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The bright side of pessimism

How many times in a meeting have you said, “HEY everyone! I have the best idea….” Your boss is nodding vigorously. Your work bestie is clasping her hands in delight. You’re beaming from ear to ear. But you can’t celebrate yet.

You forgot about negative Nelly. Nelly is already scowling. She’s just waiting to chime in with, “That’s out of budget, our CEO doesn’t have Twitter, and where in the heck would we even get a trained polar bear?” Srsly, Nelly, chill!

In the working world there has been long held cultural ideal of the perfect worker: the extraverted, enthusiastic, and ambitious optimist. Inspired by the spate of articles arguing for the value of introverts, I think we need to also recognize the value of having a pessimist on our team.

First, realize that we pessimists don’t often identify as pessimists. Our goal is not to blindly shoot down your amazing idea; it is to identify roadblocks early and determine if, given those roadblocks, the plan is still viable. Most pessimists are merely planners who think that determining where a plan could fail early on will yield a better result.

Second, optimism bias is a thing. In fact, even negative Nelly probably displays optimism bias in her personal life. It is generally good for all of us to believe, despite rational evidence, that we will achieve success, live long and prosperous lives, and become millionaires. But for projects at work, being biased towards assuming everything will just work out can put your organization at risk.

Another upside? We pessimists are SO PREPARED. According to this article, “[Pessimists] tend to be better-prepared. They may not be un-anxious, but they feel more in control. In some sense, they’ve peaked in anxiety before their actual performance. By the time they get to the event itself they’ve taken care of almost everything.” Who doesn’t want that on their team?

If you’re worried about situations where a teammate’s immediate planning could be detrimental, like an ideation session, set ground rules for the conversation like everyone must follow improv rules (Yes, and!) when someone presents an idea. You should also let everyone know that, once you have several ideas and are narrowing down options, there will be a point in time for listing pros and cons for each. Your team’s resident pessimists will feel at ease knowing there will be a space for their concerns in your process.

Ultimately, there is nothing wrong with pessimists. Some people get pumped up by positive thinking; pessimists may prefer planning and action taken. And that’s okay! It’s more than okay. Optimism is useful, but teams of all “Yes Men” won’t get us anywhere.

Together, we are responsible for creating a culture in our organizations (and as a sector) in which, despite the excitement surrounding a plan or idea, dissent is welcomed and constructive critiques are celebrated.

Pessimists will challenge you, but that challenge may be just what it takes for everyone to make tighter plans, hold better discussions, and have more impact. We should aim to have that healthy tension on every team.


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