8 Tips for Early-Stage Remote Company On-Sites

*co-authored with Kate Field

Aampe is an early-stage, fully remote and globally distributed SaaS startup with team members in San Diego, Austin, Chicago, North Carolina, Washington DC, Antwerp, Paris, Berlin, Mumbai, Delhi, and Singapore. We were founded in 2020 and at the end of 2021 we decided to plan our first full team on-site. In April of 2022, 10 members of our team flew into Amman, Jordan; visited Petra for 2 days, and then spent 5 days working at a resort on the coast of the Dead Sea. It was an incredible experience, and a resounding success.?

We learned a lot in designing, planning, and executing the trip. Here are 8 tips to help you generate high ROI from your onsite.

Tip 1: Select a place that inspires

In our experience most company trips fall into two types:?

• Meetings in boring, lifeless hotel conference rooms or conventional convention centres.
• Team trips to touristy, fun-filled, and pleasure-oriented hot spots (e.g. Bahamas or Hawaii).?

We wanted something different. Startups set difficult and grand objectives. So once you’ve filtered destinations based on your specific logistical constraints, select a destination that can teach you something about human ambition and achievement. Meet somewhere that is a testament to persistence or design or ingenuity and that will give you a strong dose of inspiration.

We visited Petra in Jordan. Notorious for its epic scenes in Indiana Jones, Petra is the incredible capital of an impressive civilisation, the Nabateans, from around 300 BC that was eventually absorbed into the Roman empire. The Nabateans grew a garden in a desert through a combination of elegant and sophisticated architectural design and plumbing. They funded it by capturing key nodes in a rich trade route and generating revenue from taxes and services. When the Romans shifted the trade routes away from Petra, the Nabateans couldn’t capture their value anymore and Petra declined. It sounds like something right out of 21st century Big Tech! Or maybe Big Tech ? is just straight out of human history…?

Tip 2: Put bonding at the beginning

Startups exist under perpetual pressure. Time spent not writing code or speaking to customers induces paranoia. The paranoia will carry over into trip planning and your schedule will fill up with urgent topics, ideas, and objectives. You imagine you’ll land at the destination and jump right into work, plough through the week, and then have a fun outing or day out at the end to celebrate all you’ve accomplished.?

We decided to flip that script.

You’re jet lagged the first few days. Folks are still slightly awkward from meeting for the first time. Let people get to know each other while having fun - it’s so much more pleasant and effective and there’s less pressure if someone just wants or needs to slip away for a nap or set their own pace.?

Laughs, struggles, and memories made in a non-direct work context will serve you well once the seriousness and natural tensions of important company decisions come into full attention.?

Tip 3: Invite life partners and families

Partners and families are key to your startup’s success. They make important sacrifices and investments to support your team-member. And yet they’re almost always invisible and under-appreciated. We didn’t want Aampe to work that way. And anyway it isn't in our self-interest. When a key team member gets an amazing offer from another company (as they always will since they’re amazing), you want their life partner in your corner, not mildly disaffected or actively embittered by what your company has done to their relationship with their significant other.?

The bonds we created in the fun/social first part of our trip weren’t just among team members, they were with and between partners and families as well. We wanted to get to know our extended team members and open lines of communication to celebrate good times, and empathise and build support ties for bad times. We selected a location and venue during our concentrated work period that was gorgeous and inspiring and enjoyable for those not directly involved in our work. They could dial into their own work from a beautiful room or poolside, or just enjoy a relaxing break and create some positive mental associations with Aampe.?

This definitely was not a requirement. The decision to join or not was of course up to every team member and their significant other(s). We just decided to clearly extend the invitation and ensure the opportunity was appealing and welcoming.

Tip 4: Combine strategic topics with regular work

When you’re a remote and globally distributed company, meetings in person are special. We initially felt an urge to devote nearly all of those meetings to similarly special topics: big strategic questions, long-term thinking, critical existential topics. And then we realized that we also just wanted an opportunity to do the work we normally do, only right next to each other. Was that wasteful? Why travel halfway around the world to do “business as usual”?

Without developing a deeply thought out answer to that question (no time!), we went with our intuition and ripped up our initial schedule. We kept just a couple of the original Big items and then identified large blocks of time to just sit together and do work that needed to be done: onboarding a new customer, preparing for a key POC, etc.

In retrospect it was absolutely the right decision. There was something powerful and enlightening about doing normal work in the same space. Not because physical colocation is always better or because we learned what we were missing as a remote company. Nope, it was simply that working next to each other for a week was just what we needed, and then we were refreshed and ready to return to our homes and keep riding our wave. Maybe one day we’ll write a thoughtful argument for why this was so good. But for now, we’ll leave it at this, and you can take it or leave it: Preserve time for normal work during an on-site.?

Tip 5: Don’t over-schedule; stay flexible

We went through three iterations of our schedule while planning the trip. We wanted to cover and accomplish so much. Big strategic topics would benefit from in-person discussion. Tactical matters could be executed quickly because the right people would all be in one room. We initially thought that if we scheduled everything in advance we could optimally balance the topics and ensure maximum efficiency during the week.?

• “If we only give ourselves 30 minutes for this topic, we won’t run over and spend more time than the topic deserves.”?
• “If we don’t put this on the schedule, we probably won’t get to it.”

There’s a concept called Probably Approximately Correct from data science that we sometimes apply to ourselves as startup operators (we are, after all, a startup founded by 3 data scientists). We are the Learners and we must Select a Function (make a decision) from a set of possible decisions. The useful point of the concept is explicit emphasis on the combination of Probably and Approximately. Only some of our decisions out of a set of decisions will be right. And then even the right ones will only be Approximately right.?

We decided to preserve flexibility in our schedule. This meant trusting our future selves to step in and update the schedule based on things we would learn as the trip progressed. If we throw out the entire schedule at the end of the 1st day, we’re probably reacting extremely based on hyper-local knowledge discovered during the 1st day. But we also don’t expect to get everything perfectly right and stick to it through the entire week.

Schedule your sessions, but let the team know that they have the power to adjust those schedules as the sessions and discussions happen. Don’t just assume everyone knows they have the power to do this. Explicitly build it into the schedule and into the team’s mindset as the on-site approaches.

Tip 6: Recover, recover, recover

It’s common to hear that a Startup “Is a marathon, not a sprint”. Startups aren’t a single sprint, or a marathon. During a marathon you don’t do ANYTHING else. You’re just running. And when you’re done you probably won’t run another one for a while. That’s not how startups work. Startups take years. There are specific and concentrated periods of time where you had better run as fast as possible; you have to sprint, not just jog. But if you try to run the whole time and never do anything else then you’re going to burn out and fail.

We prefer to think about startups as regular speed running. This means you run frequently and regularly, and you run hard while you’re running. For regular and consistent speed running, what you do between your runs is just as your actual running. This is called Recovery.?

Recovery is about efficient restoration of energy so that sprints improve over time. Resting is one of the most important things you can do in a startup. Eat well. Regularly stop thinking about work (for hours at a time, not weeks!) so that your brain is actually recovering instead of burning calories on pointless ‘what-if’ mental cycles. Devote the right time and attention to loved ones so that they don’t become embittered opponents of your work and you don’t become racked with guilt for failing them.?

Recovery matters at the macro-scale and the micro-scale. The main part of our trip was 5 days, and it was tempting to pack in as much as possible.?

• “We only have 5 days!”;
• “We need to get as much done as possible!”;?
• “People can rest when they get home!”.?

This was our animal brain screaming at us; an indicator of fear, and a scarcity mindset. The surest way to only get 1 or 2 high quality days of work out of 5 days is to cram the first 1 to 3 days full of information-dense and intense conversation and effort. After a day or two of that kind of cramming your faculties are so degraded you might as well not be working at all. In fact you’ll likely become counter-productive rather than just unproductive.?

Instead of cramming, we spliced our schedule with small and large breaks. Go for a swim. Go spend time with your partner - who may anyway be swimming with another colleague’s partner, getting another kind of work done. Eat something tasty and energising. Stretch your limbs during a nice walk somewhere pretty. If there’s a single best tip out of the 8 in this post. We’d pick this one.

Tip 7: Don’t sit in one closed room; create space

Sometime in the 20th century the noxious idea that windows distract children from learning infected the U.S. public education system. It wasn’t just windows either. Standard school desk-chairs were designed to constrain a child’s arms and legs and make the desk immobile. Those ideas permeate the way we think about productivity as adult professionals as well. The underlying thesis is: Eliminate Distraction and keep your mind rigid. Reject that thesis during your onsite.?

We arranged for a meeting room at the hotel to use when appropriate. And then we spent only part of our time there. We had a lot of small group work and sometimes we did that while walking. We sat at a rooftop cafe and had a quiet discussion; some of us found comfortable lounge areas where we could dive deep into a problem together. Physical movement is related to mental flexibility. We wanted to maintain flexible mindsets, so we didn’t rigidly constrain our physical setting.

Tip 8: When something goes wrong…it’s an opportunity!?

After a brilliant weekend we were ready to begin our period of concentrated deep work. Then we learned that one of us tested positive for covid-19 early Tuesday morning after feeling unwell overnight. Everyone on the trip was vaccinated, and by April of 2022 the severity of covid-19 no longer alarmed. It was still hard not to panic. You hate to catch a virus right towards the end of a global pandemic. And on top of the risk of illness, there were so many potential complications for returning to our home countries.?

We took some deep breaths (at a very safe distance from each other!), and thought about our options. We could all return to our rooms and work ‘remotely’ - losing the opportunity to spend time together but possibly minimizing the risk of any further spread. Or we could take some precautions and continue to work together, ensuring we still captured the time together at some additional risk of further spread in the team. The details of our decision don’t really matter here. We went with the latter option, and it happened to work out well for us. We had a great 3-4 additional days together. Nobody else tested positive or experienced symptoms, and our team member never experienced more than mild symptoms and still managed to enjoy the climate and a spectacular Dead Sea view from his balcony.?

This isn’t about Covid-19; that just happened to be what we needed to deal with this time. When you do difficult and unusual things, circumstances will go wrong. Accidents will happen, and your luck won’t always be good. What matters is how you respond in those moments. If you panic or dwell in stress or bitter recrimination about your luck, you’re likely to compound the negative situation with subsequent poor decisions. If you calmly make the best of the situation, then you’ll be training your team for inevitable adversity ahead.

Summary

None of these were obvious to us when we started planning our on-site. A few of them we only consciously recognised in retrospect. They will definitely be on our mind for future trips. And we hope they’re helpful for some of you as well. Here are our 8 tips, all together:

Tip 1: Select a place that inspires.

Tip 2: Put bonding at the beginning.

Tip 3: Invite life partners and families.

Tip 4: Combine strategic topics with regular work.

Tip 5: Don’t over-schedule; stay flexible.

Tip 6: Recover, recover, recover.

Tip 7: Don’t sit in one closed room; create space.

Tip 8: When something goes wrong…it’s an opportunity!?