Ultimate Offsite Insight #2: The Importance of Date Selection
The first installment of Ultimate Offsite Insights had to do with finding your offsites purpose; Why this should be your 1st step, why it’s so important, and then I included some best practices for identifying your events purpose.
The process for finding your offsite’s purpose is the same no matter the size of your offsite. This is not the case for the rest of the planning process, including today’s step: Date Selection.
That’s why before I proceed with my advice for this step, I felt it was important that I explain how I classify small, medium, and large groups:
Small Teams: 5-25 people (p)
Medium teams: 25-75p
Large teams: 75-150p
There are, of course, extra large groups, (150+) but I feel the guidance from the large teams can be scaled to fit. If you have any questions on how to do that, you can always shoot me an email from my Let’s Chat page. 😀
Okay, with that said, let’s jump into today’s Ultimate Offsite Insight…The Importance of Date Selection.
The Importance of Date Selection
You might be surprised to find that picking a date for your offsite is one of the tasks organizers find the most stressful, especially if they have large teams. The dreaded date dance doesn’t have to be a source of frustration and anxiety. In most cases, the reason people find this task so difficult is because they are simply being too flexible with the options.
In my humble opinion, there are really only two ways to efficiently pick a date for your offsite, but several ways to funk it up. Let’s go over the how to do it first.
How to pick dates the LL way
1. Select Date Ranges: There will likely be a few people that must attend your offsite, such as managers or session leads. Follow these steps to acquire your date ranges:
Get key players availability or preferred timelines first. Depending on how many key players you have, you could poll them or just have them DM you their availability via slack or email. Do this without looping in the rest of the team. They’ll know soon enough. 😀
Create an availability matrix: Either use the poll you sent out or collate the availability you received into a spreadsheet to share with only the leaders whose availability was submitted. Expert tip: Everything should be done in full transparency. This will help avoid a painful back & forth.
Cross-check that availability: Now use that matrix to identify 2 or 3 coordinating date ranges. Share these ranges with the leaders for their approval.
Send out a survey to attendees: Once you have manager approval send the survey to the attendees. I think it goes without saying, you should only include the identified date ranges in the survey. 😄 Expert tip: I use google forms for this survey, and it’s never more than 3 questions. Name, Preferred Date Range selection, and their back-up selection.
The date the majority of the team can attend is obviously your winner. This is the process I use most frequently, but it really only works for small and mid-size medium teams. Once you get over 50 people, it’s no longer efficient to poll for dates. (More on that “why” in the “How not to do it” section)
2. Events Schedule: When you’re doing your annual planning for the upcoming FY, also create an annual event schedule. Identify date ranges in advance for all your IRL and virtual experiences. You don’t have to pick exact dates, but identifying how many you intend to have and what month makes the most sense to have it in, is a good start. This accomplishes so many things for so many people:
Leadership can properly align roadmaps with IRL connection moments. Making for more purposeful offsites.
Current team members can pinpoint the events they can attend, and adjust for the ones they can’t. This communicates thoughtfulness towards maintaining their work/life balance, among many other positive messages.
New team members have travel expectations set from the moment of hire. This speaks volumes about the importance your company puts on transparency and connection.
Workplace & Operations teams can be well prepared to host, as this schedule can help to inform their own workplace calendars. For example, planning their monthly happy hour on the day the most teams will be visiting the office.
Offsite planners & managers will have the runway they need to plan the most meaningful events. Not to mention how much stress it relieves not to worry about picking a date.
Honestly, these examples are only the tip of the iceberg, when it comes to the benefits of an events schedule. Not only does it make every event feel more intentional, but it has positive effects in all areas of the company, including financially. Simply put, it pays to plan ahead.
How NOT to pick dates
Okay, I’m gonna assume the majority of people reading this have a lot of experience with date selection. You might’ve even thought my above suggestions were kinda obvious. However, I know there are a fair amount of you who are currently pondering this question…
“I do both those things, and somehow I still get pulled into the dreaded date dance. What gives?!”
Well, in my experience, you probably made one of these common missteps - a.k.a How not to pick a date:
Asked the entire group at once: Classic mistake of well-meaning, democratic managers. While we appreciate your desire to make it a group decision, this approach almost always ends up in chaos. 1000 dates are suggested, and you end up with more blackout dates than availability. Unless you are a super small team, like 5 people, never make it a group effort.
Discussed over Slack or email: I don’t think I have to explain how freaking confusing those convos can get. So many threads and suggestions; everyone voicing all the reasons why this or that date doesn’t work. It ALWAYS a mess. Do yourself a favor and just send a survey. You can then organize that information on your own, and only share the dates with the team once the decision is obvious.
Tried to please everyone: It is rare that you get 100% attendance on teams over 15 people, and that’s okay. If necessary, you can find intentional ways to incorporate those who cannot attend. Trying to move around dates to accommodate everyone is a frustrating practice.
Offered too many options: At most you should offer 3 date ranges, preferably in the same quarter. Like “too many cooks in the kitchen,” the same can be said “for too many dates on the calendar.” Besides, no matter how many date ranges you throw out it always comes down to 2. Why not just start there?
Didn’t communicate black-out dates upfront: Not everyone celebrates the same holidays. So when you are asking for availability for a certain time frame, make sure to include a list of black-out dates for the leaders to consider in their responses. Otherwise you chance having to repeat the process when someone books right over a holiday weekend. That said…
Offered dates on/near holiday weekends: This might seem like commonsense, but I’m not talking about obvious holidays, like Christmas. For example, a manager is struggling to find available days in June for their offsite. They finally find a few open days, but the last day of the offsite would be the Friday of July 4th weekend in the US. Doesn’t seem like a big deal, but trust me it’s a very inconvenient date for a whole lot of people. Offering dates like this will undoubtedly affect your attendance rate. Try to avoid any of your offsite days falling on, or within 1 day, of a holiday or long weekend.
Storytime
In January 2022 the world was just starting to regain some normalcy. Atlassian had officially opened up travel after 2 ½ years, and people were starting to have IRL experiences again. As the Trello employee experience manager, I was eager to start designing events for our teams. However, after what we had just been through, there were bound to be a myriad of emotions about IRL experiences - anxiety, excitement, fear, anticipation; my teams were going to feel all the things. In order for the excitement to outweigh the anxiety, I couldn’t just throw dates out there and leave planning to team managers. I had to take a full-service concierge approach. If I was going to organize 35+ events from top-to-bottom, I needed an events schedule.
As I start all event design, I Identified our purpose first. It felt pretty obvious: Providing meaningful reconnection opportunities for our teams after Covid. However, I couldn’t take a hard line with just providing only IRL experiences. In order for this programming to serve its purpose, the teams had to have options. Therefore I designed the programming so they had a choice between having a virtual teambuilding event or coming to NYC for an IRL offsite.
Considering these options, the word “offsite,” wasn’t really speaking to the purpose. Not everybody was going to be “offsite,” after all. So I decided to rebrand and I called this programming Team Times.
Now, there is a ton of detail that went into this program design, but this Storytime is supposed to speak to today’s Offsite Insight. For this reason, I’m going to skip ahead a bit and focus only on my date selection approach. Maybe one of these days I will do a Gather Guide all about Team Times. 💡
Since this was a full team program it was definitely considered an Extra Large group. About 310 internationally distributed people. Now, usually I wouldn’t mess with date ranges in this case. For EXL groups I just consult leadership and make an executive decision on date. However, the climate was different for this one. I felt it was pertinent to the success of the program; and again to help excitement outweigh anxiety; that timing felt flexible and gave the impression of a group decision. To achieve this, I used a mix of an Events Schedule and Date Range Selection.
Events Schedule: Due to the budget I had been allocated for this program, I had to complete all Team Times by the end of FY22. For Atlassian that was July 1st. Which meant I had Q3 (Jan-Mar.) and Q4 (Apr-June) to schedule all 35+ virtual and IRL events. Since it was already the middle of Jan. and any good IRL experience needs at least a 2 month runway for planning, I decided on the following structure:
Virtual Team Times would happen towards the end of Q3 - Late Feb.- end of Mar.
IRL Team Times in NYC, would occur in Q4 only - Apr.- June
This process identified my date ranges and led into the 2nd part of my design.
Date Range Selection: Before I released the date options in my comms, I first had to know who was doing what. I created surveys for the managers to share that anonymously polled their teams for their preferred offsite model - Virtual or IRL. Expert tip: I designed the surveys to be anonymous because I didn’t want anyone to have to explain why they didn’t want to travel. None of our business . Also, calling out those who preferred virtual risked alienating them from team members who wanted to travel. 😉
Once we knew what model the team had chosen, I had the managers share a second survey that identified the date ranges available to them based on their choice.
By the end of January 2022, I had a completed events schedule. 20 teams chose a virtual Team Time, with all events provided by the amazing TeamClass! 🙌; and 15+ teams were coming to NYC for a kick-ass IRL Team Time.
Team Times was a defining program in my career. I designed, organized, and executed every, last detail. I would have never been able to pull that off if I hadn’t approached date selection with a strategy.
Picking a date is much more important than it seems. If you’re still not convinced, think of it this way…
The process of selecting a date is usually the first comms touchpoint. If you go in all flaky, throwing out options with no rhyme or reason, and bending to please everyone…that disorganized chaos is their first impression of your planning style. Leaving most people thinking…
“Omg, if we can’t even decide on a date, what’s the offsite gonna be like?!”
But, if you go in with a plan, giving clear leadership, and setting boundaries, that first impression goes from…
“Omg, I’m scared…” to “Omg, that was so organized! This offsite is going to be awesome!”
Date selection is an often overlooked opportunity to start establishing trust with those you're planning for. Trust fuels engagement and authentic connection. Cultivating it early on will only level up every event you design.
Moral of the story: Every element of offsite planning matters. Don’t sleep on any of it.
