Why will this be hard for us?

I was working on a strategy and helping review another this week, and found this framing helpful. Especially in mature organizations, the challenge tends to reside not in determining how to do something, but rather in finding what makes this “how” difficult for this organization. 

The common symptom here is dust-covered stacks of past plans that look eerily familiar to what is being proposed. There’s a certain Groundhog Day quality to these. “Oh, we’re pitching this thing again? Okay, I guess it’s been a few years since we last tried it.” The “it” might range from product ideas to processes and practices. Having cross-functional communication issues? Let’s start an XFN working group. This time around, it’s sure to bear fruit, right?

Putting our systems thinking hat on, we can see that well-established orgs are held together by forces that animate them. The dynamic equilibrium of these forces tends to also preserve the status quo: the plans that failed will likely fail again in similar ways, if tried once over. Think of it as a cousin of procrastination: just like with us humans, the actual challenge might not be the work itself, but rather the inner organizational tensions and conflicts that make doing that work next to impossible.

A useful shift here might be to focus on why, given these animating forces, we are to expect a different outcome. What’s changed about the situation? How did forces change and in what way since our last attempt? The generative question that tends to help is “why will this be hard for this particular team or organization?” 

A word of caution: it’s easy to land on despair when looking into what animates an organization. Discerning and reflecting on team pathologies asks for heaps of patience and compassion. Perhaps this is why we often fall back just rolling the dice again.