by Clint Boulton

Stretch assignments help future IT leaders shine

Feb 13, 2020
CareersIT Leadership

CIOs tap trusted lieutenants for anything from strategy to applications and infrastructure leadership, ostensibly bolstering the organization's leadership bench.

The most successful tech chiefs hand off many critical tasks to trusted lieutenants, in part to groom potential leaders to help future-proof the company. Choice Hotel CTO Brian Kirkland is a master of such delegation, assigning leaders with high potential tasks that extend beyond their regular job duties.

Thanks to these stretch assignments, which help leaders bolster their strengths and shore up weaknesses, Kirkland has built an IT function that is capable of operating without him.

“I try to obsolete myself as much as possible,” Kirkland tells “The key is to identify [his staff’s] aptitude and interest. What’s their oxygen? What do they enjoy doing and what do they hope to get out of their career?”

CIOs have long tackled stretch assignments with an eye toward helping themselves level up in the business, as reported. And while it behooves up-and-coming IT leaders to push their managers for such assignments, many CIOs like to stress-test potential successors or those who may assume leadership roles in adjacent areas of the business.

Developing tomorrow’s CIOs

Chris Judson, Choice’s vice president of engineering, is one of Kirkland’s high-potentials. Judson manages Choice’s data services, machine learning and artificial intelligence efforts, guests and loyalty systems, as well as the chain’s cloud computing partnership with Amazon Web Services. Judson also helps negotiate deals with vendors and explores how emerging tech such as virtual assistants and 5G might play a role in Choice’s future. It’s a path fit for a future CTO, Kirkland says.

Playing off of Judson’s knack for strategizing, Kirkland worked with him on the company’s IT plan, mapping out tech initiatives. Kirkland delivered this strategic roadmap to Choice’s board of directors. Judson and Kirkland also regularly huddle with executives, including CEO Patrick Pacious, on IT strategy. Kirkland also routes business partners through Chris. “I like to put him at the table as opposed to handing him work,” Kirkland says.

Judson says that he enjoys the experience. These days he’s accelerating Choice’s DevOps strategy, which includes building out CICD (continuous integration continuous deployment) pipelines. He’s also fortifying the company’s enterprise data warehouse strategy to enable capturing of event data in real-time for fraud detection and other analytics.

Judson is one of several high-potentials, Kirkland says. One staffer governs day-to-day IT infrastructure, running daily stand-up meetings and employee townhalls, a role that Kirkland says could lead to a CIO appointment. Another tech leader with aspirations on the business side of Choice is paired with appropriate business leaders.

Kirkland tries to help staff fill in the gaps between their roles and adjacent roles. For instance, he ensures that many of his technical staffers learn financial aspects of the business, including what factors impact revenues per available room, top- and bottom-line growth, as well as key concepts such as capital and operational expenditures.

For each employee, it’s important not to assign stretch opportunities that “don’t fit with their brains.”

“You have to stretch them in what the individual is trying to achieve and in ways that help the organization be successful,” Kirkland says.

Building a leadership bench

A critical stretch assignment early in Milind Wagle’s career at co-location and datacenter service provider Equinix has him eager to “pay it forward,” including opportunities for high-potentials to move laterally or upward.

Wagle, whose consolidation of the company’s expanding configure price quote systems proved to be a stepping stone for his current role as CIO, is grooming several lieutenants for future success. He switched one lieutenant who was leading applications to governing architecture and moved an infrastructure head to run applications. Another leader has become the face of business transformation for the company.

Wagle also formalized the chief of staff position as a rotational opportunity for staff who have high potential but don’t have the experience or exposure in the business. The chief of staff, who hails from Equinix’s application team, works closely with him and the leadership team to gain a new vantage point of the company.

“I view it as a role in service to me and leadership team tasked with enabling the organization to be set up better for digital transformation priorities,” Wagle says.

Worth the stretch

By their definition, stretch assignments are challenging, but some organizations are tested to the limits, as Patrick McGrath learned as the CIO of real estate firm Savills. McGrath assigned a talented product developer responsibility for an iOS app, but that person is struggling to marshal resources and communicate value to power users and senior leadership.

“Frankly, they’re struggling a little bit, finding the right balance between driving forward quickly and building a cross-functional team,” McGrath says.

To provide air cover, McGrath has asked other peers to “coach” the staffer and avail them of other resources. McGrath, who sent the staffer to leadership training, isn’t giving up. “This person is a high-potential who I think will ultimately be successful,” he says.

How to seek stretch assignments

Gartner offers the following recommendations for those seeking stretch assignments, courtesy of a March 2019 research note by analyst Eric Knipp. 

Press the issue. Most leaders will bring people along, but if your boss isn’t challenging you with stretch assignments, challenge him or her to invest time in developing you, Knipp says.

Profess your passion. Managers aren’t mind-readers so be sure to tell them what you are passionate about and that you want greater challenges. “The majority of professional development is experiential, so stretch assignments that tap into your past experience, your future development needs and your passion are key,” Knipp says.

Stretch assignments are often nonlinear. While a stretch assignment may be preparation for the next step up on the career ladder, careers rarely progress in a straight line, Knipp says. Be prepared to stretch into a lateral move that gives you access to new opportunities inaccessible from your old trajectory.

Stretch assignments should mesh well with work priorities. They should provide learning opportunities that are relevant to current and planned future roles, while stretching you beyond your comfort zone. “They should also include coaching interactions before, during and after the assignment,” Knipp says.

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