3 Questions to Ask at Your Strategy Off-Site

Ask them, or there may not be many off-sites in your company’s future

Well, it’s almost that time of year again. It’s time for the annual leadership off-site, during which you will likely think, ink and drink too much.

If you are like many, you’ll leave the safe confines of your office to hang your hat in a beige, patterned hotel conference room that is painfully close to the promise of tranquil water, challenging links or virgin mountains.

But all those things will have to wait.

For now, there is work to be done and you know the drill. You’ll spend 80 percent of your time optimizing the business models that got you here; 10 percent of your time being challenged by a consultant in skinny jeans wearing “look-at-my-glasses” glasses; 5 percent of your time engaging in some fun, albeit uncomfortable, activity; 3 percent of your time hoping someone photographs a co-worker doing something embarrassingly epic; and 4 percent of your time thinking about the future. (The math error was intentionally included, just to make sure you were paying attention. If you caught it, read on.)

Maybe this year you should try to make the off-site memorable—and worthwhile.

You have no choice if you want your company to survive.

What some of you already know is that this year needs to be different. The days when you could show up and figure out how you could do just a little bit better than what you have always done ended about a decade ago.

The future is simply coming too fast to continue to employ incremental thinking.

So, if you are looking for a more productive off-site, here are three topics that I have helped facilitate—topics that always lead to a more productive year. (And as a bonus, I promise that if you take on any of them, you will have an off-site that you will never, ever forget.)

Topic No. 1: Do we trust each other?

Change is inevitable. One of a leadership team’s primary responsibility is navigating change in an efficient and profitable fashion.

But with change comes fear: fear of things you don’t understand; fear of losing your job; fear of firing a friend; fear of the unknown. And with all of that fear comes drama: a vicious cycle of complaints, persecution and rescuing that, at best, keeps you stuck in a spin cycle while you need to move forward.

Trusting each other is fundamental to breaking this cycle. It allows the victim to become the creator, the persecutor to be seen as a challenger, and the rescuer to become the coach.

Luckily, my friends Patrick Lencioni and David Emerald have written the books The Five Dysfunctions of a Team and The Power of TED that provide road maps for discussing how your team is doing when it comes to trust.

I have facilitated these discussions. In my humble opinion, this topic is critical for any off-site. It is also a topic that the best leadership teams embrace.

Topic No. 2: What should we stop doing?

This year, why not start your meeting by building a list of things you should STOP doing? Doing this will create a clearing for the essential initiatives that your top people must be focused on every day.

One caveat: One of your pet projects might just wind up on the “to-be-killed” list. When it does, don’t get furious; get curious. Maybe your team knows something you don’t about the future.

Topic No. 3: Do we have a company of inventors or innovators?

This year, instead of talking about big ideas, first try to get your team to focus on big insights; talk about innovation instead of invention.

Invention is starting with ideas and then looking for someone who needs them. Innovation is starting with insights—large, meaningful market needs that you have a right to solve—and then thinking of ideas to solve them.

Some of the best off-sites I have been involved in have centered on insight building. Our own insight conversations have led us to start four new businesses based on emerging and growing market needs.

These activities, when properly staged, align the CFO and CEO on problems worthy of solving. They literally help set a strategy that appeals to both the visionaries and the folks who like to spend their days getting stuff done.

Here’s the best news of all: These exercises often reveal that you have the ideas the future wants. You just have to get the organization to focus on them.

So, what will you be focusing on at your off-site? Getting to the answers behind any one of these topics will make your team stronger. Master all three and you will rule the future.