How To Plan An Effective Executive Team Retreat
Pro-tips for gathering your executive and/or senior leadership teams for quarterly or annual planning, plus access to a free Executive Team Retreat Agenda Template.
Previously on The Offsite Blog, we’ve discussed “The Cadence”, answering why, when, and how often to host team retreats based on your company’s goals and team size.
We’ve also covered how to plan effective All-Hands Meetings, as well as various cities we recommend having offsites, speakers and facilitators we’d recommend hiring for your next offsite, and more.
From a strategic planning standpoint, executive team retreats are some of the most important gatherings at your company.
While you don’t want to waste money on travel, logistics, and activities, the opportunity cost of those in attendance and the potential ROI of these meetings can be astounding.
Because of this, we want to ensure that every executive team retreat you plan is done with intention, preparation, and long-lasting benefits.
Below, we’ll cover some “pro-tips” for planning an effective Executive Team Retreat meeting. You may run these quarterly, so if you have questions about how to apply these ideas to your organization, please set up a free Offsite account and then reach out to me directly at jared@offsite.com.
Time is money, so let’s get into it…
Don’t forget to download our Executive Team Retreat Agenda Template and…
Join our free Team Retreat Planning slack community to discuss agenda building, budgeting, venue inspiration, and more in real-time with hundreds of other people leaders.
Of course, visit offsite.com whenever you plan your next Executive Team Retreat!
Think Intentionally About Each Retreat’s Goals
As a Chief of Staff, EA, Head of People, or even a CEO planning an executive team retreat, it’s imperative to carve out definitive goals for every executive team retreat that you plan. Even if you meet quarterly, the strategic planning needs, pressing issues, and team dynamics among your executives will evolve.
These goals will inform every aspect of the retreat's development and execution, from venue selection to activity choices to facilitation.
The process might require discussions with your executive team to ensure everyone's vision for the retreat is considered.
It will almost certainly require “pre-work” on presentations, goal-setting (such as OKRs), and perhaps other sessions you may add to your agenda.
Consider these potential objectives when planning an Executive Team Retreat:
Aligning the executive team on strategic initiatives for the upcoming year, like product roadmaps, budgets, and growth plans.
Strengthening camaraderie and trust within the leadership team to enhance effective decision-making.
Providing a platform for transformative leadership development sessions tailored to your executives’ specific needs, so they can become better managers in turn.
Reinforcing the company’s mission, vision, and values at the leadership level to cascade down through the company.
Building inter-departmental relationships and understanding to facilitate smoother operational flow.
Celebrating key leadership achievements, such as successful project completions, hitting or surpassing KPIs, securing investments, etc.
Goals for your retreat should not only reflect but also advance the company's overarching strategic imperatives. They ought to be precise, actionable, and quantifiable.
For instance, rather than a broad aim like "Enhance leadership synergy," specify a target such as "Finalize Q1 2024 OKRs." Such detailed goals will not only provide a clear measure of the retreat's success but also help in obtaining quicker buy-in for future leadership events.
Send A Pre-Offsite Feedback Form To Attendees
Getting input from your team before the retreat can make a huge difference. Here’s a simple approach to gathering pre-retreat information:
Send out a basic feedback form to your executive team well in advance (Google Forms work just fine!). This isn't just about sorting out the practical stuff like meal choices or room requirements, though that’s part of it.
You’ll also want to ask your executives to share what kinds of issues they wish to cover during the upcoming executive team retreat, what leadership development sessions they’d like to experience alongside other executives, and how they’re feeling about the company overall.
Example prompts to get the basics right:
Do you have any food allergies or dietary restrictions?
Do you have any specific needs for accessibility?
Are there any dates you absolutely cannot attend the retreat?
Beyond logistics, it's also a chance to see how everyone’s feeling about their work and the company. Ask questions that measure their sense of connection with their team, their views on the company’s direction, and their personal career growth.
Here are some sample questions to consider:
How connected do you feel to your teammates and leaders?
How optimistic are you about the company’s future?
Do you believe the company lives by its values?
Finally, get their thoughts on what they’d like to achieve during the retreat.
Find out what issues they think need addressing, what skills they want to build, and what kind of activities they'd enjoy. After the retreat, you can ask for their feedback on how it all went to make the next one even better.
Book An Inspiring and Cost-Effective Offsite Venue
Choosing the perfect venue for your Executive Team Retreat is a critical decision because it serves as the backdrop for your gathering.
It should be inspiring for your executive team if you’re looking to spark creativity, no frills if you’re seeking to imbue frugality, close to customers if you’re trying to incorporate more connectedness with the market to your business, etc.
To secure an inspiring and cost-effective venue, it's essential to consider factors such as location, ambiance, size, flexibility, and available amenities (such as meeting space, Wi-Fi speed, and activities).
While Offsite provides end-to-end offsite planning services to hundreds of remote and hybrid companies (like Buffer, Webflow, HiBob, Hampton, 15Five, Linear, Metabase, LinkSquares, Rattle, Airbyte, and others), we’ve also developed an Airbnb-style marketplace where you can discover the perfect venue for your offsite.
We’ve partnered with hundreds of boutique hotel, resort, and venue options around the world, which you can search for free once you make an account at offsite.com.
We streamline the booking process, helping you send requests for proposals (RFPs) out automatically to our hotel partners, processing their proposals for you within 24-48 hours in a majority of instances, and clarifying contract terms while saving you 20% or more on room blocks, meeting space, AV, and more.
You can compare venues, invite your colleagues and/or managers to view venues and profiles with you, and ultimately book your offsite venue directly through the platform.
Finally, expert assistance is only an email away if you want help making the best choice to meet your company’s specific needs for your upcoming Executive Team Retreat.
Develop An Agenda Focused On The Business Objectives For Your Offsite
Take your objectives, as well as relevant feedback from your team, and craft an agenda that balances key work sessions, fun team-building time, and “flex time” to relax.
You may follow a system like the Entrepreneurial Operating System (EOS), Scaling Up, or another business methodology that has the basic outline for executive team retreats.
If you do…great! That will give you the basic framework for an agenda (as will our template below), and you can plan activities, meals, and travel around those sessions.
Below, I’ve linked to our Executive Team Retreat Agenda Template.
One of many session ideas we recommend to clients is the “Vision/Traction Organizer” from EOS.
Over 90 minutes, you and your executive team can develop an inspiring 10 year vision for the company, ultimately connecting your upcoming quarter and/or annual planning efforts to “bigger picture” thinking you should want your executive team to have in mind as they help you steer the business.
We wrote detailed “facilitator notes” for this session here.
(Email me with feedback about this article, The Offsite Blog, and the facilitator notes above! Are these helpful? What else do you want to learn? We’d love to know…)
Assign “Pre-Work” To Attendees
Before the retreat, it’s vital for your leaders to prepare their contributions.
After all, your top executives will be at an offsite for 2 or 3 days instead of working with their direct reports or otherwise operating their departments.
Effective “pre-work” will ensure much greater ROI from your executive team retreats, and preparation should be done with the CEO’s guidance (or review of the most senior leader attending the meeting, like a Board Chair), to align on the strategic themes and OKR (Objectives and Key Results) development that will be discussed.
This strategic pre-work helps streamline the retreat by aligning the leadership’s presentations with the company’s strategic direction. It also allows you to:
Ensure presentations are data-driven and relevant, incorporating recent analytics and research pertinent to the strategic initiatives being discussed.
Prepare any specific materials, such as reports or case studies, that will support the strategic discussions.
Anticipate the kind of discussions and workshops that will be most beneficial to work through in-person, in real time with your executive team at the offsite.
Here’s how to set up effective “pre-work”:
Inform the leadership team about the retreat's strategic focus weeks in advance, encouraging them to gather pertinent data and insights to support their strategic planning suggestions.
Organize sessions for quarterly/annual retros, strategic planning for the upcoming quarter/year, and long-term vision-setting so that each conversation occurring during the offsite will be high ROI.
Set up a timeline for attendees to submit their “pre-work”, allowing for thorough review. This guarantees that everyone is prepared before the meeting.
By focusing on these strategic elements, you can ensure your executive team retreat is not just a meeting, but a turning point for your company's future success.
During The Offsite
In a perfect world, most of the logistics will sort themselves out ahead of your Executive Team Retreat.
If you are a Chief of Staff, Executive Assistant, People Leader, or even a CEO reading this, and want to fully participate in your Executive Team Retreat as an attendee, consider hiring a company like Offsite or working with a “day-of” coordinator at minimum (like a wedding planner!).
If you’re a Chief of Staff or EA attending an Executive Team Retreat, and you do not have outside support, it is possible that your main objective during the Executive Team Retreat will be to ensure everything runs smoothly.
Here are some tasks to keep in mind during the Executive Team Retreat:
Venue Coordination - some collaboration with your hotel and/or meeting space provider may be necessary to ensure all gathering spots are set up to your liking.
Technical Setup - you will likely oversee AV equipment and connectivity, working with your hotel and/or meeting space provider (possibly third party providers as well) to minimize the risk of technical glitches during the work sessions of your Executive Team Retreat.
Attendee Experience - you will largely be responsible for enhancing the overall participant experience. This includes providing resources, materials, and communications to keep attendees engaged and safe throughout the offsite.
Troubleshooting - during the Executive Team Retreat, you will act as the troubleshooter, ready to address any unforeseen issues or concerns that may arise. Quick problem resolution is vital to maintain the event's flow and minimize disruptions. Take the pressure off your shoulders, though. If you’re “chill” in handling unforeseen circumstances, your colleagues will be chill, too.
Many People Leaders find the weeks leading up to an Executive Team Retreat to be stressful, especially if you don’t have outsourced support. However, your colleagues will thank you tremendously for your efforts, and your company leadership should value and acknowledge your work as well. You did it!!!
Turning Insights Into Actionable Plans
The true measure of a successful Executive Team Retreat lies in the follow-through. After the offsite, it's time to transform those great ideas into tangible results.
Start by gathering all the ideas and discussions from the retreat. Organize a debrief session with key participants to prioritize the initiatives that emerged. Use criteria like strategic importance, feasibility, and potential impact to identify which ideas to implement first.
Assign one of your executives to each top-priority idea. This creates accountability and ensures someone is responsible for moving the project forward. Set clear deadlines and milestones for each initiative to maintain momentum.
If relevant, communicate the executive team’s findings (such as quarterly or annual plans, new company values, etc) to the wider organization.
Schedule regular check-ins to monitor the progress of these initiatives, even if you have quarterly Executive Team Retreats. These should be short, focused check-ins to address any roadblocks and evaluate progress against the set milestones.
(For what it’s worth, we do this every two weeks with our leadership team at Offsite, and our leadership team meets at an offsite quarterly.)
Want More?
I could write for days on how to plan an effective Executive Team Meeting, or really any type of offsite.
Every company is different, and so the team at Offsite is committed to being a resource for you as you work to ensure your team(s) remain agile and ready to tackle whatever problems and opportunities come your way.
Email me anytime at jared@offsite.com, or visit offsite.com for client case studies to see how other companies are planning their offsite cadence.
If you haven’t already, subscribe to The Offsite Blog below for agenda templates, budgeting spreadsheets, and more thought leadership like this post around offsite planning, remote work, increasing employee engagement, and more.
And of course, when you’re ready to plan your 2024 Executive Team Retreats, make a free account at offsite.com to search our curated marketplace with hundreds of amazing offsite venues, 20%+ savings on room blocks, meeting space, and more.
Plus, we offer end-to-end offsite planning services if you want a “done for you” experience. See why companies like Buffer, Webflow, 15Five, Linear, HiBob, Metabase, Hampton, and others trust Offsite for their team retreats.
Thanks for reading!
-Jared
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