4

Theresa worked two cubicles over from Simran and made a habit of stopping by several times a day. Simran wouldn’t have minded these brief visits except that Theresa did nothing but complain. “Every morning when I asked how she was, she would launch into all the bad things in her life,” Simran told me. “Her home, her commute, our coworkers, you name it!” At first, Simran thought that listening and asking questions would allow her colleague to vent some of her negativity, but that just made things worse. “I became the go-to for her daily tirades.”

Once, after the CEO called an all-staff meeting to announce that she was giving everyone in the company a bonus after a particularly strong year, Theresa went immediately to Simran’s desk to point out that the company’s benefits package was still inadequate. It tainted the excitement that Simran was feeling, not only about her bonus, but about the organization’s successes.

Simran had to work closely with Theresa and wanted to get along with her. But she found it trying, and most days, when she saw Theresa coming, her instinct was to run the other way.

The pessimist, the cynic, the doubter, the complainer, the naysayer, the defeatist.

We’ve all worked with someone who can’t seem to find anything positive to say—ever—and even seems to enjoy pointing out all the ways projects and initiatives will fail. You may be familiar with the Saturday Night Live skit featuring the character “Debbie Downer,” brilliantly played by the actress Rachel Dratch. Debbie is a drag at any social gathering, regularly bringing up the rates of feline AIDS. Anyone who interacts with her is irritated, and although this is a caricature, a lot of us can relate to the dread of having to deal with someone like Debbie. Pessimists just aren’t fun to be around.

Here are some of the behaviors that they frequently exhibit:

• Complaining about meetings, senior leadership, other colleagues, anything and everything
• Proclaiming that a new initiative or project is doomed to fail
• Adapting a “we’ve already tried that and it failed” mentality, especially in conversations about innovation or new ways of working
• Immediately pointing out the risks of a tactic or strategy
• Finding something negative to say, even when the news or meeting is mostly positive

On days when Theresa was out of the office or on vacation, or was so busy that she didn’t have time to stop and chat, Simran felt more focused and productive. She also realized that anytime she heard Theresa coming toward her desk, she would physically brace herself for the onslaught of negativity, or even pretend to be in the middle of something, hoping that Theresa wouldn’t interrupt her to complain. But these evasions weren’t sustainable, and she found herself wishing that Theresa would change her attitude or at least find somewhere else to direct her negativity.

If you want to get out from under your naysaying colleague’s dark cloud, it’s helpful to understand what’s driving their behavior.

The Background on Pessimistic Behavior

There are a lot of reasons why pessimists see the world the way they do, and gaining a deeper understanding of what makes them tick can help you decide which tactics to use and inspire greater empathy. You may even see ways in which you can benefit from their outlook.

What leads someone like Theresa to be such a downer? There’s no single answer to this question. However, there are three elements to consider when it comes to pessimism:

• Outlook. A pessimist believes that negative events or results are inevitable. Think of the classic pessimist from children’s literature, Chicken Little (or Henny Penny, as she’s called in some countries), who told every animal at the farm that the sky was falling. Chicken Little believed that disaster was imminent.
• Agency. The second aspect is whether or not the person feels they can do something that will affect the outcome of a situation. Michelle Gielan, a researcher who focuses on happiness and success and, therefore, also looks quite a bit at pessimism, defines a pessimist as “someone who doesn’t believe good things will happen and has no ability to change outcomes.”1 Negative thinking isn’t necessarily bad, she says, and, in fact, may be warranted in some circumstances. But if a person also feels as if their efforts to avert disaster will make no difference, they’re unlikely to act.
• Behavior. This is where the attitude becomes action. A defeatist’s behaviors might include incessant complaining, as with Simran’s colleague Theresa, or constantly putting down others’ ideas, or talking about how unhappy they are. These actions are the expression of their fatalistic outlook and lack of agency.

All three elements are important to reflect on. Does your colleague have a negative outlook but rarely act on it? Do they feel they have what it takes to change their situation or to influence the results of a project? Those who have a negative outlook but retain agency often fall into a category called “defensive pessimism,” which sometimes has benefits.2

For example, one study showed that defensive pessimists with chronic illnesses were more likely to take actions that could improve their health, like proactively managing their pain.3 Researchers suggest that defensive pessimists might fare better during infectious disease outbreaks because their worry leads them to adopt preventive behaviors, such as frequent hand washing or consulting their doctor. People who fall into this subcategory can be easier to work with than someone who feels there’s nothing to be done about the impending doom they see everywhere.

There’s another category of pessimist—victims—who tend to have a negative outlook, very little agency, and play out their behavior in a way that paints them as the object of scorn or bad luck. I’ll talk more about this variation of pessimism in chapter 5.

Prevention versus promotion focus

One of the ways to better understand your pessimistic colleague is to think about what’s known as motivational focus. According to this model, prevention-focused people are concerned with safety and often see tasks as a series of obstacles to overcome. Those with a promotion focus tend to think about the future in a positive way and see opportunities where others see insurmountable challenges. Social psychologists Heidi Grant and E. Tory Higgins describe the differences between the two types, as shown in table 4-1.

TABLE 4-1

Differences in dominant motivational focus

Source: Adapted from Heidi Grant and E. Tory Higgins, “Do You Play to Win—or to Not Lose?,” Harvard Business Review, March 2013, https://hbr.org/2013/03/do-you-play-to-win-or-to-not-lose.

Neither type is better or worse than the other, but they do function differently on teams and in organizations. Grant and Higgins explain, “[Prevention-focused people] are often more risk-averse, but their work is also more thorough, accurate, and carefully considered. To succeed, they work slowly and meticulously. They aren’t usually the most creative thinkers, but they may have excellent analytical and problem-solving skills. While the promotion-minded generate lots of ideas, good and bad, it often takes someone prevention-minded to tell the difference between the two.”4 Could it be that your pessimistic colleague has a prevention focus?

If you lean toward a promotion focus (note that it’s possible to have characteristics of both types), you might find your prevention-focused colleague especially frustrating. But understanding that there are valuable aspects to their behavior and that pessimism is more than just a pathological insistence that “the sky is falling” could make their vigilance less annoying and may even give you ideas about how to channel it for good.

There are other possible drivers behind your colleague’s persistent complaining, including anxiety, a desire for power, and resentment.

Anxiety

For many pessimists, imagining the worst-case scenario can be a knee-jerk response to anxiety. By thinking of everything that could go wrong, they feel like they can guard against those possibilities coming true. Of course, this is only helpful if they then take action to prevent their worst fears.

For example, think about the last time you applied for a job that you really wanted. During the process, you probably told yourself at one point (or maybe several) that you’d “never get an offer.” That critical self-talk is certainly pessimistic. However, it can serve a functional purpose if you better prepare for your interview or do more research on the company in response.

It may be that your pessimistic colleague isn’t aware that their mind always goes right to the negative, or maybe they think doing so is helpful. Perhaps, for example, they believe that by pooh-poohing ideas up front, they are rescuing the team from the agony of disappointment. Playing out their anxieties in this way can make those around them, especially optimists, uncomfortable. But recognizing that they’re doing this because of worry, not because they want to rain on your parade, can make it easier to cope.

Power

Your naysaying colleague may be motivated by a desire for power as well. When I’m in a meeting with someone who is shooting down ideas left and right, I often interpret it as a deflection of responsibility. After all, if they insist, “That’s never going to work!” they won’t be left holding the bag if the project doesn’t pan out as hoped. In some cases, I’ve also considered it a sign of laziness. If a colleague says, “We shouldn’t even try,” then they’re off the hook for making the project work or contributing to it in any meaningful way.

But research by Eileen Chou at the University of Virginia reveals a different motive. Chou’s findings indicate that pessimists find a sense of control in their negativity. Rather than avoiding responsibility, they may be asserting autonomy by disagreeing with the group. Others see them as more authoritative too. As Chou explained to me, “We assume that most people would shy away from naysayers or exclude them because they’re a drag. But it’s actually quite the opposite. People who have high status are often the people who dole out negative or contrarian remarks.”5 This creates a reinforcing cycle. Pessimists use negativity to feel powerful, and their cynicism makes others likelier to perceive them that way, and even to choose them as leaders, which turns the perception of authority into reality.

Resentment

Perhaps your glass-half-empty colleague is expressing disgruntlement. Take Phillippe. He and his colleague Audrey were both up for a promotion in the marketing department at the pharmaceutical company where they worked. Phillippe had been there for seven years and had had his eye on leading the team for a while. Audrey was a relative newcomer, having joined the organization eight months earlier. But the senior vice president of marketing believed Audrey had more potential, so gave the position to her. Phillippe spent the next six months putting down every idea that Audrey had and claiming that any new initiative she proposed had “already been tried” before her time and was “a complete failure.”

In Phillippe’s case, his behavior wasn’t a matter of an anxious disposition or motivational focus. It was his resentment that led him to undercut Audrey and hinder the team’s progress. You often see this cynical and jaded attitude in people who, like Phillippe, have been passed over for promotion, don’t feel valued by the organization or their boss, or sense that they aren’t earning the respect they deserve. So, unconsciously or not, they try to bring down those around them.

However, in some cases, a pessimist might be right to suspect foul play—especially given what we know about how people from underestimated groups, such as women and people of color, are frequently overlooked for promotions.

Regardless of what’s motivating a cynic’s behavior, there are costs to you and your organization.

The Costs of Working with a Pessimist

Research shows that pessimists themselves suffer great costs. They are more likely than optimists to experience anxiety and depression. They tend to report more stress and take longer to recover from illnesses and other setbacks. Some studies have shown that a negative outlook makes you less creative. There’s even evidence that pessimists experience greater financial trouble: they are less likely than optimists to have put money aside for a major purchase or to have started an emergency fund. They also tend to worry more about money and finances than people who are optimistic.6

Since emotions, both positive and negative, are contagious, it’s easy to get dragged into a pessimistic colleague’s outlook, and you might experience some of the costs discussed earlier as a result.7 You may become demoralized, worry about negative consequences more than usual, or start to feel like your actions won’t make a difference at work. Or you might be irritable and stressed-out as you try to avoid the pessimist. The more time you spend with your negative colleague, the more likely you are to start seeing the world through their eyes.

This is what happened to Jamal when he had a manager, Courtney, who constantly criticized the company’s leadership. This was one of Jamal’s first jobs, so he didn’t think to question Courtney’s perspective. Instead, he began to see the company’s leaders as Courtney portrayed them. “The constant negativity sapped all my enthusiasm, excitement, and optimism about the future,” he explained to me. “I internalized her criticism and believed in the flaws of the leadership and our product.” He says that he even doubted some of their teammates because whenever people didn’t show up to work, Courtney accused them of faking sick. Even though their team consistently met or even exceeded their targets, “Courtney always made us feel as though we weren’t working hard enough. This really created a divide among us. You can’t successfully sell as a team when these fissures exist.”

Just one pessimist on your team, especially one with authority like Courtney, can change how everyone interacts. Constant complaining can create divisions on a team, reduce everyone’s satisfaction at work, erode trust, and foster negativity that pollutes the team—or organizational—culture.

None of us want to bear these costs. So how can you get along with your downer colleague? Start by asking yourself a few questions.

Questions to Ask Yourself

Answering the following questions will help you begin to map out a plan for improving the dynamic between you and your pessimistic colleague.

What are the possible sources of their pessimism?

Knowing what’s leading a cynic to shoot down ideas or resist trying new approaches may point you to a solution you hadn’t thought of. What’s the underlying reason for the complaining? Do any of the motivations I just described—prevention focus, a need for power, or anxiety—seem to fit the bill? Might they be resentful of something?

If your colleague is anxious about a project failing, you might reassure them that they won’t be penalized for trying something new. If they’re afraid of “wasting time,” reiterate why experiments can be valuable, even if they don’t work out. If they’re just burned-out or too busy and aren’t keen to stretch themselves further, then maybe help troubleshoot how they can manage their workload (or reduce it if you’re their boss).

Be proactive about figuring out the underlying reasons for their attitude. That’s what Lucas did with his colleague Joe who complained nonstop about how their consulting team was sizing the market for a new medical device. The team met several times to go over the project, clearly divide up the work, and set goals and milestones. Joe did not productively contribute to any of these discussions. He would cross his arms and say things like “I don’t see how this is useful for the client.” Lucas pulled him aside and asked what was going on. After some back-and-forth, it became clear that Joe didn’t fully understand what was expected of him. His pessimism was a defense mechanism. Lucas spent half a day with Joe going over what he needed to do and practicing the work with him. Together they sized five of thirty sub-segments of the market so Joe would then be comfortable doing the other twenty-five on his own. This approach worked. Lucas told me that Joe’s “skepticism evaporated,” and he stopped pushing back during their meetings.

Are their concerns legitimate?

A little cynicism is healthy, even necessary. Pessimists play an important role in society and in most workplaces, because of the balance they bring. They can helpfully point out risks that many of us—especially the optimists—tend to miss. They encourage caution when others are quick to push an initiative forward. We need dissenting voices to check our assumptions, advance our ideas, and prevent us from costly missteps. And negativity is sometimes warranted. When you look at what’s happening around the world—soaring economic inequality, racial injustice, a rising wave of populism and nationalism—it’s understandable that some people don’t feel hopeful about the future. And insisting on positivity when we have lots of good reasons to be concerned about what comes next can make your head spin.8

Consider whether your team or organization has fallen into a “cult of positivity” where only agreement and optimism are rewarded. Do you leave room for people to openly disagree or express doubts? Maybe you are mislabeling a colleague a pessimist because they are simply willing to speak up when others are not.

Which of their behaviors are problematic?

Try to avoid painting your coworker and their gloomy attitude in broad strokes and pinpoint the exact behaviors that are creating issues for you. Is it that their negative comments discourage the rest of the team from speaking up? Or that they won’t take on work unless they’re 100 percent sure it will succeed?

I often hear people describe pessimists as “taking the air out of the room,” and I’ve certainly worked with coworkers who have this effect. But get specific about what they’re doing that’s causing trouble. As Heidi Grant told me, “You want to be sure there is an actual problem. You might not like their way, but maybe you can just tune that out, roll your eyes, groan a bit, and then move on.”9

Knowing exactly which behaviors are causing trouble for you and other colleagues will help you decide which strategies to employ.

Tactics to Try

If Winnie the Pooh, with his incessant optimism, wasn’t able to change Eeyore’s worldview, chances are you won’t get your colleague to always look on the bright side. But there are steps you can take to make working with a pessimist more pleasant and productive.

Reframe cynicism as a gift

Assuming your colleague doesn’t have malicious intentions, try to view them as having a special gift. When they point out yet another reason that the initiative you’re working on is doomed to fail, tell yourself, They are using their unique talent to help us see the risks. This ability to point out potential flaws is often an undervalued attribute. Take a look at any number of the big corporate disasters that have taken place in the past several decades, from Enron, to Wells Fargo, to the BP oil spill, to the Boeing 747 Max tragedy. Experts who examined what caused these and other catastrophes consistently found that many employees were aware of the mistakes being made (or the crimes being committed) but didn’t speak up about them.10 Oftentimes, people stayed mum because organizational culture discouraged employees from raising concerns, and they feared the repercussions of doing so.11

Accepting pessimism for what it is will also build a connection. Finding common ground with your naysaying colleague and seeing logic and even value behind their gloomy disposition can help you get to a place where you can relate and, maybe, eventually get along. But changing your perspective is just the beginning—compassion alone is unlikely to stop your coworker from spreading their gospel of negativity.

Give them a role to play

If your colleague is a natural at pointing out risks, consider making that part of their formal role. You’ve undoubtedly heard the advice to appoint a devil’s advocate who is tasked with raising difficult questions and challenging a group’s thinking. Research shows that giving at least one person the right to push back in this way leads to better decision-making for the team as a whole.12 This is a perfect task to assign to a pessimist. Since “devil’s advocate” can have negative implications for some people, I like to call it “disagreer-in-chief.”

One advantage of this tactic is that it helps the group avoid vilifying the pessimist and recasts them as a productive team member. Nilofer Merchant, a former tech executive and innovation expert, is a big proponent of the idea that divergent voices are key to both individual and corporate growth. As she writes, “Some leaders demonize people [who raise objections], accusing them of being the problem instead of solving the problem that is being raised. The reason is simple: It’s not comfortable to see your shortcomings. It is this discomfort that causes leaders to deflect and defend. And, of course, when leaders do this, they limit whether the organization advances.”13

Challenge their assumptions

Pessimist: “This is doomed to fail.”

You: “Actually, I think this might work.”

Pessimist: “You’re just being naive.”

Trying to force a pessimist to see things your way can further entrench them in their perspective. Instead, engage with their underlying ideas and assumptions. Ask for clarification or more information about what they mean. For example, if your coworker says, “This project is never going to make it past Finance,” ask them to explain why. Better yet, ask for alternative solutions: “What can we do to make sure the project does win their approval?” (Watch your tone so you don’t come off as dismissive or condescending.) You can even model this behavior by using “but” statements. For instance, you might say, “It’s possible that Finance won’t go for this, but it’s worth laying the groundwork now because next year, they’re apt to approve more tech projects.”

Heidi Grant says that there is a magical combination when it comes to engaging with pessimists: “You want to make clear that you believe it’s going to be hard and that you believe you can be successful.”14 If you act like it’s going to be easy, the pessimist will dismiss you. Conveying that you understand why they feel the way they do will improve your chances of nudging them toward a different perspective.

You can also reframe their complaints, while acknowledging them. For instance, if the pessimist grumbles that another team member is lazy, you might say something like “It’s a busy time for everyone. I bet they’re doing more than we can see.” You don’t need to be patronizing or mean, but it’s helpful to present an alternative view. Or ask your downer colleague to be constructive. For example, you could say, “I can see why you’re frustrated. Do you think there’s anything we can do about this now?” Or “What could we try next time?” You don’t need to come out and say, “Well, do something about it!” But you can increase a cynic’s sense of agency by pointing out actions they can take, or even telling a story of a time when you encountered similar circumstances and responded productively.

Help them understand when their pessimism helps and when it hurts

Because a healthy dose of cynicism can be helpful to a group, your defeatist colleague may not be aware of the negative impact their words and actions are having on others. Help them see the light. For example, you can say, “When you make negative comments, the team gets stuck.”

This is what Byron did when his colleague Morgan kept saying that their joint project wasn’t going to work. Their team had been tasked with organizing the company’s sales inventory and identifying operational efficiencies that might lead to new sales. Morgan worked for another department and was skeptical of the project from the beginning. Byron could see that Morgan’s attitude was aggravating the other team members, and he was concerned it would impede their progress. He set up a one-on-one meeting with Morgan and explained, as diplomatically as he could, that whenever Morgan made negative comments, the team looked deflated and the conversation stopped. Morgan doubled down, reiterating his skepticism that the numerous departments involved could pull off the plan. Byron asked him to offer alternatives to the ideas being proposed in addition to raising concerns. “I explained that what he was doing felt like continually putting up roadblocks, without providing a detour sign,” he told me. Morgan took Byron’s advice, and when team members responded positively, seemingly relieved, it reinforced the new behavior. Byron told me that the team’s recommendations were implemented with many of Morgan’s alternative solutions. He believes the process was more rigorous because of his contributions.

Lean in to positivity

Positive peer pressure might help, too. Although singling people out is sometimes counterproductive, you can set norms for the whole team to observe that will nudge a killjoy in the right direction. For example, you could agree as a group that everyone will ask themselves before they speak, “Will this comment be helpful?” You might also agree that criticism should be accompanied by a suggestion of what to do instead, as Byron encouraged his colleague Morgan to do in the previous example.

It’s especially important to take action if a cynic’s negativity is swaying the team. Eileen Chou found in her research that even one pessimist can influence a group’s decision-making process. Because of a group’s inherent drive to maintain harmony, she explains that “if there’s one outlier, the group moves toward the outlier to appease them.” You can counter this tendency, she says, by agreeing that decisions shouldn’t be driven by just one person’s perspective.15

Fostering an atmosphere of positivity is another way of using peer pressure to encourage pessimists to look on the bright side. Michelle Gielan suggests, for example, that you might start meetings with a positive prompt, such as “What’s one way that a colleague has made your life better or easier lately?” The specific prompt you use is less important than helping the team focus on something good.

Watch for polarizing

When experimenting with these tactics, watch that your actions don’t inadvertently make your problem colleague dig their heels in deeper. As Grant says, “Many pessimists think optimists are idiots and they’ll be eager to dismiss you as a wide-eyed moron. We think we can come at them with a fire hose and drown them with our optimism!”16

But pushing too hard for positivity could make them double down on the gloom and doom. Instead, respect their motivational style and even acknowledge what’s right about their point of view. It helps to admit that you also have negative feelings or thoughts, and then validate their perspective—or some aspect of it that you agree with. You don’t have to say, “You’re absolutely right; this project won’t succeed,” but you can say, “I hear your concerns, and I share some of them. Help me understand what has led you to these conclusions.”

Hang with the positive crowd

Spending time with more positive coworkers is a good way to bolster yourself against a storm of negativity. Seek out people who lift you up, as opposed to drag you down, and invest in building relationships with them.

Jamal, whose boss, Courtney, turned him against the company’s leadership and his own teammates (see “The Costs of Working with a Pessimist”), used this tactic. Once he realized the negative impact that Courtney was having on him, he tried to avoid contact with her as much as possible. Instead, he focused his time on colleagues who were enthusiastic about the future. As he explained, “It helped me quite a bit to spend time with coworkers who were excited about their work and the company. They wanted to get out into the field and shout about our product from the rooftops!” Although Courtney never really changed her tune, Jamal was able to flourish with support from like-minded friends.

• • •

Let’s return to the story of Simran and her colleague Theresa, who had nothing but complaints when she stopped by to chat. Simran told me that she made subtle changes to how she interacted with Theresa, and she tried to emphasize the positive. For instance, after three months of asking Theresa, “How are you?” every morning and getting a “negative earful every single day,” she started asking, “What’s good today?” The first few times, Theresa was taken aback and didn’t have a response. But soon, she started answering the question. Simran says that she never asked, “How are you?” again. Instead, she’d inquire, “What went well in the meeting you had with that client?” or “Tell me about the best parts of your presentation.”

She also learned to excuse herself when Theresa started on a tirade: “I’d politely get out of the conversation as quickly as I could.” Simran admits that she was surprised that such small actions worked. Theresa didn’t ever become a ray of sunshine, but Simran stopped dreading their interactions, and she says that she learned a lot about how to deal with negativity—not just from coworkers but from other people in her life as well. “I feel more able to stay out of the fray and not get dragged down,” she says.

TACTICS TO REMEMBER

The Pessimist

DO:

• Encourage them to play disagreer-in-chief as part of their formal role.
• Engage with their underlying ideas and assumptions, asking for clarification or more information about what they mean.
• Convey that you understand why they feel the way they do and nudge them toward a different perspective.
• Help them understand when their pessimism helps and when it hurts.
• Set constructive norms for the whole team—for example, you could agree as a group that everyone will ask themselves before they speak, “Will this comment be helpful?”
• Acknowledge that you also have negative feelings or thoughts and validate their perspective or some aspect of it that you agree with.
• Spend time with more positive coworkers to bolster yourself against a storm of negativity.

DON’T:

• Try to drown them in positivity; that can further entrench them in their pessimism.
• Dismiss their perspective as unhelpful or illogical.
• Ignore their complaints or their concerns; they may have valid reasons for their naysaying.