Making Sense of the Messy Middle

In many product organizations, there is a gap.  Below that gap, the work is well understood and known.  It’s been committed to delivery.  Without clarity here, things would devolve into chaos.  Agile delivery teams work well here and Agile practices guide the day-to-day ceremonies and activities. Above the gap, there’s strong pressure to identify the organizational goals, make promises, and meet commitments.  But, in between, in the messy middle things can get off track and go a little sideways.

Why is this a problem and how do we cross the gap?  How do go from high-level business goals to an actionable delivery strategy that works?  How do we connect business outcomes to team outputs?

Stuff at the team level will, by nature, be more prescriptive.  Do this.  Build that.  Deliver this.  Things at the business level will be too high level – presentations and spreadsheets – lacking necessary details for execution.  Somehow, we have to connect these disparate worlds.

The messy middle is the arena of product managers and owners.  This is where we uncover what might work, reduce risk, and invest in visible learning.  We remove the monster hiding in the riskiest assumptions.  We connect the intangible business outcomes to tangible product outputs. We ensure work given to the delivery team can be executed well.  

In this session, Chris shared his experiences navigating the messy middle. He explained how some simple practices could make huge differences and bring clarity to delivery teams. He highlighted common pitfalls and the role organizational culture played in this space. By the end, participants left with actionable strategies to try in their own organizations, along with a deeper understanding of product discovery, prioritization, and dual-track Agile.