5 ways to help teams step outside their comfort zone: Colorado CIO of the Year winners

How can you encourage teams to take risks and embrace change? Listen to what these top CIOs have to say
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Once you're wrapped in a warm blanket of security and familiarity, it can be challenging to pull back the covers and step into the crisp air of change. But there can be big benefits for expanding your comfort zone, especially when you work in IT where change is constant. 

We caught up with CIOs who recently won the 2021 Colorado CIO of the Year ORBIE Awards to learn how they’re encouraging their teams to get comfortable with being uncomfortable. The awards were presented by the Colorado CIO Leadership Association, a professional community that annually recognizes CIOs for their excellence in technology leadership.

From encouraging their teams to answer provocative questions to leading with transparency, these award-winning CIOs share some of the key ways they encourage their teams to step outside their comfort zones. 

1. Encourage a disruption mindset

Leadership CIO of the Year

Alan Cullop

Alan Cullop, SVP and CIO, DaVita: IT is constantly evolving, so I think that in general, most IT professionals are – to some degree – comfortable with change, and comfortable with being uncomfortable. In healthcare IT in particular, every day and every patient presents unique challenges. Flexibility is key, both in terms of the way we manage people as well as the technical solutions we develop.

We try to encourage a mindset of “disruption.” For us, this means encouraging our teammates to take calculated risks. We want everyone to be comfortable with using mistakes as learning and growth opportunities, particularly as we explore new technologies and approaches. We balance that with a constant focus on patient safety, and protecting the privacy and security of information in the healthcare setting, before we move forward on a deployment.

The disruption mindset is more than a leadership tactic; for us it also plays a role in recruiting and talent management. 

As we build our teams, I challenge my leadership group to factor this into the recruiting process. We want to get a feel for a potential teammate’s comfort level with the unknown. We try to gauge a candidate’s willingness to keep “disruption” top of mind. In our work, not only must we be solving today’s issues, but we must also be thinking two to three steps ahead so we keep our organization well positioned for the future. This is more easily achieved when your teams are built to embrace change, and the opportunity to innovate.

[ Get exercises and approaches that make disparate teams stronger. Read the digital transformation ebook: Transformation Takes Practice. ]

2. Uncover the "provocative proposition"

Super Global CIO of the Year

Brian Gabbard

Brian Gabbard, VP of IT Services, Ball: There are two words that I use to move people outside of their comfort zones: provocative proposition. I often ask my team what the provocative proposition is for what we want to achieve. Provocative propositions, for me, are those uplifting statements that describe the end state – the “what” we are trying to achieve. Some key questions that I like to ask related to provocative propositions are:

  • Is it provocative? Does it stretch, challenge, or interrupt the status quo?
  • Is it grounded? Are there examples that illustrate the ideal as real possibilities?
  • Is it desired? If it could be fully actualized, would the organization want it? Do you want it as a preferred future?
  • Is it stated in affirmative and bold terms?

When I think of the importance provocative propositions can play in the day and life our IT professionals, I am reminded of the story of the three stone cutters. I want our team to be like the third stone cutter, understanding and connecting with the meaning behind their work. 

3. Understand what makes you uncomfortable

Global CIO of the Year

Chandra Venkataramani

Chandra Venkataramani, CIO, TTEC: To be able to work outside your comfort zone, one needs to first understand what makes them uncomfortable. Then, I encourage them to seek a small task that they can take on, without fear of failing. It is important to start small and get a feel for the excitement and satisfaction completing a task that you thought was outside your comfort zone. 

As a leader, it is my job to provide my team with an environment where they are not afraid to fail and where they are encouraged to innovate and try new things. This, combined with the encouragement to be curious every day and also question the status quo, is what will differentiate a normal team from an extraordinary one. It is good to keep Eleanor Roosevelt’s quote in mind: “Do one thing every day that scares you.”

4. Be transparent 

Enterprise CIO of the Year

Bill Case

Bill Case, CIO, WOW!: Creating a company culture based on a shared vision, mission, and core values is paramount to building trust among the team. At WOW!, we've intentionally taken time to establish these building blocks to produce a high-functioning, dynamic team that trusts one another and can perform even in the most challenging environments. These components provide a solid foundation for our team to take risks and support one another when things get uncomfortable.

One of the tactics I've found most successful with teams is to create a high degree of transparency with our strategy, our strategic initiatives, and the road map we have outlined to achieve our goals. We take the time to not only explain what we're working to achieve, but we also provide broad context and explain why the work is especially important to a thriving organization in a competitive environment. Transparency reinforces our values which, in turn creates a sense of greater comfort among the team. At WOW!, we know that to be an exceptional broadband provider we have to listen and respond to our customers and find ways to provide the WOW! experience by being reliable, easy to work with, and pleasantly surprising to each of our customers every time. To help my team be comfortable with the rapid change, I continuously reinforce our strategy and provide the context to help the team support and align with our vision.

5. Create safety

Corporate CIO of the Year

Mike Bush

Mike Bush, Senior Director of IS, Colorado Rockies: You can’t step out of your comfort zone if you’re scared that doing so will result in some sort of punishment if you’re wrong. Leaders can create this safety by communicating that it is OK to make a mistake. This certainly is not a free pass. As leaders, we must decide where the line is and make that clear. You will be shocked how far people can reach when you give them support and encouragement to go beyond what they believe their limitations are. 
It may sound cliché, but a good tactic to help people get comfortable with being uncomfortable is to take blame and give credit. That is, when someone is navigating uncharted waters and they make a mistake, a good leader will take part (or all) of the responsibility to upper management if things go wrong. Conversely, if the employee sees some success, a good manager deflects all credit and praise and makes sure it goes to that employee. Creating this level of safety within your teams will encourage your people to try new approaches.

[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]

Ginny Holden is an independent consultant who brings the practice of IT to life through memorable storytelling.