In January of 2013, I made the decision to take our fourteen-person technology startup offsite for an annual kickoff meeting.  At just under $20,000, it was the single largest investment in a non-payroll item that I had ever made as the co-founder and CEO, and I had more than one person (outside the company, of course) tell me that I was being frivolous.

It was the best investment I could have made. In fact, the outing was so successful that we've done it every year since then. In January, we'll bring 140 people offsite and we'll kickoff what we all hope is another banner year company growth and development.

I've learned that there are four things that you have to do if you're going to run a successful all-company offsite, and one thing that you absolutely shouldn't do.

1. Invite everyone.

One of my goals in running our annual offsite is to build stronger relationships between teams that ordinarily don't work together. To accomplish this goal, it's critical that we have 100 percent attendance at the offsite; nobody stays back in the office.

"But what about critical customer support issues?" you might ask. My short answer: create a plan to deal with them such that everyone can be present and focused. It might mean your offsite takes place on certain days of the week, or during off-peak hours, but I can't stress enough the importance of having everyone present.  It sends the message that everyone in the company is critical to our success and we want you here with us.

2. Create activities that build trust and relationships.

At each of our offsites, I've kicked things off with a speech that lays out my goals for the offsite and sets up the agenda for the next two days. At the end of my opening talk, I've always laid down the following challenge: Do not spend time socializing with people with whom you already spend most of your time at work. It's your responsibility over the next 48 hours to seek out every person you don't know, introduce yourself, and learn one thing about them both personal and professional. 

Every year, I'm amazed at what happens when these incredible connections are made. Barriers are broken down, trust is built, and understanding and empathy are increased.  I think our biggest ROI from our annual offsite comes from the improvement in execution velocity resulting from cross-functional team members getting to know one another.

3. Have a unifying theme.

An all-company offsite is your opportunity as the leader to set the tone for the entire year and you should take full advantage of it. In my experience, there's no better way to do this than to brand the event and to use that theme to rally your team to the mission at hand.

Your theme should focus on the single most important business issue or growth challenge that you face; it should be simple to understand and deep enough to touch everyone's work in a meaningful way. Two years ago, we were having challenges in our hyper-growth environment: 75 percent of our team members were new to the business and a lack of understanding about "who did what" was leading to poor execution. We wanted to give everyone permission to tackle issues head-on and empower them to take fast action. That year, our theme became "Own It!"

4. Bring in outside voices.

In a startup, there is no shortage of issues that must be addressed, from the tactical ("we need more leads!") to the existential ("this isn't working, we need to pivot").  As a result of the intense analysis that's required to navigate these waters, your team can find itself trapped in a bubble, overly-focused on a narrow set of solutions. Getting an outsider's perspective can break the logjam.

For the past two years, we've invested in one or more outside speakers to address our team on topics that expand our thinking and improve our professional toolset.  We've heard presentations on everything from customers sharing their biggest challenges to industry experts forecasting the future. The most exciting thing about bringing in outside voices is that the opportunities to learn are limitless. 

5. Don't get fancy.

What we never do: spend money on ostentatious displays of startup culture. We're renting space at a modest training complex about 30 miles outside of our headquarters--not flying everyone to Iceland for a weekend on a glacier. At every step of the experience, we're communicating to our team that we're responsible stewards of our company's balance sheet; we're making this investment with the expectation of a high return.  

Financial frivolity has killed its fair share of startups.

No matter your company's size, it's critical to start off your year on the right foot.  The best tool for the mission is an all-company offsite.

Published on: Dec 15, 2017