Issue 30: How to Leverage Strategic Offsites - Executive Team Retreats & All-Hands Meetings
A “Secret Weapon” for Chiefs of Staff leading Annual Planning, OKRs, and Employee Engagement Efforts
Welcome back, aspiring and current Chiefs of Staff!
In this week’s issue, we’re featuring a guest post from Jared Kleinert, Founder/CEO of Offsite. Offsite is the “go to” resource for any Chief of Staff planning a team retreat. They offer a curated marketplace with hundreds of offsite venues, all at 2️⃣ 0️⃣➕% discount for room blocks and meeting space, plus end-to-end offsite planning services for teams of 1️⃣ 0️⃣ to 5️⃣ 0️⃣ 0️⃣ attendees.
Click here to make a free Offsite account (no credit card required) and submit your first request for a spectacular offsite venue in a matter of minutes.
Disclosure - I’m an angel investor in Offsite, but only because I wish something like this existed when I was a Chief of Staff planning team retreats at Hugging Face!
*Interested in sponsoring a future issue of Ask a Chief of Staff, hit reply. Note, we’re already booked till next year!
Are you currently working on annual planning for 2024? Do you have a hand in creating OKRs each quarter, or ensuring the team engages with company-wide initiatives so they are completed successfully?
If you answered “yes” to any of the above, then you might consider strategic offsites as a “secret weapon” for getting your leadership team together regularly, working through pressing issues, and presenting a united front to the rest of your company.
In this week’s issue, I’d like to cover the 2️⃣ most strategic offsites you’ll plan throughout the calendar year, which are Executive Team Retreats as well as your All-Hands Meetings.
My hope is that you evolve from having to convince your principals of certain initiatives to running a well-oiled strategic planning machine among your executives that continuously drives happier employees, greater performance, and increased alignment across the company.
🕵🏻♀️ Determine Where Strategic Offsites Fit Into Your Rhythm of Business
As Ask a Chief of Staff has documented before, Chiefs of Staff play a key role in determining company strategy, communicating strategy through frameworks like OKRs, and ensuring execution of strategic initiatives.
You may have a rhythm of business already, outlining moments during the year where you’ll create, follow-up on, and revisit company-wide and department-level strategy.
At Offsite, for example, our rhythm of business includes:
Kickoff of annual company-wide goals and Q1 OKRs the first week of January
Quarterly OKR development the last two weeks of the quarter (for the following quarter) kicked off by a quarterly Board Meeting
Company-wide presentation of new OKRs the first week of each quarter
Mid-year opportunity to “upgrade” or change the annual goals, if needed, after the Q2 Board Meeting
Annual planning cycle most of December, for the following year
Leadership team meetings every-other-week to keep track of OKRs
Weekly All-Hands Meeting on Zoom for everyone to check-in on progress towards OKRs
Weekly 1-on-1s between managers and direct reports (as CEO, I do 15 minute check-ins on Mondays, and other department leaders run 20-30 minute meetings on Mondays or Thursdays with their teams)
Daily async check-ins on Slack using Geekbot
Based on this rhythm of business, we can plan strategic offsites, or offsites leveraged specifically for strategic planning.
For Offsite, this means two All-Hands meetings in person (one in January, and one in late June or early July) to kick off Q1 and Q3. It also includes quarterly Executive Team Retreats with our leadership team at the end of each quarter to finalize OKRs for the following quarter.
Based on your company’s size, it may only be feasible to do one All-Hands Meeting each year, in which case you’ll have to decide if an annual kickoff or a Q3 offsite is most strategic for getting everyone at your company together in-person. But, Executive Team Retreats should be held quarterly or layered into your rhythm of business wherever they’ll be most strategic.
💰 Plan Ahead To Save Time, Money, and Stress
While strategic offsites should be easier than other team retreats (like incentive trips, celebratory gatherings, or holiday parties) to justify with your principal, planning ahead will allow you to set (and keep) a reasonable budget.
Additionally, when it comes time to plan these offsites, you’ll be less stressed because venues can be booked ahead of time and attendance should be close to 100% if everyone has plenty of advance notice on offsite dates.
Once you’ve determined when you’d like to host strategic offsites, you can make a free account at offsite.com to search our curated marketplace with hundreds of amazing offsite venues around the world.
Within minutes, you can submit request to hotels, resorts, and other venues you think might be perfect for your All-Hands Meetings and Executive Team Meetings, and within 24-48 hours, you’ll receive detailed proposals with a breakdown of room block rates, meeting space costs, food and beverage minimums, activity options, and more.
Plus, with Offsite you’ll save 20% or more on these various budget items, giving you thousands (perhaps even tens of thousands of dollars) in savings that can be reinvested into flights, meals, and other costs associated with your offsites.
We even have a free budgeting template you can use as well: you can simply copy this spreadsheet for each offsite you want to plan in 2024 to get a high-level overview of your annual budget required to run your strategic offsites.
One of the benefits of planning ahead is you can tie the business objectives of these offsites (such as planning and rolling out strategic initiatives, increasing employee engagement and alignment, and solving the company’s most pressing problems) to the investment in retreats collectively.
With your principal, you can then determine if spending on certain elements of your retreat (such as outside speakers or facilitators, select team-building activities, or destinations and venues close to key clients or investors) are worth the associated costs.
In essence, your budget becomes a narrative of how much your leadership values setting and executing company-wide strategy, and your “pitch” to principals is that the use of these well-placed strategic offsites will yield high ROI because they will improve things like annual planning, OKR creation and execution, etc.
📝 Develop Intentional Agendas For Strategic Offsites
Your most frequent offsites (likely Executive Team Retreats) will have similar high-level agendas, providing you and your leadership team with the space to work through pressing issues in line with your company’s rhythm of business.
These executive team retreats are some of the most important gatherings at your company. While you want to be mindful of the budget associated for 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.
As a Chief of Staff, it’s important to define specific 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 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.
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.
Here, you’ll find our Executive Team Retreat Agenda Template which ties together many of these ideas. As you can see, most of your team’s time together will be spent in high ROI sessions like retros on previous quarterly or annual goals, planning for the upcoming quarter or year, and professional development that can have a meaningful ripple effect throughout the organization.
For your All-Hands Meeting, you’ll also want to be mindful of programming, as the investment of your team’s time is substantial. Your company’s culture is also on the line, so you want the experience to go well, leading to increased employee engagement, retention, and alignment.
Here is our All-Hands Agenda Template which, again, prioritizes strategic planning sessions, brainstorming, problem-solving, training, and other business-building “sessions” before determining meals, fun activities, and other logistics.
🙋🏻♀️ Ask For Feedback Before And After Every Offsite
One of the main benefits of planning your offsite cadence in advance is being able to track pre and post offsite feedback throughout the year.
At the start of the year, you can send out a basic feedback form to get logistics out of the way, asking questions like:
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 offsites this year?
What is your T-Shirt size (for swag)?
What airport(s) do you typically fly out of?
Then, before and after offsites, you can send additional feedback forms asking for feedback on certain sessions, employee engagement stats like an employer net promoter score (eNPS), and other prompts related to company-wide strategy and alignment.
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?
What strategic initiatives are most important to figure out for the upcoming quarter?
By sending pre and post offsite feedback forms throughout the year, you can get “smarter” with every offsite you plan.
Not only will you learn what types of activities, meals, and experiences resonate with your team, but you can develop sessions to work through the most pressing items of business, share feedback with your principals so they can stay connected to employee sentiment, and hopefully showcase that your offsites are leading to increased eNPS scores, employee engagement, and alignment across time.
📈 Create Momentum With Every Offsite
The real work begins after the offsite. As a Chief of Staff, it's your responsibility to capture the momentum generated and channel it into sustained action.
Strategy means nothing without execution, and one of the many benefits of strategic offsites is receiving team buy-in on bringing strategic iniatives to life in the days, weeks, and months following team retreats.
Begin by distributing a summary of the offsite's key takeaways and agreed-upon OKRs to all participants. This document should serve as a reference point for the upcoming quarters, a constant reminder of the commitments made and the goals set.
Next, integrate the outcomes of strategic offsites (such as the following quarter’s OKRs, or new company mission, vision, and values) into your company's regular reporting and review cycles.
This continuous monitoring ensures that the objectives remain front and center, driving frequent decisions and actions. It also provides a framework for accountability, allowing for course corrections and reinforcing the importance of goals determined at offsites.
Organize follow-up meetings virtually to discuss progress on strategic initiatives determined during offsites and address any challenges that arise. These check-ins should be an opportunity for collaborative problem-solving, ensuring that no team or individual feels isolated in their efforts to meet their key results.
Don't forget to celebrate the wins, no matter how small. Recognizing progress towards strategic initiatives fosters a culture of achievement and motivates teams to continue their efforts. Use company-wide communications, such as email newsletters or Slack, to highlight successes and learnings along the way.
Finally, announce upcoming offsites with excitement and give people something to look forward to once they accomplish their current initiatives. Strategic offsites can, and should, have time allocated to celebrating the previous cycle’s wins, ensuring everyone who attends your Executive Team Retreats and All-Hands Meetings feels excited about attending future offsites and continuing to create more momentum over time.
Leverage strategic offsites as a “secret weapon” in your rhythm of business and you’ll turn your organization into an unstoppable execution machine.
🤑 Last Chance to Participate in our Chief of Staff Compensation Survey
Calling all Current Chiefs of Staff! Do you know how your salary stacks up against other Chiefs of Staff with similar years of experience or stage of company? 💸💰
We’re running Ask a Chief of Staff's annual compensation survey for the second time to help bring some more transparency to this role and empower folks who are re-negotiating their salaries or stepping into a new Chief of Staff role.
The survey shouldn't take you more than 4️⃣ minutes to complete and results will be published in mid December ☃️ 🎁 All results will be anonymized and shared on this newsletter! Results from last year’s survey here.
🎥 Upcoming Events and Workshops:
November 28th: PowerPoint, Memos & Co: How to Master an Audience-Adjusted Narrative and Storytelling
December 4th: NYC Holiday Dinner Party [In Person, limited to 20 participants]
Free for AaCoS Community members but paid for others.
December 7th: Establishing a Learning & Development (L&D) Program
December 19th: Harnessing 2023 Reflections to Set Actionable Goals for 2024
As a reminder, events and workshops are free for all Ask a Chief of Staff community members and the recordings will only be provided to members. There is a suggested ticket price on all workshops on but the first 25 registrants can waive your ticket price with code ASKACOSREADER.
Additional Chief of Staff Related Reads:
The Chief of Staff Guide — Part 4: Career Path
How a Chief of Staff Can Help Your Startup
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👋🏼 Until the next issue,
Clara
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