Sell the pain, not the solution, the theory, or the blame

A strategy that ignores the obstacles is liable to fall at the first hurdle. That’s if it even gets that far – who will take seriously a strategy that ignores the issues? Turn those obstacles into outcomes Agendashift-style, and organise them so that you can establish a sense of direction, identify places to focus your efforts, and measure progress and success, well you’re in much better shape.

Most things Agendashift-related come with leadership lessons too, hence Leading with Outcomes. Here, in a psychologically safe environment, it must be ok to talk about obstacles. As a leader, you have a responsibility to encourage that to happen. But we can take that basic lesson further: how we talk about obstacles matters too.

Ever since a workshop in Berlin in 2019*, we’ve paid closer attention to how obstacles are framed. What started out as an effort to debug one breakout group’s frustrating experience turned into a new exercise, Good Obstacle, Bad Obstacle (yes there’s a nod to Rumelt in the name there).

Ostensibly, the exercise’s job is to frame obstacles such that the conversations to turn them into outcomes will be productive and satisfying, even enjoyable. What we repeatedly find though is that it helps us get to deeper issues and at the same time puts a spotlight on the organisation’s discourse. A bugfix becomes a key feature!

The exercise’s goal is to produce obstacles that are real, relevant, and representative – describing things that colleagues would quickly recognise, that affect their everyday work, and worded as they might word them. As per the title of this post, the trick (if “trick” is the right word – it can take real effort) is to sell the pain, not the solution, the theory, or the blame.

Some examples of “bad” obstacles:

  • Lack of a knowledge management system
  • Lack of people, money, or time
  • Lack of WIP limits
  • Lack of the Agile mindset
  • Lack of leadership
  • Lack of quality

The problem isn’t the “lack of” language (or “scarcity language”, as I sometimes call it), though that’s a strong smell. The problem is what those obstacles are selling: solutions, theories, or blame (or a combination), all of which get in the way of agreement. They’re easily dismissed (they may exclude better solutions or theories, for example), they call for things that everyone knows are unlikely to be forthcoming, or people feel judged by them.

Instead of those “lack ofs”, tell the more interesting side of the story. Sell the pain. Identify the real issue. That way lies the path to agreement on outcomes, a more coherent and robust strategy, and a more purposeful innovation process. And if you want your organisation’s discourse to improve, try paying attention to how obstacles are articulated. The conversation to turn a bad obstacle into a good one (in your next retro, perhaps) might be more important than you might think.

*See Events below – I’ll be back in Berlin in February, my first trip outside the UK since Covid!

Image: anonymous, CC BY-SA 3.0,

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  • Events: Added Berlin, 7-8 February
  • Media: interviewed by Jeff Keyes of Atlassian, December 11th


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