4 Solutions For Avoiding DevOps Training Pitfalls

April 26, 2021 | Reskill Your Workforce | 8 min read



Technology organizations are the driving force of business success. With the rapid pace of technology change, moving faster with more agility is not an option, it’s a necessity. Yet, delivering on a DevOps transformation is hard work. With DevOps there is no set standard – every team, business, and industry has a different way of doing it. It’s chaotic. Chaos can cause delays, miscommunication, and lost revenue. Businesses can’t afford chaos. Here we'll explore several solutions to employ in online DevOps training to cut through the chaos and build high-functioning teams.

  1. Train your existing teams
  2. Recruiting and training novice talent
  3. Train for DevOps Management
  4. Train employees outside of tech

“Organizations that adapt quickly and provide a delightful customer experience (CX) will have the opportunity to thrive in this new digital economy, while those that continue to rely upon long application release cycles and legacy waterfall software development life cycle (SDLC) processes will likely not be able to survive, or at least won't thrive as they might otherwise, given the right technology decisions.”
-Jim Mercer, IDC: Addressing the Challenge of Adopting and Scaling DevOps

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There are stacks of evidence extolling the virtues of DevOps and an almost equal amount of studies indicating how difficult DevOps is to harness successfully in large organizations. IDC’s “Addressing the Challenge of Adopting and Scaling DevOps”found that most Enterprise organizations are using DevOps for less than 20% of their application estate, with the rate doubling in 2021 with organizations planning to have nearly 31-40% of their application estate using DevOps.

Skillsoft recently polled a group of Tech Executives and found that nearly 20% of respondents indicated that DevOps projects are started but are not going well. Another 25% indicated that they have not even launched a DevOps project, while a third group of 15% has no plans to launch a DevOps project.

This is 60% are either just failing (not failing forward fast) or not in the game at all. But why?

  • DevOps is more than using popular and effective tools that enable better DevOps.
  • It is more than a mindset shift for your development and operations teams.
  • It is more than being good at Agile.
  • It is more than being adept at automated testing.
  • It is more than building software as a team and creating communities of practices.
  • It is more than aligning your business imperatives with your tech development.

To truly make DevOps effective in your organization, it’s about harnessing all of them together.

To get to the state where everything is working well together, you can do a few things. You can hire the best, most experienced people/talent to bring in the knowledge needed. And good luck with that approach in this hyper-competitive market with shortages of experienced developers worldwide.

You can bring in vendors to discuss how their tools solve lots of the troubles, pitfalls, and difficulties implementing DevOps. Good luck with that one, too, especially if you want an objective view of what success looks like.


DevOps is not about the tools because we all know how quickly tools change and how quickly the problem space or solution domain shifts. So what works? The best way to successfully deploy DevOps is with a reskilling and upskilling program targeted to your Dev teams first and then to the rest of the organization. This is a holistic approach.

Let's explore what this holistic approach to DevOps looks like.

SOLUTION #1: Train your existing teams

Role-based training to reskill an existing population of learners

Most organizations have large cohorts of people who have been building software for quite some time. They are not all new to building software. In some sense, it might be easier if they were DevOps Natives, where they only know DevOps as their way of building software, services, and products. But the reality is you have people who have used traditional SDLC approaches to development.

This brings in the notion of reskilling—people who need to unlearn their old approach and re-learn a new approach.

These people typically need to understand what is expected in a new role and how to transition to that role. We believe it is important to make that transition prescriptive but not rigid. We do understand that learners want to know what to learn next and what their journey will look as they move to a more native DevOps role. Part of this journey must include plenty of opportunities to practice what is being taught. These people know the value of durable skills being developed by experience and hard-knocks in some cases. But a practice environment that quarantines the hard-knocks so that your tech infrastructure (networks, security, applications, etc.) is not compromised while someone is learning to do new deployments or new automated testing or just merely practicing with a new tool. Having prescriptive content that is built around the roles that your learners will need to master is an essential ingredient for this segment of your population. It helps reskill a group pretty much every organization has today.

SOLUTION #2: Recruiting and training novice talent

Role-based training to upskill a cohort that has very little experience with software development.

Another way to get DevOps talent is to upskill a group of potential candidates. We see this around the globe. Many companies are hiring generalized talent from colleges and academic institutions and upskilling them to their way of building products, services, and software.

This is as close as you will get to producing your own DevOps-native team members.

They likely have very little to unlearn but plenty to learn. They will undoubtedly need to have a broad and deep curriculum that offers plenty of feedback and practice. This cohort likely needs the prescriptive part of a role-based curriculum the most. They have minimal expectations of what to learn next, so guidance and feedback (criterion-based assessments) are needed. And like the prior experienced group, this group also needs plenty of practice to build, test and deploy what will become their durable skills.

DevOps Online Training Custom Onboarding Journey
Create tailored learning paths blending Skillsoft, custom, free, and paid-provider content to meet your strategic needs. Target specific audiences to ensure the right assets are discovered by the right teams.

SOLUTION #3: Train for DevOps Management

Role-based training that combines both an understanding of the tech skills needed for DevOps and the human components of people, communications, collaboration, and teams.

Another way to get more DevOps talent is to ensure that you keep the talent you have by having leaders that inspire their teams to build great products. We've heard from many organizations that some leaders truly do not understand what DevOps is or how to help it flourish in a development team.

This may be the most important group.

This approach, which is developed in your organization, is to nurture and build teams that work together effectively. This helps avoid team dysfunction and prevents seeing members leave the company (institutional knowledge drain) because their leader does not understand what they are collectively trying to accomplish.

This group of aspiring leaders needs some basic training in all of the components of DevOps.

They will need a broad understanding of the adjacency areas that make DevOps work well, from Agile methods to gaining executive buy-in and business alignment to creating communities of practice and a culture of learning and failing forward fast. On the technical end, they will also need to understand how to build process and test automation into your development, address the drain of legacy applications, measure progress with metrics, and finally, how to best leverage 3rd Platform technologies/platforms.

Then for good measure, we need to throw in the adjacency skills they will likely need to understand the changing nature of their world. An understanding of Security, Cloud, Programming, and Infrastructure/Operations advancements. Whew, that is a lot for anyone to digest.

Then throw in all the other "business requirements," and leaders can become overwhelmed. Having learning assets that help them with both the tech side of learning and the people component is crucial for success. Having them combined is even better.

Top Non-Tech Skills Courses Used by Tech Professionals (In descending order of consumption/usage)

  1. Contributing as a Virtual Team Member
  2. Developing a Growth Mind-set
  3. Coaching Techniques That Inspire Coachees to Action
  4. Developing and Supporting an Agile Mind-set
  5. Developing Your Business Acumen
  6. Enabling Business Process Improvement
  7. Managing Pressure and Stress to Optimize Your Performance
  8. Trust Building through Effective Communication
  9. Managing for Operational Excellence
  10. Being an Effective Team Member

Coming Soon! Aspire Journey - DevOps for Leaders and Decision Makers

SOLUTION #4. Train employees outside of tech

Role-based training for people to pre-skill into a needed role.

Yet another way to find new talent for your DevOps efforts is to look internally again. This time not in a formal upskilling or reskilling effort, but rather pre-skilling.

Look for people in other disciplines in your organization that may have qualities you want to develop and keep. There are several cases of this working well. Imagine a Design director (not technical) who is really adept at managing projects and getting all assets to come together by a certain date. If that person is great at what they do, they could make a good Scrum-master with some appropriate training and nurturing.

Especially if this person has the Institutional knowledge of what your company does, it is likely less of a leap to find success. The pre-skilling part lets them try to a role without expectations or an "all or nothing" mentality. If they like it, let them decide to pursue it if they don't, let them continue in their current role.


“It is not possible to build a well-designed and strong application without embracing DevOps principles across the entire application. Developers need to be mindful of best practices. DevOps ensures faster release cycles using continuous integration of tests and continuous delivery of releases.”

In all of the above solutions, I envision that adjacency skills attainment becomes one of the most important indicators of success in the future.

The prototype professional is someone who has solid core tech skills, conversant in adjacency domains and skills and has a well-honed digital dexterity mindset. Those people will be in high demand around the globe, and unfortunately, there is a shortage. So most organizations are realizing they need to upskill, reskill and pre-skill the people they have.

Mike Hendrickson, VP of T&D Products


Mike Hendrickson is Vice President of Technology and Developer products at Skillsoft. Prior to Skillsoft, Mike spent 15 years at O’Reilly Media, Inc., where he most recently was the VP of content strategy. Mike is a technology strategist with extensive experience establishing, building, and maximizing relationships with industry leaders, companies, and partners.