How to Run an Annual Team Retreat

Hey 👋 - Brandon here.

Happy Saturday to 1,535 growth-minded accountants.

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I just got back home from hosting our annual team retreat at Disney World and I’m going to share some tips with you on how to run a successful team retreat.

We have been on six retreats over the years to Charlotte, Destin, Nashville, Port St. Lucie, Cancun, and now Disney.

I have experimented with various agendas ranging from all business, to all fun, to somewhere in between.

I’ll also give you some insights on costs.

Let’s go!

First, why should you have a team retreat?

I run a 100% remote firm which makes our annual team retreat a highly anticipated get together. But even if I had an office and saw my team in person each day, I’d still host a retreat.

Here are some of the expected benefits:

• Improved morale and culture - special stories come out of each team retreat that are referenced in the future

• Increased alignment - getting everyone out of their daily work environment enables employees to better consume firm trainings and information that are important for growth

• Strengthened relationships - your team gets non-office face time with you and peers which strengthens the overall community-feeling in your firm

• Recruitment tool - we always post pictures of our team retreats to market our firm to prospective talent

You may assume these are non-quantifiable benefits but the results will speak for themselves.

You’ll see lower turnover over time, have an easier time collecting resumes for open positions, and find that your employees are more motivated to take up leadership positions in the firm.

Now let’s get into the nuts and bolts.

How much does it cost?

I’ve run retreats that are short and inexpensive and on the flip side long and costly.

My early retreats with a small team cost ~$1,000 per person.

When we went to Cancun we spent ~$1,500 per person because we stayed at an all inclusive resort.

Our Disney trip cost ~$2,850 per person.

Our recent Disney trip cost per person breakdown was:

• $500 for airfare

• $100 for transportation

• $1500 for lodging

• $200 for park tickets

• $50 for swag

• $500 for food and beverages

Our food and beverage costs were higher that prior years (usually $250 per person) because we threw a welcome party and had a minimum to hit.

How many days should it last?

I have experimented with both short and long retreats.

In my experience, a three night retreat is the perfect length.

You fly everyone in on night one and host a dinner or welcome party.

Then you have two full days to host business meetings or have fun.

And you fly out the morning after night three.

On our recent Disney trip everyone flew in on Monday and out on Thursday.

It was the perfect length of time.

I do recommend locking down lodging 8-10 months in advance of the date. You don’t have to disclose the location to your team if you want to keep it a surprise, you can just block the days on everyone’s calendar.

Most resorts will have clauses that allow you to adjust the total rooms, and subsequent price, as you get closer to your date and have a clearer idea of headcount.

What is the ideal agenda?

To nail down an agenda you have to first ask:

What is the purpose of the retreat?

For me, it’s gaining alignment and fostering relationships.

My ideal agenda to meet that goal is a mix of business and fun.

Here was our agenda for our Disney trip:

Monday

• Welcome party 6:30-8:30

Tuesday

• Breakfast 7:30-9:00

• Bike building (for a non profit) 9:00-11:00

• State of the firm 11:00-12:00

• Lunch 12:00-1:00

• Hollywood Studios 1:00-9:00

Wednesday

• Breakfast 7:30-9:00

• DISC presentation and breakouts 9:00-10:15

• Growing your career 10:15-11:15

• Leadership Q&A 11:15-12:00

• Lunch 12:00-1:00

• Epcot 1:00-9:00

Thursday

• Depart

Making business meetings required and starting them early ensures drinking doesn’t get too out of hand the night before (important for risk reduction as you scale).

There’s a lot more that goes into a retreat but these are a few big things that can help you get started.

Don’t plan a retreat alone.

I lean heavily on my EA, McKeller, and she does a phenomenal job executing on the details.

I’m curious if you have any questions about holding a retreat.

Shoot me an email if you do.

That's all for this Saturday. See you next week.

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See you again next week.

Cheers,

Brandon

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