How to tell if your strategy session is successful

By December 16, 2020Blogs
Successful Strategy Sessions

What makes a good strategy session?

With the new year just around the corner, it’s time to start thinking about a strategy session for your business.

Strategy sessions are a great time to pause, evaluate, and plan for the future. 

Especially after the rollercoaster of a year we called 2020 – your business, your industry, and your goals may have changed – causing you to plan a new roadmap for 2021.

Clients often ask us, “but what makes a good strategy session?”

Easy. Here are three benchmarks we use to tell if a strategy session was successful. 


1. It’s clear.

A good strategy session will result in clear targets that give you and your team a path and a goal. Often these are revenue goals, profit margins, scalable models, or project deliveries. They depend on your business vision and long term planning – but the important thing is they’re identified, they’re clear, and they’re agreed upon.


2. It’s focused.

The next component of a good strategy session is how focused it is. While topics and questions inevitably come up; it’s important not to get too derailed from the goal of the session. A strong agenda, assigned pre-work, and clear action items will allow you to stay on topic and move through conversations efficiently, make appropriate decisions where needed, and take note of any follow-up conversations that are needed. 

One of the biggest complaints we hear from executives is that their strategy sessions never seem to get much accomplished. Too many times they get ‘stuck in the weeds’ or distracted by topics that aren’t as high priority. 

If you’ve struggled with that in your strategy sessions, we recommend hiring a skilled facilitator to keep your team on task and focused through the agenda.


3. It continues to live.

Finally, the third way we know a strategy session was successful is how well it continues to live after the meeting. Accountability and follow-through are crucial to maintaining the momentum and expected results.

A poor strategy session is one that is forgotten a week after the event. Make sure all objectives, targets, and priorities live and breathe throughout the year by identifying metrics you will watch and report on periodically, as well as plans for progress updates. 

This can be the most challenging aspect of a strategy session, and it often requires the most work. You’re going to need to create a plan that is unique to both your team personalities and work habits, as well as tailored to the specific goals you’ve set. 

Accountability is one of the biggest values executive coaches can bring to a leadership team. Their experience and trained skills are perfect for following up with teams regularly to stay on top of progress, as well as helping you analyze any setbacks and respond strategically.



And there you have it. The three things that make a GOOD strategy session for your business. 

Regular strategy sessions are key to running a successful business. However, far too many have experiences that demonstrate the difference between a ‘good’ and a ‘bad’ strategy session. If you want to set your team up for a successful session, remember to keep it clear, keep it focused, and keep it alive.

Need help getting those done? Our executive coaches are trained to help with just that. Reach out and get some guided help to ensure you’re on the right track to complete your goals. 

Happy strategizing!

Ilana Zivkovich

Author Ilana Zivkovich

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