Be more like me: a pessimist!


I attended a conference last week, and one of the talks was about people and how we think. The presenter also talked about pessimistic and optimistic people during this talk. Is the glass half full or half empty? For some reason, we believe everyone should be optimistic, always believe in a good outcome, always believe it will be better, and always know we can improve. It is almost like society doesn’t like people who are pessimistic. For me, the glass is often half empty. I tend to see problems and don’t automatically believe things will be better in the future. I am really trying to be more positive; sometimes, it works, and sometimes it does not. What about teams? In my experience, teams are always optimistic! Most teams should be more like me and be more pessimistic. Or at least be realistic!

In modern organizations, teams often use a process where they create a plan for a short period and try to deliver value after this period. Scrum is one of the most popular frameworks. In Scrum, teams work in iterations, aiming to deliver value in every iteration. However, a plan is just a plan, and often the reality is different. This is okay; teams adapt the plan and continue. At least that is what you expect.

However, the reality is often different.

When teams have a delay, they often believe they will catch up. They are optimistic. Most teams will keep their plans and keep on working. “We will be okay in the end, no worries.”. My experience after working with many teams for many years, that that sentence is something that does worry me. There is a reason for a delay, and when nothing changes, this delay can occur again. Knowing Murphy, it will happen again! The delay will increase, or more topics will be delayed.

How to deal with this challenge? How to make teams more pessimistic or at least be realistic? Let me share some tips with you.

#1 Create full transparency

If there is no transparency, how do you, the team, or stakeholders know there is a delay? Therefore the most important step is to create transparency. Make sure everyone can see what the (lack of) progress is. I worked with one team who was against publishing the progress in their weekly report, and it would create a wrong impression for stakeholders if something were behind schedule. Err, that is the idea, not to create a false impression but to talk about it. But fine, we will not add the progress in the weekly report. After a few months, the team was behind schedule, although they said it would be okay, and it surprised many people. We decided to include the progress in the weekly report, and from that moment, we did have the right conversations. Leadership ensured it did not become a blaming session but a valuable conversation between the team and stakeholders.

#2 Confidence vote

Do you recognize the scenario where the team did not make their plan, and somebody suddenly says: “I already knew a week ago we would not make it because ”? At that moment, you think: “Err, did you not consider sharing this information?” One of my regular practices with teams is to ask them for a confidence vote halfway through the planned period or iteration. On a scale of one to five, how confident are you that we will deliver what we need to deliver? Where a thumb up is 100% Yes, and an open hand is 0% totally not. When different people show different values, you can discuss why. Do some people have information that is not known to other people on the team?

#3 Plan less work, be realistic

Help the team commit to less work. Let’s assume a team plans ten units of work and only delivers eight units of work. This is often a disappointment. Two units less than planned. Let’s assume a team plans six units of work and delivers eight units of work. This is a good feeling! They delivered more as planned. To help a team, it can be interesting to coach them on planning less work. However, be careful as there is also an unwritten project management rule that the planned work will fill up the available time. This approach requires that the team does not slowly extend the scope or start to goldplate the units of work.

#4 Forecast for tomorrow is based on the weather of today

There is this famous quote: “Insanity is doing the same thing over and over again and expecting different results.” By the way, it was not Einstein who said this! When a team delivered ten units in the last weeks, why would they suddenly deliver twenty units? It is the same weather. When you would like to make a forecast for tomorrow, just look at the weather of today, and it will probably be the same as today. (Unless you live in the Netherlands 😬). Challenge a team when they suddenly change their expected value delivery; what did they change that they feel confident it be more or less?

Being optimistic is a good habit, but sometimes it is better to be realistic. I am less pessimistic and more realistic, and that is already helping me a lot. It is your challenge to help teams become less optimistic and more realistic. Nobody benefits from teams who are always too optimistic and must always disappoint their stakeholders. In the end, this will even result in less trust. Why would they believe the team? They never deliver what they promise!

How do you help teams who are always too optimistic?

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