How to Upskill Your Cloud, SRE, and DevOps Experts to Empower Your Organization

How to Upskill Your Cloud, SRE, & DevOps Experts to Empower Your Organization

Today, every company is leveraging technology to innovate, streamline operations, and create value for their customers. When it comes to software engineering, developers have a natural and prominent role in creating new capabilities, but that doesn’t happen without a greater support infrastructure. Cloud, SRE (site reliability engineering), and DevOps engineers are central to value delivery and business continuity. It is essential for engineering managers to understand how they can coach and upskill these experts to both enable their career growth and increase business value.

Distinctions Between Expert Roles 

Modern software development teams work in a DevOps way, by bringing people with different competencies together and enabling a faster, higher-quality value delivery and development lifecycle. 

Writing the application business logic is only part of the engineering equation needed to deliver customer value. The other part, operations, includes many tasks that are mostly driven by Cloud, SRE, and DevOps experts. Good examples of those tasks are designing scalable and reliable systems, ensuring that code can be tested and deployed using continuous integration and delivery pipelines, monitoring system health, and implementing security and compliance guidelines.

Personally, I dislike the title “DevOps Engineer,” because DevOps is applicable to the entire engineering team and is a more abstract concept. SRE, on the other hand, is a concrete implementation of the DevOps philosophyexperts in an SRE role bridge the gap between developers and operations. A DevOps engineer (what I prefer to call the “automation/cloud specialist) differs from an SRE, as they only focus on systems operations.

There are some natural derivations in lateral roles that come from further specialization in certain technology areas such as DevSecOps engineer, chaos engineer, or cloud and solution architects at more senior levels. 

SRE and cloud specialists are crucial to the success of the product or service. Yet, they are too often disconnected from the business reality; this is where coaching and mentoring makes all the difference. 

Mentoring Is Vital to Career Growth

Engineering managers have the lead role in mentoring and coaching these experts: guiding, providing feedback, showing different career possibilities, and building bridges within the rest of the organization. Engineering managers can act as human routers to make the connection between experts and business stakeholders, ensuring experts get first-hand knowledge and visibility on the value and end-user experience of the product(s) and service(s) that they work on. 

Similarly, managers can then demonstrate to stakeholders the positive business impact of these experts’ actions. Does the solution have a great reliability track record and always meet the agreed SLAs? Tell them about it! What would it take to enable solution architecture to scale ten-fold and be available in other geographical locations to support new business cases? Great conversation starter! 

How to Make It Happen

Unfortunately, business stakeholders usually only connect with these experts when something goes wrong (e.g., a system failure), and need to understand what happened and why. Engineering managers can change this pattern and create a new paradigm.

Here are a few things managers can do to establish this paradigm and foster its culture:

      • Translate business and industry-specific jargon into technical concepts, examples, and terminology that experts can relate to. 
      • Help experts develop the necessary non-technical skills to communicate effectively, and translate complex engineering scenarios into simple, relatable terms and ideas with business impact.
      • Facilitate sessions where experts can present and showcase potential opportunities that new cloud and data technologies can unlock in the organization, generating new business models or streamlining existing operations and processes.
      • Create and explore opportunities for experts to shadow and connect directly with colleagues in different roles across the organization, such as working alongside a customer support representative or joining a sales meeting.

This enables constructive cooperation across competencies, breaking silos while helping these experts grow and gain a better understanding of their impact in the organization.

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Upskilling, Community, and Thought Leadership

There is no substitute for hands-on learning, and engineering managers have a unique role in creating those opportunities. It’s important to maintain a continuous dialog to understand the expert’s career goals and interests, while simultaneously facilitating situations that enable them to gain new hands-on experience.

Simple and small steps, such as inviting them to a steering meeting, participating in a technical brainstorming workshop, or joining a new, exciting project (even if in a minor role) can make a huge difference and impact. Venturing out of one’s comfort zone is always an opportunity to grow and learn.

Further, hands-on experience should always be accompanied by other learning and input, such as insights from other experts, industry certifications, or non-technical skills development.

Certifications and Digital Content

Consuming digital content—articles, videos, whitepapers—and pursuing industry certifications—such as those offered by AWS, Microsoft, Google, and the Cloud Native Computing Foundation—are both excellent practices for validating existing knowledge and discovering new services, expert insights, and best practices.

Each of these organizations offer certifications that go from the fundamentals to complex solution architecture scenarios, focusing on areas such as security, networking, and data engineering. When combined with hands-on experience outside of typical work tasks, content-learning and certifications provide natural upskilling and specialization pathways that stay with the expert even when changing jobs or companies. 

There are also plenty of advantages to an organization that has certified experts. It nudges the organization toward good practices and ways of working, while enabling the company to level up their cloud partnership status and showcase their expertise to customers.

Technology Communities

In organizations, from SMBs to larger corporations, there is a natural tendency for individuals to become siloed in their team and/or business unit. Cloud, SRE, and DevOps are domains transversal to all development teams and organizational structures. Fostering an internal technology community where these experts can regularly meet increases alignment and promotes a healthy exchange of ideas. Moreover, it enables these experts to drive the technology governance and foster a culture of engineering excellence across the organization.

Similarly, external communities and events are also a great way to gain new insights and fresh perspectives. DevOpsDays, ServerlessDays, as well as AWS and Azure Community Days and Meetups, to name a few, are fantastic options to learn and meet like-minded people. With practically all events now fully virtual and often free to attend, this is something that should be highly encouraged and promoted in your organization.

Sharing Experiences and Thought Leadership

Engineers, especially less experienced ones, might be intimidated at the prospect of sharing their insight and experiences in technical articles or public speaking engagements. Regardless of the level of the content, whether beginner’s guides or more advanced deep dives, there is considerable value in creating content and sharing knowledge. Entry-level content from a Cloud, SRE, or DevOps expert can offer tremendous value to a developer or business stakeholder not familiar with the topic, and it can help bridge gaps between different competencies.

From a career growth perspective, an expert that invests time and effort in thought leadership activities—including written content and speaking engagements—is more likely to accelerate their professional growth and seniority. This is not first because of the positive visibility that those activities bring to themselves and their organization (that helps!), but rather, it enables the expert to radically improve and develop valuable communication skills. Simply, with practice comes change; the more we work to translate and express complex thoughts and ideas into written and verbal content, the less subject we are to our own silos. 


Coaching and upskilling Cloud, SRE, and DevOps experts reveals new possibilities for impacting how an organization operates and delivers. With these experts, it’s critical that direct managers and senior leadership start seeing and treating them as value creators, not cost centers.

When mentoring these experts, help them understand their potential career paths and growth, and highlight the value they create and the impact they make in the organization. Most importantly, be transparent, provide constructive feedback, and foster a psychologically safe environment that encourages them to venture beyond their comfort zone and try new things.

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