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How to foster an IT team culture that breeds success

Team culture is hard to foster and difficult to maintain. CIOs Jack Wood and Paul Brady offered their tips to fellow CIOs at the recent SIM Boston Technology Leadership Summit.

In part one of this CIO tip, Paul Brady, CIO at Arbella Insurance Group in Quincy, Mass., and Jack Wood, CIO at Wayfair, the Boston-headquartered e-commerce home décor company, talked to fellow CIOs at the recent Society for Information Management's SIM Boston Technology Leadership Summit about their leadership styles and what they look for in recruits. Here, they share how they build -- and preserve -- IT team culture.

Diamonds in the rough: Wayfair Labs

Finding high-quality IT talent is never easy, but for Wayfair's Wood, the e-tailer's explosive growth -- doubling in revenue every year -- required some creative thinking on his part. At the relatively young company, the object was to find "rising stars, but not the top of the market." Five years later, the aim is still "to get your value-add," Wood said. "We don't want to lower the quality of engineering in our organization ... but we still want to go after the diamonds in the rough."

With that goal in mind, Wood's team has created Wayfair Labs, a training ground exclusively for noncomputer science people -- employees good in math, perhaps, or interested in coding, but lack the degree.

"We bring you in and train you for four months. We put you in code base and we slowly roll you out into our environment. At the end of four months, you either move into a full-fledged software/database -- whatever it is -- or we part ways," Wood said.

The training is done by Wayfair employees -- "future leaders" in IT who want to be in a management track. "Before we give them full ownership of an engineering organization ... we carve out a piece of the class and give them four or five people" to train, he said. "They still have their day jobs, but we allocate 20% to 30% of their time to be a mentor to these four or five people." 

The program has a 98% acceptance rate and a 95% graduation rate. Internal people account for about 10% of the applicants, but the program has become so popular that Wood's team has to turn people away. No recruiters are dedicated to the program -- word of mouth and brand recognition fuels the interest, Woods said. The lab has proved so successful that Wood has added a second component -- the DevOps Cabinet -- a six-month program addressing the need to align application development and operations.

"It is hot in market, and we just refuse to pay some of the salaries that people are demanding. We'd rather grab someone, train them for a few months and know that whoever comes out of it is an amazing Agile team," he said.

In addition to the training programs for entry-level and junior people, all new hires, wherever they are located, "come to the mother ship" for two to three weeks to soak in the Wayfair team culture. "We write it off as training, and when they are in Boston, we do things that give them a sense of what it is like here," Wood said.

Lifestyle perks reel in senior talent

Location matters in recruiting IT talent. Arbella Insurance has found its headquarters south of Boston to actually be an advantage, especially when it comes to senior IT professionals.

"We have had a lot of success getting people who were looking for a specific change," Brady said -- from consultants looking to travel less to people weary of the commute into Boston. "We have hired people who are taking pay cuts, because they want to be at their kids' football games or are tired of being on the road," he said.

SIM Boston Technology Leadership Summit panel on fostering team dynamics
Jack Wood, CIO at Wayfair, and Paul Brady, CIO at Arbella Insurance, discuss IT team dynamics at the SIM Boston Technology Leadership Summit.

Getting entry-level IT employees is more challenging for Arbella, Brady said. He has built strong relationships with local colleges and universities, and starts recruiting in the fall, well before graduation. "Over the course of the last four years, we have brought in 20 hires from local universities and colleges," he said, 18 of whom are still with the company. Entry-level IT employees are put into a structured technology program that includes business training, group projects and awards.

"In our experience, kids coming out of college want that stuff," Brady said. The cohort is tracked closely to help them find their best fit, Brady said, citing an actuarial science grad who came in as a database administrator and showed a talent for development. "So, we have made those transitions."

IT team culture includes fun

Both Wood and Brady have instituted voluntary programs that build IT team culture and reinforce company values. At Wayfair, Wood started a weekly event involving a "fun thing to do in the office" -- for example, a chili cook-off; the company also "empowers" people to do events off-site, with stipulations: "It has to include someone not on your team, include more than five people and be an activity," Wood said. Examples include fishing cruises and camping trips. A recent exception to the activity rule is a group trip to the new Star Wars movie at a theater Wayfair rented out for the event. "We have to walk to the movie theater together," so that qualifies as an activity, he said.

We have to sit them down and let them know what our culture is. At the same time, you have to evolve the culture of be left behind.
Jack WoodCIO, Wayfair

At Arbella, Brady's team is encouraged to participate in company-sponsored charities and also has a full schedule of fun activities. Because it is difficult to sneak 130 people out of the building at one time, most events happen on-site. Holidays are big, Brady said, citing a Halloween costume event that "was totally outside my comfort zone." At a recent chili cook-off, Brady's entry for the "hot category" didn't win because he said he backed off on the hot stuff to spare people. "So, we're going to redo the chili cook-off," he deadpanned.


Esprit de corps is a hard thing to keep alive, however, said both CIOs, who talked a bit about future concerns. Wayfair's recent public company status -- it went public in October 2014 -- changes the workplace, including IT team culture, "no matter what people say."

"Your day to day is going to be impacted," Wood said, citing access to data as just one example that changes once a company must follow the Securities and Exchange Commission's disclosure laws and regulation.

Also, Wayfair's hypergrowth is a double-edged sword. The steady influx of so many people -- each wanting to make a mark on the company -- means that the IT culture changes, and not always for the positive. "We have to sit them down and let them know what our culture is," Wood said. "At the same time, you have to evolve the culture or be left behind."

Arbella is also facing headwinds, Brady said. Once far ahead of the curve on work-life balance perks, the company sees competitors catching up -- offering causal clothing even at downtown Boston high-rise offices and flex time.

"Work-life balance is no longer a differentiator, so we have to think about, how do we stay ahead? Is it a four-day work week? A lot of companies are doing it," Brady said. "But we know that what we do today is par for the course tomorrow, and that is one of our big challenges."

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What are some of the ways you build IT team culture at your company?
I guess the main question is what kind of culture. "Success" is a tricky criterion because everyone would interpret it differently.
Based on my observations smaller companies seem to be more effective in building a culture (of any kind) because they're not so compartmentalized. In larger companies typically the existing culture is a huge factor to consider in change management.
Hi Albert,

I recently interviewed a CIO headhunter who had an interesting take on company culture. He basically argued that a big company can support many cultures but that it is unified by values that everyone, no matter what department or location, subscribes to. So, for example, the IT culture might be different from the marketing culture, or the New York office have a different vibe from the Seattle office, but the values -- think mission statement -- is the glue. 

Here's the post I wrote about the interview: CIO headhunter dismisses rock star CIO, extols corporate values 

Curious what you think.

Hi, Linda..

1. Values and mission. Yes, they should be the glue. But typically employees won't even remember the values and what they mean.
It's not enough just to write these words on the walls.
Management must embrace them first, and continuously - constantly - work with the teams promoting and steering. This is rarely done, so the CIO headhunter misses the real contexts.

2. I liked the article. Commented there.

Yes, it is hard. And it's on management.

"The idea of reusability is not new for the manager with technical experience in software. When code used in one place can be reused, the savings can be enormous, as can the increase in reliability and decrease in variability. Once we have fabricated a collection of useful, reliable, and reusable modules, we are prepared to lower the cost, raise the quality, and improve the predictability of software development.
One of the arguments against reusable software is that it doesn't come free. We cannot reuse just any old software we slap together. We must make an additional investment to render it truly reusable. The higher the initial investment, the more times we must reuse the module to recoup the investment.
A similar argument is often made against using teams for software development and maintenance. Teams do require a startup cost, and in many projects this startup is so long we never recover the loss during the life of the project.
This argument, however, is not against the use of teams, but in favor of better management of team formation.
Even if management were poor, the cost of team startup could be recovered by reusing the teams over a series of projects.
Unfortunately, only the better software organizations seem to reuse their teams. Breaking up successful teams is economic nonsense, so why is it so common? Long before the days of software, people understood the practice of dissolving well-functioning teams ultimately derives from the insecurity of management:
What is feared of integration within a small group is that it may organize itself in opposition to the larger whole —and this it certainly will do if its existence be threatened; but equally, a protected group will endeavor to satisfy its wider interests by collaborating with the organization of which it is a logical part. In this way, its loyalty will extend to the firm as a whole."

- Gerald Weinberg in "Managing Teams Congruently".