2023 Cultural and Growth Foundation: Why Plan Your Strategic Offsites A Year in Advance?

In the aviation industry, it can be disconcerting for a novice passenger to watch the pilot walking around and checking the condition of the plane. Seasoned travelers, however, know the pre-flight check is a mandatory part of every air journey, whether the pilot is helming a small private aircraft or the massive 787 Dreamliner

It may seem redundant for the pilot to check everything that the ground crew also recently checked, but in fact, it is a testimony to the great care the pilot has for the passengers–that he or she will leave nothing to chance. 

Executive Responsibility

The same can be said for planning for the success of your business. While your crew should be highly skilled, you as CEO still take final responsibility for successfully moving your business from one place to another. 

As the CEO, your culture and your team are your growth foundation. You want your entire leadership team to be experts in your market and customers. That is best done in person.

With more people working remotely or in hybrid settings, company offsite meetings are the perfect opportunity to bring your leadership team together to bond, strengthen company culture, and talk about high-level strategies that may get neglected when your team dives into the day-to-day tasks that need to be done.

These regularly held strategic meetings are where CEOs can give and receive the key feedback to keep the proverbial planes running on schedule. 

Develop a Regular Cadence

If you’re a frequent business traveler, you know the exact times your preferred airline departs. In fact, you rely upon the airline and the airport to keep things running smoothly. And when flights start to back up, chaos ensues

You don’t need news headlines blaming everything from weather to supply chain shortages to ground grew sickouts to know that delays and cancellations are not good for business. The same is true for your strategic planning meetings. 

Put the meetings on the books at least a year in advance. Make sure everyone knows when and where they will occur and give everyone plenty of time to prepare for the meeting. And keep to the schedule as if you expect the New York Times to blast you for any cancellations or changes that may occur. 

Quarterly Meetings

We recommend holding your high-level strategic meetings once per quarter, either at the beginning of the quarter as a way to codify your plans for the coming 13 weeks, or waiting until the end of the quarter after your numbers drop as a way of wrapping up and reviewing the previous period. 

We find the CEOs we work with are equally divided in their preferences with respect to which schedule is best. 

Another timing consideration–hold your quarterly strategic meetings two weeks before your scheduled board meetings. This gives your senior leadership the opportunity to come together to measure and future-plan your corporate strategy. How have things progressed as planned since the last meeting? What will you be measuring at the next strategic meeting? How will you report on these metrics at your upcoming board meeting? 

Beyond reporting back to your board, holding quarterly strategic meetings gives your A-Players the opportunity to build routine feedback loops. They become more accountable to one another and they also establish the ideal foundation to review and present high-level strategies to their entire team back at the office. 

Modern Day Water Cooler

If you’re of a certain age, you remember the idea of the water cooler chat. People would supposedly gather around the water dispenser to chat about work activities and to catch up on gossip. Whether or not that was ever a real office ritual, the idea behind it was sound. 

“We exist to connect with other human beings”

–Jen Fisher, Chief Well-Being Officer, Deloitte US (via Salesforce.com)

People enjoy the social interaction of working together. And a lot of that has been lost as more companies are going hybrid or fully remote.

Your strategic planning meetings give your executive team the opportunity to reconnect on a personal level. Not only do they get to discuss strategy in person, they learn a lot in the little side discussions that may be largely missing on Zoom as people worry that maybe their side chats are being monitored. 

The offsite meeting provides a forum for getting to know colleagues on a personal level. The side events, the dinners, and the random hallway conversations with colleagues all lead to building deeper connections that are more difficult to establish in an office environment.

Event Format 

The format of the meeting–whether you choose to hold it in a high-end hotel setting or a more casual retreat site–should match your corporate culture. CEOs differ on their preferences and there is no “right” way to plan the format. 

If you absolutely can’t get to an off-site location, a virtual meeting will work. But whenever possible, plan for an in-person format. 

And whether you’re holding the meeting in person or virtual, be sure you leave enough time for personal interaction and reflection.

We also highly recommend using a coach to facilitate your meeting. Coaches can help keep your meeting running on time, making sure you hit all the high points, which leaves more time for you as CEO to join the discussions and require you to watch the clock less as you look to ensure everything happens as you’ve planned it. 

Great coaches book out early, however, which is another key reason to schedule your off-site meetings as early as possible. 

If you’re looking for more ideas on implementing a successful strategic meeting, PFD Group can help. Contact us now for more information, or read about the PFD Stewardship Summit in Alaska


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