Messy Middle
This past week has been one of those weeks where work takes you across a journey of multiple roles to play with the different teams I work with, both in the immediate and extended organizations I belong to.
In the extended organization, I’m working towards helping with initiatives that tackle all or most of the teams. In some cases, this might involve reviewing APIs or gathering and writing down the architecture principles or strategies currently at play.
Helping the teams that belong to my immediate organization looks different across projects or timeframes. Right now, my time seems to have been focused on making sense of the “messy middle”. This is an interesting problem in itself. People tend to agree on long-term visions and kind of what we’re working on in the present.
what is the messy middle?
The problem with the “messy middle” piece of projects is that it feels like the “How to Draw an Owl” meme. The organization knows the end goal, and the teams know of certain steps they are currently working on to help achieve that goal.
But the “messy middle” is harder to handle, as we need to define enough future work towards that “North Star” but not so prescriptive that it restricts teams. I’ve seen projects derail very easily due to giving very minute steps in a multi-year project, where some phases are prerequisites of the next steps, rapidly creating dependencies among teams or even halting progress due to everyday issues or changing priorities getting in the way of the plan.
At the end of last year, we defined some goals to accomplish during 2023, and while teams have started to work toward them in their own ways, the whole “middle” part is missing.
how do we generally need to work around here?
The messy middle is filled with lots of unknowns. One way I’ve seen work is by defining milestones that would help teams align and give them enough input to know where to allocate work next and leeway to choose their own adventure and how to achieve it.
If your company works in”sprints”, you might want to review how teams are tracking their goals based on how often they deliver, like every 2 or 3 sprints. This allows time to let them work uninterrupted and review and re-align if necessary.
In general, if you have a core group of people able to define the guardrails and constantly review the output of teams, and if we’re reaching the desired goal, they should be accountable to not only do this but also communicate how they see the teams tracking, and the learnings of this process.
Conclusion
If your role includes managing the messy middle to help teams deliver towards the larger company goals, or “North Star,” how are you handling it? Do you have any tips or tricks? Let me know! Program tracking is one of those things that, if your company has a Program Management Office, you should leverage.
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