By Ellie Hearne

"It was mind blowing to realize the number of misunderstandings that arose from little things - easily fixed and preventable things, too. Careless emails, offhand remarks, or simply different approaches to the same challenges. We'd just never made time to address them." - VP of Marketing, large SaaS company

The context was that his team had just completed a day-long offsite meeting which I had facilitated. In my experience of such days, every type of group - no matter its industry, age, or makeup - benefits from a team-wide check-in from time to time. A check-in on goals, culture, communications, and all the other aspects of working well as a unit.

You likely spend more waking time at work than you do at home, and business is personal. Emails sent in haste, bad days, remote meetings, individual burnouts, "watercooler" gossip - they're facts of life for so many of us.

Maintaining perspective and working well together against the backdrop of that kind of noise can be challenging. Investing a few hours (or days) in an offsite or retreat can pay dividends in morale, productivity, and improved communications.

But it's not just about feelings and job satisfaction. A strong offsite will help you define and move closer to achieving your company's goals.


Why have an offsite?

A good offsite meeting leads to a happier, more productive team. They get to know one other better in the process and emerge more bought into the company or team vision. Problems are solved, bonds are strengthened, and culture is solidified and improved. To quote another senior executive whose offsite I ran, "This is a must for any team."


But how do you run a good offsite?

With a few years of offsite experience to my name, I've compiled some guidelines.


1. Be inclusive, without breaking your budget

Offsites don't have to be expensive or even held offsite to be successful.

If you can't afford to bring your whole team, re-think that luxury resort. As your team grows, it's more important to include everyone than to wow a select few with a ritzy destination. 

Ask any experienced, successful leader: some of the best and most surprising ideas come from newer or more-junior team members - fresh perspectives are often necessary to solve persistent challenges. Inclusivity also shows those newer recruits how things are done and the culture you're trying to instill and develop.

Wherever you hold your offsite, include everyone you'll be rewarded with loyalty, boosted morale, and new ideas.


2. Break the ice - trust falls optional

Open the program with something that gets people out of work mode - and ideally helps them learn about each other. Personality profiling, "two truths and a lie," twenty questions - the options are many and don't have to be expensive or time consuming. Sometimes an elaborate game or activity can become more of a distraction than a boon.

A strong offsite will likely include a few tough conversations, so it's important build in some lighter moments. You're asking people to put in a little more - work on weekend perhaps or travel out of town and/or a disruption to their routine - so remember to have some fun and reward people for investing their time and ideas.


3. Bring an agenda

Plan on having a plan. It'll make the difference between a fun weekend that's soon forgotten, and one that leaves a lasting, positive impact on the company and team. 

What are your goals? To solidify a founder-driven culture as your company grows? To define the next quarter's KPIs? To improve communications among teams or remote workers?

If you're unsure, ask yourself what a successful offsite might look like. That's your starting point. Figure out your goals and build your agenda accordingly.

Make its creation a team-led process. If your people aren't bought into the agenda, it will only get derailed anyway.


4. Drive towards action - and encourage discussion

Once you have an agenda, keep it on track. An offsite will quickly present all the challenges of a stale weekly meeting if the same people take over while the wallflowers shut down.

Call out the people who don't typically contribute (perhaps giving them a heads-up beforehand to lay the groundwork). Politely jump in when someone is dominating discussion and pivot back to the topic at hand. Remind people throughout of your common goals to keep everyone bought into the discussion. 

Ask questions. Open, closed, obvious, and tough. You learn nothing if you're the only one talking, so be sure to pull diverse voices into the dialogue whilst drawing them out on tougher topics and driving towards action. Encourage meaningful conversation and play devil's advocate where necessary - your team is counting on you to keep the discussion fruitful and on track.


5. Define next steps

Close with a summary. What are the next steps? Who will own each item? When will you do a progress check?

This closing piece is often an afterthought, but it shouldn't be. Defining clear outcomes and next steps will ensure your offsite leads to positive changes.


5. Follow-up

This helps make the difference between an impactful insight and a costly waste of time. Consider using your next team meeting for a brief post-mortem. What worked? What didn't? Check in on the offsite action items and hold individuals accountable - yourself included.



To close, another client sums up her offsite experience: "I was skeptical going in, but I quickly saw the value. It occurred to me that as a team we're hardly ever all together and we're rarely in a position to discuss culture or communications. It took work to make the meeting a success, but even a few months out we're still feeling the benefits."



Ellie Hearne is a leadership-communications expert and founder of Pencil or Ink. Over the years she has facilitated offsites and workshops for teams at Google, Spotify, Starwood Hotels, Love Child, Oracle, Morgan Stanley, BlueCrest Capital, and numerous small businesses and startups. Ellie can be reached here, here, and here.