Making The Most Of Company Off-Sites: More Productivity, Less Boondoggling!

Hawaiian Beach

Company off-sites are important to boost business and morale. Ever year, Financial Samurai goes on a company off-site to plan fo the following year.

The sun now sets at 5pm and it only gets to a high of ~64 degrees nowadays in San Francisco. Despite the cold, winter is one of the best seasons in Northern California thanks to epic powder up in Lake Tahoe three hours away. I've got my season pass on hand and I can't wait to carve it up at Squaw Valley. What's better than shredding down a 2,800 foot vertical and then grabbing a beer with friends in a hot tub? Nothing!

Before the snow falls there's this awkward time between November 1 – December 1 where it's cold, but not cold enough to bring about consistent natural snow. My resort closes down for three weeks in November for maintenance and artificial snow production to build the base as an example. Can you imagine living in a cold climate without anything to do? That's like living on top of a hill with no view.

Making The Most Of Company Off-Sites

As CEO of my business, I've decided to make an executive decision to host an annual company offsite in Hawaii every November to December. Going to Hawaii during the winter maximizes one's appreciation for the islands since the weather ranges from 70 at night up to 82 during the day, everyday without fail.

Hawaii is also one of my key retirement hubs I've got to do more research on before permanently relocating for an estimated six months a year. The other six months will be spent between San Francisco, Lake Tahoe, and traveling.

After attending a disappointing company offsite in NYC where we were locked up in conference rooms the entire weekend, I promised myself if I was ever the big boss I'd do it right for my people.

A company off-site should exist to build relationships, improve profitability, and make work fun. I'd like to share some thoughts on creating a company offsite agenda for maximum business efficacy.

Related: Top 10 Reasons To Start A An Online Business Today

Company Off-Sites: Planning The Agenda

1) Financial overview.

Analyze the month over month, quarter over quarter, and year over year sales, operating profit, and net profit figures for every product line. Is the business trending up, flat, or down? The goal is to get an idea of which products are selling best to maximize profitability and deemphasize those products which are selling poorly. Analyze the profit margins for each product and see whether they are expanding or contracting.

Getting a good grip on a company's expenses is vital. The goal is to create an optimal cost structure so that as sales grow, operating profits grow even faster thanks to leverage. Operating leverage is the main reason why I love internet businesses and would never want to do anything else. It costs $20 a year to register your URL regardless if you have 100 visitors a day or 1 million visitors a day. We are talking 80%+ operating profit margins online. The key is to keep marginal costs to a minimum without impeding growth.

It's also important to understand the seasonality of the business so you can adjust production accordingly. I discovered after you reach a certain traffic level online, there's a noticeable slowdown during the summer months online given most of my traffic comes from search engines. There's nothing I can do to prevent school from getting out during the summer and families from going on vacation. As a result, I plan to join the world in taking lots more vacation between June – September as well. I'll probably do my other semi-annual board meeting in a new location during the summer for at least a couple of weeks to make sure I don't slack off too much.

2) Goals overview.

Company off-sites are crucial for reviewing goals. Compare the progress made to the initial goals. For those goals that were not completed, have a candid assessment as to why. Perhaps you were too optimistic, too pessimistic, or some exogenous variable created a change in the competitive environment. For those goals that were completed, discuss whether the goals fulfilled their purposes. Goals often change throughout the year and it's important to make sure such goals are relevant to the business' success.

One of my main goals is to build at least one new online income stream. 2012 was the launch of my book on severance package negotiations. The book has ben updated for 2021. For 2021, I'm considering creating a subscription membership forum instead for more serious investors and a second book.

One of my main goals is to build at least one new online income stream or one new web feature a year. 2012 was the launch of my book on severance package negotiations, and 2013 was the launch of the FS forum which needs more participation by me if I want it to grow. For 2014, I'm considering creating a subscription membership forum instead for more serious investors and a second book. Making 50-100% on Chinese stocks was huge, and it looks like serious investors are willing to pay for more such insights through a subscription newsletter or forum.

3) Goal setting for the new year.

Now that you've analyzed the past 12 months, it's now time to make new goals for the next year. It's a good idea to just follow the calendar system of goal setting because the business environment, including the IRS follows the calendar system. No need to be a rebel in this regard unless you have an extremely cyclical business.

I've found that the higher you set your goals, the higher the outcome. Setting low hurdles only serves to make you feel better about yourself at the end of the year. What you really want to do is push yourself to the limit to see what you can do and then adjust accordingly. I like to deploy a Blue Sky, Aspirational, and Base Case scenario for my goals.

Related: 2021 Outlook And Goals

4) Team building exercises.

Team building events are great to boost morale. When colleagues get along, synergies are created. You're more likely to go that extra mile for a colleague you like versus a colleague you hate. I plan to host some scuba diving, hiking, surfing, and golfing events with my colleagues and prospective clients to build camaraderie. We'll also have team dinners to sample local cuisine as well.

It's hard to boost employee morale if your business offsite is in some office building where the skies outside are grey and the weather is freezing. Seasonal depression (SAD) is a real thing and you don't want to start associating business off-sites with depression. Going to a warm place like Hawaii, Bora Bora, Fiji, Playa Del Carmen, Mallorca, South Of France, and Cabo are ideal places for team building.

5) Compensation and promotion decisions.

Company off-sites are good for figuring out who gets paid and promoted in the next cycle. Thanks to technological progress, competition is more fierce than ever in practically every single industry. Retaining the right group of people and not letting them go to competitors is one of the biggest challenges every manager faces. It's important to be up to speed on the latest compensation figures and perks to stay competitive.

The company offsite is a chance to discuss with other senior management who are the indispensable employees. Employees who are up for promotion should be aware that year end off-sites are crucial for providing a final last impression. This means no getting slopping drunk at the company party. Underperforming employees also have one last chance to demonstrate their worth.

6) Acknowledging performance.

It's important to always recognize great performance. A company off-site is one of the best times to host a small award ceremony highlighting employees who truly went above and beyond normal company culture. My favorite awards are: Best Team Player, Best Culture Carrier, and Most Dedicated.

More than money, employees want to receive recognition. A simple “thank you” by the boss or a blast e-mail highlighting a subordinate's achievements to others is a cheap and highly effective way to retain employees and keep motivation high. I strongly believe companies don't recognize employees enough for their loyalty, dedication, and hard work.

Here are some prizes I have in mind for my colleagues: 1) Dinner and drinks for two at any restaurant on the island, 2) An all expenses paid vacation for two for one week anywhere in the world, 3) A $1,000 shopping spree, 4) A new MacBook Pro laptop, and 5) Use of my place up in Tahoe for a week in the winter or summer.

Company Off-Sites Can Be A Lot Of Fun

As travel returns, we plan to host another company off-site in Hawaii. Hawaii is always a great place to enjoy life and plan for the future.

Utilize your company off-sites to boost profits and employee morale. Post-pandemic, people are really going to want more work-life balance going forward.


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33 thoughts on “Making The Most Of Company Off-Sites: More Productivity, Less Boondoggling!”

  1. I’m a beginner surfer. I love to body board but haven’t gotten too into surfing yet bc I’m kinda lazy to lug around a board! Can’t fit in the trunk and don’t have a big vehicle in Hawaii.

    Will think more about the newsletter. Thx!

  2. Sam, we have traded a few comments before I bought a home in Oahu. Drop me a line when you’re on-island.

  3. Levi B @ Wealthnote

    I’m suggesting a company offsite for my current employer. Probably going to get laughed at if I suggest Hawaii since we have 3,000 employees and small budgets. I think it would be great for us though because right now it seems like we are suffering from cubicle fever and our productivity is way down.

    Also, sign me up for the paid newsletter. Sounds like a great idea.

    1. Suggest it for just the team. A great offsite is an intimate offsite of fewer than 50 people IMO. Smaller the better! Where so you work? Just finished our scuba team building exercise today.

  4. Stefanie @ The Broke and Beautiful Life

    I think a trip to Hawaii with hiking, scuba, etc would be enough to retain any great employee ;) (I need a boss who’ll do that for me!)

  5. Sam,

    Two questions…

    1) What do you think of BYD?

    2) Do you rent out your Tahoe place? My wife and I just moved from Denver, we’ll have the Epic Local pass this year (as with every previous year).


  6. Sounds more like a tax deduction to me! Personally, I like Maui (Kaanapali Beach) little better. When I was CFO, my company entertained the top 30 bicycle dealers at the Acapulco Princess (Acapulco, Mexico). The executives brought their wives to help entertain these dealers. It was a great excuse for a vacation with the company paying for it. We entertained the dealers for 5 days and stayed for 2 additional days to unwind. My only (personal) expenses was a shirt I bought and I think I even put it on the expenses report. I am glad I cannot get audited over it, it was 22 years ago.

  7. Enjoy the trip! I’m a big fan of Hilo, on the Big Island, and all of Kauai. If you go to Kauai, make sure to rent a 4 wheel drive vehicle and visit Polihale. It’s one of my top 3 beaches in the world, hands down. You’ll love it!

    1. Kauai is great. I stayed up in the Napali Coast area last time and enjoyed the hiking and beaches. I’m going to stick to Oahu for the next couple of company off sites but may consider the switch in the future!

  8. Hi Sam

    From someone with a “staffer” mentality, this exotic offsite does sound much better than the average location. I like the idea of the prizes too, that will certainly boost the morale.

    I’m still impressed that you (or anyone else for that matter) get anything significant done after they reach financial independence.

    1. Jason,

      It really is just about the challenge of doing something better and being more productive. For example, let’s say someone won a small lottery. I dare say they’d be giddy as school kids to come to work because they’ll work for the love of it and not stress as much!

      If you are a gambler, it’s like playing with houses money.



  9. The traveling that I’ve done for work has really helped me build relationships in ways that just isn’t possible over email and phone calls alone. Company off sites are really great ways to connect to your coworkers, get to know clients better, and get closer to completing goals and targets you’ve set. And what a bonus when the off site is in a fantastic place!

    1. For sure. Not sure if there are many company off sites being booked to Detroit over they winter. Aspen or Lake Tahoe absolutely! Got to make work fun so that it doesn’t feel like work to get more production.

  10. I’m looking forward to your report. We are planning a business trip to the Big Island early next year. I’ll see if it’s a viable retirement spot for us. Oahu is probably a better fit for us, but it sounds like the housing price is out of reach. Keep us updated.
    Can you see if there are any good multi unit properties on Oahu? How much would a 4 plex cost? Thanks!

    1. Very cool. The Big Island is going to still be much more expensive than Portland, Oregon unfortunately.

      May I suggest taking a business trip to Houston or the southern states? Much cheaper than Portland.

      1. I think close in Portland is actually comparable to the Big Island. I was just looking at a triplex and it cost $675k. It’s much cheaper in the suburb.

        1. Really? I guess it depends where as I usually will look for ocean views or somewhere close to the beach.

          I think it’s better if we divide and conquer. I’ll report back on Hawaii and you report back on Texas and the southern states.

    2. Hello Joe,

      The parents are retiring out to the Puna region of HI and we’ve spent a good amount of time out there over a few trips. The big island is basically divided in two, East and West, with East being a jungle “alternative lifestyle” type paradise and the West being sun and fun. I prefer the East myself for the raw nature aspect, but the mentality is very different from the mainland. It’s almost 3rd world in mentality, but not materially, if that makes sense. Kona (the west) is about 2x as expensive as Puna for my lifestyle. Kona is more of a packaged vacation destination IMO. Fantastic coffee of course.

      Cap rates all over Hawaii are pretty bad as far as long term rentals go. Maybe 4-5% last time I checked around a year ago. I wouldn’t buy anything that doesn’t cashflow with the 50% rule.

  11. As usual, good insight. When I traveled for work overseas we had weekends off and toured the local sights. Sometimes, colleagues traveled with me. The good times.

    Suggestion…for the early FI types, how about a post on your thoughts for year end tax planning. With a focus on how to best live off of the investments with minimal tax impact.

    Thanks in advance!

    1. I’d love to get your thoughts on year end tax planning and living off investments. Always good to get insights from the community. Shoot me an e-mail with your draft when ready. Cheers!

  12. I recommend visiting an outrigger canoe club and making plans to canoe surf as a fun team building activity. Ocean canoes seat 6; surfing canoes seat 4. So many possibilities for exploring team dynamics, trust, communication, goal attainment. And then there’s the Ohana and thrill of riding waves together!

  13. I think people would definitely pay for a newsletter highlighting Chinese stock picks. That’s such a difficult market to penetrate that serious investors would probably eat that up.

  14. I guess everything is relative. I can’t imagine how cold things get in Canada since it is ridiculously cold in North Dakota, Michigan, New York, and New Hampshire during the winter!

    My other promise I made if I ever became my own boss was to stop working both before sunrise and after sunset. One or the other is fine, but not both.

    Good luck with your 2014 brainstorming!

  15. Sam, how many people work for you? If I was the only employee in my company, could I legally have an offsite like this and count it as a business expense? I’m just curious.

    1. Not sure. Probably best to check with your accountant if you want to have an offsite with yourself and report back your findings! I do know there should be an annual shareholders meeting. I’ve got a small team of people working with me to keep the magic alive.

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