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Tech Debt how to point during times of tech debt work where you are investigating and developing at the same time?

Question asked by 992709ab3a0461f29c0a350b9b6f3f87 on Oct 15, 2015
So my team is working on a current backlog that we have picked up from another team.  Right or wrong the work needs to be done.  We have tried doing out traditional team pointing, we use tshirt sizing then move to points.  However we are finding this does not work very well for this work we are doing now.  The spec is bascially moving the backend code from the original work to a more defined approach using states.  The goal is to make the code more useable and workable by others. 

The problem is that doing this work is challenging to the point that our normal points don't seem to work and so the team is frustrated with the inconsistencies that we seem to be showing.  But the team also understands the work is like peeling an onion, things that look easy or would be easier if we new code history etc - but we don't so we find all kinds of issue in the code that require us to "code while doing and making architectual decisions that effect other" thus slowing work down or sometimes stopping work completely to get answers or the make decisions.

How should we handle this?  How have other handled this?  (Yes I know, never incur tech debt, always do the right thing - but reality is where I'm at so I'm looking for any real world ideas to keep the team engaged, moving forward and to keep mgmt. from being so concerned that the points are dropping from a normally consistent team.

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