Shifting Underwriters to the Agile Mindset


Hello, I am engaging with a team of underwriters for a large-scale effort; the underwriters are the business partners, so they will be Product Owners, Product Managers, Business Owners, etc.

Underwriters are UBER risk adverse, like excruciatingly low levels of detail and are highly numbers driven (yes, broad categorization, but the underlying meaning is clear - they are or can be very change-resistant and detrimental to the iterative and incremental nature of Agile).

Does anyone have any good pointers, tips, techniques for helping to shift a group of underwriters to the Agile mindset? Helping them to make the mental shift to being more iterative, more engaged and collaborative members of the team and program team?

Thanks in advance for anything you can share!


FWIW, my process would be something like…

  1. Try to understand why they’re resistant to the change. How are the changes challenging their world view. Is there a way to show them that the changes still respect their world view and can meet their needs in a better way?

  2. Explore and then explain why you care about this change. Why is this important for you? Why is this important for the teams, the organization, how will this benefit the underwriters and why should they care anyway? Is there a competitive advantage that this will give us? Is this going to be less waste with better quality? Will we be more focused on the customers’ goals?

  3. It sounds like they prefer BDUF because they feel like it addresses uncertainty and minimizes risk. Show them that just enough planning will provide the insights they need for work further out. How much information is necessary to make the decision you need to make today? What decisions can be deferred until we have more information? Deferring decisions can help avoid or mitigate risk more effectively because we’ll have additional information at that time.

  4. Demonstrate that through empiricism, frequently inspecting and adapting, and using real-time information we can make more sound decisions without incurring a lot of extra wasted work. Waste is also adds risk since it takes our attention away from the matters that do need our immediate attention.

  5. If possible, put numbers to this. Cost of waste, benefit of doing something now vs waiting, level of detail needed to make a for now decision that can be adjusted when we have more details.

  6. If they’re worried about not having a BRD or something like that, engage them in a story mapping activity. They can see then that this replaces a BRD and we’ll progressively elaborate on the details as we get closer to working on them. Make the backlog visible and encourage them to work just a bit ahead of the teams to head off any risks that might be coming.

  7. I’d play a game with them. Maybe the ball point game or some game that shows that a lot of detailed planning doesn’t help very much, but a little planning and a lot of inspecting/adapting are critical to making decisions. Try to demonstrate that starting with a just enough plan and refining can yield better results.

  8. Don’t take the rejection personally. Be patient and empathetic, this is scary for them. Ask them what they are willing to try and celebrate when they try a small step (A reminder for me as much as anything :slight_smile:)

Hope this is helpful.

Would you be willing to share what you’ve tried, what’s worked, what doesn’t work? We all run into these scenarios and I think it helps to hear about other experiences.


+1 to the ballpoint game

  • Meet them where they are.
  • Help them articulate a near-neighbor “future vision
  • Find behaviors that will help them bridge between the current and future states, without too much of a leap (keep things safe enough for now)
  • Help the brave move out of their comfort zone by testing out those new behaviors
  • Learn from the small safe-to-fail experiments
  • Rinse and repeat.