Let me set the scene... You're a manager, Director, VP, or CEO. You run a remote or hybrid team. You KNOW that getting people together builds high-performing teams, you know your team enjoys these opportunities, and you recognize why they're important. You have the budget, you've figured out the dates, you've waited maybe accidentally a bit too long to figure out what you'll actually be doing with this time, but now it's coming up, so you ask your group "what should we make sure to cover in our time together?"

What you hear sounds reasonable. Your direct reports want to hang out together and just have some team bonding time. One or two people have some ideas of a process or approach they want to try out and they want to use that time together to brainstorm and/or get feedback and buy-in. So that's that. You divvy up the agenda, post in a few Slack for good "team bonding activities", and move on to the next things you have to get done.

Does this sound familiar? Probably. It's what I see a vast majority of leaders do when they're planning and thinking through these gatherings.

Here's some hard truth... even though it feels fine, good enough, maybe even productive, it's not. Your expectations are too low.

What's actually happening here

When you ask your team "what should we cover?" you're asking them to tell you what would make a good birthday party, not what would truly drive business goals forward. They're going to tell you things like:

• We should hang out more
• It would be fun to do an activity together
• I have this one idea I want to workshop

And look, none of these are wrong. But they're not strategic. They're not going to move the needle on the conversations you've been having or thinking about for six months without resolution. They're not going to get you unstuck on the challenges that keep you up at night. They're not going to create the kind of alignment that makes the next quarter run smoothly instead of continuing to run to the next fire.

And even if your team can tell you what they need, it's up to you to frame and tackle these challenges in the right way, so that they're looking at the heart of the issue and not just a piece of it. They're measuring success against other gatherings they've experienced, which (let's be honest) have probably also been just "fine."

You can think of it like customer interviews. When you're talking to customers or constituents, they'll give you ideas but you don't build each of those things into features or programs. You take a deeper look at what threads are connecting those requests, examine your customer's journey and their pain points in order to get to what they don't even know to request. THIS is your goal when designing a gathering.

What you're actually optimizing for

Here's what typically happens with this approach:

1. You spend time together
2. People enjoy seeing each other
3. You talk about some things
4. Everyone leaves feeling pretty good and probably with some next steps from some discussions but not all of them
5. Three months later, not much has actually changed

You're optimizing for "did people have a good time?" when you should be optimizing for "what's different six months from now?"

The conversations that have been stuck for months? Still stuck. The alignment issues? Still there (or went away but have since resurfaced). The priorities that feel fuzzy? Still fuzzy. The energy and excitement from the gathering? Gone by the following week when everyone's back to their usual routines.

And look, I get it. People having a good time isn't a bad goal. But when you're investing thousands of dollars (when you count salaries, travel, venue, and opportunity cost), you deserve better ROI than "people enjoyed themselves."

What better actually looks like

Better gatherings accomplish three things simultaneously:

1. Real strategic work gets done (decisions made, priorities clarified, stuck conversations unstuck)
2. Deep connections form through tackling those challenges together
3. Clear action plans emerge that people are still executing (or have completed) six months later

Notice I said "simultaneously." Not team bonding on day one and strategy on day two. Not fun activities in the morning and serious work in the afternoon. The connection happens THROUGH the strategic work. Trust builds when you tackle hard problems together in creative ways and offer people different, more meaningful ways to get to know one another. People leave knowing each other better AND with clarity on what's next.

This is what it looks like when you're asking the right questions during planning:

• What conversations have we been having for 6+ months without making progress?
• What decisions do we need to make that we keep putting off?
• Where do we lack alignment that's causing friction in our day-to-day work?
• What would be different about how we work together if this time was truly successful?
• What do people need to know, feel, and do differently after we're together?

How to actually get there

Stop asking your team what activities they want to do. Start asking yourself what outcomes you need to achieve.

Then work backwards:

1. What are the 2-3 most critical outcomes for this gathering? (Not 10 things. Pick the vital few.)
2. What conversations need to happen to achieve those outcomes?
3. What's preventing those conversations from happening effectively in our regular meetings?
4. How can we create the right conditions for breakthrough on these topics?
5. How do we ensure we're creating an agenda that flows and doesn't just exhaust people with multiple days of heavy or intense conversations?
6. What accountability structures will ensure the decisions we make actually stick?

And here's the thing - you might realize that designing this kind of experience requires expertise you don't have. You can do AN activity. But sequencing 15+ interconnected activities so each builds momentum toward your goals? Facilitating real-time when someone opposes every idea? Navigating power dynamics so all voices are heard? Turning discussions into decisions with real accountability? That's not something you figure out on a Slack thread two weeks before your gathering.

The real question

The next time you're planning a team gathering, ask yourself: Am I planning a birthday party or a business transformation?

If the honest answer is birthday party, that's fine - but own it. Don't expect it to solve your strategic challenges or create lasting change.

But if you actually need business outcomes, if you have real challenges that need solving, if you want your team to be different after this time together - then you need to approach it differently. You need to set your expectations higher. You need to invest in making it actually worth the time and money you're spending.

Your team deserves better than "fine." Your business deserves better than "good enough." And you deserve to walk away from a gathering knowing that something real has shifted, not just hoping it made a difference.

---

Ready to plan a gathering that actually produces lasting change? Book a free consultation call with me today. I'll help you identify what outcomes you really need and design an experience that delivers them - not just another "fine" gathering that everyone forgets about by next quarter.