How to thrive at your offsite

2 days at an offsite can accelerate your career – don’t waste the opportunity.

👋 Hi, it’s Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.

Last week, we had our second offsite of the year in New Orleans. We’re fully remote, and most days, it's net-positive. But twice a year, we get the whole team together in person to amp up our collaboration, knowledge sharing, and team bonding.

Offsites are a big investment – of time, money, and energy. They come with pressure for the leaders planning the event (make it worth that investment) and employees attending (make a good impression in a new environment). They can be stressful, anxiety-inducing, inconvenient, or all of the above.

I think our offsite last week was our best yet. Some of that came down to planning (we picked a new city, had a great hotel/working setup, and planned good sessions). But a lot of it also came down to how individuals on our team showed up. 

As the leader, I noticed this – who made an impact in big and small ways. As an offsite attendee, that should be your goal: the offsite is a better experience because you were there.

If you do this, you’ll get more value out of the sessions yourself, and make a lasting impression on your boss and colleagues. So fresh off our offsite, here are our tips for how to do this, based on our observations as leaders and a quick survey of our team. 

– Taylor

P.S. We’re running a private 1-hour workshop on using AI as a thought partner on next Thursday, October 17, from 5-6 p.m. ET. It’s for Personal Math subscribers only – sign up here.

Why offsites matter

It’s easy to complain about offsites – they require travel, arranging childcare, finding time to get your day-to-day work done, all-day sessions with your team (tough for introverts), and doing it all in an unfamiliar environment with shitty coffee. 

But as a leader, they’re important – you’ve invested time, energy, and money into the offsite, so you want it to go well. And if you’re at a remote or hybrid company, your CEO or executive team probably also believes being in person is critical for the team’s success. 85% of leaders say the shift to hybrid work has made it challenging to have confidence that employees are being productive.

Therefore, leaders are paying attention. So offsites are a great way to shift their perception of you from a high-potential IC to a leader. If your company is remote, you have 1-2 times a year to make this impression. Don’t waste the opportunity.

Your offsite playbook

In short: A successful offsite starts before you get there and doesn’t end when you get on the plane home. Here are our tips to getting the most out of the offsite, before, during, and after you’re there.

1. Invest 30 minutes to maximize three days

It’s natural to wait until the last possible minute (the first session) to fully engage. Resist this urge – spend 30 minutes on the plane and do two things:

Reflect on the business – Offsite sessions usually require you to zoom out from your day job. Avoid scrambling for something to say by thinking this way beforehand. To prepare, you can ask yourself three questions:

• What am I most proud of that we’ve accomplished as a business this year?

• What’s something I believed at the beginning of the year that I’ve changed my mind on?

• What’s the most important thing we need to prove as a business next year?

Set a personal goal – choose one personal outcome that if accomplished, will make the offsite worth your time. Is there a problem you’ve been grappling with that could get solved? Is there someone on the team you want to know more? I love this quote from one of our team members: “I think having the goal of making two new/closer friendships really helped. Made it feel much less daunting, even within a small company, to have a specific and achievable goal."

You’re about to spend 3 days of your work week at the offsite (1% of your year if you work 45 weeks a year). Spend 30 minutes and plan your time.

2. Participate, don’t observe 

Resist the urge to do work while you’re in sessions. When we surveyed the team on the best thing they did to get value out of the offsite, 39% said they did work in advance to make sure they were free for the sessions. This isn’t easy – as it often requires working longer hours before the offsite.

But leaders notice who’s actively participating and who’s checked out during sessions. Closing your laptop and adding value to a session helps you stand out, and makes the session better for everyone. If you’re too busy to participate, don’t go. It’s better (for you and the team) to not attend than sit in the back and type on your computer the whole time.

3. Find small ways to help

Offsites never go 100% according to plan. There’s lots of moving pieces and things fall through the cracks. Be the person who pays attention, and volunteers to help when it's needed. Find a whiteboard or easel to write on. Get extra water for others when you get your own. Welcome the new member of the team who’s not talking to anyone yet. 

When we’re on zoom, we’re more one-dimensional. Getting together in person makes everyone seem a little more human – your boss, your colleagues, and your team. So leverage this opportunity, and find even small ways to show your humanity.

At our offsite, I was doing some filming, and forgot a black shirt to film in. Four people went through their wardrobe and volunteered their clothes. Two more volunteered to sit in on the session to help with a new filming style. I remember all of them. The little stuff goes a long way, makes the offsite run smoother for everyone, and helps you stand out.

4. Get out of your clique

The most common advice from our team post-offsite? Talk to someone you don’t usually talk to. “I sat next to someone I wasn't as close to, and it turned out to be one of the best decisions of the offsite.” 39% of our team said something similar to this – and we’re only a team of 25.

For better or worse, in-person interactions are more memorable than virtual ones. So don’t use the offsite just to interact with your existing work friends – be there person who initiates cross functional conversations, either in sessions or dinner. 

5. Own the follow up

A lot of plans and ideas get made at offsites that in reality, no one has time for. Be the person that leads the discussion after the offsite to agree what to work on and what to discard from the offsite. Reflect on all the ideas and energy from the offsite, organize it into potential projects, then convene your team and choose which next steps really matter. If you can’t lead that meeting yourself, suggest the idea to your boss or team lead, and get them started with a list of what you heard.

6. Don’t whine

Once you’re there, you’re there. Even if you’re stressed about the kids at home, your plane was delayed, the offsite is at the Airport Sheraton not the Virgin Hotel, save the complaining for home. 

Our Advice

Offsites aren’t going away – if anything, they’ll likely become more common. Other remote companies are like us – 43% host two or more retreats a year. So it’s in your best interest to learn how to show up and perform well in these environments.

Being a net contributor at the offsite doesn’t make up for not being great at your day job, but in a team of strong performers, it is one way to stand out. It’s a moment of differentiation – and one that takes some extra effort, but not much in the grand scheme of a year or career.

Have a great week,

Greg & Taylor