Should and Will Discussions

by: Chris Barrett (VP Engineering)

We’ve all been there – sitting around a table with a bunch of bright passionate colleagues fiercely debating a plan but getting nowhere fast.  Sometimes it seems nearly impossible to reach agreement on a direction for a new endeavour – whether it’s a sales campaign, a marketing plan or a product roadmap.  There are always many variants of a possible solution, but some are derided as short sighted while others are criticized for needing years to execute.  When no one can even agree on how to start working towards a resolution, things can really start heating up!

One trick I use to break this type of logjam is what I call a “should and will” discussion.  It starts by saying, “Lets agree on what we should do, then we can talk about what we will do”.  I find that if we can first come up with what we “should” do in the long term – given all the time and resources in the world to craft the perfect solution – it is often easier for the team to agree on a strategy.

Once we have agreed on what a successful end game should look like, it is much simpler to have a constructive discussion on the trade-offs and compromises needed to deliver a realistic plan for what we will do within the time and resource constraints that face us.  In my experience, the exercise of agreeing on the first step creates positive momentum and clarifies the context within which short-term decisions aligned to the long-term vision can be made.

I’ve found this approach to be an effective way to have a system-level discussion with technical teams that have radically different experiences and perspectives on a complex subject.  But the same process works just as well for any kind of tough strategy debate – whether it’s a major account sales plan, a marketing launch campaign or a product roadmap.  Give it a try when you have a deadlocked situation… it won’t resolve every impasse but it might just enable your team to put their heads together without too much cracking of skulls!

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