How to Improve Your Strategic Conversations

October 28, 2021
October 28, 2021 Jamie Notter

Whether you’re leading a management team or a project team, the quality of your strategic conversations is hugely important.

A strategic conversation is one that digs into a complex issue that has serious strategic implications and may require a shift in approach or tactics. Obviously your quarterly or annual planning meetings are strategic conversations, but at any point during the year you may need to address a strategic issue that could require a shift.

So take a minute to be brutally honest with yourself and give you and your team a rating on how well you do your strategic conversations. I’ll keep it simple with a 3-point scale, but obviously you might be in between two of the categories:

  1. Poor. They don’t happen very often, or when they do, many viewpoints are shared, but conflict is avoided and there is no resolution about what shifts we need to make. No/low accountability on follow through. Line between strategic and tactical often blurred.
  2. Average. Better job with the big strategic conversations (e.g. annual planning) compared to dealing with emerging strategic issues. Conflicts are tackled (generally) but decisions skew to the high-level, making follow up harder. Strategic and tactical kept separate, but not necessarily different processes for each type of conversation.
  3. Exceptional. Continuous sensing of emerging strategic issues with swift response. Conversations are clear, direct, and decisive about what needs to change. Accountability standards high and managed without drama. Specific process for strategic conversations involving adequate prep and data.
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If you didn’t score a confident “3,” then you have work to do. This is a major focus in our Priority-Based Execution system, which is one reason why we prefer to run our coaching program for the entire management team, rather than only the CEO. Strategic conversations can be improved by:

  • Building your conflict resolution skills
  • Designing the right process for your strategic conversations
  • Having the right data in front of you when you have the conversations
  • Putting in place a system for tracking follow-through

If you’d like to have a 60-minute conversation with me about the current state of your strategic meetings and get some more specific advice on what you might do to improve them, book it here (make sure to mention “strategic conversations” in the appointment).

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Photo by Campaign Creators

Jamie Notter

Jamie is an author and growth strategist at PROPEL, where he helps leaders integrate culture, strategy, and execution to achieve breakthrough performance and impact. He brings twenty-five years of experience to his work designing culture-driven businesses, and has specialized along the way in areas like conflict resolution and generations. Jamie is also the co-author of three books—Humanize, When Millennials Take Over, and The Non-Obvious Guide to Employee Engagement—and holds a Master’s in conflict resolution from George Mason and a certificate in Organization Development from Georgetown, where he serves as adjunct faculty.
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