In the Messy Middle reflects where Wicked Outcomes™ thinking is being shaped and not through neat definitions, but in the space between challenge and outcome. As early ideas are shared, three tensions surface: how to clearly describe the journey from Wicked Challenges™ to Wicked Outcomes™, how the Six ITs™ operate as an engine for lasting change, and a growing desire to understand those ITs more deeply in practice.

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WHAT WE'RE WRESTLING WITH

As we’ve started sharing early thinking on Wicked Outcomes™, the most useful responses haven’t been answers(!) they’ve been better questions! Here are three themes keep coming back, and they feel important enough to capture here, not as conclusions, but as markers of where the work is taking us:

BRIDGING

The first is the bridge between Wicked Challenges™ and Wicked Outcomes™.

We’ve talked about both, but not enough about the journey between them. What’s emerging is the idea of the Six ITs™ acting as an Outcomes Engine, not a linear process, but a set of capabilities that convert challenge energy into something that lasts. That bridge needs to be made explicit, visible, and testable. That’s very much work in progress.

FLEXING

The second is a renewed focus on individual Six ITs themselves.

There’s growing interest in how things like Resource-IT behave less like a fixed operating model and more like a flexible transformation backbone, flexing and reshaping as the challenge evolves. Iter-IT in particular keeps coming back to the foreground, not as “doing it again”, but as the discipline that builds clarity, confidence, and capability over time.

Resource it

Securing the different kinds of Resources required that are essential for resolving Wicked Challenges™. Not solely People but the Knowledge, Skills, Budget, and Time.

Collabor-it

Bringing colleagues together in the same room on the same page. Insights shared, dots joined, turn challenges into opportunities and outcomes!

FRAME It

Describing the situation so that all stakeholders engage and develop shared meanings. As a result, embrace a shared commitment on what success will mean.

INNOV-It

Encouraging innovative thinking to help make difficult choices and trade-offs and not be put off by the messy, combative, iterative ways decisions are often made.

Measure It

Scoring a realistic standard of success rather than a goal that is perhaps unrealistic. Towards improving Wicked Outcomes™ made-up of Solutions and Benefits.

Iter-It!

Committing to multiple iterations is essential to maintain flexibility and build confidence in the journey. Regular checkpoints provide accountability for the whole team.

SCOPING

The third, and perhaps the most fundamental, is scope.

What we call Wicked Challenges aren’t the classic, society-scale “capital-W” Wicked Problems. But they’re also far bigger and messier than the tame, well-bounded problems most organisations are set up to solve. That in-between space, organisationally bounded, human, systemic, unresolved, still lacks the clarity around good language. Naming it well feels like part of the work.

This is where we @YourBigPic tend to operate. In that messy middle. Using visual thinking, collaborative sense-making, and practical frameworks to make progress without pretending things are simpler than they are.

We’re sharing this not as a finished position, but as an offer to get amongst it. So, if you’re wrestling with something that feels “wicked” in this way, we’d love to learn from it, and weave those experiences into what comes next. Thanks to our intrepid reviewers willing to counter and challenge with their years of wisdom!