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Paul McAvinchey
Co-founder of Product Collective
Asked a question last year

What are some tips for leading an organization/team through a transformation from waterfall to agile?

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Danie Karaplis
Product Leader | Treasurer, getWITit Cleveland Chapter
  1. The first thing to do before starting the transformation is to have the team read Scrum69 by Jeff & JJ Sutherland.  
  2. Print out the 12 Principles of Agile116 (preferably large posters) and display them where the team will be sitting (co-locate the team as much as possible). 
  3. Get an agile coach on contract to help with the transition. If you can't do that, see if someone within the org can take on the role. (It might be you.)
  4. Practice makes better. Every sprint, dedicate extra time than normal to a retrospective. Create actionable items to improve the process from sprint to sprint. You likely won't find the right formula for your specific team until 5-6 sprints in. 
  5. Focus on the customer and delivering iterative value. This sounds like a given, but coming from a world of waterfall where you're focused more on solutions and accounting for all edge cases it's easy to fall back into solution mode and forget. Focus on vertical, valuable slices of work. (Mona Lisa75 analogy.) 
  6. the most important thing is to offer yourselves some grace. You won't get it right the first or second (and probably not the third) time. Keep practicing, keep learning and reading about agile/scrum, and collaborate often.
Ant Murphy
Product Coach and Consultant | Occasional Cat Herder 🐈

First and foremost is to understand the why - the motivation behind why the organization wants to transition.

Over 80% of transformations fail and in my experience, it's predominately because of undertaking them for the wrong reasons - cost-cutting, making teams do more work with fewer people, "because google does it", etc are all the wrong reasons.

Any kind of change (both personal and org change) is taxing, hugely disruptive, and takes time. The only way to get through the tough times and prevail is to have a compelling 'why' that you (and in the case of org change, the majority of your people) truly believe in.

You can read more in my blog post, 'Is Your Transformation Failing, Too?'75, but after being a part of half a dozen of transformations myself and looking at other case studies I find the most successful all have the same winning formula:

The right motivation + enough people in the org who believe in it = success.

How do you put this into practice?

Well as I said at the start, the first step is understanding what the motivation is for undertaking the transformation. There needs to be a real need. A real problem to solve - half a dozen 'successful' transformations have all started at a critical point for the business, like failure/real decline. 

One that I personally led (this was a product-led transformation, not agile) was for a media company that was seeing a real decline in their viewership as the rise of streaming media like Netflix was disrupting them - there was a real problem and a sense of urgency. Something that rallied people and made us act now, not later.

This brings me to the second part of the equation, "enough people who believe in it"

Starting a movement starts with the why, but it really hinders on execution.

A great example of this is a case study I share in my blog about a transformation consultancy called K2K Emocionando165 who require their clients to have over 80% of their employees117 vote yes to the change otherwise they won't proceed with it. 

This is all about ensuring that you have the critical mass, or least the confidence in building that mass which is necessary to sustain the movement.

Rallying people behind the why is one thing but you need enough internal champions who will carry the baton and motivate others to really pull any kind of org-level change off. Without it the movement will simply die-off as it struggles to get the critical mass it needs to push past the threshold.

How this can look in practice: 

  1. Leaders go first. The first step is a crucial one and that's for leadership to 'lead by example' and model the new behaviors they wish others to follow. Moving to a more agile way of working is not about practices or process it's about mindset so the change must begin with leaders displaying this new mindset and behaviors. This is the only way to shift culture.
  2. Start small. One way leaders can lead by example is to help create the space for at least one or two teams to start operating in this new way. The key here for these teams are for them to be in a good position to be exemplary examples. Get the leaders to help rope them off from the rest of the organization and provide them with the ability to create their own culture and operate in this new way.
  3. Start to make noise around it. Like I said you want them to be exemplars. You want people to be jealous of them and WANT it themselves. This is again where leaders can help, they can help be the team's cheerleaders and must be the evagalists for this new way or working. This will help inspire others and get that movement going.
  4. Expand the bubble. Once others start to ask for working in this new way too, allow the new culture-agile-bubble to expand to include these new people as well. Then make some more noise. Now you have multiple teams all operating in this new way and being advocates for this new way or working. Now the movement is rolling.
  5. Continue to iterate and expand the bubble until it consumes the whole organization. There will come a tipping point as you approach that critical mass and you'll almost lose control of its expansion. People will start to pick things up themselves and operate in this new way as if it's no longer even a question or choice.