Why Most Company Offsites Fail (And How to Make Them Amazing)
In Alpine’s early days, about 25 employees and portfolio company CEOs flew to Orlando to attend a speaker series hosted by Fortune. The speakers were incredible, including former Secretary of State Colin Powell. We all enjoyed the conference, took great notes, and left feeling like it was a home run.
Two weeks later, at a board meeting with one of the CEOs who had attended, I asked what he had implemented from the conference. His blank look told me the answer. Subsequent blank stares from similar conversations over the next month led me to the conclusion that the result of the conference was nothing. No change. No progress. Zero. Zilch.
This was not our only failed offsite. Other times, our firm rallied around a set of new initiatives, wrote them down and committed to them. But by the next week, we were once again busy in the whirlwind of our jobs, returning emails and attending meetings. The following year, when we pulled out that list of initiatives, we realized we had achieved very little.
After several false starts, we began learning the principles of conducting effective offsites. In our 21 years, we have likely had over 200 firm, departmental or CEO offsites. When I trace back the most game-changing innovations we made over the past two decades, nearly all of them came from firm offsites.
Do’s and don’ts in conducting offsites
Don’t … focus on entertainment
Our most expensive offsites were typically our least effective. Several times we paid for big-name speakers. While these were some of our most highly-rated offsites by the participants, as described in the Fortune example above, they were nearly worthless from an impact perspective. The goal of an offsite should be to meaningfully improve your company. When people are passive spectators, they rarely retain information, let alone make a meaningful change in their businesses or lives.
Do … the work at the retreat!
Pep talks and motivational speeches have a place, but in the most effective retreats, you do work. You have just taken your senior team off site and away from Zoom, Slack and email for two days. So don’t talk about making a new customer journey — make one! Don’t talk about your five -year goals — map out a plan to hit them! Create a goal for the retreat that is clear, simple and attainable. Examples of specific outcomes of an offsite could be: creating a five-year vision, refining the customer journey, defining the ideal customer, or retooling your company’s recruiting processes. Don’t try to do everything.
Don’t … create too many initiatives
The biggest problem for most companies is that they have too many initiatives, not too few. Having too many priorities is like the Mark Twain quote, “I didn’t have time to write you a short letter, so I wrote you a long letter instead.” It is a sign of intellectual laziness. Having too many priorities creates confusion for the team, sets them up for failure and diffuses energy on priority eleven that should be invested on priority one.
Do … take the time to write the “short letter”
On the final day of an offsite in Napa many years ago, former Alpine partner Mike Duran stood up in front of the room and posted a big white sheet on the wall. He wrote down the numbers 1 through 4. And he said that we weren’t going to leave the room until we had reduced the dozens and dozens of initiatives from the offsite into a list of four items with no sub-bullets. Reducing the list from 17 to 4 was the real work of the offsite.
Don’t … leave an offsite without clear accountability
Ever get all excited about some new change? “Hey, from now on let’s make sure we are recruiting from a more diverse set of schools.” And everyone agrees and nods — and then nothing happens. This advice sounds obvious, but it is so uncommonly followed that I feel the need to state it. No goal will be achieved without three things:
A single owner;
A clear deliverable; and
A deadline for the deliverable.
(Note: “Accounting Department” does not qualify as an owner. “Sally Smith” is an owner.)
Do … ask presumptive questions
Presumptive questions are questions that presume success and often help you challenge the status quo. These can nearly always be interjected into offsite sessions. Examples of presumptive questions are:
“How would we achieve our 10-year goal in six months?”
“If we were the best in the world at [acquiring new customers, creating new code, sourcing founder-backed SaaS companies], what would need to be true?”
“What are our competitors unwilling to do?”
And the famous Peter Thiel question, “What important truth do very few people agree with you on?”
Don’t … have too many cooks in the kitchen
Getting the whole firm together is amazing. Like many firms, we have remote workers and multiple offices and rarely have everyone in one place. But according to a Wharton study, true brainstorming and problem-solving is most effective with five to six people. If you are going to bring your entire firm to an offsite, make sure you are breaking into small groups to do the actual work.
Do … think big
Why not use the two to three days that your entire team just took off work to ask big questions and make real changes to your business or the world at large? Why not try to be the best in the world at what you do? Someone is going to be the best in the world … Why not you? Why not now?
Bertrand Russell said, “Most people would rather die than think; many do.” With the large number of stimuli that hit us daily, as leaders we need to proactively schedule time for our team to think. We need to create a clear, focused purpose for that time, and to structure that time effectively. If you can consistently schedule this time and give your team permission to think, you will be amazed what you and your team will create. Creativity is the ultimate weapon in business to spark innovation and exponential forward progress. Help your company unleash it.
Sources
Is Your Team Too Big? Too Small? What’s the Right Number? Knowledge at Wharton: https://knowledge.wharton.upenn.edu/article/is-your-team-too-big-too-small-whats-the-right-number-2/