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7 leadership skills that will make or break your DevOps transformation

Christopher Null Freelance writer

As a DevOps leader, you need to manage an array of complex systems during a digital transformation. But none is more complex than the network of humans you'll be working with to get the project done.

TechBeacon spoke to top DevOps leaders. Here are seven core skills they say you'll need to manage your teams effectively and push your digital transformation to the finish line.

1. Patience

Cultural transformations are lengthy and difficult. Failures are inevitable, and it can be hard for all involved to step back and wait to see their work pay off. Daniel Barker, currently leading the technical and cultural transformation for the National Association of Insurance Commissioners (NAIC), said a lot of people will be quick to blame the transformation for any failures and may actively fight against your initiatives. Much of this reaction is driven by fear.

"Most people, maybe even the leader, won't know what's ahead for the organization or their specific role in the company," Barker said. "That creates a lot of anxiety. You can work through these concerns, but it will take time and many conversations."

Barker said he learned a hard lesson about patience at a previous company where he wasn't seeing results and teams were growing disengaged.

"I just kept pushing harder and trying to force everyone down the path. This really backfired on me. Even more people became disengaged, and I lost some supporters. I've learned to bite my tongue a lot more and never force anything."
Daniel Barker

2. Listening

Communication is an essential leadership skill, but many leaders focus more on the speaking side at the expense of the other side: listening. Without this ability, you won't be able to understand what information your team members need to do their jobs or to ease their anxiety about problems they'll face during the transformation.

Barker said he encourages as much dialogue as possible when he's leading a transformation. While he can't be everywhere at once, he tries to make himself available when someone asks and takes proactive steps to engage groups that might be less likely to reach out.

When you solicit feedback this way, you might not always like what you hear, but Barker urged leaders to keep their minds open. You are going to hear a lot of harsh comments throughout the transformation, he said.

"It's very important to accept those comments, internalize them, and even reward the person presenting them in order to encourage more. Never punish those commenting or try to fight back against them. They are helping you gain context."
—Daniel Barker

3. Self-awareness

In addition to being in tune with your team members' emotions and motivations, success depends on you, the leader, understanding your own. A realistic grasp of your strengths and weaknesses prevents you from being either overly confident or too self-critical, both of which can undermine your leadership. It also sets a tone that helps team members manage themselves during the ups and downs of the transformation journey.

"When you're known to be part of the leadership, people will look to you for examples of how to behave, how to react, [how to approach] next steps, and so on," said Aubrey Stearn, an independent DevOps consultant and interim head of DevOps at Solicitors Regulation Authority, the national regulatory body for attorneys in the UK.

"I have to constantly think about how I'm framing my reactions to situations. When something doesn't go to plan, sure, I can feel a bit down personally. But at the same time, I have to make sure I keep morale high on the team and that we extract all the good learnings from the event."
Aubrey Stearn

4. Coaching 

During a digital transformation, a leader needs to be able to deliver structured, curated messages to disparate groups. But NAIC's Barker said it's important those don't come as demands. He takes a coaching approach, asking a lot of questions to prompt team members to come up with their own answers and solutions.

He also presents content in a variety of ways, not all of them coming directly from a place of his own authority.

"I need to increase the team's knowledge about tools, techniques, or strategies we'll need to use in the future. I do this through traditional presentations, newsletters, sharing articles with specific people or teams, and bringing in presenters from outside the company."
—Daniel Barker

5. An ability to learn—quickly

The knowledge you bring to a project will only get you so far, however. Eventually you'll have to step outside your comfort zone, so an ability to learn on the fly will serve you well.

DevOps veteran Chris Short, who currently works on the Ansible team at Red Hat, shares this example

"You know Kubernetes, Ansible, and are familiar with every public cloud provider? Great! Now help me move this 15-year-old .NET monolith into a cloud-native environment. One's ability to pick up things they've never touched, and meet people where they're at and bring them forward, is critical for a leader."
Chris Short

6. Systems thinking

NAIC's Barker said a DevOps transformation leader needs the ability to think about the system as a whole. This assumes a very deep knowledge in several areas of the technology stack and general knowledge about everything else in the stack. If all that leaders know is development, he explained, then they probably won't be very effective with the network team. They'll need to understand DNS, OSI layers, routing, switching, firewalls, MTUs, and packets in order to gain the team's confidence.

The opposite is also true, Barker added. "The development teams won't want anything to do with you if you don't understand how to write a 'Hello, World!' app in your company's primary language, why they need to deploy quickly, or why time-tracking of creative endeavors is basically useless," he explained.

"[It's important] to not pretend to know something you don't, because the people who really know will see right through that. Be genuine and transparent."
—Daniel Barker

7. Diplomacy

Each role and relationship in a company has a unique perspective, and sooner or later some of them will come into conflict with others, or with you. The ability to understand and respond sensitively to different ideas and feelings while still asserting your own will help improve communication, build mutual respect, and ultimately lead to more successful outcomes.

"I’ve been doing change for a long time, and diplomacy is the one skill you'll always need. There will be disagreements on specifics, fear of change, and some pushback. Diplomacy is the one skill that will allow a leader to help bring about change as effectively as possible."
—Chris Short

Can you add to this list? Share your DevOps transformation takeaways in the comments below.

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