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7 Deadly Mistakes That Turn a Well-Intended Leadership Team Offsite into Another Time-Waster

Nobody plans for  a bad offsite, and yet we’ve all heard the horror stories. Let’s dive into where things go awry.

Mistake #1: Not Having an Offsite at All

The list of excuses is endless: no time, no budget, memories of offsites past that floppedYet, I’ve never heard anyone say, “Gee, I really regret that fantastic time with my team.” The magic word here is “fantastic.” I’ve seen firsthand how a well-executed offsite can be transformative for teams and companies alike. So, are you sure you want to miss out? (Hint: My Offsite Strategy Tool can help you decide if an offsite is right for you and ensure it delivers tangible outcomes.)

Mistake #2: Obsessing Over the Logistics Too Soon

Jumping straight into the ‘how’—picking a spot, fretting over the budget, or imposing arbitrary restrictions like “one day only” or “$25K max.” If this event could redefine your business’s growth trajectory, would those details really matter in the grand scheme of things?

Mistake #3: Slapping a Label on It Prematurely

Labeling your offsite too early can box you into a corner of preconceived notions—like needing a remote, swanky locale with feel-good fluff. That’s a straight path to missing the point. Start with your goals, not the gimmicks.

Mistake #4: Lone Wolf Planning

Whether it’s the CEO, HR, or any well-meaning team member planning solo, it’s a no-go. People value their time and want to ensure it’s spent on matters important to them. No one likes surprise party planning at work. Get input, involve others, and build it together.

Mistake #5: Not Clearing Mind Space

Arriving with a suitcase full of distractions isn’t ideal. Whether you clear the decks before or create space to do so during the offsite, it’s crucial. The offsite starts now before the actual event.

Mistake #6: Forcing “Fun”

Let’s be honest: manufactured fun is as enjoyable as a root canal. Every activity should align with your business, learning, or experiential objectives. Remember, time is money—quite literally when you gather your team. (Use my Offsite Strategy Toolto figure out the goals first)

Mistake #7: Skipping the Pro Facilitator (when you need one)

(Eye rolls tolerated.) If you want everyone fully engaged, an external message reinforced, or just don’t have the bandwidth to micromanage the offsite details, consider bringing in the pros. It can make all the difference.

Feeling overwhelmed? Don’t be.

I’m here with a two-pager wonder toolthat helps you nail down the why, what, who, and how of your offsite (in that mandatory order)—or decide if you need one at all.

It’s my no-strings-attached gift to you, aimed at never hearing about “bad offsite” ever again. Grab a 30-min chatwith me to walk through the tool, or dive into the DIY route with my 10-minute masterclass.

Here’s to fantastic offsites that prove to be the best investment of your time and money!

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