DevOps: 5 habits of successful leaders

Building and improving a DevOps culture requires a special kind of leader. The most successful DevOps leaders model habits including consensus-building and continuous learning
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A strong DevOps culture usually spreads widely and organically. It also requires strong leaders who manage their teams in ways that are generative to that culture – and possess many of the same attributes that they’re hoping to cultivate.

“DevOps ultimately requires a high level of collaboration to be successful, so it’s critical that team members have the communication and interpersonal skills to work well with others,” says Gou Rao, CTO at Portworx. “DevOps leadership needs to set the tone.”

Setting the tone with action is often more effective than by mandate; while leadership can still require some top-down prescription, a healthy culture is better served by building habits conducive to DevOps success.

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5 habits of high-performing DevOps leaders

Let’s dig into five characteristic habits of strong DevOps leaders.

1. They hone negotiation and consensus-building skills

The ability to bridge gaps among individuals and teams could benefit most executives and managers, but it’s absolutely essential for DevOps leaders. Negotiation and consensus-building skills – as well as a knack for balancing those with prescription when necessary – are key.

"A good DevOps culture is all about collaboration and breaking down silos."

“Leaders in DevOps organizations need these more than traditional technology leaders,” says Ravi Lachhman, evangelist at Harness. “A good DevOps culture is all about collaboration and breaking down silos.”

These skills are particularly important to DevOps leaders because they are usually more concerned with the impacts of their processes and tools on internal customers or partners, and therefore are as much interested in how things get done as they are in what gets done.

“Engineering efficiency changes can have an immediate impact across the organization, so the internal customers of DevOps teams can be wary and potentially pessimistic about changes they implement,” Lachhman says. “The adage ‘your customers don’t care how you achieved something’ is not true for DevOps leaders because DevOps teams are in the business of [defining] how you achieve something.”

Indeed, the “how” (and “why”) are crucial – that means broadening your focus to include not only outcomes but how those outcomes are produced.

“Good leaders invite everyone in the organization to the table,” says Derek Weeks, VP at Sonatype. “They understand everyone needs to buy into building a DevOps practice and agree on the desired outcomes. Managers and leaders that implement these strategies create healthier change, happier people, and better outcomes. And remember, healthy and happy teams outperform talented ones.”

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2. They promote continuous learning and growth

Inflexible silos allow people to stay static in their specific roles. They don’t need to care about how someone in a different role does their job. As in #1 above, they don’t need to care about how things get done – just that their singular part of a larger process or pipeline gets done.

That’s antithetical to DevOps.

“In many organizations, the members of a value chain [who] deliver faster, better, and more secure apps and services are too focused on their own piece, and the engineers and individuals working on their piece of the value stream don’t have the time or ability to look upstream (from testing into the design work, for example) or downstream (from development to operations),” says Eveline Oehrlich, chief research officer at DevOps Institute. “This causes a narrow view and does not allow for improvement and understanding of the bigger picture.”

It’s not necessarily the individual’s fault, however. There may be little incentive for learning and development; there might even be a downside for doing so.

“The pressure to deliver in many cases does not allow for room to learn and understand other key areas within the value chain which can be improved when working together,” Oehrlich says.

DevOps leaders regularly give their teams the time and space to learn and grow – from each other, from experimentation, from training or professional development, and so on.

How do you widen skills? Think cross-training and shadowing, for example.

“Building a team that supports each other and has a wide set of skills is crucial,” Lachhman says. “As a leader, you need to encourage an environment where learning and development will thrive. Someone on the team might have infrastructure-as-code skills, while another has more familiarity with building out a CI/CD pipeline. Cross-training and shadowing would help both team members learn.”

Oehrlich similarly points to shadowing other roles as a good means of encouraging learning, alongside other means such as professional training and creating a sense of safety for experimentation and failure. That particular tactic is one way in which strong leaders foster more collaborative cultures, too: By walking a mile in a colleague’s shoes, you understand and empathize with them more. This can also undo bad habits, especially if you’re pivoting from a more siloed organizational setup.

“Continuous learning will improve habits and sharpen skills,” Oehrlich says.

Weeks from Sonatype also points to continuous learning as a mainstay of strong DevOps leaders. And it applies to you, too – not just encouraging your team.

“Strong leaders aren’t just reading the tech blogs or watching the conference videos (though they do that as well) – they’re reaching out to people and asking them for 30 minutes to chat and share experiences,” Weeks says. ”The best of those conversations are more dialogue than discourse.”

3. They lead with empathy and patience

Leadership often means making tough decisions, including of the variety that won’t make everyone happy. And the pace of many modern IT organizations means a completely hands-off management approach might miss the mark.

That doesn’t mean micromanagement or command-and-control styles should come into vogue.

Sprint-based development teams might sidestep prescribed best practices during intense responsibilities.

“When building platforms to support both [continuous delivery and uptime], DevOps leaders need the patience to understand organizational change won’t happen right away,” Lachhman says. “They also need empathy for sprint-based development teams, which might sidestep prescribed best practices during their intense responsibilities two or three weeks at a time.”

4. They listen continually and don't blame

Empathy and understanding require listening: DevOps leaders listen to their teams habitually.

"The notion of 'fail fast and learn fast' can only evolve if feedback is received regularly and activated often."

“Listen to your team and your team will listen to you,” Rao from Portworx says. “Good leaders can give and receive feedback while building a DevOps culture from the ground up. The notion of ‘fail fast and learn fast’ can only evolve if feedback is received regularly and activated often. This also sets the standard for what is expected of your team when things get challenging.”

We should also note that cultures of blame or fear don’t engender productive feedback and collaboration. Strong DevOps leaders consistently look for ways to grow a blameless culture where people aren’t worried about the negative consequences of trying new things or sharing new ideas.

“You can’t expect a DevOps team to collaborate if they don’t feel comfortable sharing their opinions and ideas,” Rao says.

5. They empower people to change

Change is hard, especially in companies that have moved toward DevOps from a legacy model. But it’s even harder when leadership simply demands change instead of empowering people to make changes themselves, whether to culture, processes, or technologies.

“Once goals are set for improvements, leaders must empower the individuals who are part of the journey to change bad habits into good habits to achieve the goals,” Oerhlich says.

For example, if communication and collaboration across functions needs improvement, the teams involved shouldn’t need to ask for approval to try new practices such as regular standups or coffee chats. This also feeds back into #2 and creating real space for learning, especially from other members of the existing team.

Leaders must work to make change feel less painful.

“Great DevOps leaders focus on making change easier for people,” Weeks says. “Creating and evolving DevOps practices within large enterprises requires a lot of change, so those leading the charge really need to keep everyone in the loop by communicating as transparently as possible.”

DevOps leaders regularly work to help individuals strike a realistic balance between what needs to get done today (or this week, or this month) and the long-term goals. Oerhlich likes the “outside-in” approach, meaning you take a customer-centric focus that pursues continuous improvements to customer (or user, or patient, etc.) experience over time while recognizing budget realities and other constraints.

Rao offers a similar but separate approach: Make clear the relationship between changes (or goals) and business (or customer) outcomes.

“Autonomy with accountability means engineers need to be trusted to make decisions quickly but understand the impact of their actions,” Rao says. “Team members should have a clear understanding of the business outcomes they are trying to achieve and be able to adapt and improve processes to meet those outcomes. For example, do you want your DevOps engineers to be in the business of building tools, or building innovation that your customers can experience?”

Another way to think of this habit: DevOps leaders continuously shift away from a mindset of change as mandate – or change as something that must occur for the sake of it. Instead, they turn change into something valuable – for individuals, teams, and customers – and enable others to do the same. They shine a bright light on the big picture instead of cutting people out of the loop.

“Good leaders are developing a roadmap for their teams to follow and easily understand where they are heading in both the short- and long-term,” Weeks says. “This enables their teams to better understand why it’s worth it to wade through some of the more challenging changes each day.”

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Kevin Casey writes about technology and business for a variety of publications. He won an Azbee Award, given by the American Society of Business Publication Editors, for his story, "Are You Too Old For IT?" He's a former community choice honoree in the Small Business Influencer Awards.