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Agile Transformations: Where to start

  • erinlmedlin
  • Feb 29, 2024
  • 4 min read

Orchestrating an Agile transformation can feel overwhelming.  If the company has been working in a waterfall world for a long time there are many ingrained practices that will need to shift with the engineering team and with the stakeholder base.  Here are 8 steps to start you off on the right foot.


  1. Find your champions.

    1. Look for people who are going to champion this idea.  Ideal candidates are those that have worked in an agile environment before and loved (or even liked) it.  These should be a combination of stakeholders and people within the engineering & product management organization and should represent a variety of roles and seniority.

  2. Align with leadership on what a successful Agile transition looks like.

    1. Have a base structure for what your Agile organization looks like - will you be implementing a scaled Agile framework or letting each team organize on their own?  What are the areas where teams will be able to choose their implementation and what will be standardized across the organization?  

    2. Let teams self-organize and watch what works well and where there are challenges and triage from there.  Each team will evolve their practice in a slightly different way - ensure Scrum Masters and leaders have time together to discuss best practices, what’s working well and what isn’t and learn from each other.

    3. Set clear expectations with leadership around the time and resources needed for the transformation.  Depending on the size of the organization - it may take a few months or a few quarters before they’ll begin to see the results of the shift.

  3. Pick one or two teams to begin the transformation first.

    1. I recommend picking teams that are loaded with at least two team members and one stakeholder that are agile advocates.  Pick advocates that are seasoned agile practitioners, are vocal about their team’s work, and are well respected in the organization.  Having a combination of team members and stakeholders that are committed to the transition’s success means they will be dedicated to conquering roadblocks and make it easier for the next round of teams to complete the transition.

    2. Make sure these teams are excited to be the first teams to transition.  Discuss the roll out strategy with the entire team and ensure they have adequate support within engineering and with their stakeholders to be successful.  Plan to regularly check in with the team and evolve the support they’re receiving as the transition occurs.

  4. Provide consistent training for the entire engineering and product management organization.

    1. This could be something as structured as an official 2 day Scrum Master training course or something more simple like my one day Beginner Agile training.  The goal is to get everyone on the same page about what Agile is and how it will look at your organization.  Ensure that the training covers both the tactical elements of Scrum and Kanban (roles, responsibilities, rituals) and also the why behind it.  Make sure everyone is able to speak the same language and understands the goal of working in an agile environment.

    2. It’s important that everyone in the organization take the same training, regardless of each person’s agile experience. 

    3. It’s also important that the training be customized to the organization.  People should exit the training with a clear understanding of what their role and responsibilities will be and how their team will interact with each other and stakeholders.

    4. Provide time, either in the training or directly after the training, for the team to talk through how they will evolve their practice based on what they learned in the training.

  5. Provide a roll out plan to the engineering and product organization.

    1. Include key information such as:

      1. Dates the transition begins

      2. What team (s) are going first

      3. How teams will be identified to begin their transition

      4. Any changes to roles and organization structure that included in the transition

      5. When training(s) will be provided

      6. What support is available for teams as they go through the transition

      7. What success looks like at the end of the transition

    2. Know that most people find change a little scary (especially if they’ve been working in the same role at the organization for a long time).  They will be thinking “what does this mean for me?”

    3. Set up several checkpoints to elicit feedback and respond to the feedback.  It’s not enough to just collect the feedback - make sure that there is also a time to answer questions or make adjustments to the rollout.

  6. Provide an Agile coach to help guide teams through the process

    1. Some teams may have a few seasoned agilists and be ready to start right away while others may have a hard time getting started.  A seasoned Agile coach can help teams find their footing faster.

  7. Start slowly and help those that are reluctant see the benefits.

    1. Teams that have had bad experiences with Agile before should start slowly.  Find the areas where they’re having the hardest time delivering (do they not have user stories ready before sprint planning, are they having a hard time getting work to done, is there confusion on what it means to have work be done?) and use agile principles to help triage the issue.

  8. Celebrate success!

    1. Ensure there’s a forum for best practices to be shared across the organization.  Loudly promote teams that are seeing success.  These might be very small wins at first but it’s important to have a regular cadence of sharing them.  It will also help other teams realize they’re seeing the same or similar wins and build their confidence in their new agile practice.

 
 
 

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