Six Ways to Effectively Lead a Planning Session

Here's the advice I almost always give to leaders: Ask yourself, "What does this session need right now?"
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Ever seen leaders play one of these roles at a planning meeting?

  • The Lecturer - In meeting 1, you're locked in a planning session and the leader is controlling everything. She says too much and says it too strongly. The rest of the leadership team starts to wonder why they even showed up. They politely go along, acting like they agree even when they have reservations. It's a charade. Everyone is just waiting for it to be over so that they can get back to real work.
  • The Passive Enigma - In meeting 2, you're locked in a planning session and the leader is strangely passive. You know he has opinions. You hear them in private all of the time. But in an effort to "not dominate the conversation," the leader has completely zipped and padlocked his lips. The rest of the group politely fills the air-time, but you wonder when you will find out what's really going to happen. And you wonder who stole the real boss and sent the mannequin.

Leaders face a dilemma when they involve their teams in planning. I hear their confusion almost every time I lead a planning session. They quietly approach me just as we're about to roll and say things like:

  • "OK, I'm going to try hard not to say anything today."
  • "What role should I play today?"
  • "Don't let me dominate the meeting."
  • "Where should I sit?" (My personal favorite.)

Their dilemma is understandable. On the one hand, who wants to be that domineering boss who monopolizes the session and chokes the creativity of the team? On the other hand, who wants to be the lame boss who allows chaos to swamp a valuable planning session?

Here's the advice I almost always give to leaders: Ask yourself, "What does this session need right now?"

For instance:

  • Ask questions: If you see a team member who hasn't contributed for a while - and who you know has strong opinions or good ideas - draw them out. Ask a simple question like, "Sherry, we haven't heard from you on this issue and I'm pretty sure you have ideas about it. Would you share your thoughts?"
  • Provide boundaries: If the team is straying into an area that you know is going to be a waste of time or if they're debating something that has already been decided, provide boundaries. "Gang, I appreciate the conversation. Something you don't know is that we've already decided as an organization not to pursue that market. So let's redirect our conversation over to these other issues that are still open for debate."
  • Draw out differences: There should be differences of opinion on your team. Instead of allowing them to lurk beneath the surface, get them on the table and crystallize them for all to see. "I'm hearing three different points of view on this topic. Let me see if I can articulate them and then we'll debate the merits of each."
  • Enforce ground rules: In any contact sport like planning meetings, fouls will be committed. Part of the leader's job is to be sure that the team plays the game fairly. "OK, I just want to remind everyone that it's fine to disagree. But we cannot allow disagreement to get personal or to let disagreement stop us from getting to a solution that we're all committed to acting on. So Rob and Gina, let's try that conversation again and see if we can get to a better outcome."
  • Manage tempo: It's an art to know when to slow down the conversation and dig into a topic, and when to call time and get the group to move forward. As a leader, you often have a better read on that call than most. "Alright, it sounds to me like we need to close on this issue. Here's what I think we need to do..."
  • Let it run: Sometimes, the best thing to do is... nothing. The team is wrestling with an important issue and they're doing it well. Yes, it's messy. Yes, it's taking time. No, you're not quite sure where it will land. But it's a substantive topic worth the effort. Sit back. Watch. Ask yourself, "What does this situation need?" And if it needs precisely nothing, then give it happily.

All of these options look like active engagement and guidance without domination. That's probably what the session needs most from you.

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