In my last blog, I spoke about how your existing team’s skills and knowledge are assets in your cloud transformation. Upskilling and reskilling are both a smaller investment and provide a quicker return on investment than hiring and training new employees. Today I will highlight a path to help your team both develop the necessary skills for cloud as well as maintain and grow that knowledge over time.

What is the CALMS Model?

This growth mindset is a continuous learning culture. Continuous learning is self-explanatory -the process of learning new skills and gaining knowledge on an ongoing basis. Skills and knowledge can be acquired in many ways from learning on the job or online education, to formal courses and certifications.

A continuous learning culture requires individuals to be self-starters, to voluntarily share information, to feel safe sharing their failures, and to constantly adjust based on new information. These values also need to be enabled by the organization in a variety of ways, including making space for experimentation, learning, and sharing.

Develop a culture of continuous learning that is initiated and led by technical professionals, and that is encouraged and sponsored by organizations. (Gartner – The Cloud Engineer: Skills Guidance for Modern Technical Professionals, by Elias Khnaser – October 2019)

6 Ways to Foster Continuous Learning for Cloud

Building a strong but flexible structure for upskilling and reskilling for cloud can be the catalyst to launch your team into the transformation effort. Here are 6 key tips that have proven successful for enterprise cloud teams in creating the support for continuous learning:

1. Perform a Skills Gap Analysis

A first step in your cloud upskilling and continuous learning journey is determining what skills are necessary now and in the future, and what skills your team already has. This baseline isn’t meant to police the team, but to help provide clarity to all as to where you are today and where your team needs to go. Some of the skills to evaluate are:

  • Technical Skills like scripting/coding, automation and orchestration, cloud networking, security & governance, database, application architecture, cloud account management, and specific cloud platform and tooling expertise.
  • Interpersonal Skills such as collaboration, communication, the ability to work globally and cross-functionally, and how to receive and provide mentorship.
  • Business Skills – technical teams should be able to translate business goals into development terms and know how to be a customer champion at any level of the organization. Cloud financial analysis skills are also important for your team to reap the scalability benefits of cloud.

2. Publish a Cloud Skills Roadmap

One way to enable self-starters in your organization is to be clear and transparent about your company goals and how they can support those goals. By aligning your tech skills gap analysis with your cloud and product strategy, and then publishing this as a roadmap for your team, they will be able to take clear actions to help fill the gaps. In addition, by keeping the roadmap up to date and rewarding those who help ‘fill the gaps,’ you will encourage both transparency and learning throughout your organization.

3. Build Individual Education and Development Plans

A learning management system (LMS) or similar tool can help both management and employees track progress at an individual level. This not only adds a bit of accountability but helps ensure no one gets left behind in the transformation. Be sure to not only include the formal or online training available in these plans. Give your employees the flexibility to learn in other ways such as writing internal documentation, attending industry events, writing papers or books, joining online communities, public presentations and webinars, or starting a growth project. Make sure there is a way for peers to regularly share feedback on what worked and what didn’t work in their individual education plans.

4. Support and Fund Certifications

Certifications are an essential way to educate your team while helping support their careers. Additionally, many cloud certifications come with hands-on labs and experience requirements, proving that they can perform the tasks necessary to support your business. One way to encourage certifications is to allow reimbursement for the test and/or provide a bonus to those who achieve certification. Promoting their accomplishment can also encourage others to follow suit.

5. Build an Apprenticeship Program

It’s not always easy for individuals to become self-starters. To encourage cross-training and reskilling, teams can build a mentoring program that partners experts with those who are just learning a new subject or skill area. This empowers early adopters to learn to mentor and share their knowledge while giving those who are newly acquiring the skills somebody to learn from and work with directly.

6. Support Internal Communities

After a few teams have successfully upskilled or reskilled and moved their applications to the cloud, it’s time to build some momentum. Encourage teams to build a resource center where they can share best practices, lessons learned, education plans, etc. This can be an informal or formal Cloud Center of Enablement (CCOE) that helps propel your team into the growth mindset.

Supporting your team to develop the skills for cloud by building a framework for success can help launch and sustain your cloud transformation long term. This also helps you retain talent while building an innovative culture that will be ready for the next big thing.

2nd Watch has supported thousands of enterprise cloud migrations with a cloud migration and modernization acceleration program designed to get you up and running in the cloud fast while maintaining business continuity. Our comprehensive methodology focuses on understanding your current state and goals and moving you to the cloud in a productive way. To learn more, visit

-Stefana Muller, Sr Product Manager, DevOps & Migration