How to build a resilient startup team

Published in

The Startup

14 min readDec 23, 2017

TL;DR

Think actively about building your team culture
Do expectation management with your co-founders
Check-in daily to see how your team members feel
Build team culture during your weekly meeting
Schedule recurring social team events
Do regular personal evaluation
Do team process evaluations
Hug it out
As a startup, you have the opportunity to create your own rules for how you do these things.

You’ve got an idea, you’re finding a way to finance the product development and you build your team. Your only focus is to build that product and meet the needs of the customers. But what about your team? Is everyone working as hard as you? What happens if someone gets burned out or need to quit? Or someone is being super annoying and you just can’t deal with it?

You’re fragile to changes in the team early on. Team trouble is talked about, but not enough. And it lacks actionable advice. Especially for the first five people. Every person counts. This is not some small problem. Actually, 65% of all startups fail due to what we call “people problems”, something Noam Wasserman writes in his book The Founder Dilemma. And being co-founders is very much like a marriage, without the sex, but still, 65% is way higher than the divorce rate!

A startup is like a roller-coaster. One of the main reasons teams fail is that they don’t know how their co-founders or team behaves under stress or very challenging conditions. Thus, you need to have processes in place so that you and your team are prepared when challenges arise. All startups will experience challenges!

I’m now on my third startup journey, co-founder and COO of Megacool. Our headquarters are in San Francisco with remote teams based in Mexico, Norway, and Denmark. At Megacool we are 3 co-founders who have experienced a long roller-coaster ride together over the last two and a half years. The tips shared are the learnings from our startup journeys and focus on teams up to 10 people. We’ll walk through the things we do to build a strong team culture and how to handle tough times.

Expectation management

The earlier you start talking about expectations among the founders, the better. Yet, most startups I speak with are not talking about these things, and therefore a mismatch in expectations often occur. Something that can be deadly for your young companies. Most assume everything is aligned. To help you get started with expectation management, here’s a few questions that you should sit down and discuss together with your co-founders. When you discuss them, make sure that everyone participates and that you write down what you agree on.

Every team is different and has different needs. These are suggestions on where to start:

Why do we do this?
What can I expect from my team?
What can my team expect from me?
What’s expected of each role?
Who gets what role?
How often should we evaluate the roles and who’s the best fit for each role?
How much work is expected of each team member?
Where do I/we work from and how do we work?
What happens if I leave the company in 6 months/1 year/2 years/4 years?
For how long can we give this startup our 100% if there’s no funding/revenue?
What salary do I expect?
What costs are covered by the company and what are costs we need to cover individually?
How do we split our costs?
How do we deal with vacation?
What if someone needs to take extended time off for any reason?

This is not supposed to be an easy conversation and not done in one hour. But starting a company is a tirade of tough conversations. Get used to it! Do one session today, then let everyone think through the discussion, and have a deadline of two weeks later to have it all in writing. And it’s totally fine to not be happy with everything, but “disagree and commit” to the decision to move forward. This is a practice that has been important to Jeff Bezos of Amazon and something he shared in their letter to shareholders.

In general, think of expectation management as when you start dating and you are wondering whether you are in a relationship or not. You need to have the conversation! So start having the conversation with your team members as well.

Check-in (Daily)

The daily check-in is the first of our routines that can help you to detect team issues on a daily basis. It has inspiration from the stand-up meeting in SCRUM. We have our check-in every day at different times to accommodate the different time zones. Before we became a distributed team, and for those at the same office, we do daily check-ins standing in a circle. Each person tells the team

what they did yesterday,
their plan for today and
addresses any challenges that may have occurred.
And last but also most important: how are you feeling this morning!

The last part is important because there can be reasons for someone to not perform that day, due to being in a bad mood or their head is somewhere else. If you are not prepared for this, the lack of performance may start to create friction within the team, as everyone makes their own assumptions about why someone is not performing. Examples can be: lack of sleep, issues at home, or generally stressed about something.

For instance, when we don’t address how we feel in the morning, and if someone is in an obviously bad mood, my default is to think that I’ve done something wrong since he or she is in such a bad mood. Then I start thinking through the past for things that can have caused this, “am I the problem?” All of this takes time and focus away from what I’m supposed to do that day. If we’d only addressed that the person was stressed from lack of sleep during check in!

The check-in scales well with the team, and once your team becomes larger than 10 people, you should split the check-in into smaller groups depending on what everyone is working on.

Now that we’re remote, we also write our check-in and check-out digitally on our #checkin channel on Slack. This is because we start at different times due to the time zone difference. The digital check-in address how I feel today and what I’m working on today. The check-out addresses what you of your tasks you were able to get done and why you weren’t able to get through it all.

If you don’t have any sort of check-in in during the day where you can get the pulse of your team, I encourage you to try it!

And as a cheesy bonus, we do a circle high-five when the check-in is over. This gives you that extra kick, puts a smile on everyone’s face, and you’re ready to do your work. And yes, this proves that we are the most awkward team in our co-working space.

Weekly meeting

Next up is our weekly team meeting. When we were all in one location, the Megacool weekly team meeting was every Friday at 5 pm. There were usually beer and dinner involved, provided by the team member responsible for cooking that week. Now that we’re distributed the meeting is every Monday at 8 am PDT.

During the meeting we summarize the week, discuss important topics more thoroughly and make decisions together. Everyone needs to come prepared and have pre-filled the agenda with notes about their work from the previous week and areas that we need to discuss. Everyone has to read through it before the meeting starts and then we’ll only discussion notes highlighted for discussion.

Moderator

Every meeting has a moderator which is a role we rotate between each team member. This is to ensure that everyone participates and takes responsibility for the meeting. The moderator makes sure that everyone prepares for the meeting, moving it forward, facilitate discussions and that we stay within one hour.

Cultural section

The main part of the meeting is similar to what most team meetings do: discuss the product progress and admin things. Where we believe there’s a good opportunity to build a strong culture early is in our culture section. This has especially been important for a distributed team to get to know each other better.

Important lessons learned from our previous startup journeys are that it’s easy to forget the elements you want to improve on if not addressed on a regular basis. This increases the chance of actually following through and be kept accountable for it.

As you can see from the screenshot of our agenda, each member is reporting on each part of the culture section. I’ll highlight the four most important ones for you to get inspiration.

Learning / New knowledge

Generally, we are all good at learning in a vacuum, the challenge is how do we share the learning across the team. Here we try to highlight individual learning from the week.

Examples: It can be a specific methodology or technology you work with, smart APIs, an article with valuable marketing insight, life hack, etc.

Challenges / Mistake of the week

Another thing we want to highlight on a weekly basis is what challenges or mistakes we’ve encountered during the week. At Megacool we strongly believe in failing fast and learning from failures and being humble about it. Here everyone is encouraged to share what went wrong and what you will do to avoid making the same mistake in the future. It’s an important trait to facilitating this habit early.

Activity / Exercising

When we started Megacool we made being active a priority. Don’t neglect the energy and focus you get on physical activity! Usually, we can correlate the level of activity with our mental well-being. E.g., my goal is to exercise 4 times a week. I believe the extra energy makes me better at staying focused on tasks at hand. Addressing this weekly helps each other to focus on this!

Fun

Most important part of the meeting is how we end it: with laughter. This is very important as people will leave the meeting with a smile on their face and be ready for the weekend.

There’s a lot of prestige in providing the best fun, and it’s a role that the moderator needs to take very seriously.

Here’s a fun example from a previous week:

The culture section can be included in the team meeting for small teams up to seven people, but it may not scale well from there. As your team grows we recommend testing this section within smaller groups within your company. For larger team meetings (8+ people) we recommend you to reduce the culture section by removing talking through all the individual reporting.

My encouragement to you is to identify what areas you want to grow and find important for the culture you want to foster and address them weekly.

Social (Monthly)

Social events are the first recurring event that I encourage you to schedule in your team calendar. Having fun together outside of work is super important for the team culture and a place to build trust.

This is one of the tips that seems to surprise people the most as they feel like they are doing a lot of social stuff with the team already. Yet, that is today, as things are going well. I am preparing you for those dark days, where the time between every beer increases, and more often than not, the social events disappear. Once the hard days arrive, you may start to avoid one another when it’s most crucial for you to put a smile on each other’s face and help each other remember why you do this together. This is a huge warning sign that something is not right with your team. By scheduling it, we avoid dropping it because it’s uncomfortable for some reason. The social events may help you start talking with each other again. It may be easier to do that outside of your office walls.

Suggestions can be:

Going for drinks
Playing games
Going skiing
Doing a sauna
Escape room
Cooking dinner

Anything that is not directly work related that helps everyone to laugh and enjoy each other’s company.

Social events are also great to encourage people to get to know each other better, especially those who don’t work directly together. These events are also an effective way to onboard new team members. My recommendation is to have one extra social event the first week of a new hire.

And last: social events don’t have to cost money. Several of the suggestions above are possible on a low budget!

To tackle this head on, appoint someone as “responsible for social,” or sign people up for each social event and have them accountable to plan it. Have one social event scheduled each month. The goal is for everyone to take part and have fun together.

Personal evaluation (Quarterly)

Next up is the personal evaluation. This is our secret sauce for addressing conflicts at Megacool before they get out of hand.

Four times a year we sit down together and give each other and ourselves feedback: two constructive and two positives. This allows us to praise what we enjoy and value with each other, at the same time as we address areas of improvement. I also have to give myself feedback. This allows me to reflect on how to become a better team member, and I try to review myself and my performance through the eyes of my team members.

Before we start, everyone gets post-it notes to write on. This is to make sure that everyone prepares for the session and don’t comment on the fly. The one to start will begin by sharing his/her two constructive improvements about themselves, followed by the positive. Without commenting between, the rest of the team will take turns on giving feedback. Once everyone has given their feedback, the recipient will comment on the feedback. By the end, the recipient will receive all the post-it notes with comments to keep and work on for next time.

When we do this session, we go somewhere comfortable, and after the session, we try to do something fun together. It can be quite overwhelming as it’s one of the toughest, yet rewarding, exercise we do.

Doing personal evaluations was something we started at our previous company, Dirtybit, with 8 people. It took about two hours. I remember how surprised my teammates were about all the positive things their co-workers appreciate about them! Everyone was always entering the sessions stressed and worried, and leaving the session with a big smile! And if it was their first time, they would say: “Oh, it wasn’t that bad!” or “I thought it would be way worse!”

This exercise does require people to be open to input and actually try to work on their “issues” and at the same time do more of what others like about them. This is for people who want to grow.

When we started Megacool we did this every other week. As our company matures, we have settled on every four months.

I encourage you to start doing something along these lines if you don’t already have a system in place for giving feedback. It will give you a forum to discuss the hard things that you want your teammates to work on. If you are uncertain of how your teammates will respond to critique, you should start scheduling them every month and start with the simple things to see how your teammates react.

Team retrospective (Quarterly)

When I worked at Dirtybit, we launched a game that turned out to fail. The day before we launched it, we decided to evaluate the development process. This was the first time we evaluated it. By evaluating it the day before it launches, we avoided evaluating based on the outcome, but rather focused on the process. We used “Retrospective” as the method for the evaluation process and found it so valuable that we are using the method for most of our evaluation efforts at Megacool today.

When you do a retrospective, you focus on:

Continue: What is working?
Start: What can be improved next time/should we start doing?
Stop: What should we definitely not continue doing?

As our startup evolves, we now do a retrospective for each sprint, hackathons and quarterly on the team process. For the team retrospective, we walk through different topics and do individual retrospectives for each. For Megacool those are:

Product & Process
Admin, Accounting, Communication, Strategy and Office
Personal growth and culture

These topics have been personalized for us and may not work for you. When we do this exercise, we need everyone to contribute. The larger the team, the more important! Everyone gets two minutes to write down their thoughts on each topic, before going around in a circle to collect input. When everything is listed we talk through and agree on the appropriate actions and delegate responsibility. After each session, do a quick poll to see if your team liked the process and whether something can improve it.

Here’s an example from our last team retrospective on the topic: Product & Process. As you can see, we have about evenly distributed comments on Continue and Start, while Stop is empty. Usually, there are only a few items listed on stop, but we still find it valuable.

Team hugs

A bonus tip for all those that have small teams in the same location. This is a quirky one, but it works wonders.

To be co-founders is like being married, except the sex. Like in any relationship, you shouldn’t go to bed without working through your issues. Since we’re co-founders it’s not possible to have make-up sex after a frustrated discussion, but instead we “hug it out”.

Thus, we have made it a habit to always give each other a goodnight hug before heading out of the office at the end of the day! Given that you don’t want to be close to, or touch someone, that you are very frustrated with, this forces us to either talk it out or reflect on whether it’s a big deal after all. Like any relationship, you have to pick your battles, and hugging each other reminds us of why we are doing what we are doing and why we want to do this together.

This started when the founders shared a small apartment in San Francisco. We now live separately but have continued doing this as you leave the office for the night. So, at our co-working space, everyone now believes that Norwegians are super comfortable with physical contact and hugging each other all the time, which for those of you that knows Norwegians are generally not the case!

These notes are based on a presentation I gave at Slush Founders Day 2016. I want to thank Andreas Saari for the opportunity. Thanks to Tiff for reading drafts of this.

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