What we’ve learned about organizing effective leadership team meetings

Once a year, I gather Knak’s leadership team for an annual planning meeting. We look at numbers, set targets, and generally figure out what we want to focus on for the coming year.

Sounds straightforward, right? It’s not. I’m an entrepreneur, not a business planner. While I knew annual leadership team meetings were essential, I had no idea how to run one when I had to put together my first meeting. I’d never even participated in one at that point! I ended up desperately searching online for tips on what to do.

With time, I’ve figured out what works for us. In this posting, I want to share those learnings – in the hope of saving budding entrepreneurs a lot of time on Google and YouTube.

Hold in-person meetings

There’s a huge payoff to gathering the leadership team in person. People are much more engaged when they are all in the same room, feeding off each other’s energy. It’s way more productive, and more pleasant, than an eight-hour Zoom call.

When we were forced to meet virtually, we tried half-day sessions. They worked better than full-day virtual meetings, but they were nowhere near as effective as in-person meetings.

Hold the meetings away from home

We don’t just hold our leadership team meetings outside the office, we hold them away from home, in a resort or in a different city. That’s because we’ve learned that getting people away from their daily environment has huge benefits.

On a personal level, people have to arrange to be free of domestic obligations. If they’re away from home, they can’t beg off because they have to walk the dog or pick up the kids from school. They are able to concentrate fully on the task at hand.

And because they are out of the office, they can’t be easily distracted by work responsibilities either.

When they travel away from home, people seem to get into vacation mode. Getting them into a new setting with new stimuli seems to open them up, and make them more creative.

Without their usual domestic obligations, team members are also free to gather socially in the evening after the work is done. That social element – which allows team members to get to know one another as people – is hugely important for relationship-building. Getting to know everyone’s strengths and quirks is as important as number-crunching or goal-setting; in fact, it makes those tasks more efficient. And you can learn a lot about people in relaxed social settings.

Book your meetings well in advance

The best way to have every member of the leadership team available at the same time is to schedule the meetings months in advance. The team members are usually among the busiest people in the office, with insane calendars. Get them to commit early!

Make sure you have the right people at the meeting

You probably have a good idea of who the key members of your leadership team are, but over time you may have to amend that list.

You can either add people to the team meeting as a whole, or you can invite specific people to come and participate in certain parts of the meeting. Either way, the point is to make sure the people at the meeting have the information they need to make decisions. We once made the mistake of deciding something, and when we brought that back to the office, the person who was going to be tasked with implementing it explained why it couldn’t be done. That person should have been consulted.

Be prepared but flexible

Have an agenda. Know what you are going to talk about, and arrive prepared.

On the other hand, don’t be too rigid about the agenda, otherwise you may not leave time to focus on what your team feels is important. We spent one two-day meeting talking only about hiring, because it was quickly apparent that because we’d just obtained funding, nothing else was as important.

Start the meetings on an upbeat note

We like to start our meetings with good-news announcements, either personal or business-related. We’ve found that these put everyone in a positive mindset and get everyone engaged.

Make sure your team members are aligned

If you’re going to be planning the year ahead, it’s important for all members of the leadership team to be on the same page about where you’re headed. We’ve found that the best way to do that is to answer the question: Why does Knak exist? When considering initiatives or projects for the future, we remind ourselves that they must align with the answer to that very basic question.

In our case, we’ve determined that Knak exists to help empower marketers to be creative – that’s our “why.” Making sure everyone at the meeting keeps that why in mind helps align us and ensures we are working towards the same goal.

(This is the basis of Simon Sinek’s book Start With Why. I’m a fan.)

We also make sure our decisions have a positive impact on each of the four pillars of our company: culture, customers, product and growth. We also use our core values to help us evaluate issues we struggle with.

Go beyond the usual SWOT analysis

We do a SWOT analysis – a look at strengths, weaknesses, opportunities and threats – at every meeting. This really allows us to take a proper 50,000-foot-high view of the company.

Every year, we start that SWOT analysis from scratch. In other words, we don’t take the previous one and build on it.

Then, after we’ve built our new SWOT analysis, we haul out previous years’ ones and compare them. Are the same threats from last year still there? If so, why haven’t we addressed them? Did we see the same opportunities last year? Why haven’t we taken advantage of them?

We’ve found that this comparative approach provides solid, useful information that helps inform our decisions.

Come to the meeting with proper data

You can’t run a proper leadership team meeting without proper data. As we have gotten more sophisticated, so has the data we use. We now have a financial model that takes all of the data involved in running the company up to the day of the meeting, and with different inputs it projects scenarios for the future. For example, if we plug in a figure for revenue, the model tells us how many employees we would need to generate that figure, and what the budget for different departments would have to be.

But that is only a starting point; we’ve also learned to allow for a certain gut feeling about what is actually possible. As a result, we often challenge the projections.

For example, if Marketing knows they average 100 leads a month, and our model tells us we need 500 leads a month to generate the revenue it’s projecting, we can see the projections are not realistic. But if our model says Marketing needs 200 leads a month, then maybe it’s doable if we give Marketing a bigger budget.

It’s all about figuring out what’s reasonable based on solid data.

Encourage people to challenge each other

We’ve gotten great results by encouraging team members to challenge each other. In our meetings, no one gets offended if someone from another department gives you pushback about your department’s projections or asks a lot of questions about your figures.

In some companies, no one cares much about other departments; we think everyone should at minimum be curious about everyone else.

Use the meetings for team-building

As I noted higher up, having the meetings away from home lets team members be together after the work is done. But because team-building is so important to us, we put team-building activities into the schedule – activities that go beyond dinner together. These might include games, or outdoor activities, like hikes. The point is to build and strengthen relationships between members of the leadership team. Strong relationships make hard conversations easier. In fact, sometimes I think the activities part of the meeting is the most important part of the meeting.

Don’t let yourself get bogged down or sidetracked

Discussions can sometimes veer off onto an unimportant tangent or move around in circles. Whenever we find we’re getting bogged down, we stop, make a note of the topic or issue, and if necessary come back to it at the end of the meeting.

Manage investor expectations

Investors generally want you to grow as fast as possible. My job is to find the right balance between aggressive growth and what’s realistic, while keeping our core value of work/life balance in mind. Our employees can only do so much; working them 80 hours a week is not productive.

When we’ve found that balance, I need to communicate it clearly to investors.

Give yourself time

I’m always overly optimistic and expect that we can do everything we need to do in a single day. The reality is that we generally need two full days. When evaluating how much time you’ll need, be realistic.

Follow up immediately with a summary of what was discussed

We’ve found it’s very important, after the conclusion of a meeting, to communicate to everyone in the company what was discussed and what was decided. Everyone wants to know, and it’s only natural that we should tell them, for the sake of transparency and to give them clarity in their work. It’s also important to do this quickly, while the meeting is still fresh in everyone’s minds. Otherwise, memories fade and you forget the context in which decisions were made.

So there you have it: a list of our best practices. They work for us, and we hope they’ll work for you!