So, your boss has picked a location for the next team meeting or off-site event.

But here’s the problem: it’s not just inconvenient; it’s practically on Mars, costs a small fortune, and no one really wants to go there (because it’s just as hot and dry, like their sense of humor). You’re stuck in a classic dilemma—how do you tell your boss their idea might be a terrible one without risking your job or coming off as the office downer?

Don’t worry, we’ve got you covered. Here’s how you can diplomatically steer the ship away from an iceberg without ending up in hot water yourself.

1. Start with the Positive

Before you jump into why the location might be a bad idea, it’s crucial to acknowledge the thought process behind the decision. Maybe the boss picked this place because they think it will inspire the team, offer a unique experience, or impress the higher-ups. Start by highlighting these positives.

For example, you might say, “I can see why this location could be appealing—it’s definitely different and could provide a fresh environment for brainstorming.” This shows that you understand the intention and aren’t just shooting down their idea without consideration.

2. Present the Practical Concerns

Now that you’ve softened the blow, it’s time to introduce the practical issues. Frame these concerns around the team’s well-being and the overall success of the event. Think logistics, budget, and team morale.

You could say something like, “I’ve been thinking about the logistics, and I’m a bit concerned about how this location might impact the team. It’s quite far and the travel expenses alone could eat up a big chunk of our budget. Plus, some team members might find it difficult to get there, which could affect their participation and enthusiasm.”

Here, you’re not just pointing out problems; you’re showing that you’re thinking ahead and considering the bigger picture.

3. Suggest an Alternative Solution, with Data

Don’t just be the bearer of bad news—be the person who comes with solutions. Suggest an alternative location that ticks the same boxes but avoids the pitfalls. This shows you’re proactive and supportive, not just critical.

You could say, “What if we consider [Alternative Location]? It’s still got that creative vibe, but it’s more accessible and would keep costs down. I think the team would be just as excited about it, and we wouldn’t have to worry about the logistics as much.”

Offering a well-thought-out alternative proves that you’re on the same team as your boss and that you’re working towards the best possible outcome.

(Team, Assemble! can help here. Hint hint.)

4. Bring the Team On Board

Sometimes, it’s not enough to have a one-on-one with the boss—especially if you suspect your concerns aren’t going to be taken seriously. This is where teamwork comes into play. Get a feel for how the rest of the team feels about the location, and maybe solicit opinions on where else it might be great to go.

Phrase it like this: “It might be worth gathering the team’s thoughts on the location. I think a quick e-mail reply with your thoughts might give us a better idea of any potential challenges and help us make sure everyone’s on board.”

When it’s not just you raising concerns, your boss might be more inclined to listen and reconsider.

5. Suggest Using Team, Assemble!

Finally, propose a solution that could make the entire planning process smoother and more efficient: Team, Assemble! This platform allows teams to suggest location destinations (while providing their travel preferences and home-bases), helping travel planners (and the big boss) ultimately land on the best choice collectively.

It’s a great way to ensure everyone’s voice is heard and that the final decision is one the whole team can get behind.

You could pitch it like this: “I’ve been looking into tools that can help us streamline these decisions in the future, and I think Team, Assemble! could be really useful. It lets everyone contribute their thoughts and helps us find the best solution that works for the entire team without the bike-shedding.”

Conclusion: It’s All About Teamwork

At the end of the day, it’s not just about where you’re going, but how you get there. By approaching the situation thoughtfully, considering everyone’s needs, and using tools like Team, Assemble!, you can help guide your boss to a better decision—one that benefits the whole team. Plus, you’ll earn some serious brownie points for being a thoughtful, solution-oriented employee.

Ready to make smarter decisions together? Sign up for Team, Assemble! today and ensure your team’s next destination is one everyone’s excited about.