Playbook
The Power of In-Person Collaboration — and How To Bring People Together
Planning a trip is way less fun than being on one.
And planning a work trip is way more work than it should be.
It usually involves sending desperate RFPs to whatever hotels you can find, playing endless email ping-pong with 50 colleagues who all need "just one small change" to their booking, and sweating the logistical nightmares of getting everyone from airport to hotel to meeting space without losing half your budget on Ubers.
A travel manager shouldn't spend 50+ hours of their life hunting down room blocks when they could be focusing on what actually matters – making the gathering meaningful.
It’s exhausting admin work, and not the best use of valuable time.
Whether staff is in-person, hybrid, or fully remote, planning group travel is a huge pain. And that’s a bummer, because the headache gets in the way of the good part: bringing people together.
“We always just found that there was so much value in this [in-person] connection between our teams,” says Workgrounds co-founder and CEO Nikhil Sethi. “And we always try to figure out what's the right format to do it. How do we do it best?”
Spoiler alert: The best format isn’t "torture your team lead with endless phone calls and spreadsheets."
But that's exactly what’s happening.
Manual booking is a messy system that only gets you halfway to what you want.
When you’re working hard, trying to do the best you can, you’ll probably end up with one of these compromises:
- Every person for themself: You let team members book their own travel, which is flexible but uncoordinated, and cuts into any group savings
- Invest in the best: You only flex your group chops for the biggest events, leaving the smaller ones in the dust
- Bring on a travel team: You hire people whose whole job is making your events happen, which adds a lot to your overhead
While all are decent ideas, each has issues—and none of them are a real solution.
Taking team planning out of the stone age
Sethi has seen how much gruntwork goes into a great work event. “It was mind-numbing how much energy we'd spend to make sure these things were really good."
It was like he’d been thrust into a time “before the Digital Age, an almost prehistoric way of figuring out how to put these events together.”
It’s not exactly cave drawings, but in 2025, most manual travel booking systems do feel pretty out of date.
And when an employee is sending RFPs by hand, that means they’re losing 50+ hours per logistics meeting and 8+ hours per booking. They’re wading through all the usual business gunk: multiple approvals, no view into the total travel spend. It’s a shot in the dark with a healthy pile of paperwork.
Future-looking orgs know that team gatherings are strategic investments that deserve the full power of smart tech.
They’re making moves to:
- Use transparent, adjustable systems, with all the info in one place
- Cut back on repetitive to-dos (RFPs, for example)
- Cast a wider net without creating more work for leaders
The travel industry’s moved pretty fast to bump up prices, but it’s not moving as fast to fix up, well, much of anything. Ever been on a more-expensive flight on a super-old plane? A pricey hotel room with a questionable stain on the carpet?
It’s definitely not hustling to make booking systems more in line with this century.
That’s why companies are taking up the mantle themselves.
AI, racing to the finish line
"We bet on the fact that there will be a solution to this problem — a more efficient way to get both aspects of the equation,” Sethi says, “meaning maximum flexibility for people, but also super-coordinated, economically-viable super leverage on the buy side."
Companies save 28% on average when they book group events with automated systems. And, with automation, the 3-5 days it can take to book a group event comes down to minutes.
What does the ideal automated platform include?
1. An info hub and outreach system with no middleman
No more lost confirmation numbers. No more scrolling through Outlook, begging the search function to actually work for once and show you what you’re looking for.
Just one spot, with everything you need.
That includes:
- An overview of team locations and travel patterns
- The ability to change single reservations on the fly
- A way to chat with hotels without, well, having to talk to them at all
2. A wider search (no extra work required)
"Most people who do these plans, who are looking for a meeting hotel space, end up reaching out to three, maybe four places tops,” Sethi says. “Sometimes they default to the same one over and over again because it just seems good enough, and it seems easy.”
But that’s not a great way to operate. You don’t know if it’s the best option, even.
Plus, it still takes plenty of time to set up your usual place. So why not spend less time for more results?
The best possible venue sourcing lets you select multiple hotels with a single click, specify room needs and dates (no call required), and send RFPs to 50+ options at once.
And above all, it gives you your time back — negotiating on your behalf and getting those best rates lined up — so you can focus on the work you do best.
3. Easier ways to handle events
When you have more options, you need a good way to figure out which option comes out on top. And once you’re happy with the logistics and planning, you need to package it up with a bow on top to get the final budget approved.
How automation can help you do that:
- Give everyone access so they can be involved without missing a beat
- Compare venue proposals
- Keep a clear ledger of everything that you (or someone else) has done
- Track the dollars and cents — both for now and for next time
- Handle last-minute flakes/changes
All clicks, no calls — sounds like a perfect WFH situation.
4. Get the team excited!
With everything booked and ready (!) it’s time to show the team what you’ve been working on. A splash or event page lets employees communicate directly with the organizer, and lets the organizer lay out a detailed itinerary for the event.
It also lets them send updates to everyone if event times and locations change, or if there’s anything new for people to know.
Once you’re all booked, you can still make tweaks to your plans, too. After all — there’s no group event without some hitch.
An automated platform can smooth out the unavoidable road bumps by making last-minute fixes easier, like “decoupling” (no, we’re not talking about those will-they/won’t-they coworkers). If something changes, you can switch up plans: go with just rooms and no workspaces, or add workspaces on.
What life looks like when you get your time back
Usually, companies that don’t use automation leave 30-40% of savings on the table — no small amount of missed opportunity.
And it’s why AI RFPs are designed to maximize savings, with time savings as a huge bonus.
Some examples:
- Team leaders stopped spending 50+ hours on calls and being-on-hold, which let them focus on strategy and the reason for meeting instead
- Get 70 hotel group booking offers across 6 cities to find the perfect location (in just an hour of searching)
- Companies that looked at more venues saved 28% on average
- Plans got made faster, down from weeks to just days
- With less friction, everyone’s happier (always a bonus!)
Fine-tune your travel for 2025 (and on)
When companies use AI for team bookings, they see more savings (money AND time). There just isn’t enough time in the day to wrangle as many properties as automated systems can — or you shouldn’t have to spend that time, anyway.
It’s important to focus on:
- The value of bringing everyone together
- How your coordination looks now, and how it can be better
- See how the team feels about planning and about the event itself
- Getting all your info in one place, and make it easy to tweak
When companies reimagine how their teams get together, they can focus on the why of the team meeting, which is what really matters.
Schedule a demo to start saving an average of 31% on every hotel booking.
