Business leaders are often compared to quarterbacks. A quarterback huddles up with the team before every play so players understand how to execute in an organized fashion. This comparison may work for some team leaders, but it no longer applies to IT.
Why? Because more and more IT functions are being outsourced: data centers, applications, development, help desk, and more. When your team is so decentralized, and often working around the globe, it is hard to huddle before every play.
Oddly enough, the outsourced parties huddle all the time on their own to lay out their next plays—which typically aim to increase their revenue, not yours! As a result, we counteract with procurement policies and red-lined legal documents. How can an IT executive be a true leader when their team consists of external relationship managers, and internal people from the procurement and legal departments?
To make matters worse, IT executives often lack the support they need from top management. Quarterbacks share the same vision as the coaching staff and the team owners: to win the championship. In reality, management often pays more attention to the cost of IT than to the fact that IT holds the key to the organization’s future.
IT leaders must take a unique approach.
Let’s forget about trying to align vendors, procurement, legal, and top executives. With no goals in common, it’s impossible to expect these disparate parties to ever run a single successful play together.
The most you can do as an IT leader is to paint a clear picture of a common goal, and rally everyone to work toward that vision. Specifically, there are three perspectives for communicating the vision and execution, each tailored to a particular audience: other leaders, peers (in Procurement and Legal), and vendors.

Each perspective requires a different communication mechanism, plan, and set of techniques.
Leading Other Leaders
Top executives are not often receptive to new ideas in a group setting. Maybe you can pitch a few ideas at an offsite, during a brainstorming session. But in that setting there are so many ideas exchanged, yours is likely to get lost in the shuffle. The best way to align on a digital vision with top executives is to talk with them individually.
A professional setting could work. Schedule a quarterly IT performance review meeting with each top executive and allocate time to establish priorities. Chances are, each top executive has several ideas about transforming the organization into a digital superpower.
The ideal setting for a conversation about a digital vision is outside work: at lunch or dinner, over a drink, in a car on a way to a conference, etc. This might feel like selling. In fact, it is. A leader must be able to sell their vision to top management.
Leading Peers
While IT’s goal is to deliver on the mission of the organization, Procurement’s goal is reducing cost and Legal’s is minimizing risk. There is no natural alignment among these objectives. Often, IT executives look for ways to avoid dealing with Procurement and Legal. As a result, when those departments do get involved in an investment decision, they often dig deeper and cause delays.
The cornerstone here is in business process ownership. The more you try to avoid those groups, the more they will compensate by making the process longer and more convoluted. A joint business process that accounts for objectives of all groups is the only way to work with and not against each other. Admittedly, defining such a process takes time and effort, but it is well worth the energy.
Leading Vendors
While you may be able to get into a proverbial huddle with Procurement and Legal, getting all your vendors to huddle together is a pipe dream. It is not possible to get vendors to align with each other. It is, however, very much possible to align with each vendor individually. It comes down to people, scope, and incentives. In that order.
Vendors try to instill trust through reputation, experience, expertise, breadth, size, and all sorts of other general traits. What they are trying to do is to have you contract their company, not individuals. There is no way that an IT leader can expect another company to align to their vision. But what matters to the success of your relationship with a vendor is not macro parameters, but specific representatives. Finding a great vendor representative is as hard as finding a full-time employee. When selecting a vendor, it is more important that you are comfortable with their representatives than with their price or packaged service offerings.
If you can get great vendor representatives locked in to work with you, it is easy to align with them on a mutually beneficial mode of operation. More often than not, if you have win-win-minded individuals from multiple vendors, you can get them all working together as a unified team.
IT leadership means setting a vision and making it personal.
IT leaders today are expected to play an increasing role in strategy execution. In fact, most organizations have a vision that is digital in one way or another. But IT leaders don’t always have designated teams to lead toward that digital vision. On the contrary, IT is expected to execute with help from internal and external personnel, many of whom don’t report into IT.
The most effective way for IT leaders to align all resources and stakeholders participating in strategy execution is to approach them individually, and find targeted ways to help each other out.