162: How to Do Team Retreats
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In this episode, Steli and Hiten discuss the importance of company retreats. A retreat is a valuable part of a company and should be planned and executed well—start to finish. Listen as Steli and Hiten share their own company retreat experiences. They reveal what worked, what didn’t, and provide pointed suggestions on how to get the most value out of the company retreat experience.
Time Stamped Show Notes:
- 00:10 – Steli introducing company retreats and its value
- 00:44 – Steli just returned from their team retreat
- 02:19 – Most of the companies that are doing retreats nowadays are remote companies
- 02:30 – Retreats are valuable to the team because employees get an opportunity to have those personal interactions
- 03:20 – Retreats that are similar to vacations don’t really work out well and are not too productive in regards to team building
- 03:47 – A retreat is also a cultural experience
- 04:24 – Make sure that retreats are culturally aligned with the company
- 05:05 – A “good retreat is how a company started”
- 05:30 – Steli shares how a retreat helped him and his co-founders
- 07:20 – How a retreat changed the purpose of Steli’s new startup
- 08:00 – Steli describes the spectrum of retreats—from working all day long to it being a vacation
- 08:58 – “What are we trying to accomplish in this entire retreat?” Assess and plan each day intentionally
- 09:16 – “There are small things that have a really big impact”—separating where people sleep and work
- 09:57 – Steli shares why he chooses a coworking space for the team
- 10:41 – Have a theme for the retreat
- 11:10 – “We’ve gotten really good at prioritizing”—you can only accomplish so much so having a theme keeps your work goals focused
- 12:35 – During mealtimes, Steli’s employees would be assigned to different team members to share a meal together
- 12:50 – Steli provides three questions that they can ask each other over lunch
- 13:40 – Make sure the members are getting the value of the experience
- 14:14 – A retreat is not just about going out to some other location
- 15:59 – Evaluate the impact of the retreat and make a more challenging one for the next time
- 16:45 – Hiten shares an experience of a retreat where they brought a customer on stage to share their difficult experiences with the product
- 17:16 – Hiten’s company worked immediately to address those difficulties and fix what the customer wanted as quickly as they could
- 17:47 – Organize customer visits to get that direct feedback, even within a retreat
- 18:40 – Reach out to Steli and Hiten and share your company team tips and experiences
3 Key Points:
- Be intentional with the planning of a retreat—from where people sleep to the coffee on tap next door.
- Evaluate your retreat and whether you hit your goals when it’s over and make a more challenging one next time.
- Create a balance between work goals and personal interaction and fun to make it a valuable experience.
Steli Efti: Everyone, this is Steli Efti.
Hiten Shah: And, this is Hiten Shah.
Steli Efti: And, in today’s episode of The Startup Chat, we’re going to talk about how to do team retreats, company retreats and how to do the well – why you should even consider doing them, how companies do them – how to do wrong, how to do the well. What is the practical value of them? I just want to explore the city with you – one of the reasons why I want to talk about this with you Hiten today is that I just returned from our last team retreat of the year. We were – we just spent a week in Santa Barbara.
It was beautiful – beautiful weather and we spent a week there with 20 people. This team and our team has grown quite significantly from eight people in January to 20 people. It’s still a tiny team but it’s going quite a lot for us and this just – every retreat is different every week we’re learning new things. I’m really very mindful about designing these retreats to accomplish certain things.
And we’re very I think careful about tracking how successful they were and what was surprising – was changed and we kind of – we’re designing these. We’re not just showing up at some kind of a co-working space and go – let’s have a week of fun or something. And, we’ve been doing team retreats from day one, so we’ve been doing this for four or five years now we’ve done quite a few company retreats. We’ve experiment quite heavily with its – have some strong opinions on this, but I also would love to hear your input your opinions. I don’t know if you –have you ever done company retreats with any of your companies? I’m not even sure.
Hiten Shah: Yeah, definitely done – we did we did a bunch of them at KISSmetrics, and I participated in quite a few company retreats of other companies as well.
Steli Efti: What is your take on so even before I jump in and check out of my two cents – I’m curious what is the – what do you think is the value of company retreats? Is it invaluable? is it more about kumbaya like the extended version of a Ping-Pong table – we want to be cool type thing, but it’s not really practical with – what’s your opinion in general about like companies that do retreats?
Hiten Shah: Majority of companies that I see doing retreats these days happen to be companies that are remote like your company or my companies. At KISSmetrics it was helpful because we were a remote team as well and we had an office at that point, so I find it very valuable when the team doesn’t get to have face time that often because it’s nice to see other humans that you work with in person. So I think it’s – it can be really valuable with it as the team grows – like in your case the team’s grown and people probably don’t know each other really that well so that can be helpful.
And then, in the case of like even now I know you probably know a lot about this but sales teams have their own sort of off sites for retreats – marketing teams, product teams, growth teams, engineering teams – all this all these teams do that. You know especially as they grow and scale, so that’s another type of retreat I would say. Yeah, and then recently I’ve heard of things that are even worse where it’s like it worse – I don’t know I have opinions. But, they go on a vacation not a retreat.
And, nothing gets done and it’s more of a relaxing vacation. In most cases I haven’t seen those work out very well because the company gets used to vacationing all the time because even if – because even if you go a couple times a year, that’s vacation. Now, that’s only in ones where nothing gets done and it isn’t productive to the organization, and then it’s just all about just hanging out with each other which you know has its own merit. And, after this, I’m going to say the final point that I have about these retreats and stuff – and then I’m sure you have a lot to share because you just came from one – I think it’s very cultural.
So, I could say that hey going on vacation three times a year four times a year is bad if you don’t accomplish anything – beyond just hanging out with each other. But, in some cultures and some companies that could be the most amazing part of the company, it could be why people join the company. It could be that the company and the in the market there is really really stressful – truly tried stressful like you know like an Uber like company, and by doing that they keep the team motivated as they go through hell so to speak.
So, I can’t complain and say there’s a wrong or right way to your retreats. What I can say is you have to make sure that they’re culturally aligned with your company and that they don’t become something where like it’s all about the retreat – and people are really looking forward to it in a way that’s sort of like oh so the companies like we just work and we go on a retreat, and that’s our reward for working. So, I don’t think it should be like. That being said, there are companies that do that and it works for them.
So, just like many other things in companies this it’s on culture and team and its structure and all these all these other factors. So, yeah pretty much at this point really curious to hear like about how you guys do it and what you think about it, but that’s my high-level take.
Steli Efti: So, I think that culturally – for us doing retreats is pretty much how this company started. So, we were doing a start-up, and it wasn’t working and we’re banging our heads against the walls and it was still not working and eventually got to a point where we decided all right let’s do this, let’s change let’s get back to some level of getting the creative juices flowing again. Let’s do this – let’s take three weeks each founder, we’ve three founders, pick a city – because we all love traveling – a city they’ve never been to that they want to visit.
We’ll Airbnb an apartment, and will do three different throw away ideas for three weeks and then come back and maybe that little bit of like time off creatively working on other things and not just like banging our heads against not just like banging our heads against the wall trying to fix this thing for the last year. And, that will help us and re-energize us – maybe we’ll find a solution for this or maybe we’ll find a solution or do something else.
And, we never got to do the three ideas in three different cities because we had the idea for what turned into elastic sales, and then turning to close out, but we still went on the traveling. I started – we started outsourcing sales while in an Airbnb in Austin and then in Miami and I started making cold calls for different startups in a while traveling. So, kind of been always part of the enemy because the founders love traveling – we all love to travel. And, that’s kind of how the company even started.
I think that over the – there was a time where we had everybody in the same office. We were in a remote team and we would still do these retreats and usually the purpose of them was that they would be typically kind of in the middle of the year at the end of the year was more of a the day in day out – we didn’t want to have lots of meetings and lots of like strategic discussions and decisions and arguments especially as the team grew to a large amount. So, we kind of always we used those retreats as this is going to be the time we’re going to sit down and think about the business long term.
We’re going to do some of the long-term planning and we’re going to create some space to have discourse and discussions and arguments and think about things much more deeply and do that transparently with many people in the company – versus meetings over a meeting every day. And then, we also wanted to have some – you know a good time and blow off steam a little bit with everybody, and just have created some good memories. Over time as we moved into more a remote company – now we’re fully remote business – the retreat has changed its purpose.
It’s still some of this like long-term strip strategy sessions and stuff like that, but the spending some quality time with people that you’ve never met, or you you’ve only seen the last time – you know six months ago a year ago – that has become I think more valuable than it used to be when we were all the same office right? I think with all the retreats that we’ve done, we had everything in there. We had retreats that were way too heavy on the work, and that basically just turned into seven work days that were 14 15 hours a day with like no brakes and people were burned out after the retreat.
And we had the exact opposite, just like you said we – it was basically a fucking vacation right? And, we went out every night and people go away and we had way too much fun. We created a lot of funny memories and we’re just too – but it was just a fucking vacation no work was really done. Nothing meaningful was accomplished. We swung on both ends of the spectrum and most of most of our retreats have been somewhere in the middle, but we’ve experimented with it we’ve gone to the extremes I think of the of what’s available.
And now for the past I think two or three retreats, we’ve got – we’ve become – as the team has grown, as the business has grown, we’ve become a lot more intentional in designing the retreat, so now you know we take like two to three weeks before the retreat – myself and some of the leadership of the company. Then, then myself and a team member that’s basically – you could call her like head of HR recruiting – she’s the good spirit of the business.
We start really planning and thinking through the entirety and really designing the experience every single day – like what are we trying to what are we trying to accomplish in the Tyra retreat? What are some of the challenges? How do we design every single day, how we take out friction, and we’ve got a lot more intentional about using a retreat as a strategic – to really move the business forward and there is a lot of small things that that have a really big impact like picking the place where people are gonna sleep, and where they’re going to work making sure that the work – like the we’ve got into a practice where we try to have separate you know where people sleep and where they work but make it close enough so people can walk.
So, people can walk in the mornings can, walk if at any point need a break, to take a nap that could you know potentially walk back to their hotel room and take a nap or have a little bit of their own space. So, to design that to be close – then we will look for work spaces that all that allow us to be loud and that’s kind of disconnected from everybody else not like open floor, co-working spaces. It doesn’t work to have really intimate, really challenging discussions.
But, also we choose co-working spaces or office spaces where there is a there is a great coffee place very close nearby and we have like an open tab with them and we have we take care of the tire like food. No decision needs to be made on own food, so you know we planned the lunches ahead, and usually lunches are being ordered, and delivered. And then, we break the teams into smaller groups to have lunches and kind of a more intimate settings. And we have more like team dinners at nicer places outside so we can decide every single little detail so that people don’t have to decide where do I live, how to get to work?
I’m at work or I need a coffee or I need a quick break of scenery – where do I go now? What’s for lunch what’s for dinner – like all these decisions are being taken care of? And then we try to now really come up with like a moto – a theme for the retreat. That’s been a kind of a really useful tool where you know we just realized when you have 20 people from all kinds of places in the world, and you bring them all to one place, and you have like five days and many people have never met each other. We’ve hired most of these people recently.
How much can you really accomplish? There’s a limitation of how many things you can practically get done in a good quality way. so we we’ve gotten just really good at like prioritizing – that prioritizing for like this is the theme the retreat and the last retreat that we did in Berlin for instance – one of the – the theme that came out of it is that we wanted every new person, everybody the company to just ask themselves two questions – what can we need to get to make our customers more successful, and what can we do to get more successful customers?
Those were the only two questions people were allowed to ask, and the two questions we wanted to focus on. As we experience that, a lot of the new people that we have on board because they were new and because we were trying to do an incredibly good job onboarding them – we spent too much time kind of babysitting baby feeding taking two little steps people were too careful about making mistakes, not rocking the boat making sure they’re doing everything right.
We’re moving a little too slow so that turned into the theme of like you just ask these two questions and that those should be your guiding postal what kind of things you do what projects you work on. And that was kind of a big thing a big theme of the entire weekend projects that people broke out in smaller groups and all that. We try to have like one thing for the entire retreat. One big thing we’re trying to accomplish that we focus the company on or a problem to fix your decision to meet or whatever. And then it’s a lot of like allowing people to get to know each other and allowing for certain conversations take place that would never take place as we’re remote company.
so we do we do lunches for instance and we will design who’s going to have lunch with him so we don’t do 20 people lunches, we do four or five people lunches, and we decide – we tell you in your calendar you’re going to have – you know somebody, in marketing you’re gonna have lunch with one person from engineering one person from support or one other random person. And, we will even suggest sometimes –you don’t guys don’t know what to talk about here’s three questions you can ask each other for lunch right?
we’ll make sure that certain conversations happen where you know people get to know each other ways they wouldn’t and people the debate and discuss problems that they don’t usually – and there’s all kinds of like projects that pop out of that and decisions and problem solving or uncovering that there are problems of misalignments that wouldn’t happen if we just remote. It wouldn’t probably happen if we just all came together for a week and we just had a good time went out to party and just all worked alongside each other but we didn’t design the experience and put people in places with questions and environments to stimulate certain things to happen if that makes sense.
Hiten Shah: Yeah, no, makes sense. I think the moral of this is to me it has a lot to do with just making sure that you’re scripting the experience as much as you can so that people are able to get value. Value means like you’re making the most of the time together. And I think that so many companies forget about that basic thing.
Steli Efti: Yeah I think that most companies when you think about team retreat, you think about let’s find a cool place, get everyone together and have a good time together right? Or, your retreat, a remote company you might think well we almost never see each other so let’s just come together and work alongside each other a lot of good things will happen we just do this.
But, then if you’re not mindful is the group grows it’s very hard to accomplish anything – it’s a very loud noisy environment and everybody else everybody has their own problems and challenges and if you don’t design the experience, it’s more likely than not – it’s just like creating and creating a conference. If you just say we’re going to invite 500 people interested in critical business and we’re gonna bring this into one room and that’s a conference it’s going to create a problem. You need to have an agenda, you have speakers you have to break out session, you have to have talks you need to have a theme, you need to know who is the audience what do they need out of this?
There’s a lot of things that need to be designed right? The after-parties, everything you need to think it through carefully to get a really practical and valuable result in other things that we do is like we query. We will we will ping every single member at the end of every single day and kind of just send them a quick survey and figure out how did this day go? Is there something we’re missing is? Is there something you wanted to happen in this retreat that still hasn’t happened that makes you nervous?
Was there something in today’s program or agenda that you thought was a huge waste of time and was kind of painful to go through? So we do this during the retreat so we don’t just learn it at the end of it, but we also do it a week after when people had time to digest and see what really what difference did it make to see like – basically if you look at every employee as a customer and the retreat is the conference that you put together for them – you want to see what’s your MPs score?
Like, are these customers successful and happy? Did they get something out of it that was valuable and even further not just carry them daily, and then at the end of the event. but before we do the next retreat will always go back into our notes will always go back and see what were the decisions we made in the things people – projects people tackle during a team retreat? And what was the impact of it – like it six months have passed since the last team retreat.
What did we say back then – when project we started – what were the decisions we made? What was the impact of all of this? Did it really mean anything? Did we get anything valuable out of it? Has the business really changed? And, if not we’ll start the retreat with challenging ourselves to make this retreat more meaningful, and if they have will again kick-start the retreat by highlighting. Last time we made all this fucking great should happen let’s make sure this time around we do the same thing.
Hiten Shah: Yeah I really like it I think. It’s like one of the things – I give one of the things that I found really valuable a team retreat that we did – and it is just really valuable and useful for people, but we actually brought a customer in and had them talk about their experience using the product. And we have somebody on stage with the customer – or in you know not on stage, right there getting the worst parts of the product out.
And, hearing all the difficulties, and once a lot a lot of the team doesn’t get to talk to the customer. So once – and you can always arrange this if you go off to like another country or something – you don’t have customers there, although most of us have customers almost everywhere I would imagine at this point – especially if you’re doing team retreats and you’re like 20-30 people or more.
But yeah it was game-changing because everyone could hear the pain and the customers voice and things got started getting fixed aligned with what the customer wanted really fast like within hours if not days, and it was incredible. So I would highly recommend if you have the opportunity at a retreat to bring a customer in for an hour and have them talk about their usage of your product and all the things that cause them to distraction that they can be really valuable and a really good opportunity when everyone’s together.
Steli Efti: I love this is – such a powerful thing. What we tend to do is actually try to organize some customer visits where we go and visit the customers at their offices.
Hiten Shah: Great.
Steli Efti: And there’s a lot of value in seeing the customer in the natural habitat and see kind of the end users use your software on their screens and be able to like roam around the office and get a vibe for the culture and then talk about the problems and all that. But I also see it being really powerful to invite a customer to the whatever space you have for the retreat and have them just give a little bit of a – kinda m our pain points – here’s the things we like with this like things were struggling, and kind of give them the intention the attention of the big part of the company.
That can be a super-powerful think that’s something we’ve never done, and it’s definitely something we’re going to try to do the future because I love that. I think that’s super powerful.
Hiten Shah: Awesome
Steli Efti: Awesome – there’s a ton more things but I think we’ll wrap it up on this when it comes to riches. I’m actually really curious if people out there have read articles or if attended team retreats that we’re in – more valuable than the average of that did something new interesting or cool – just reach out to reach out to us, and me personally it’s Steli on Twitter.
I’m super curious to learn more about – and they’re constantly improving this as we – as I foresee this to keep being a part of the way that we’re going to be running the business. I want to get – we want to do the best company retreats that exist on this planet so I’m always used to learn more and hear more. So, please share you have any advice or tips on this and. And, I think this is it from us for this week.
Hiten Shah: Yeah on company retreats
Steli Efti: Alright. Bye.
[End of Audio]
Duration: 22 minutes