Remote design sprint. 16 lessons learned

Recently I facilitated my first fully remote Design Sprint. Mistakes were made and here I will share them with you. Let’s go straight to the points.

Photo by NEW DATA SERVICES on Unsplash

• Timezones. Trying to schedule for different regions (aka big time difference) is nearly impossible. For instance, if you take a workday in Estonia (where I am located) from 9 to 5 and overlay it with a 9 to 5 in California you will have no overlap. If you are lucky enough and you get someone from East Coast you might squeeze in 2 hours of Design Sprint (from here on will be mentioned as DS for sake of keeping this short). Long story short, someone will have to wake up early or work late if you want to do a cross-region sprint. The next point might suggest that doing so is not the best idea.
• People get tired. Design Sprint requires all the team members to actively participate and give their input as much as possible. It is a highly challenging and energy-draining collaborative effort. Intense. Honestly, if you just make someone sit there for 3–4 hours they will get really tired as well. It is not a good idea to go over time with participants workday. On contrary give them a bit of time in the morning if the DS starts in the first half of the day or in the evening before the end of the workday if it is in the second part of the day.

I liked that there were resting pauses which allowed the head to rest a bit. Maybe on this is to aim it to start earlier but I know that with busy schedules it is hard to do. 2pm Estonia time is not the worst. 6pm Estonia would be something where I stop thinking.

• Eat that frog first. Comparing the amount of energy in morning versus evening sessions I can conclude that having the first 2 day sessions in the second half of the day was a mistake. As I mentioned before, DS involves a lot of ideation, brainstorming, voting, and most importantly, decision making. All the participants will go through their workdays before joining your session in case you held it in the second part of the day. They already made tons of decisions and they are way more tired now and decision fatigue kicks in.
• I didn’t plan enough breaks. Just an additional combo to the previous 2 mistakes was not having enough break time. The rule of thumb is to have a break at least every 90 mins for longer meetings. I would maybe even argue that you should have a break every 60 mins. Bear in mind though, you have to be really rigid and precise with breaks so that everyone is back on time. You can play around with this by introducing some fun rules during the ice breakers. More about rules later.
• Commitment. DS takes around 18–19 hours from a week for a core team member. It is not easy to convince people to spend such a big chunk of time on something that doesn’t have a defined outcome of success. However, we as facilitators have to make sure that the team is fully packed and that participants commit to these timeframes. The mistake I made was accepting some managing stakeholders to drop in and out, and in moments when they were needed for the discussion they were unavailable. Therefore, ask people if they can commit to participating all the time, try your best to make sure that they understand the value of DS. Still, hesitating? Move on to the next one and find a substitute.
• Icebreakers shouldn’t be random. I can’t say that the icebreaker I chose to go with didn’t work but I felt like transitioning from the icebreaker to the DS itself felt like jumping from a cliff. In my opinion that transition pulled us back. With a more smooth transition you can move on with a built-up momentum. Next time I would choose an icebreaker that would allow me to have a smoother transition into sprint activities.
• Time is important, allocation is not. Everyone I have discussed the DS with told me “Assign extra time to any activity you plan to have during the session”, which I did and we rarely went overtime with activities. That being said, since I assigned extra time to every activity sometimes we finished earlier than planned and there was some time left on the timer. What did I do? Was happy that we are on time and moved on to the next activity. What I should have done? Take notes of every minute and second you win on the course of DS. These are golden minutes that you can use when a really important discussion is going over the time or everyone is exhausted and need more than 10 mins on the break. Otherwise, when something like this happens you have no idea how much time you can give for extra discussion or break. The illusion of finishing early the other activities might give you a feeling that you have a lot of time won. Well, usually it is not the case.

We should be more strictly following the time-box.

• Be flexible and don’t get stuck. In a logical continuation to the previous point, you should plan as much as possible but be ready to react to changes. Don’t get stuck on rules that won’t impact the final outcome. Someone really wants to give 3 points during the vote instead of 2? See the reaction of the team, let them do it. Does someone have similar points on the stickers? Combine them and move one. Especially in the first 2 days of the DS, it is about quantity, not quality. Some decisions should be made just by feeling the pulse of the DS team. Luckily, we as product designers should already be good with reading the room.
• Rules are important. Rules are specific to every DS. Make it fun or at least explain everything you ask them to do, no one likes to be bossed around. You can ask participants not to discuss things on individual ideation. You might introduce different methods of voting. Anything that makes sense. If something not working it is never too late to change or introduce a new rule. For instance, the first day when someone was done with individual ideation I had no idea if they are done or not, I had to individually ask towards the end of every activity. I guess that was just annoying for others and took valuable seconds that we could have used later. The second day I introduced a rule of posting an emoji next to the individual’s name as soon as they are done. Easy.
• Examples and explanations. Having a sticky with an example of the activity saved me tons of time when I was explaining to participants what they should do in an activity. You spent weeks preparing for this, for some of participants this will be the first time they participate in a DS, so be specific, don’t use jargon, and be as simple as you can in explanations.
• Don’t lose the bigger picture. At times, especially as the ideation went into complicated topics participants began to wander away from the main narrative and went into too much details. Even though it seems easy to pull back everyone to the main goal there are 2 problems:
  a. You have to be careful with how you cut back on the extension of ideas that participants have.
  b. Sometimes you will be stuck on details with them.
  Keeping long-term goals and sprint questions in the eyesight for participants might help, whenever you all drift away go back to these sentences and see if you are still aligning with them. Next is my idea of how to avoid problem “b”.
• Listen properly. To avoid previous problem in my opinion you simply need to be always aware of what’s going on. In theory, it sounds really easy, but on the DS you are not a participant. You are a facilitator that needs to track the time, activities, sort things, make decisions on the fly, and sometimes while doing all of that your focus might wander away from the process of ideation. To be honest, I have no idea how you can be on top of all the things during the entire sprint. Try your best to listen and take notes.
• Mapping = value. I really believe that Mapping activity is one of the most crucial parts of the whole DS to get everyone aligned with the process and actors. Considering not only the persona that we were trying to deliver for but also different actors involved in this process and their touch points improved the alignment for the whole team.
• Interviews are tricky. On the one hand, these interviews can be done in advance and save everyone some time. On the other, it gives alignment and an opportunity to ask questions from different perspectives since people involved in DS have different backgrounds. Considering that the timeframe I choose for the interview was just 20 mins it felt like some questions that could have been asked were left out. That leads me to a conclusion that there should be an interview that will happen before the sprint to identify key findings, present these at the DS and then have one more round of interviews during the DS itself. And that perfectly leads to…

I think we didn’t get to hear from everybody during the expert interviews. Maybe letting the participants prepare in advance could save time on individual interviews?

• Homework sucks. Even if participants promise you that they will do everything after the sprint and send it to you by tomorrow’s session, don’t trust them (personal pain). Don’t get me wrong, I probably wouldn’t do it as well. As soon as they leave the DS they are not mentally there anymore, they are tired and they have billion personal things that they need to take care of. And remember the point “People get tired”? That’s the reason they didn’t finish it on the sprint itself. Essentially they were just tired, which was my mistake in the first place. But still don’t trust homework.
• 4 part sketching works. We know that it works, but it actually works in a remote environment as well. Since it had to be anonymous so that others don’t know which sketch belongs to whom this was my flow to move the sketches to Miro. Ask them to have pen and paper before the session → Take a photo of the sketch → Send it to me via Slack (most of them have Slack on their phones, alternatively they can use Airdrop) → I upload it to Miro. If everyone meets the requirements of having slack on their phone + pen and pencil in real life then it works perfectly.