Probing Questions For Executives Approving A Rewrite

A while back, I wrote a guide for developers preparing for a system rewrite.  This time I’m talking to the other side of the table; executives being asked to approve a system rewrite.

Here are three probing questions to help you and your developers dig into the realities of a rewrite and gain confidence in the project:

  1. What are the client’s pains, and how does the rewrite solve them?
  2. How will you support current users during the rewrite?
  3. What lessons have you learned from the original system, and how will you prevent repeating the same mistakes?

What are the client’s pains, and how does the rewrite solve them?

There is no business value in a the next generation of your software.  Have your developers put in the work to understand how the current system causes client pain?  

Do they know the frustrating pain of needing features that can’t be delivered? The maddening pain of redoing work destroyed by a bug? The teeth grinding pain of slow systems that steal minutes with deadlines hours away?

Which pains are they addressing, and how much of the system do they need to rewrite to give clients some relief?

Pain provides focus and a metric for success. Without a specific pain goal, the project will metastasize and grow into “replace everything”. 

How will you support current users during the rewrite?

Feature freeze is the most common answer, but it should not be acceptable.  Neither is only patching critical bugs.

One solution that has worked well for me: The Senior proposing the rewrite gets to architect and oversee the new solution, but all the coding will be done by the juniors.  The senior will be responsible for fixing bugs and implementing new features on the legacy system.  

With that much skin in the game, and no juniors doing junior things, you’ll be amazed at how quickly the legacy system stabilizes. I have seen this be so successful that the rewrite gets canceled, and the work written off as a moral boosting learning experience.

What lessons have you learned from the original system, and how will you prevent repeating the same mistakes?

This is really a question of ownership.  Are your developers ready to acknowledge and own their mistakes?

Are their expectations for the future realistic, or do they expect the shiny new technology to prevent them from making the same mistakes?

Going from monoliths to micro services, micro services to serverless, or serverless back to a monolith won’t help if your developers are repeatedly implementing a fundamentally flawed design.

Rewrites can destroy your company

Companies have been destroyed by endlessly stalled rewrites.

Work with your developers to answer these questions.  It’s likely that you’ll find a much less risky path than the full rewrite.  If you do agree to the rewrite, asking questions will give you confidence that your developers have a realistic plan that they can deliver.

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