Corporate Outings by Design

You can forget all your troubles, forget all your cares
So go downtown, things’ll be great when you’re
Downtown – no finer place, for sure
Downtown – everything’s waiting for you

Downtown by Frank Sinatra

Ole’ Blue Eyes may not have been an event planner, but he sure knew the secret to showing a team a good time: get out of the office! Nothing helps a team forget the cares of the cubicle like a trip out on the town. The only tasks before you now? Deciding where to go, what to do, and what to accomplish.

Nailing the Numbers

You’ve been tasked with showing your colleagues a good time, have you? As you’ve likely discovered, while the task can sound a load of fun, making the fun happen is a serious assignment. Before you do anything else, reach for a pen and paper and take down some vital stats. First up: how many people are you inviting? Of those, how many do you expect to attend? Will you be affording each guest a plus-one? How much notice do you have to work with? Do you have any flexibility in terms of dates or times? And finally, how much are you planning to spend? (More about that touchy subject is coming right up.)

Setting a Budget

There’s a common concept in negotiation textbooks: never be the first to mention a number. The theory is that the second person to talk numbers will always have the upper hand, ensuring that they won’t leave a dime on the table, but could always ask for more if the first number if woefully insufficient. In event planning (as with corporate outings) this rule of thumb is a quick way to waste a lot of time.

Consider this: there are families who throw birthday parties with $20 budgets and those who entertain with $200,000 budgets. Were the $20 family to simply ask for a list of suggestions for their celebration, untethered to any budget, the list would likely produce a long list of completely unrealistic options. On the other hand, the deep-pocketed party throwers would likely find the bounce house and cotton candy vision insulting.

Take it from us: before you start brainstorming, you need a budget. If you’ve been tasked with calculating what a party should cost, perhaps returning with high-level options is your best bet. “Here’s what $50 per head will buy, here’s what $100 can do, and here’s what $250 could make a reality.” Then and only then, get down to the nitty-gritty.

Clarifying Your Purpose

For some, an outing is a chance to connect. To hear about the little details of kids, families, hobbies, and trips that haven’t broken through the hustle and bustle of work life. To others, an outing is a chance to conquer a task. And to still others, it has a singular goal: fun. No depth, no importance, just fun. Your outing could be one or a combination of all three. But it’s up to you to decide the purpose of your event and shape your budget, timing, and activities around it. Write your purpose down and make it clear to each attendee and every vendor. Then define your outing’s success by one question: did we satisfy our stated purpose?

Snagging a Ride

For small teams, few methods of transportation are easier than Uber or Lyft. Even if your people are willing to carpool, the event will feel like more of a treat if your star accountant doesn’t have to move her pile of laundry to the trunk. Don’t want to make your employees mess with reimbursements? Both companies have programs that allow you to pay for rides, up to a certain dollar amount, that originate or end at a location you determine. Guests simply enter a code and set their destination to your venue. When they arrive, you’ll get the bill. For larger groups, consider enlisting the services of a shuttle driver. Your team will arrive at the same time and you’ll guarantee that the group won’t get split up due to poor navigation or–dare we say it–speeding tickets.

Landing on a Length

Benjamin Franklin famously said, “Guests, like fish, begin to smell after three days.” In corporate outings, we can safely swap “days” for “hours.” Unless your outing includes a major distraction or activity, colleague chit-chat gets old pretty fast. Three hours is a good cap for a team meal that isn’t supplemented with engaging entertainment or adrenaline-pumping activity. (Plus, your outing will be much more likely to be viewed as a treat if it doesn’t mean a night of emails.) Work piling up is not a gift. Striking the right balance between length and time is an art. Speaking of which…

It’s All About Timing

It can be said for most things in life, but it’s especially true for events: timing is everything. Choosing when to venture out together is almost as important as deciding what precisely you’ll do. Each industry comes with its own considerations, but a company outing will typically be most welcome when…

• Other activities aren’t competing for scarce weekend nights (e.g. the holiday season)
• Workloads aren’t overwhelming (e.g. tax season for accountants)
• School schedules aren’t taking breaks
• Major local team events aren’t being played

Once you’ve landed on a date, you need to decide on a time of day. If an afternoon away from the office will be viewed as a burden to those worried about the email avalanche that could follow, perhaps an evening out would be better. Right? Well, not necessarily. It depends on the team. If yours is a team of family people, asking them for a night away from the kids will probably just sound like more work–really sacrificial work. For a group of recent college grads, the concept of a free fine dinner would be much more appealing. One way to treat your people to an evening of fun without taking their family time? Invite their families along.

The Plus-One (or Two, Three, or Four)

Everything’s better when you can choose your company. Even work parties. Actually, especially work parties! Giving your employees a plus-one will make the conversation more comfortable while giving their spouses or significant others a chance to meet the people they’ve heard about. If you can afford it, consider widening the net even further, especially if you’re planning a family-friendly event.

Think of this as your opportunity to thank the kids of the moms and dads they’ve shared with your organization. Treating them to an experience (such as a theme park, movie, or themed restaurant) will give them a new appreciation for mom’s job. Even if you can just move the “what I think of my mom’s work” needle an inch, it will go a long way in helping your team members feel less torn about their work-life balance.

Food and Drink

If you’re like most Americans, you likely think, “What is an even without food?!” Believe it or not, plenty of such events have been thrown. And many, quite successfully. Skipping a meal can cut costs, so long as the timing is right. A simple after-work happy hour can be a fabulous outing that gets the conversation moving for the modest price of a beer. And the special guests invited to skip work to come to a 2 pm private movie screening won’t even notice that the invitation didn’t come with calories.

If you do plan to serve food or drink, keep a few things in mind: first, delegate. Whether you’re planning a simple picnic spread following the completion of a ropes course, or have visions of an elaborate dinner complete with wine and dessert, don’t reinvent the wheel. Focus on the needs of your people while someone else focuses on the food. Second, consider allergies and intolerances. Food allergies have skyrocketed in recent years. Most can be accommodated with a subtituded meal, while others could product anaphylactic reactions with the mere association (like peanuts). Send a quick email before your event, surveying for any food restrictions.

Not sure which path to take? When in doubt, feed your people. Even the smallest of snacks will be welcome nibbling for a deserving crowd. Absolutely positive that your crowd will be full? Set up a surprise coffee station and watch the smiles spread like wildfire.

A Note about Liability

Just because your outing takes you away from the office doesn’t mean you’re out of the woods in terms of liability. Should an unfortunate event occur (such as a car wreck) or a colleague be accused of misconduct (a risk increased exponentially by the presence of alcohol), your company could easily be on the hook. Such risks can’t be eradicated altogether, but they can be mitigated. Two helpful precautions include hiring a professional driver to shuttle participants to and from the location and eliminating alcohol from your menu. The latter may make conversation a bit more taxing, but few factors are more tied to risk that booze. It’s a trade-off to be certain, but one you may be wise to make.

Blending In vs. Taking Over

Picture the ideal outing in your mind. Are you gathered with your coworkers around a white table cloth as a bustling restaurant fills the air with energy, or secluded in a forest, free from distraction and isolated from anyone outside of the company bubble? There are two approaches to team outings: blend in, or take over. Blending in is ideal for smaller teams, or for especially large events. Think of professional sports games or special museum exhibits. The primary purpose of your outing is to satisfy the purpose you defined above, and treat employees to whatever public activity will accommodate it.

In a takeover, you’re likely affording your guests an opportunity they couldn’t otherwise afford. Perhaps it’s horseback riding in a small group, or seeing a blockbuster movie the day before its highly anticipated premiere. The added benefit of a takeover is you’ll have the entire setting to yourself. No onlookers, no run-ins with junior’s teacher, and no company reputation to manage. Answering this question requires asking another: do you want to keep your entire group together, or break into smaller groups? The larger your group, the more likely it is that you’ll need to secure an entire venue or activity just for your purpose.

What Outings Won’t Fix

A corporate outing is an opportunity to show your team that you value their contributions and their efforts are worthy of a break. And yet, plenty of corporations treat their teams to fancy outings while maintaining a rampant culture of underappreciation. So where’s the rub? As any trust fund baby can attest, no amount of money can compensate for a lack of authentic connection or recognition. Before you try to fix a problem with a bandaid, consider the origins of any sore spots in your company culture. If you hear that team members are in dire need of some off-the-clock connect time, an outing may be just the fix you’re looking for. But if complaints of a hostile work environment, impossible requests, or insufficient resources are buzzing around your halls, a mere outing may not be the remedy your team is looking for.

Going Above and Beyond

Want to make an unmistakable statement that you see and understand the needs of your teammates? Spend some time thinking about the smallest things an outing may affect on an individual basis. That after-work dinner could cost a parent $60 or more in babysitting. Trekking downtown could trap your attendees in rush hour traffic. And choosing a setting that mandates specific attire could cost a staff member more at the department store checkstand than any entree is worth. To truly treat your company to such events, some additional generosity could be required. Namely, an envelope of babysitting funds, Uber credit, or even a gift card for a fresh outfit. Expected? Absolutely not. And that’s precisely the point.