Executive Strategy Session

At least once a year, every executive team should take a chunk of time to dig deep into their company’s strategy and re-align on mission, purpose, and priorities. This session follows a proven structure for such a meeting.

Usually, executive strategy meetings like these are either a half-day or full-day. When you have such a long session, always open with a welcome and make sure everyone knows what to expect from the day.

From there, move on to reviewing your key metrics, taking a long view to look at trends over time, from at least as far back as the last time you had a strategy session. After having this quantitative look at the company, move to a qualitative discussion that focuses on where the organization is, what is going well, and what isn’t.

Now that everyone understands the current situation and where the company would like to go, it’s a good habit to return to the company’s vision, mission, and purpose. This is both a sanity check and calibration exercise. If the company’s purpose doesn’t match the planning, either the company’s vision should be updated, or the plan is getting off track.

The rest of this executive strategy meeting agenda template will help you figure out your strategic priorities and how to act on them. You will find a path forward, and then have to choose one priority as your main focus—a useful exercise in figuring out what is truly important.

For any tasks or action items that come up in the meeting, note them in the section for next steps at the bottom of the agenda sample.

Best Practices For Executive Strategy Sessions

Here are ten best practices for executive strategy sessions:

1. Be Prepared – As with any organizational meeting or personal discussion, it’s important to be prepared. Sourcing the latest information is critical. Are you ready to have the meeting? If not, make sure you have your notes and research from the last few months or years in order to fully answer any questions.

2. Practice Transparency – This is a common mistake with most internal meetings. As soon as something happens within an organization, people try to cover it up or understand it themselves. However, this only leads people to cover things up or not understand them at all. So make sure you are open and honest with your team and provide strong feedback to them.

3. You are Part of Your Team – It sounds self-evident, but it’s important to think of yourself in the room just as you think about your own team. We tend to play favorites or have blind spots when it comes to reviewing ourselves. Make sure see where you are going wrong, and make corrections so that you can continue being a strong leader for the organization.

4. Be a Good Listener – To be a good leader, you need to be able to mediate effectively. You need to listen to yourself and others. It’s important that everyone feels heard and that decisions are made based on what is best for the organization as a whole as opposed to individual agendas.

5. Keep Your Eye on the Exit, Not the Entrance – It’s important that you have a clear view of company goals and what they look like. The best way to spend your time is to make sure everything you do is aligned with achieving those goals, not rehashing the past.

6. Read People – When you attend meetings with executives, be sure you know how to read people. If someone is getting more upset than you think they should be for a particular situation, then there is probably something deeper going on. You need to be able to read people and organize your notes based on what you are seeing and feeling in the meeting.

7. Define Your Success with Positive Action – This is an important part of being prepared for an executive strategy session. When it comes time to make decisions, it’s not enough just to see improvement. Be clear in terms of numbers, actions, and results. Be specific!

8. Raise Concerns – We’ve already talked about it, but it’s essential that you make sure that your team knows about the concerns you have with the policies that are being considered and with decisions being made. If you don’t raise any concerns or questions, then they will not be addressed and may be ignored.

9. Ask the Right Questions– This is an important part of being prepared for any meeting. It’s also vital that you ask the right questions based on what you want to get out of the meeting. If you have a preconceived idea about something, then that will affect what you end up asking when it’s your turn to speak. Make sure you are focusing on asking questions instead of telling.

10. Stay Focused – It sounds obvious, but many executive strategy sessions lose focus very quickly. It’s easy to get caught up in your team-mate’s stories and forget why you’re there. Be sure to stay focused on the goal of the meeting: help your team move forward. The executive strategy meeting agenda template here will help with that.

5 Worst Practices for Executive Strategy Sessions

Let’s talk about some practices that you may want to avoid when working with executives. As mentioned, it’s good to have these in mind before you start a meeting so that you have a solid foundation and can avoid making mistakes:

1. Being Too Prescriptive – We mentioned that it’s important to be specific and clear in terms of the goals you want to achieve. Sometimes people will do this by trying to make decisions based solely on their own experience. This can be disastrous if they are making decisions without looking at the whole topic and listening to others. The wrong decision can lead to negative results or failure.

2. Promise Things You Can’t Deliver – This is a common problem that plagues executives in any organization. Make sure you don’t promise things you can’t deliver. Don’t only think about yourself – promise things you know you can get done. This will make it easier to provide the necessary results and will help when stakeholders ask you for more than you initially think is possible (which they likely will).

3. Not Getting to the Point – You have a lot to cover in a meeting like this, so take time to collect and organize your thoughts before speaking. Remember that you have just as much of a story to tell as they do, and it’s important that you deliver your message in an organized manner.

4. Not Understanding the Goal – Remember the goals you chose with this meeting in mind. Be clear on what those goals are, and make sure your team knows them as well. This is an important part of making good decisions. If you get sidetracked onto a conversation that's not related to your main goals, steer back on topic.

5. Not Measuring Results – Sometimes, people will consider a strategy session a success simply because you listened and made decisions. A good strategy session should have some sort of measurable results to follow up on. Be sure that you set up results to track in the future to determine success and failure of your decisions.