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Driving Forward vs. Fully Acknowledging What’s Here

“Teamwork begins by building trust. And the only way to do that is to overcome our need for invulnerability.” – Patrick Lencioni

Of the many questions I get from clients each year, how to do collective planning well is at the top of the list. Having a clear vision is one thing. Leading a discussion and conversation about the vision and what that means for each function is another. How does one lead a dialog about important issues? How do we lean in to disagreements? How do we decide to move forward as a team? 

The ‘how tos’ and ‘when tos’ fall into place and come naturally from tending to the larger container that holds the planning discussion. How we are together becomes a more important metric to hold. What do we need to have in place interpersonally before we can talk about the agenda items and the issues and perspectives? 

Doing collective planning as a leadership team well is an art of such interpersonal skills and inner-personal skills. Because, as Andy and Jerry note in this conversation, planning begins before the planning happens. The planning process framework — no matter what you choose to use — is less important than the interpersonal dynamics among the team. When both ingredients are at play, however, then you have a workable and possibly fun and invigorating planning process.

“You can use planning not to exacerbate the tensions on the team but to make the team stronger at the end of the process,” Jerry reminds us. Consider these questions below and reflect on how the team functions, your planning process, and your feelings and impressions about the dynamics that might hinder your processes and projects. 

Take a moment to reflect: 

  • How well do we function as a team?
  • What issues or dynamics arise on the team currently? 
  • What is the quality of the container for the group? 
  • What are the relationships between members? Where is there unaddressed tension between people or around issues? 
  • Where is there a lack of trust, or unresolved conflict? 
  • How do we debate? 
  • How do we talk through hard topics together? 
  • How do we make decisions? 
  • How do we confront areas of misalignment on the team or around issues? 
  • How does the strategy get translated into a roadmap and used effectively across the company?
  • How do we manage disagreements?
  • How would we know when we were functioning well? What would that look like?
  • Where can we improve? What would be different?
  • How is our planning process?
  • What are the constraints around the planning process (are they clear)?
  • In what ways might our current and past planning processes be performative?
  • Have the desired outcomes for the planning process been named?
  • Where are we paralyzed by perfectionism, thus delaying decisions?

More questions for reflection from where you sit:

  • What conversation(s) do you need to have that you are putting off or want to be better prepared for?
  • What decisions need to be made that have not yet been made?
  • Are there recent conversations or decisions that happened where you felt you were not heard or that did not go the way you wanted?
  • What is something that is on your mind consistently that should be addressed?
  • Where do you need help or support that hasn’t been communicated yet?
  • What could be even better regarding your relationship with your peers? What action might you take to make this happen?
  • Where do you not have trust on the team?


Connect. Think. Lead. Adapted from the forward I wrote to a friend’s new book… Connect. Think. Do. I’d first gotten the call, an inquiry call for coaching, two weeks previous. In a follow-up…
Still Standing Still Years ago, I wrote that founding, running, and working in a startup can often feel as if you’re often feel as if you’re standing still while your hair’s on fire.…
Since Feeling is First My most favorite lines of poetry are from ee cummings: since feeling is first / who pays any attention / to the syntax of things / will never wholly kiss…



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