How to Build Lasting Success in your Agile Transformation

by Michael Sahota

The most important thing I have learned about starting an Agile transformation is to ask the question "Why Agile?" The result is that we begin focusing on what really matters. To look beyond teams and process. To look at the organizational context. When we start from this broader perspective, we gain the chance of building lasting success.

This article is for anyone who is involved in an Agile initiative. You may be starting one. You may be in the middle of one. You may have Agile well established at your organization but are now faltering or stuck.

In this article I will give you the step-by-step instructions on how to set up and run a one-hour workshop to turn your "Agile" initiative into something valuable and sustainable that will open the door for real change (transformation).

Why Ask Why?

Agile, and Scrum in particular, is wonderful for helping us develop and grow effective teams. Lasting organizational success with Agile requires that we look holistically at the organization, not just products and teams. The most common challenge I have witnessed is that Agile is seen as a technology initiative or just something that happens at the team level. When we clarify our goals, the focus usually shifts from just Agile training and coaching to include strategic and cultural aspects of organizational growth.

Set up Meeting: Stakeholders and Objective

Who should be included in this meeting? This will, of course, completely depend on your context. My general approach is to include the most senior leaders involved in the change initiative. It could be CEO and reports. It could be VP of Technology and down. It could be a manager or even a team. My general goal is to go as high as we can and still have coherence and alignment. See How to Build a Culture Bubble for why the choice of participants is crucial.

People will want to know why they are coming to the meeting. The meeting objective could be "To increase alignment on why we are doing Agile." Depending on the level of awareness, this meeting may be sold as checking alignment or creating alignment. Pick something that resonates with your stakeholders.

Step 1: Ask Why Agile?

Ask them to brainstorm a questions like "Why are we doing this Agile Initiative?"

There is no magic question. Participants should pick questions that fits their context. Here are some other example questions:

  • Why do we want Agile?
  • Why do we want to improve how we work?

Give everyone sticky notes and sharpies and ask people to brainstorm questions on their own for three to five minutes. I find it useful to explain or remind people How to Go Fast with Sticky Notes.

Sometimes there is a fear of asking executives to use sticky notes. If they will not use sticky notes, then there is little support for collaboration (and Agile) in your organization. So shift your focus to a culture bubble lower down in the organization.

Step 2: Explain What, Why, How

While participants are writing sticky notes, set up three flipchart pages with labels What, Why and How. (See diagram below.)

The trick: It is really important to ask why when brainstorming. Only during playback should you separate the reasons into what, why, how.

Once everyone has finished writing, explain that the results of the brainstorm will need to go on one of three different pages. Explain what those pages mean.

Here is my explanation:

  • What (outcome) – This is about the result: what we want to achieve. The outcome we are looking for as an organization.
  • Why (rationale) – The motivation for this undertaking. You may also see leading indicators of success here.
  • How (process/practices) – This is about the mechanism or means that support getting to the outcome. How we actually do things.

Step 3: Collect Data Around What, Why, How

Ask them to put each sticky note on the most relevant page and cluster based on matching concepts. Instruct them that you are all working as a group to reach a shared sense of everyone’s reality.


  • It doesn’t really matter where things go as long as it generally makes sense to participants.
  • Challenge the group to get items in places that make sense. Most leadership groups I have worked with are not in the habit of challenging one another.
  • Each person ultimately has control and choice over where their item goes.

Once all the items are up, conduct a shared sense-making of the result. Ask the group what patterns there are. This may trigger a round of re-organizing. Sometimes I invite the group to come up to the board and reorganize to make the patterns clearer.

Circle each cluster and, optionally, label each circle.

Step 4: Pick Most Important Elements

Use dot voting to have the participants select the most important elements for this initiative.

Important: Have them vote in reverse seniority order to avoid hierarchical bias. See Highest Paid Person in the Room (HIPPO) bias problem for why this is very important.

Summarize the results to check for understanding: "So it seems like the outcome for this initiative is X and we see Y and Z helping us get there?" Check for nods. It may take a couple of goes to get this right.

Step 5: "Agile" Is Not the Goal

Let the group notice that Agile is gone! The outcome that they seek has nothing to do with Agile! Agile is not the goal.

Help them notice how Agile may help with the what, why and how (if that is true). Help them also notice that there is a much broader initiative beyond Agile to support the goals.

I have been doing this for a while and here are the most common items that I see coming out of this workshop as the important goals.

  1. Quality Product
  2. Productivity/Effectiveness (Faster Time to Market)
  3. Happy, Engaged Staff
  4. Financial Security/Stability
  5. Collaboration/Teamwork

Step 6: Replace the "Agile" Initiative with Something Else Suggest officially dropping Agile as a goal, and instead, re-brand the initiative to focus on whatever their desired outcome was. This will help people focus on the outcome, and not on "doing Agile." In a recent transformation, this turned out to be a key element in our success. Do not underestimate the value of a name and the stories we tell about ourselves.

Being Agile and Transformation

It is scary to Let Go of Agile as an official goal. It turns out that this is necessary to Stop Agile from Being Used as a Whip or a Shield. My experience is that the only way we can really get to an Agile mindset is to let it arrive of it’s own free will. Coercing a system as an evangelist prevents the results we hope for. I have done this many times and have seen the error of my ways.

The Critical First Step

This workshop is a critical first step for starting or re-booting your Agile initiative. My first meeting on site with a new client starts with this one-hour workshop. I hope you can use it to foster success in your organization and start a beautiful journey of organizational growth.


I would like to acknowledge Simon Sinek’s wonderful book, Start with WHY. One caveat: in this workshop, the goal is alignment on any of why, what or how. Alignment will get us started on our journey, and we need not clarify our why at this step.

Also, don't miss the 23 November Agile Leadership webinar, Top 10 Secrets of Agile Transformation. Register today.

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