The 2 Mortal Sins of Team Leadership Pt. 2

Click Here to Read the Executive Summary

In my last post I shared why I hate teams and talked all about how to avoid the first mortal sin of small team leadership – Misusing People

(If you missed that post you can read it HERE.)

In today’s post I’m going to talk about the second mortal sin of small team leadership – Long Boring Meetings

While my last post was all about respecting the members of your team, this post is all about using your team’s time and energy less like a sledgehammer and more like a katana to slice through your objectives while helping every member on your team sing with joy.

SIN #2 – The Sin Of Long, Horrible Hair-Pulling-Out-Gut Wrenching Meetings
Everyone thinks they know how to run a meeting. But mostly they don’t. Of all the meetings I’ve attended, the ones that were poorly run, far, far, far, outnumber those that were run well.

But it’s nobody’s fault really, because most of us learned how to facilitate meetings from people who also didn’t know what they were doing.

Here are few ways to avoid meetings from hell –

1. Start meetings on time –
No matter what! If a meeting starts late, then people show up late. They aren’t focused, and no one takes the meeting seriously. It should feel awkward walking into a meeting late. You should feel bad. The meeting should be started with such clarity that coming in late makes you feel like an ass.

2. Have Clear Desired Outcomes –
You should never meet without a purpose. And just discussing ideas is not a purpose. If you want to sit around and chat, fine, but that’s not a meeting, that’s cocktail hour so bring the booze and don’t worry about getting anything done because you won’t.

But if you do want to get something done know what that is. Have at least one and no more than 5 desired outcomes for a meeting. Having 3 is a really good place to start as it’s simple without being too simple.

State these outcomes at the beginning and review them at the end. That way everyone will know if the meeting was a success or what is standing in the way of that success.

3. Have A Specific, Time Bound Agenda –
Discussions are great but endless discussion leads to endless discussion. Time bound discussions lead to simple actionable ideas.

So create a written agenda. List the items you want to cover and set time limits. Yes you can fudge by 5 – 10 minutes but remember that the more you fudge the worse it will get.

Also shoot for meetings that are 20 – 60 minutes long, the shorter the better. Most meetings are too long and they suffer because of the extra space. The only meetings that should be longer than 60 minutes are big picture strategic meeting which should only happen rarely.

4. Be or Find a Machiavellian Facilitator – (Noble but Ruthless)
People suck at staying on track. It’s hard to get a group to stay focused, which is why you need a facilitator who can guide discussion, pull out key points, and keep people on track.

Most people are actually pretty bad at this, so make your choice well or learn to do this yourself.

If the meeting facilitator doesn’t interrupt several times in the meeting to keep things on track, if they don’t solicit advice from people who have special knowledge, and if they spend more time talking than facilitating, then they aren’t a good choice.

If you run a business and you’re running a big strategic meeting where your input is needed, DON’T BE THE FACILITATOR. It’s hard to tell the boss you don’t like her idea when she is running the meeting.

5. Strategic meetings should be separated from coordination meetings –
This is the biggest mistake I see teams make. So let me explain the difference.

Strategic meetings are for coming up with ideas: for thinking about the group’s purpose and long term direction. These meetings are important but should happen rarely. Because once you’ve chosen a direction, you should try it for a while to see if it’s working.

These meetings should be about getting big ideas on the table, looking at strengths and weaknesses, and making sure everyone agrees with the larger mission.

These meeting are for developing strategies, but not for putting those strategies into action. The only things to consider on the implementation end is: do we have the talent or can we find it? Do we have the resources or can we find them? Otherwise don’t get bogged down in the nitty gritty, it’s just a waste of time and muddies the creative waters.

One clear plan that works 80% of the time is better than 5 unclear plans wedged in around your imagined limitations.

Coordination meetings are for only one purpose: Executing the plan laid out at the strategic planning meeting.

That’s it. It should just be focused around who is going to do what when. That’s it. If you have a great idea for a new potential direction great! Write it down and bring it up at the next meeting, this is not a “What If” meeting this is a “WHAT IS” meeting.

This is the meeting where you create a specific plan, set deadlines, and assign tasks. It’s not for discussing big ideas. If you realize that you can’t make the strategy work, GOOD! You need to know that and that will happen. But that’s when it’s time to drop the implementation and get back to big picture.

Some people need to be at a strategic meeting; in fact as many stakeholders as can come should attend these meetings. But execution meetings should be limited to the people who 100% have to be there and no one else. Not everyone needs to have input on how the event is promoted. Not everyone needs to have input of how the sound check will be done. Keep strategic meetings big and coordination meetings small. And don’t hold one big coordination meeting unless the left hand needs to know what the right is doing.

6. STOP LETTING EVERYBODY TALK! Too often everyone is given input in meetings. And sometimes that’s okay, but usually only a few people need to share ideas. Everyone has ideas and everyone has assholes but you don’t need to endure both.

If the discussion needs to happen between two team members let them share first. If they can’t come up with a solution throw it out to the group.

7. Some Meetings Should Be for Connection –
Every now and then you should have an informal meeting where people get to know each other. This helps with group cohesion. But don’t mix these meetings with the other ones, or schedule this after the meeting time.

8. Most of the Time You Don’t Need A Meeting –
Good meetings are meetings where everyone in the room is there because you need them to be. But most of the time you don’t need a meeting. Instead spend time one-on-one. Create shared documents. Have mini super short meetings. Use tools like Slack to stay in touch. Or make sure to talk to each key team member each day.

If you do these things, then you will reduce your total number of meetings. And the best meeting of all is the one you don’t have to have.

Final Thoughts on Groups:
Leading a small group or team with excellence is perhaps one of the most difficult things to do on the planet. Great leaders know when to listen and be open to new ideas while at the same time also know when to stop discussion and move ahead. And while you may not have been born a great leader, you can learn to be one.

All it takes is a desire to serve, a willingness to be vulnerable, and the intention to lead with humility and clarity even when it means that you’re the one that has to change the most.



Small groups and teams are hard to run, harder to run than a much bigger organization because each member is so crucial to success. So, if you’re going to run a small team or business it’s essential that you avoid the two biggest sins of team management.

Sin #2: Holding Long Meeting.
Here are the keys:

  • Start meetings on time – coming late should suck.
  • Have clear objectives for the meeting.
  • Have a specific time bound agenda (Shoot for 30 – 60 mins).
  • Have a Machiavellian facilitator (a.k.a. kind but ruthless).
  • Understand the difference between strategic meetings and coordination meetings and keep them separate.
  • Strategic meetings – are for coming up with ideas and making plans, should includes the whole team and should occur rarely.
  • Coordination meetings – are for putting strategies into action, should be short, should only include essential members, and should happen more frequently as needed.
  • Don’t mix and match meetings – pick a strategy and try it. If it doesn’t work pick a new strategy and try it. Just don’t pick and try at the same time.
  • Have some meetings where people can just connect, but don’t try to get anything done.
  • Finally the most important rule is don’t have meeting unless you absolutely have to. Meet in small groups, send emails, use project management tools like Slack or anything else first. Then if you really have a meeting make it coun,t and make it awesome.