7 Benefits of a Leadership Offsite

We’ve seen periods where our clients were big on over-the-top boondoggle getaways for the leadership team and times when they stopped all workshops and retreats for austerity reasons. That’s two ends of a spectrum and neither end is ideal for most organizations.  

Instead, somewhere in the middle – a getaway from the day-to-day challenges of the office without being too costly – brings a huge return on investment to most organizations if the time is well planned.

Why leadership offsite and why does it work?

An ideal leadership offsite will have an agenda that is focused on the big goals of the organization. Participants will work on big questions, talk about important ideas and work together to figure out a plan going forward. Or, there could be workshops on topics that will strengthen the group as a team — also helping to better achieve those big goals. 

Of course, some of the real benefits will be all the extra stuff that happens outside the agenda. 

What kind of extra benefits come from an offsite?

  1. Finding common purpose: When companies are planning their leadership offsite they seek to find “whole-organization” issues to work on instead of the “single department issues.” That’s great because it gives the team a chance to work together. While struggling to solve problems, folks will learn to work toward shared goals.
  2. Teambuilding: Connecting peers outside of work often means getting to know each other as people, as individuals and as humans outside of the work environment. And that goes a VERY long way to building trust  – and trusting each other, deeply, is at the foundation of moving from a GROUP to a TEAM. Strong work relationships are critical for success.
  3. Gaining perspective: Getting up from behind the boardroom table – literally getting a different point of view and walking away from the to-do list for a couple of days – gives people a chance to gain a new perspective on things. Many times different perspectives lead to new ideas and innovation.
  4. Overcoming fears: Participants get to explore new ideas and possibly share fears about the company and its direction that just don’t come up in task-related meetings.
  5. Building Skills: An offsite is a great time to bring in help to build skills in areas where individuals might be struggling. Maybe you help your leaders learn how to take a Coach Approach to Leadership to help grow the staff who report to them, or you help them have difficult conversations (we’d say help them have essential conversations) with each other. Perhaps you really want to take steps to build a truly cohesive and effective team. Think about the goals of your organization and what you need to build in your team to achieve them.
  6. Finding hidden talents: Changing the environment and making room for new perspectives often means participants start behaving differently and start showing new sides of themselves. This can open their eyes, and yours, to some talents they have that they aren’t using “back at the office.”
  7. Transforming from a leadership group to a leadership team: We often work with our client organizations to help them build their leadership team at offsite meetings. So that may seem odd – they’re a team but we help them be a team. You see, many, maybe even most, leadership teams aren’t really a team: They call themselves a team but they’re really just a group who meet once a week.

What’s the difference between a leadership group and a leadership team? 

A leadership group is a bunch of individuals, each quite likely highly talented in their field and successful in their careers who meet regularly. At those meetings, they offer up their expertise in their own area, they defend their budgets and their teams, they update the group on what they’re doing in their area and occasionally discuss issues with their colleagues at the table, when there are overlaps in their areas. 

  • They tend to “stay in their lane” and not challenge each other on the other’s area of expertise. 
  • They tend to be there as advocates of their own role and their own staff.  

In other words, the VP of Finance is there as the finance expert and to keep things on track financially, the VP of Sales is there to ensure the sales team is well supported and to make sure Sales keeps its position of importance in the company’s work, etcetera.

A leadership team has a shared stake in everything. While members of a cohesive and successful leadership team acknowledge each other’s expertise, that isn’t why they’re there. The VP of Finance is there to support the leadership team and to lead the company, the VP of Sales is there to support the leadership team and to lead the company, the VP of HR is there for the same reasons.  

  • They offer helpful suggestions to each other, regardless of their area of expertise.  
  • They challenge and ask questions of each other, regardless of their areas of expertise.  
  • They have built a level of trust with each other that allows them to do that and to know they’re doing it for the good of the company and the good of the team.  

On a leadership team, the VP of Finance knows when the VP of Sales is challenging her on a topic, it’s not to make himself look smarter than her, it’s not to build an empire in the Sales division and it’s not because he’s trying to protect his sales staff. He is doing it to see if he can help the VP of Finance make an even better decision for the good of the company.

Now that may seem like a fantasy world for some companies, but it isn’t. It’s the outcome of a group that consciously works to become a team. We regularly help leadership groups become cohesive leadership teams with our Five Behaviours programs.

Coach’s Questions

Do you think you have a leadership group or a leadership team? What can you do to become a stronger leadership team? When can you take your team for a leadership offsite and what would you like to work on?

Is there room for humor in executive leadership?

How often do you and your team laugh and joke at work? 

That might seem like a strange question, but humor at work can drive success in a variety of ways. Now, arguably some office cultures that are more open and creative are going to have very different examples of humor than perhaps an office with a more hierarchical workplace or very serious business mandate – but even a chuckle can be as important as laughing out loud.

Generally, people joke with people they are comfortable sharing experiences with (remember that one of the five behaviours of a cohesive team is trust!). Laughter and friendly banter are good signs for teamwork and productivity.

Skeptical? Medical schools are researching how humor affects health, psychology schools are looking into how humor is linked to mental health and wellbeing and elite business schools are investigating how humor helps with business success.

Humor helps

Consider that laughter:

  • Releases those feel-good endorphins
  • Lowers stress (and blood pressure!) and releases tension
  • Increases oxygen intake (which is good for your heart and muscles as well as your emotional well-being and focus)
  • Helps people cope with physical pain or feeling overwhelmed (the idea of the wisecracking cop or macabre-funny coroner is grounded in the reality that laughter helps us cope with painful situations)
  • Encourages a feeling of connection with others
  • Improves your mood and immunity
  • Boosts morale, creativity, and productivity

It’s easy to see how humor can really help to engage your team, encourage teamwork and motivate everyone when things are challenging. 

Humor and positivity can even help with corporate branding and engaging with customers (if you ever ordered from ThinkGeek before they were recently bought out, you may have laughed out loud like me at their cheeky customer emails from the ThinkGeek overlords and hilarious product descriptions). It’s why many big corporations pay big bucks for funny advertising and cleverly worded social media.

The trick is that humor is rather subjective and if you miss the mark, you risk having the opposite effect. Just like a good comedian, leaders need to read the room and know their audience.

A misplaced wisecrack or bad joke could risk the respect of your team members, offend people or even demotivate. I’m thinking of the many wince-worthy and cringe-inducing moments with Michael Scott, the Regional Manager on NBC’s The Office or David Brent if you’re a fan of the British original! The fictional character of the cringy boss was so funny because those moments sadly ring so true.

You can’t force funny. But it could be valuable to look for ways to encourage laughter and levity in the workplace.

Humor in leadership

Here’s what we do know about ways to use humor as a leader:

  • To make a joke and encourage a jovial atmosphere, you have to be able to take a joke
  • Positive, uplifting humor is far more powerful than negative (laughing WITH people is completely different than laughing AT them!)
  • The best jokes or funny moments are authentic and natural
  • It’s best to be careful not to cross any lines providing a harassment-free workplace includes not making team members uncomfortable with jokes that are offensive to, say, women or minorities or members of the LGBTQ+ community 
  • A bit of self-deprecating humor is funny, but research by a doctoral student at the London Business School shows employees have less respect for leaders who constantly make fun of themselves
  • Maintaining professionalism doesn’t mean your humor has to be PG, but tasteful will never be a bad choice (think: would I want this moment on YouTube or repeated to others outside this circle?)
  • There are different kinds of funny – find your own style (clever, witty, wry, teasing or haha)

If you’re not sure if people are laughing to be polite, watch their eyes. Someone who is genuinely amused will have a “Duchenne smile” (named for Guillaume Duchenne, a 19th Century French physician who studied facial expressions) with not just a smile at the mouth but crinkles around the eyes. Most of us can fake the smile but not the mirth in the eyes.

Opportunities to use humor

As leaders, we can look for opportunities to use humor to advantage. There are many opportunities, even when you’re staring down a deadline or wrestling with a never-ending project. Here are some ideas:

  • Poking fun at systems or something that everyone is worrying about
  • Inside jokes (preferably that are inside to everyone on the team) about shared experiences or relatable feelings
  • Laughing when you make a mistake (it puts everyone else at ease!)
  • Clever puns or retorts

There are several ways to actually set up occasions to encourage laughter. Consider things like:

Endorsing friendly wagers or office pools. I heard about one team comprised of Americans and Canadians, who had a bet for the winning US-Canada hockey game where the losing side had to create a top-10 list of why the other nation’s hockey team is better (the US won that year and the Canadians cleverly had “Your Canadian-born players are better than our Canadian-born players” as number one!). If sports aren’t your thing it could be predicting who will win something else — maybe Dancing with the Stars.

Picking moments for silly contests. You could challenge your marketing team to scoring the most baskets with crumpled paper balls before a brainstorming session or see if everyone will post a baby photo in the break room (whoever gets the top score on who’s who wins lunch). When the boss is able to smile and relax, the rest of the team feels more at ease and comfortable laughing. 

Holding social events and off-site activities. No matter what you do – see a ball game, go skating or airsofting, see who can get out of escape rooms the fastest – being together in a more relaxed environment is conducive to fun and laughter. Plus, funny and zany memories offer laughs to share for months to come. This can be especially helpful if the culture of your workplace is serious and not fun.  If you run a funeral home, it’ll be best to take the team out for your jokes and laughter!

Post a funny meme or comic in the staff break room or on your office board. Have a contest for the funniest office meme. I knew a quality leader who labeled his inbox, “The hip, the happening, the INBOX” just because and it was so ridiculous in an otherwise serious place that it always made people smile. Simply attaching a funny, apropos comic (thank you, Dilbert!) or gif (thank you, The Office!) to an email and sending it to your team underscores that you’re in it together – and might make them chuckle.

Use humor in presentations or speeches. You don’t have to write your own material! Just find a good joke or anecdote and attribute it to the creator. Find one-liners you’re comfortable using and try them out. I remember one veteran CEO who was known to be uncomfortable speaking in public being asked out of the blue to give a speech and he stood in front of everyone, paused with a bemused smile at the awkward silence and said, “I can hardly wait to hear what I have to say!” Everyone roared. Laughing puts everyone at ease and encourages dialogue.

Not too long ago we talked about ways to develop your executive presence. Highly effective leaders have certain qualities that people gravitate toward, including confidence, charisma, and compassion. 

When leaders use humor effectively, they’re seen as not only likable but also intelligent and more trustworthy. It’s emotional intelligence that differentiates great leaders from the rest.

And so it’s not surprising that a leader who is able to use natural, off-the-cuff humor to put people at ease and connect with them is going to be someone that people want to work alongside. Someone who smiles and can be genuinely funny (or appreciate humor and creativity!) is much more human and approachable – and even if it’s not a natural strength, you can work on it.

Coach’s Questions

Can you think of times you’ve seen executive leadership use humor effectively? How do you use humor at work? What could you do more often or differently?