A collaborative approach to IT leadership (Part 2)

Originally posted on  6/24/2008

In the last post, I began sketching the context for the development of a collaborative approach to IT leadership, taking as my starting point the challenges faced by a newly-hired head of a large technology organization. I want to pick up here where I left off: laying out the framework for addressing those challenges with a unified approach to winning the support of executive leadership, developing the current state, future state, and roadmap, and winning the support of IT. But first, a little recap from last time.

It’s been my observation that newly-hired CTOs, CIOs, EVPs, etc., tend to prioritize their challenges as follows:

1. Win the support of the executive leadership of the organization
2. Develop current state, future state, and road map
3. Win the support of IT leadership, IT management, and IT non-managers

Furthermore, they tend to view the first two as solo activities, something they have been tasked with doing on their own, as a way to prove their worth to the organization.

There are a number of problems with this way of approaching things:

1. It establishes a culture of top down leadership, the effects of which are difficult to undo once the new technology head turns to the task of winning over the IT department.
2. It isolates the head of technology from IT executive leadership.
3. It increases the likelihood of making uninformed or impractical recommendations to executive leadership.

In order to tackle their challenges while avoiding the problems of the typical approach, leaders need to rethink the interrelation of their goals based on the following assumptions:

1. A new head of technology cannot develop the most accurate and effective current state, future state, and road map in isolation (or only in partnership with folks brought in from the outside). Input from all levels of IT (operations, management, and leadership) is critical to success.
2. The support of IT leadership will be more easily given if they are included in the process of winning the support of the organization’s executive leadership.
3. The support of IT managers will be more easily won if IT leadership supports the new technology head.
4. The support of IT non-managers will be more easily won if IT managers support the new technology head.

There are two things a new technology head needs to work towards in light of these four assumptions:

Bring IT leadership into as much work with the executive leadership as is practical and appropriate right from the start. Doing so keeps them feeling in the loop and flatters them by giving them face time with upper management. It also facilitates observing them on a larger enterprise stage to evaluate their strengths and weaknesses, which helps with future professional development, knowledge management, and succession planning activities.

Use IT management to drive the development of the current state, future state, and road map. These are the folks who are on the ground, getting the job done in the current state–they know a lot more about it than anyone by themselves could learn in 60-90 days, and likely a lot more than IT leadership already does. In addition, they have daily contact with the people who know absolutely the most about IT: IT non-managers doing the work that keeps the lights on. And both groups spend a good deal of their time discussing IT’s problems and debating possible solutions with each other. Failing to draw on this pool of ready expertise increases the likelihood that the current state, future state, and road map will miss the mark and that IT won’t support the new technology head.

One way to accomplish both of these is to create two tiers of collaborative teams: a leadership team (the head of technology’s direct reports, with frequent, although not constant, participation from the head of technology) and a management team (managers selected by the leadership team). Both of these teams, despite the other goals they accomplish, are essentially a succession planning and professional development mechanism: leadership team activities groom folks to take over higher level positions in the organization, most immediately the head of technology, but, if run properly, also other positions across the organization; management team activities function analogously, but feed lower levels in the organization (culminating with the leadership team level).

These teams are useful (indeed, critical) beyond the first 90 days of a new head of technology’s tenure (something to be discussed in a future post), but for now, let’s look at how they might function from a high level during these 90 days:

Weeks 1-2: The head of technology should spend at least 50% of the first two weeks working with the leadership team, bringing them at every opportunity into the process she or he is going through by  discussing as much as is possible (and appropriate) with them and including them in work with executive leadership.

This is also the time for the head of technology to build consensus with them on implementing a collaborative approach to developing the current state, future state, and road map during weeks 3-12. This includes getting them to nominate IT managers to form the management team, the first responsibility of which will be reporting on the current state in each area of IT. Note that the members of the management team should not necessarily be the most senior people, but rather represent the pool of folks from whom the next generation of IT leadership would likely come.

Weeks 3-5: During the next 2-3 weeks, the management team will draft current state assessments of each area in IT, present them to the leadership team for feedback, and, after the review cycle has ended, finalize them. This process gets the new head of technology, the IT leadership team, and the IT management team all working together closely in the first 5 weeks to create a current state assessment that is broadly informed and widely agreed upon.

Weeks 6-8: During the following 2 weeks, the management and leadership teams will work together on the future state vision. First, the entire group brainstorms together to generate a list of goals for the future state of IT: i.e., what does IT need to accomplish in the near-, mid-, and long-term? Second, they break into teams to come up with strategies to meet each goal. With this done, the entire group meets to review the results. Once the final list of strategies is complete, the group as a whole can come up with a list of expected benefits associated with achieving the future state.

Weeks 9-11: The next 3 weeks are spent determining what needs to be done to reach the milestones of the future state. This falls primarily on the management team, who will work with their direct reports (as well as the other IT managers and their direct reports) to flesh this out. What is needed here is the list of projects that must be completed to realize the future state in the near-, mid-, and long-term along with rough, order of magnitude estimates on resources (numbers, skill sets) and cost (dollars and hours) required.

Depending on the organization, the level of detail will vary. The more historical project data, process documentation, and operational metrics there are in place, the more detailed the estimates can be. But even having something as general as “$”, “$$”, “$$$” for cost and one stick figure, two stick figures, three stick figures for resources is acceptable at this stage. They key is to make sure that the final deliverable demonstrates that planning, thought, and design went into the results. All of these SWAG estimates will be revisited when and if the projects go forward, at which time they can be rendered in more detail.

Week 12: Finally, the head of technology pulls together the current state, future state, and road map into a presentation for executive leadership, using the leadership team for review and feedback.

At the end of such a collaborative process, the head of technology not only has a more accurate vision of the current and future states (and a more realistic plan for how to move from the one to the other) but also strong support for her or his work. In addition, because a wide range of folks from all levels of IT have had a hand in it to varying degrees, she or he speaks to the executive leadership not as a talented outsider with an individual take on the matters at hand, but as new leader who has already gained the support of his or her team in a substantial way.

Easier said than done, of course, and making such a collaborative approach work within the particulars of any given organization will be the real challenge. But consider the alternative for a newly-hired head of technology: Split their time between winning over executive leadership and building their own current state, future state, and road map from scratch, spending whatever time is left with their direct reports, all of whom are wondering what’s being said in the meetings with upper management and exactly what the vision for IT will be, and hoping that the rest of IT will eventually come around.

And if a collaborative approach like the one outlined here fails, you can bet that an autocratic, top-down first 90 days wouldn’t fare much better…it would simply take longer for the failure to manifest itself (perhaps more like 12-18 months than 90 days).

In the next post, I’d like to turn to the ongoing work of the head of technology and how the use of collaborative teams (the leadership and management teams introduced here, as well as one more, the operations team) can contribute to his or her effectiveness.