27 Questions to Ask Before Hiring a Corporate Travel Planner

Experience and track record (questions 1-6)

Start with questions that reveal whether the planner has handled groups like yours, not just groups in general. A planner who regularly manages 20-person executive retreats may not be the right fit for a 300-person sales kickoff, and vice versa.

Listen for specific numbers in the answers - vague responses like "we've done plenty of groups" without details on size, destination, or recency are a signal to probe further.

• 1. How many corporate group trips have you planned in the last 12 months?
• 2. What is the typical group size you work with, and what's the largest you've handled?
• 3. Have you planned trips to the specific destination we're considering?
• 4. Can you share references from clients with a similar group size and budget?
• 5. What industries do your clients typically come from?
• 6. How long have you been operating as a company, and what is your team's background?

Contracts and risk management (questions 7-12)

This is the category that most directly affects your financial exposure, and it's where inexperienced planners often fall short. A planner should be able to explain attrition, cancellation, and force majeure terms clearly and in plain language, not just point to boilerplate contract text.

If a planner can't explain the difference between attrition and cancellation penalties off the top of their head, that is a meaningful red flag given how central these terms are to the financial risk of a group contract.

• 7. Who reviews and negotiates the hotel contract on our behalf?
• 8. What attrition percentage will you negotiate, and what happens if we fall short of it?
• 9. What are the cancellation penalties at each stage before departure?
• 10. Does the contract include a force majeure clause, and what does it cover?
• 11. Who is financially liable if the venue fails to deliver contracted services?
• 12. Do you carry liability insurance, and can you provide proof of coverage?

Pricing and transparency (questions 13-17)

Group travel pricing structures vary widely - some planners work on a flat fee, others on a per-person markup, and others take commissions from hotels that may not be disclosed upfront. None of these models is inherently wrong, but you should know which one you're agreeing to and what it means for your total cost.

Ask directly about commissions, because a planner earning commission from a specific resort has a built-in incentive to steer you there, which isn't necessarily bad but should be transparent.

• 13. What is your fee structure - flat fee, per-person, or commission-based?
• 14. Do you receive commissions from hotels or vendors, and do those affect your recommendations?
• 15. What's included in your quoted price, and what counts as an additional cost?
• 16. How do you handle currency fluctuations or price changes between booking and departure?
• 17. What is your payment schedule, and what triggers each payment?

On-site execution and logistics (questions 18-22)

A planner who is excellent at contract negotiation but has no plan for on-site execution leaves you exposed on the day that matters most. Ask specifically about who shows up, what their role is, and what happens when something goes wrong in real time.

The answers here should be concrete: a named role (not just "someone from our team"), a described process for handling issues, and examples of problems they've solved on-site before.

• 18. Will someone from your team be on-site during the trip, and in what role?
• 19. How do you handle rooming list changes or last-minute attendee substitutions?
• 20. What is your process if a flight delay disrupts the group's arrival schedule?
• 21. How do you coordinate with the resort's own event and banquet team?
• 22. What happens if a vendor - transportation, entertainment, AV - fails to show up?

Communication and process (questions 23-27)

Finally, ask about how the planning process itself will run, since this determines how much work lands on your internal team versus the planner. A good planner should be able to describe a clear cadence of check-ins, a single point of contact, and a defined process for attendee-facing communication like registration and travel documents.

If the answers suggest you'll be chasing the planner for updates or doing significant coordination work yourself, that mismatch will surface repeatedly over the following months.

• 23. Who is our single point of contact, and how quickly do you typically respond?
• 24. What does your standard planning timeline and check-in schedule look like?
• 25. Do you manage attendee registration and communication, or does that stay with us?
• 26. How do you handle attendees with special requests - dietary, accessibility, extended stays?
• 27. What happens if our headcount or budget changes significantly mid-process?

How to run this as a single discovery call

You don't need to read all 27 questions verbatim in order. Group them into the five categories above and allow 10 minutes per category in a 50-minute call, taking notes on specificity rather than just whether an answer was given. A planner with real experience will often answer two or three questions at once because the categories naturally overlap in practice.

Pay attention to which questions the planner seems eager to answer versus which ones prompt a vague or deflecting response - that pattern tells you as much as the content of any single answer.

Red flags to watch for across all categories

A few patterns show up repeatedly when a planner isn't a good fit: reluctance to put fee structures in writing before a contract is signed, inability to name a specific attrition percentage they typically negotiate, no clear answer about who is on-site during the event, and references that are more than two years old or from a very different type of event.

None of these alone is necessarily disqualifying, but two or more together is a strong signal to keep evaluating other options before committing.

How Latitude Group Travel answers these questions

We built this list in part because it reflects the exact questions HR and operations leaders ask us during discovery calls for retreats, incentive trips, meetings, and sales kickoffs across Mexico and the Caribbean. We have a dedicated on-site lead for every trip, a standard practice of negotiating attrition and force majeure terms before any contract is signed, and a flat, transparent fee structure disclosed before you sign anything.

Running through this checklist with any planner, including us, is the fastest way to know within one conversation whether they're equipped to handle your specific trip - and it puts the risk conversation on the table early, where it belongs, rather than after a contract is already signed.