large number of activities that you presently perform that provide very little strategic value. These are the things that you must simply stop doing. You must put the well-being of the organization above your fears and find the most cost-effective manner in which you can provide those services—even though it is likely to be from an outside resource.

That takes courage. It will leave a large part of your team feeling very vulnerable. It may result in a smaller budget and footprint for your organization. It could even result in a staff reduction as you identify that you no longer need some purely technical resources. But it is the right conversation to have. It is the only conversation that will ensure your continued relevance. And it is what will be required to take you to a truly strategic level.

Conversation #4: With Yourself

“Am I ready to go the distance?”

Despite all of the angst that may have been generated by the first three courageous conversations, the toughest, most courageous conversation that you will need to have is with yourself. When I was playing the role of the CIO during the hypothetical in Australia, I was asked a question about what I would do given the circumstances. My answer was, "Keep my resume updated." It got a good laugh, but it wasn't much of a joke. There is a reason that the tenure of CIOs is relatively low compared to other executive roles. It can be a thankless job. Choosing to have these kinds of courageous conversations will not make it easier.

If you elect to follow my advice, you must be prepared for the fact that the resistance will be forceful and unrelenting. As an industry, we suffer from a type of selective amnesia. We seem to forget (or just willfully ignore) the cautionary tales of organizations that failed to have these kinds of courageous conversations—and suffered the dire consequences. Yet, the halls of IT leadership are swarming with IT executives who continue to repeat the mistakes of the past.

Having the kinds of courageous conversations that I am suggesting will certainly set you apart. But that may not be a good thing. The conversations will likely set you apart as someone who may be considered a "contrarian" or a "naysayer." Being courageous will demand that you tell the proverbial emperor that he has no clothes on. It will not win you any popularity contests. So the final, and perhaps most important, conversation you must have is with yourself. You must ask yourself if you are willing to go the distance—to have these conversations, to stick with them and to live with the consequences.

Four Courageous Conversations For Every IT Leader

This is important for two reasons. Personally, you need to know what you're getting into. If you are not prepared for the consequences, then you have no business beginning these conversations. The second reason is more altruistic. These are conversations that must occur. But having them without the necessary follow-through is a recipe for disaster. If you are not prepared to go the distance, then there is a good chance that you will do more harm than good. So before you begin, have a quiet, reflective conversation with yourself and ensure that you are prepared to follow this wherever it takes you.

The Need for Courageous Leadership

Our industry is desperate for leadership. We need true leaders. Leaders that are courageous and prepared to have difficult conversations with their customers, with their bosses, with their teams and with themselves. It is the only path that will enable us to function effectively in the future. Are you ready to be courageous? Are you ready for these conversations?

About the Author

Charles Araujo is the founder and CEO of The IT Transformation Institute, which is dedicated to helping IT leaders transform their teams into customer-focused, value-driven learning organizations. He is the author of the book The Quantum Age of IT: Why Everything You Know About IT is About to Change, is presently at work on two new books. Araujo is also the creator of DeepRoots, an organizational change methodology designed for IT teams. He frequently speaks and writes on a wide range of subjects related to his vision of the future of IT. You can follow him on Twitter as @charlesaraujo.

This article was originally published on 09-05-2013