“On Monday, we’re having our meeting. It’s like D-Day to decide what happens next. I’m thinking about how to manage the conversation. I wondered if there were a better way to ask, ‘What do you think should happen next?’ other than asking ‘What do you think should happen next?’” That message was on my phone at 10:39 p.m. Sunday evening. It is from a friend and client. She’s staring down a strategic conversation with her board today.

The important strategy question?

Keeping the organization’s core initiative going, changing it dramatically, or shutting it down.

4 Ideas for Managing a Critical Strategic Conversation

Managing a critical strategic conversation is something to plan for in advance.

To answer her question, there are four ideas for structuring the critical strategic conversation on what the initiative’s future should be.

1. Gain a sense of individual perspectives before the critical strategic conversation.

I always want to understand upfront what each person is thinking. We use this information to shape the discussion. You can gain early insights through personal conversations, surveys, or online collaboration (where the entire group is participating but not seeing others’ answers). If something prevents developing that early understanding, I’d design the group’s strategic conversation to gain a sense of individual perspectives before group discussion happens.

One way? Create a worksheet or exercise with several questions that individuals complete at the start. After recording individual ideas, then they share their input. From the initial written perspectives, you can understand and manage how perspectives change during the meeting. You may also get a true sense of perspectives before hearing others’ views changes what people are willing to say in the meeting.

2. Address potential biases early, if possible.

Group members may make assumptions or believe certain things are so important or so harmful. These beliefs may bias their perspectives. If possible, remove these points. In this situation, the person asking the big strategy question will likely exit the organization based on the group’s decision. That could bias certain peoples’ perspectives. She’s already addressed by providing a pre-determined time window for her departure. Nobody need worry about the decision forcing her out of a position she hoped to remain in for years. Diffusing bias points can free up the strategy conversation dramatically.

3. Split the group into smaller ones with similar perspectives.

If the group is clearly divided, split it into smaller groups sharing share similar viewpoints (in this case, perhaps, groups that have landed on continuing, dramatically changing, or stopping the major initiative). Ask them to collaborate and recommend a course of action for their assigned scenario. Have them briefly describe their recommendation, the rationale (including upsides and risks), any assumptions they’re making, what they think will have to be done to start implementing the recommendations, and critical success factors. Doing this before full-fledged group discussion can create a physical representation of the recommendations. This physical depiction (perhaps on flip charts) leads to a more clear and concrete strategic conversation.

4. See if recommendations change as the scenario changes.

After gaining the individual or small group perspectives, describe a few variations in the scenario. See what happens if the personal stakes or other big factors change. Potential variations you could pose in question form include:

  • What if you had to devote 50% more time than now to accomplish this recommendation?
  • Suppose you had to raise money for this recommendation?
  • What if the initiative’s leadership had to change?
  • Would you be willing to invest two years to accomplish your recommendation?

There you have it.

You have an insider’s view of our phone conversation today. You also have a resource for the next time you must manage a critical strategic conversation that feels like your organization’s D-Day. – Mike Brown


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