Leading agile transformations for those of you who are doing it or have done it. What were some of the unexpected blind spots or challenges that arose during the transformation? How did you overcome them or adjust your approach?

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VP of IT - Digital Sales Platforms in Healthcare and Biotech, 10,001+ employees
We started our agile transformation within IT and quickly found out it doesn't help if you only train IT with agile methods. Agile is a culture and you need to include the business stakeholders. We found that in most cases, our peers in the business unit weren’t ready for the agile setup. We approached them and they agreed to adopt it, but they still wanted to have a clear scope, budget, and timeline and weren’t available every week for questions. Our solution was to create a Business/IT hybrid team and we trained them together.

This was a big learning for our organization: just doing a couple of agile trainings won't make the organization agile. It takes a lot of practice, reiterations, and finding out what is blocking before you really get on this path. And the process is ongoing.

In some areas of the organization, we started adopting agile as many as 10 years ago, in areas where the amount of interfaces to other teams was relatively low. In these areas, it was easier to adopt and they are really running well now. In other areas, we struggle more because there are just too many players involved.

My advice is to start in small areas where the scope and the area of responsibility are still clear. From that, based on those success stories, scale up to the rest of the organization. We are currently in the middle of the scale-up.
CIO in Government, 10,001+ employees
At the Virginia Dept of Social Services, we are all on on Digital Transformation.  We established a Digital Transformation Office (DTO) to work jointly with IT and the Business.  We addressed the functions of the DTO in coordination and consultation from Gartner.  These include, Agile Coaching, Human Centered Design, Organizational Change, Business Process Reengineering, Project Management, and DevOps.  We then fortified all this thru the implementation of Product Teams to align business and IT
Director in Manufacturing, 1,001 - 5,000 employees
Our company culture places immense emphasis on meeting deadlines, precise cost control, and fulfilling Wall Street expectations. This approach aligns with traditional Waterfall project management methods. However, Agile, being fundamentally different from Waterfall, presented us with numerous cultural challenges in introducing its flexibility while operating within our established Waterfall environment.

To adapt to this situation, I suggest beginning with smaller projects and gradually expanding your portfolio of success stories. You can start by incorporating Agile principles into a small percentage of projects and closely monitor the results. As you demonstrate tangible ROI and improved success rates within the Waterfall corporate culture, you can gradually increase the adoption of Agile practices

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