How to work with a pessimist

As you go about your day-to-day business, you’re bound to eventually encounter the wicked workmates we’ve come to know as collabohaters. Some collabohaters hate the very idea of collaboration, but others are perfectly happy to put in their two cents; it’s just that their two cents are always such a drag.

Morrissey Gets a Job

There’s a persistent pessimist on almost every payroll, an eternal Eeyore who thinks your newest idea will wind up belly-up, a Prophet of Doom wearing a sandwich board to say the end is nigh.

If you’ve taken our 9 Collaborators quiz and discovered yourself to be a skeptic, don’t be alarmed: there is some overlap, but skeptics are not necessarily pessimists. Skeptics question commonly held assumptions; this can be annoying, but also very valuable. Skeptics often have something to contribute. Pessimists often anticipate the worst case scenario while seldom advancing a better course forward. For bonus points, they sometimes mistake their Morrissey-like business outlook as “realism.”

(Sidenote: everyone is eligible for a temporary and occasional Morrissey pass. Botch a big meeting, lose a big client, realize that there’s a grand canyon between your Q1 projections and your Q1 reality? By all means, queue up “Everyday Is Like Sunday” for a few spins.)

What do you do when you’re frequently finding yourself stuck beneath someone else’s cloud? What if you’re the pessimist’s boss? What if—shudder—you’re the pessimist?

Call ’em out (but treat ’em like adults)

This is a rule of thumb you’ll find applying to collabohaters of every type: at some point, you have to call them out for their nonsense. In the case of pessimists, the stakes are too high to just dismiss it as a personality quirk or to resign yourself to skewering the pessimist behind his/her back on IM.

“Negativity can fester and eventually kill a team’s momentum and motivation,” wrote Harvard Business Review‘s Amy Gallo. “Don’t let negative comments linger. Ask for clarification or more information about what the speaker means.”

The latter point is critical. Hold pessimists accountable for their pessimism. The new campaign you’re pitching to a client is DOA? Why? What would the naysayer do better?

Be candid about the effect that rampant pessimism is having on your team. Be frank rather than patronizing. My daughter isn’t even four years old and I already feel like “And how do you think so-and-so felt when you did such-and-such?” is a line of questioning that will need to be revamped in the near future.

Don’t take it personally

If you’re on the receiving end of a blast of pessimism, there’s no point in getting defensive. “It’s not you, it’s me” is actually true in this case.

Also, pessimists usually aren’t saboteurs; they aren’t necessarily rooting against you, even though it may feel that way sometimes. (We’ll be getting to saboteurs in a different post.)

Identify the root cause(s)

Has your collabohating pessimist always been a pessimist? Was there a catalytic event that caused them to break bad? It’s imperative to treat these cases as individual cases, particularly if you’re in management.

Even if there’s no obvious event—like being passed over for a promotion, or disagreeing with a company’s change of direction—talking to your pessimists about what’s bothering them will help you to identify what could satisfy them.

“Anybody can be a team player if he finds the right motivation…and the right team,” business psychology professor Tomas Chamorro-Premuzic told us. “Conversely, when people are demoralized, disengaged, or bored, they will be natural collabohaters.”

Make yourself less pessimistic

Even if you are the “victim” in this pessimism scenario, you almost certainly still harbor your own negative thoughts from time to time. Think about ways you can train your own brain to accentuate the positive. If you’re successful, this will give you a more credible talking point with your pessimistic colleague than to simply tell them “Hey, this article reminded me of you.”

Embrace the gloomiest sort of team bonding

It’s not that pessimists have nothing to offer us.

Polarizing philosopher and writer Alain de Botton takes no comfort from inspirational peers and go-getters. Instead, he credits the “bracing wisdom of some of the world’s great pessimistic philosophers” for shaking him from gloom. If you find yourself in a particularly cultish or rah-rah business culture, a pessimist may help puncture the façade in a useful way.

“Our dread that we might be the only ones to feel anxious, bored, jealous, perverse and narcissistic turns out to be gloriously unfounded, opening up unexpected opportunities for communion around our dark realities,” he says.

So… there’s that.

How have you come to collaborative terms with pessimistic teammates? Are you an ex-pessimist who flipped the script? We’d love to share your tips with the community.

Adam McKibbin
Post by Adam McKibbin

Adam McKibbin is the content marketing manager for iMeet Central. His writing has been featured in Adweek, the Chicago Tribune and The Nation, and he’s produced content for some of the leading tech brands on the Fortune 500.

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