Issue 21: The Chief of Staff's role in Offsite Planning & Execution
An unofficial job of the Chief of Staff: planning and executing offsites
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.
For those who want to outsource their offsite planning, Offsite is also providing 20% off your first contract with them if you mention “Ask A Chief of Staff.”
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!
So You’ve Been Asked To Plan An Offsite…Now What?
As Chief of Staff, you’re already working 3️⃣ jobs in 1️⃣. Likely, you’re working for a principal who puts in demanding hours themselves and expects you to simply “figure it out” whenever there’s a job to be done.
Your latest task? Planning a leadership team retreat, board meeting, or *gulp* an All-Hands retreat for the entire company. You’ve probably been left with limited information about the goals, budget, and expectations for the offsite, which might make the task at hand even harder to manage. Maybe you’ve never planned an offsite before, or the team has grown considerably since you last took on this job.
In this week’s issue, we’ll be giving you a framework for saving time, money, and stress in planning your company’s offsites.
📝 Set The Offsite Objectives With Your Principal
As a Chief of Staff, the first step in planning a team retreat is to establish clear objectives with your principal. Identify what you aim to achieve with the offsite—be it team-building, strategic planning, skill development, celebration of a major milestone, or a few different objectives. However, we suggest no more than 3️⃣ objectives so as to keep the offsite focused and not try to accomplish too much in a limited number of days.
These objectives will serve as your guiding light throughout the planning process and ensure that the retreat aligns with the broader goals of the organization. It will also help you determine how much to invest in the offsite and provide a framework for determining if the offsite was successful or not.
You want to get a high-level budget, objectives, venue search parameters, special requests, and other feedback from your principal before you start planning, or you will be faced with endless delays when seeking approvals, dead ends on your hard work, and less options for venues and activities.
⛺️ Secure Your Venue (and Watch Out For Hidden Costs 👀 )
Choosing the right offsite venue is crucial. Look for a location that offers a conducive environment for both work and relaxation. Consider factors like proximity to nature, amenities, comfortable accommodations, and the ability to accommodate various team sizes in meeting spaces, breakout rooms, dining establishments, and activities on-property.
Over 50% of your offsite budget will be spent on lodging and travel to/from your chosen venue. Where you decide to plan your offsite is the single most important decision you’ll make. We recommend using the free “forecast” tool at AllFly to determine which destinations will be most cost-effective for your team.
You can also create an account at offsite.com at no cost, and with no credit card information upfront, to search through hundreds of curated offsite venues where we’ve pre-negotiated 20% or more off room blocks, meeting space, resort fees, food & beverage, and other boutique options.
Be on the lookout for any additional clauses, costs, and fees that seem out of place. Negotiate everything. Then, sign the contract and share the exciting news with your team: You’re going on an offsite!
📋 Send Your Team A “Pre Offsite” Feedback Form
Just as you would manage your principal and get their feedback as early as possible in the offsite planning process, you should do the same with the rest of your team.
Send one pre-offsite feedback form to your team in order to learn about their:
Dietary preferences and/or allergies
Travel sensitivities and/or accommodations needed
Preferred activities (and/or how active or relaxed they would like activities to be)
Preferred agenda items (or what type of content they’d like to receive at the offsite)
Other logistics as needed (such as comfort level in renting a car and driving other colleagues, T-shirt sizes for swag orders, etc).
Plus, you can use pre-offsite feedback forms to ask for an employer Net Promoter Score and other employee engagement metrics to get a pulse on the company. You could ask questions related to your business objectives for the offsite. For example, if you’re seeking to achieve greater clarity on company-wide objectives, you can ask, “On a scale of 1-10, how clear are our company-wide objectives?”
Asking for the same scores after the offsite will also give you more data to bring back to your principal in determining the ROI for your offsite. You can easily collect this information with a Google Form or, if you’re looking for something a bit more robust, Airtable.
🗓️ Plan An Engaging Agenda
Crafting an engaging and purposeful agenda is a hallmark of a successful team retreat. Work closely with the team leaders and stakeholders to determine the ideal balance of activities, workshops, and downtime.
Read the input from your pre-offsite feedback forms to understand team preferences, ensuring activities are inclusive to people of different physical abilities and interests. Include sessions with everyone in one room, breakouts where you pre-determine who goes where (to increase cross-department collaboration and break up silos), and choose-your-own-adventure options.
Consider bringing in outside speakers and facilitators, especially if you’d rather focus on enjoying the experience yourself, or if you and your principal are inexperienced at running certain types of workshops like OKR planning or feedback listening sessions. Bringing a keynote speaker could be a great way to set the tone for the offsite and also badge the event as “not your typical meeting.”
💸 Manage The Offsite Budget and Team Resources
A successful offsite requires upfront budgeting, as well as management of your team’s time if you’re asking leadership to prepare presentations, give talks, or lead breakout groups. As the Chief of Staff, you’ll need to take charge of budget allocation, expense tracking, and vendor management. Optimize your resources by seeking cost-effective options without compromising on the quality of the retreat.
For example, if you are running short on budget for activities, you might consider a volunteer outing that will cost little, yet still provide a unique shared experience for attendees and photo opportunities for the “employer marketing” you do surrounding the offsite.
If you are planning the offsite with additional support from an executive assistant, someone with an operations role, or a company like Offsite, then your job is to “architect” the experience and provide budget parameters around certain decisions. That way, when you outsource the research to others, they can provide you with great options for you to say “yes” to quickly, ensuring those options remain viable and everyone’s time is used effectively.
👀 Oversee Communications and Triple-Check Logistics
Keep all stakeholders well-informed about the retreat details, including the agenda, travel arrangements, accommodation, and any pre-retreat preparations. Namely, this includes your principal, your offsite venue, and other leadership that is being asked to approve budgets, prepare materials for the retreat, and otherwise ensure the objectives for the offsite are met.
When communicating with employees, they will want to know details in advance surrounding travel policies, whether or not they’re allowed to bring a “plus one”, any expectations surrounding time spent with the team during an offsite (compared to meeting up with friends or family if you’re hosting an offsite in a major city), where to share photos, where to upload notes from the offsite, and more.
With regards to vendors, triple check that they will show up on time, have all the details for your offsite, know about your team and objectives in advance, know of any last-minute agenda changes, and have emergency contact details with you or an outside facilitator.
Utilize various communication channels, such as email, Slack, and team meetings to disseminate information and address any questions or concerns promptly. Document a “run of show” in case you get sick, your travel is delayed, or some other issues arise and you are unable to continue executing the offsite logistically: Over-communicate.
🎤 Facilitate The Offsite (and/or Coordinate With Internal and External Speakers and Facilitators)
If you utilize internal speakers (such as executives) or external speakers & facilitators, you will play a key role in identifying and coordinating with guest speakers and facilitators for the retreat. You might engage key clients, subject matter experts, or industry leaders who can share insights, provide inspiration, or conduct skill-building sessions.
Provide these individuals with your “run of show” and let them know exactly where to be (and when), unless you have event production staff taking care of this for you.
If you choose to facilitate the offsite yourself, be mindful of time and keep everyone on track. Your job is to keep everyone on-agenda so you can accomplish the business objectives for your offsite while ensuring everyone makes it to activities, meals, and breaks on-time to keep everyone engaged.
If something goes wrong, stay calm and use some of your break time to catch up, outsource problem-solving to your venue or other dedicated support, and be positive. Others will follow your lead.
🙋🏻♀️ Reconcile Bills, Gather Feedback, and Evaluate Success
Once the offsite concludes, it’s crucial to evaluate its success and gather feedback from the participants. Send a post-offsite feedback form for general feedback as well as data points to get the “before and after” for any metrics you surveyed for in your pre-offsite feedback form.
Ensure action items that were committed to during various sessions are documented in Asana, Notion, or whatever project management tools and company wiki you keep. And don’t forget to send follow ups to the relevant parties.
Triple check all outstanding bills from your venue and other vendors, and then pay everyone promptly. Reconcile your budget and let out a big exhale: You pulled off an epic offsite!!!
⏰ Determine A Cadence For Offsites In The Future
One of the best ways to leverage offsites for employee retention, engagement, and alignment (especially for remote and hybrid teams) is to develop a regular cadence for offsites.
These should not be one-off experiences. They should be predictable so you can plan in advance, utilize feedback from previous offsites to make future experiences better for your team, and increase the ROI on each offsite you host. With a regular offsite cadence, you and your principal can also plan for the appropriate staff to take on this responsibility in the future, whether you continue to plan offsites but reduce scope in other areas of your job description, bring in other team members to support you, or choose to outsource offsite planning to a trusted resource like Offsite.
➡️ In conclusion, planning an offsite takes a lot of work! As Chief of Staff, you play a critical role in ensuring its success.
From setting objectives and designing the agenda to managing logistics and evaluating outcomes, a Chief of Staff is instrumental in creating a transformative experience for the entire company.
Hope you’ve enjoyed the latest issue of this newsletter and we’re looking to you for future newsletter topics! If you have any questions around being a Chief of Staff, tactical takeaways that you can apply, or other curiosities about the Chief of Staff role, submit a question below and we’ll answer it in a future newsletter issue:
📣 In case you missed the announcement, Ask a Chief of Staff has reopened our waitlist and is accepting new members. We’ve also introduced a new “Aspiring Chief of Staff” membership tier for folks who are looking to focus on their job search and transition into a Chief of Staff role!
If you’re an aspiring, current, or former Chief of Staff, we’d love for you to join us in our Slack community to share best practices and knowledge with each other.
🎥 Upcoming Events and Workshops:
July 13th: The Anatomy of Great Offsite
July 19th: Moving from Imposter Syndrome & Inner Critic to Inner Guide
July 26th: {IN PERSON EVENT} SF Chief of Staff Happy Hour (registration must be approved to attend)
As a reminder, events and workshops are free for all Ask a Chief of Staff community members (including our newest Aspiring Chief of Staff tier!) 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:
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👋🏼 Until the next issue,
Clara
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