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"Behind The Scenes" On How To Plan An Offsite (After Planning Hundreds Of Team Retreats Globally)

Offsite founder/CEO Jared Kleinert interviews Senior Client Success Lead, Kim Ford!

Whether you’re planning your own offsite and wish to learn some of our “pro-tips” after planning hundreds of team retreats for clients, or you are considering working with us via our done-for-you services, we have something special for you!

I asked Kim Ford, our Senior Client Success Lead (responsible for managing all our offsites and other Client Success Leads) to share a high-level overview of our offsite planning processes with you, in an effort to hopefully save you a lot of time and money whenever you plan offsites while increasing the ROI of your retreats.

Offsite is also partnering with Ask A Chief of Staff, the go-to community for “people leaders” who serve as Chiefs of Staff (or desire to do so in the future) on the first-ever Chief of Staff Offsite Survey.

If you could take 3 minutes to fill it out, we will share anonymized data back with you through a lovely, easy-to-share-with-your-team report so you can be better informed about the average budgets, offsite duration, locations, and more across dozens of like-minded companies. Click here to take the survey, and thank you.

Kim covers the following for us:

  • the importance of having a step-by-step process when planning offsites

  • the importance of knowing your specific goals and vision for an offsite even before setting your budget, choosing a location, and planning other logistics

  • budgeting, seasonality, and leveraging our various partnerships to support clients

  • the value over-preparing and having all necessary supplies on hand

  • pro tips around choosing offsite venues with good communication, which you can learn during the proposal and contracting process as well as site visits

And so much more…

We didn’t want to share ALL our trade secrets, and I only asked for about 15 minutes of Kim’s time for this interview, but if you enjoy this, please let us know at jared@offsite.com so we can make more content like this in the future.

Special thanks to Kim for taking time to be “on camera” with me.

If you haven’t already, subscribe to The Offsite Blog below for agenda templates, budgeting spreadsheets, and more thought leadership around offsite planning, remote work, and increasing employee engagement.

Planning an offsite, team retreat, or conference?

Whenever you plan offsites in the future, make a free account at offsite.com to search our curated marketplace with ~1000 amazing offsite venues globally where you can save 20%-40+ savings on room blocks, meeting space, and more.

Plus, we offer end-to-end offsite planning services if you want a “done for you” experience. See why hundreds of companies like Buffer, 15Five, HiBob, Metabase, Hampton, and others trust Offsite for their team retreats.

Thanks for reading!

-Jared


Below is a transcript of the interview (it was a ~15 min convo). I fed the interview into Otter.ai, and while I took a few minutes to break up some sentences for readability, I didn’t edit everything perfectly (the AI was supposed to do that, lol!). It’s hopefully “good enough” if you prefer to read the transcript, or you can watch the interview above.

JARED - Welcome, we're live. I'm on the road because we're a remote first company. And we can work from anywhere.

So I'm at a WeWork right now, in the Washington, DC area. Kim was telling me before we hit record that she actually helped open up this location in a past life. But I got to meet Kim, a little over 10 years ago, when she was supporting Tony Hsieh from Zappos fame, and the Downtown Project.

They were bringing entrepreneurs like myself to the area, planning these conferences, and Kim was one of the masterminds behind that. And so fast forward all these years, we get to work together. She's amazing. And I wanted to invite her onto our blog here to share a little bit about her work at Offsite today, and what we do for clients. So Kim, welcome to our unofficial show.

KIM - Awesome, thank you, first time doing something like this. Like you said, for anyone interested, I do have quite a bit of a background in event planning. For a long time I was in the tech space planning kind of tech startup events, then kind of merged in they're doing community building events with communities in downtown Washington, DC, and then in some suburbs of Texas. And then most recently, I've kind of combined the two in helping create communities for companies that are doing off sites all around the world. And I love it. So excited to be here.

JARED - We are grateful to have you on the team. And when Kim joined us, she was a Client Success Lead planning team retreats herself, I'll let her go a little more into that. Now, she not only plans some of our larger offsites for clients, but she's also essentially running our client success team.

And all the other client success leads are reporting to her as well as other team members. And so Kim knows a thing or two about also planning now.

And you know, if you would…I would love to hear what actually happens these days, you know, after myself, Jake, or Andy from our sales team is able to onboard clients. And we hand it off to you guys to tell the people what goes into planning an offsite, I think, you know, this is a really cool opportunity for us to open the kimono and let people into the Offsite process, if you will.

KIM - Well, before I kind of jump into kind of like what our step by step processes are, like, we do have, we've done our best to kind of create offsites into, you know, play by play in creating it into a science.

In fact, like, a month ago, I broke it down into over 100 steps that we do. But that being said, we love our clients, we love how everyone is so different and so nuanced. And every company has a different culture. And so we love to really lean into that and encourage creativity and thinking outside the box.

So that is something that we really push in trying to like pull that out of you in these meetings that we have with you. So once we get handed off from the sales team, we're gonna do an onboarding call, and we're going to ask you a million questions. So be ready for that.

But before we kind of like get to the logistics of things, we really want to understand your goals and your vision. And like what success looks like for you and your company. And putting on this offsite, we understand it's a huge investment. And we want to make sure that we really hit that target. And that when all is said and done everyone on your company, like loved it, and that we really met those goals.

So those are the very first questions that we're going to ask you. Then as someone who is kind of a numbers gal, myself, we want to see what your budget is. And so we will do like a really deep dive in your budget.

And because we've done so many of these events, we can really break down like just how much we can spend on your activities and your budgets and where we think the price point needs to be for your hotels and how many nights you can afford to stay so we can really break that down for you.

And we can suggest like maybe you you know, want to make sure your team is going to a warm place but it just San Diego just doesn't fit in the budget. We know seasonality, we know events around the country, we can really make some suggestions that can make you know still great off site fit within your budget.

So after the budget, we're gonna throw out some like creative ideas and kind of play to some of those goals, your culture, things like that. And like see, you know, if kind of we're hitting the mark with the culture of your company, I'm there Sorry, I have a couple of notes over here.

We're gonna use our experience and what we've seen that worked with other clients. And suggest some programming ideas and really kind of like pencil out what we would suggest for your agenda.

One mistake we see happen a lot is overpacking the agenda, we want everyone to not be too exhausted and hate each other by the end of your offsites, we need to make sure that we pack in, you know, enough breaks and enough time for those introverts to get some time to themselves and recharge and stuff like that. So that is something that we try and make sure that we work into your agenda.

Another thing that we can bring to the table is we have relationships throughout the industry. And we like to leverage our relationship and industry to give you guys the best deals and work with the best companies out there. So in things like transportation, and flights and hotels and activities, we have worked with hundreds of 1000s of companies. And so we really work to get you guys the best deal and work with the best companies.

Also, we are going to keep you guys on a schedule. So in the very beginning of the process, we're going to create a, you know, a calendar of deadlines of these are when these deposits are due. And this is when you need to decide this for your swag. And this is when you need to submit your rooming list. So we're going to keep you guys on a schedule and make sure that we're not rushing at the end, and that everybody can be as stress free as possible throughout this process. And then leading up to the event, sometimes off site will be on site with you guys to help him on the event. But sometimes we empower you guys to do it yourself.

And so the weeks leading up to the event, we're going to make sure that everybody on your planning team feels empowered, has all the information that they need will create facilitator roundups, with contact information, links to contracts, everything that you could need on site will have meetings to connect you to all the vendors. And just make sure that everybody feels good and that there's no stress leading into this, then during the event, we will be your on call people. I hate to say this, but something always goes wrong. And that's just part of events.

But we are here to alleviate and put out any fires that happen. Just because we might not be on site with you doesn't mean that we are there with you advocating on your behalf. And so we will still make sure that everything goes as smoothly as possible.

And then after everything is said and done, we want to hear about everything went here, all the great stories, and then we're going to be there for you to help reconcile your budget and, you know, kind of put like, quote, close the book on it and survey your team, get those results, see how much everybody loved it and make sure that we like actually hit those goals that we asked you in the beginning. So that is kind of my my overview of what we do for our clients.

JARED - Yeah, and that was just, you know, 10 steps out of the 100 people on our list. And I've been with you on the ground personally with some of our larger clients like 15Five, seen you sort of run the show for a 130 person sales kickoff. And now you've taken on some of our higher end clients like the YPO event that we just did in Las Vegas, which is super high end.

What would you say are some of the pro tips that you're sharing with the rest of the client success team so they can help their clients more effectively? And then what would you tell either a potential new hire that we have or someone that decides not to work with Offsite for their end to end planning, but just uses the marketplace to get their venue and then tries to play it on their own? Yeah, what are some pro tips for offsite planning that you've learned after doing this 40 or 50 times at our company?

KIM - I wrote down a few one I mentioned I am a budgets person. So one thing that I do in the beginning is I actually pad the budget and make sure that even in a padded situation that we stay within budget because things are going to happen lights, people are going to have to buy last minute flights or you know things happen and so make sure that you aren't cutting your budget so close that you're going to end up going over budget. So that's probably something that I would recommend as kind of a pro tip.

Another thing that I think is really important is in choosing a hotel. Like money is not the most important thing or only important thing I would say like having a hotel that has good communication and that you can build a good relationship for is really, really important. So if a hotel is not, you know, takes forever to respond and is not helpful and stuff like that, that's, that's kind of a red flag to me. And so I typically would not push a hotel like that.

And then a couple other I think, on the ground tips, I hate like to really over prepare. And like every document you have, I like to just print off every schedule, contact information, have it already, I have kind of like, I'm one of those people with that with the like, one of those club clipboards, that you'll see me running around with all like my highlighters and my pens. So over prepare, think about every situation maybe like, you know, your boss needs to leave, but you're missing one person, and you can't find that contact information, just like have everything readily accessible.

And then kind of in that same ballpark, I like to just buy a bunch of a like event in office supplies, and ship them to your hotel. So buy box cutters, Sharpies, paper, Post It tape, like maybe you have no idea what you need tape for, but you're probably going to need it. So like just buy those things, it'll cost you $30 and just have it at the hotel. So you're not like trying to find someone who has a pair of scissors for you.

And then I think my last piece of advice is like don't stress the small things, things are gonna go wrong. But nine times out of 10, your attendees have no idea and they're just enjoying themselves. So just like soak up that energy. Don't worry that the appetizers are 15 minutes late, like nobody notices. So just don't stress the little things. It's not a big deal.

JARED - “If you're having a good time, they're having a good time.”

So as as our senior clients access lead with the rest of the team, looking up to you, you know, asking you for advice. What are you most excited by these days as as far as what off site is working to provide to our clients and you know, how far we've come in the process of documenting and leveling up our off site planning process?

Hmm, um, one thing that we try to provide clients is kind of a microsite that's been something that we've been working on. And so we've been trying to like, level up and kind of like, you know, working with graphic designers and creating, instead of kind of having all these documents that I talked about having a place for all your attendees, that appears very professional looking, branded, branded, you know, for our clients, but also it kind of captures the vibe of your offsite with where you're going.

And it has all the information in one place like packing lists, weather information, how, you know, map information about how far they need to walk for dinner. Like what dietary restrictions are accommodated, all that information is in one place. So you kind of alleviate all the hundreds of questions from attendees that they'll have. So that that is something that I love that we've been pushing and hoping and working to improve for our clients.

JARED - And maybe just last question, what are you most proud of given your time at all side all the work you've done for clients with the rest of the team.

KIM - Um, I think creating systems to help kind of part of being an events is trying to catch all the details and be very detail oriented. But with having lots of clients and so many nuances and working with so many vendors, we try and create systems that alleviate possibilities for sometimes having mistakes and stuff like that. So that is something that I'm working hard with our team. And also making sure that that every client gets the same amazing experience with no matter what client successfully they get assigned to.

We all have different backgrounds and different experiences. We want to make sure that everybody has an incredible experience with the off site. And so we're trying to make sure that we level up in all areas and that, that if you know someone doesn't have that background of knowing hotel industry or knowing how to like create a meeting agenda, you know, stuff like that, that we train all our employees to like level up and have that experience.

JARED - I'll tell you privately all the time, but I'm so grateful that We're working together. And I'm really grateful that you're leading the team now. I think we're better than ever at off site planning and roll. We're getting better with every passing day. So thank you so much for your time, just giving people a sneak peek into what it's like to work with Offsite.

If you liked this content, we can do more deep dives into this. Maybe I can have can write some, some more stuff up for you. But thanks so much for watching this and we'll talk to you soon. Thanks again.

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