3

When Aiko’s new boss, Cora, first joined the company, things were going smoothly. Aiko was happy to have someone she could learn from and who promised to bring new ideas and approaches that would improve her projects. But several months into her new manager’s tenure, she started to see some red flags.

Aiko had long been the go-to person on any questions or meeting requests related to the department’s initiatives. This seemed to upset Cora, who would ask, “Why aren’t they coming to me for answers?” She got angry with Aiko whenever this happened, treating Aiko as if she was trying to undermine her. Attempts to redirect their colleagues’ inquiries to Cora didn’t stick, which only infuriated her further. “It’s just what they were used to doing,” Aiko told me. “But Cora took it personally.” In her previous job, Cora had managed a large team and budget, and now Aiko was her only direct report. “I think that always bothered her,” she said.

Cora’s overly emotional reactions and snide comments wore on Aiko. “She nitpicked everything I did to the point where I felt I had no power to make decisions, even small ones. I was always afraid she was going to get upset and explode. My confidence in my ability to do my job eroded,” she explained.

Aiko had never questioned her competence before. But now, Cora’s insecurity was rubbing off on her.

If you’ve ever doubted yourself because you work for a boss who doesn’t have faith in you, shoots down your ideas without explanation, and blames you for their lack of success (like Cora was doing to Aiko), you’re not alone. There are, of course, many flavors of bad bosses, but insecure managers wreak a particular kind of havoc. They can be notorious micromanagers who drive you up a wall with their incessant nitpicking, or paranoid meddlers who make you question your every move. They may even go so far as to intentionally hurt your career if they perceive you as a threat.

How do you know if you’re dealing with an insecure manager? Here are some of the most common behaviors exhibited by this type of difficult coworker:

• Being overly concerned about what others think of them
• Suffering from a chronic inability to make a decision (or stick with one), even when the choice has little consequence
• Frequently changing the direction of a project or meeting, especially at the suggestion of someone in power
• Taking opportunities to highlight their expertise or credentials, especially when it’s not necessary to do so; in its more toxic form, this may include putting others down to make themselves look more important
• Attempting to control everything about a team or project, including when and where and even how people accomplish their work
• Requiring that every decision and detail have their approval
• Not allowing the team to interact with colleagues from other departments or senior leaders in an attempt to control the flow of information and resources

Aiko’s boss, Cora, wanted everyone in the organization to go through her because she thought that would prove her value. But she spent so much time trying to manage how others perceived her that she failed to do what she’d been hired to do: provide fresh ideas and mentor Aiko. Instead of innovating, she was micromanaging, and Aiko, as her sole direct report, was the unfortunate target.

Aiko felt stuck. Every time she took even minor steps to advocate for herself, Cora seemed to become only more paranoid and controlling. No one should have to work for a boss like this, ever. But if you can relate to Aiko, and aren’t able to leave your job, and want to find a way to work with your self-doubting boss, there are ways to respond that won’t further incite their insecurity. The first step is to understand what might be making your insecure manager act the way they are.

The Background on Insecure Behavior

Self-doubt is a universal part of the human condition. We all have times when we wonder if our coworkers think we’re smart, if we have what it takes to nail that presentation, if we said something wrong in a meeting, or if strangers are judging the way we dress or look. I’m not proud of this, but when I’m talking with someone who I suspect doesn’t respect me or is silently questioning my capabilities, I sometimes mention that I went to an Ivy League school or that I work at Harvard Business Review. I have even talked about how busy I am to prove I’m “in demand.” I’m cringing as I type, but I do know these are normal reactions to feelings of inadequacy.

Seeking approval and even praise from others stems from the fact that human beings once relied on community to survive and still need it to thrive. As psychologist Ellen Hendriksen explained in an interview with Vox, “A little bit of insecurity, a little bit of self-doubt, is helpful because it allows us to monitor ourselves. It causes introspection and self-examination and motivates us to grow and change.”1 There’s an instructive label for the 1 percent of people who have no self-doubt: psychopaths. Complete freedom from insecurity is not something to aspire to.

While feeling insecure at times is natural, we start to see problematic behaviors, such as micromanaging, unfairly criticizing direct reports, or constantly seeking reassurance when people attempt to conceal or compensate for their self-doubt.

Leaders may be more susceptible to self-doubt

Research has shown that insecurity increases as you move into leadership roles. A UK-based leadership consultancy surveyed 116 executives, for instance, and asked about their biggest fears.2 The number one reported anxiety was being considered incompetent. The executives in the study also said they feared underachieving, appearing too vulnerable, and coming off as foolish—all revealing deep insecurities around others’ perceptions of their performance as leaders.

Why would managers who tend to have more power and authority than others be more insecure? Shouldn’t it be the people without power who worry about their jobs and how others see them? In a series of studies, professors Nathanael Fast and Serena Chen have shown that when powerful people feel incompetent, they tend to act more aggressively toward others, needlessly sabotaging them or being vindictive.3 Incompetence alone doesn’t lead to aggression though. Those in less powerful roles who feel insecure don’t typically resort to the same bad behaviors.

The gap may stem from increased pressure to perform when you’re promoted to a senior position. “The expectation is that people higher up in the organization will have enhanced leadership ability, knowledge, access to information and data—that they’ll be more competent than others,” says Ethan Burris, the Neissa Endowed Professor at the McCombs School of Business at the University of Texas, Austin.4 The discrepancy between how confident or capable leaders actually feel and the high expectations that come with their role results in what’s called “ego defensiveness,” where leaders engage in actions to protect their self-esteem or justify their actions.5

Take Ralph, a sales VP at an IT services organization. Ralph had knocked it out of the park as a sales director and earned a big promotion, but he was reluctant to give up his relationships with clients, since he’d worked hard to win their business. He wanted to do two jobs—his old job and his new one—but the company’s leadership team insisted that he hire someone to report to him. Roberto was that unlucky hire. When he joined the team, unaware of the full story, Ralph resisted handing over his accounts. He often inserted himself into Roberto’s communications with customers and demanded that all decisions related to his previous clients go through him. Roberto was doomed before he walked in the door because Ralph was doing everything he could to protect what had led to success in his previous role.

For people who aren’t stereotypically seen as leaders, the problem is even more complex. Women or people of color, for example, may experience self-doubt, not because of any flaw or inability to lead, but because they receive both overt and subtle cues that they aren’t equipped to do the job—that they should feel like a fraud. Or they’re sent conflicting messages, such as “Be assertive but not confrontational” or “Be yourself but don’t show any negative emotions.” In a wildly popular Harvard Business Review article, “Stop Telling Women They Have Imposter Syndrome,” consultants Ruchika Tulshyan and Jodi-Ann Burey wrote about this phenomenon. They explain that, in many organizations, women, especially women of color, are blamed for feelings of inadequacy when the real issue is that the workplace culture has signaled that they don’t belong or aren’t deserving of their success.6

In addition to worrying about being outed as incompetent, some insecure bosses may be concerned about job security. If you’ve ever lost your job, you know how shameful it can be—a feeling that most of us want to avoid at all costs. When you pair the fear of being fired with concern about being perceived as incompetent, it can lead to acute insecurities.7

A few months ago, I was talking with a middle manager at a biotech firm about an innovation initiative that had stalled at the company. One of the obstacles the leader of his division identified was that people were afraid to disagree with anyone senior, not wanting to bring up new ideas that might challenge the status quo. When I asked the middle manager to help me understand this hesitation, he said, “I don’t want to get fired. I need this job.” When I dug deeper, he conceded that to his knowledge no one had ever lost their job at the company for speaking up. He’d seen people who spoke truth to power go on to be promoted. Still, he was worried. “I don’t want to be the first casualty,” he told me.

It’s possible that your insecure manager feels concerned not only that they’re not up to the job they’ve been given but that they may lose that job at any moment. Fear and shame, as I discussed in chapter 2, can wreak havoc on our minds and provoke us to mistreat others.

The Costs of Having an Insecure Manager

Let’s return to Aiko’s situation, described at the beginning of the chapter. Aiko’s dip in self-esteem wasn’t the only consequence of the bad blood between her and her boss, Cora. There were ripple effects. It was difficult for Aiko and Cora to make progress on their team’s projects, for instance, with so much confusion around who should be the point person. Colleagues in other departments started to doubt the competence of both people and hesitated to involve them in important meetings about the company’s strategy.

There are many other costs associated with having a boss like Cora. First, there are the psychological consequences: an increase in job-related stress, anxiety about your future, and, as Aiko experienced, a creeping self-doubt.

There are also potential consequences for your career prospects, especially if your manager is taking credit for your work or singing their own praises at your expense. In extreme cases, your manager may even intentionally discredit you and your work to make themselves look better. Teresa Amabile, a professor at Harvard Business School, found that self-doubt led managers to give harsher performance reviews. “Those who are intellectually insecure come down hard on others,” she wrote, “perhaps as a tactic for proving how smart they are.”8

Insecure managers are also bad for business in general. Because their egos are fragile, they tend not to listen to other’s ideas and resist feedback. In one experiment led by Nathanael Fast and his coauthors, managers at a multinational oil and gas company in the Middle East were asked how competent they felt in their role on a scale of one to seven. The lower they rated their competence, the less likely they were to solicit feedback from their employees, and as a consequence, their employees were less likely to offer up ideas.9 Insecure managers like those in the study may worry that employees’ suggestions reflect negatively on their own competence and ability to do their job. If people believe changes need to be made, the logic goes, then perhaps it will appear as if the manager doesn’t know what they’re doing. So they send signals that they aren’t willing to hear input. And employees who have their ideas ignored or rejected are less satisfied at work, are less creative in coming up with novel solutions to problems, and are more likely to quit.10

What can you do to prevent the harm caused to you and your organization by a boss who lacks confidence? Start by asking yourself a few questions.

Questions to Ask Yourself

As with any colleague who fits into one of the archetypes in this book, it’s helpful to reflect on the situation before you act. So, ask yourself:

What evidence do I have that my boss is insecure? Could I be wrong in my assessment?

Before you label your manager “insecure,” try to be objective. Just because someone doesn’t lead in the way that you want doesn’t mean that they are unsure of themselves. If the person is acting tentatively, they might have good reason to be risk averse or they might come from a culture where caution is celebrated. Many people, especially women, have been socially conditioned to downplay their successes or positive attributes. It’s possible that your manager has been encouraged to avoid bravado and defer to others.

Is the insecurity causing a problem? If so, what is the negative impact?

Your manager constantly seeking reassurance is probably annoying, but is the behavior in and of itself a problem? Perhaps once your boss’s ego has been assuaged, other negative consequences are minimal. Consider what, if any, damage your boss’s insecurity is doing to you or your team. In what ways is it detrimental? Having a clear sense of the problem will inform if and how you act.

Am I feeding the insecurity?

It’s always helpful to explore the role that you may be playing in creating (or perpetuating) a negative dynamic with a colleague. That’s not to say that you are the cause of your manager’s confidence problem, but could you be triggering it in some way?

Do you generously share the spotlight with your boss? Do you show appreciation for their work? Perhaps, because of your own self-doubts, you try to play up particular skills or expertise you have, which in turn highlights your boss’s flaws. Maybe you’ve challenged their ideas in front of others? Or signaled that you don’t trust them to get the job done? Think carefully about whether you are inadvertently feeding your manager’s insecurities and possibly making the situation worse.

What does my boss want?

No matter the source of their feelings of inadequacy, what most insecure managers want is to experience less fear and feel surer of themselves. And can’t we all relate to that? Everyone wants to feel as if they’re good enough. What else might your manager want? What are their goals and aspirations?

As with any situation that requires managing up, it’s crucial to understand your boss’s objectives. In answering this question, you may instinctively favor negative interpretations: “My boss wants to destroy my career” or “My manager wants everyone else to look bad.” But go a step further. Even if they want to “destroy” your career (which is unlikely), what’s the motivation behind that impulse? For instance, maybe they’re afraid of losing their job in an upcoming round of layoffs or maybe they believe that their critiques (which really come off as harsh criticisms) will motivate you to perform better. Keep asking yourself “why” until you uncover a drive to which you can relate.

With the answers to these questions in mind, it’s time to think through the steps you’ll take to change the problematic dynamic between you and your self-doubting boss.

Tactics to Try

No one wants to spend their workdays (or sleepless nights) dreaming up new ways to appease their boss’s ego or get them to stop weighing in on tiny, meaningless details, like what font to use in a presentation. But having a healthy, positive relationship with your insecure boss will make your work life much easier, and there are some proven ways of making that happen.

After reading through the following tactics, figure out which are most relevant to your situation and try them out. You can make adjustments as you go.

Think about the pressures they face

Far too many bosses are overextended, overwhelmed, underqualified, or undertrained. So step back and look at the big picture. It’s possible that legitimate pressures like hitting year-end targets or dealing with constantly changing rules about where and when employees work is raising your manager’s anxiety level and prompting them to take out their insecurities on you.

They may have stressors you don’t see or fully understand. Exercise empathy. Remember that your manager is human, even if their insecurity is causing problems that need to be addressed.

Sveta’s boss tried to control every aspect of how she did her job and would even lie about having important projects coming up to keep Sveta from taking her vacation. Because this was Sveta’s first job out of graduate school, she was hesitant at first to push back on her manager. But eventually she felt she had to say something. Confronting her boss only made her double down on the lies though. She tried to shift her mindset instead. “What worked best was thinking of my boss as a child who wasn’t aware of the harm she was doing. With that picture in mind, I was able to keep a calm composure as I might with a kid,” she told me. Exercising patience took a lot of self-control, especially when her manager got under her skin. But Sveta was careful not to lose her temper, often excusing herself from the room to calm down before going back to a heated conversation with her boss. She never loved working for this manager, but she did learn to live with the relationship, at least temporarily. Controlling her anger kept tensions between her and her boss down and allowed Sveta to do her job—and take her well-deserved vacation time.

Help them achieve their goals

If your insecure boss tends to put you down or take credit for your work, it might spark your own competitive tendencies. But one of the worst things you can do is to retaliate. If your self-doubting manager senses that you can’t be trusted or that you have disdain for them, their defensiveness is likely to ramp up. Instead, consider what it might take to appease them and whether you’re willing to do that.

This is what Sanjay learned to do with his boss, Vineet. Sanjay was incredibly frustrated by Vineet’s lack of trust in him, which was most evident when Vineet questioned Sanjay’s data analysis in front of their clients. When Sanjay asked why he was doing this, Vineet said that it was really important to him that they have the numbers right. So Sanjay stepped back to see what he could do to address his manager’s concerns. He experimented with a new approach, and a day or two before any appointment with clients, Sanjay made sure to share his data and ask about Vineet’s goals. “I wanted to know what he wanted out of the meeting,” Sanjay told me. With Vineet’s objectives in mind, he would suggest several ways they could achieve them together. He used phrases like “We’ve got this” and “It’s good that we’re in this together.” It felt hokey to say these things, but Sanjay noticed that Vineet started to trust him more as a result. This took extra time and effort, of course, but the payoff was that Vineet stopped undermining him in front of clients.

Framing your work as a joint effort could help to alleviate tension between you and your insecure boss, as it did for Sanjay. Start sentences with “we” as much as possible. And when you succeed, be sure to share the glory.

Be careful that you don’t downplay your talents, however. Research shows that employees who are the object of envy will often hide their positive attributes and try to avoid taking credit.11 But that can backfire. Your insecure manager may feel even more anxious if they think your work isn’t up to snuff or that your poor performance might reflect badly on them. And others in the organization may start to think you’re not as capable as you are. The goal is for your boss to see you as a trustworthy partner, without damaging your own career and reputation.

Signal that you’re not a threat

You want your boss to think of you as an ally, not a rival. It’s best if you can do this from the start with your manager, but it’s never too late to reset the tone of your relationship. In a meeting, you might say, “I admire what you do and I’m hoping to continue learning from you.” At the same time, you don’t want to make them think they can walk all over you.

The key is to watch what you say in a way that you don’t make them feel even more threatened than they already are. For example, I don’t understand that” can feel like a challenge to their intelligence, even if it’s just a simple statement and you genuinely want to find out what they’re thinking.

Lindred Greer, a professor at the University of Michigan who studies conflict, shared this trick with me: when dealing with a superior who sees her as a threat, she imagines herself as a cute little squirrel, and she tries to project the warmth of that persona. She says this picture softens her edges and helps her come off as nonthreatening. This may seem silly—do I really need to pretend I’m a squirrel?—but Lindy says she’s come to enjoy doing it. It makes her smile and takes her attention away from her frustration with a difficult colleague.12

Pay compliments and express gratitude and appreciation

You can also help calm your manager’s ego by rolling out the compliments. Research on managers who feel incompetent has shown that genuine flattery helps.13 Note the word genuine. Most people will see right through empty praise. For example, if you’re trying to get your boss to ease up on micromanaging, don’t tell them how much you admire their attention to detail.

Many people understandably fear coming off as sycophants. Instead of paying compliments, you can also express appreciation for something they’ve done for you. “Direct reports often don’t realize how hungry their leaders are for evidence that they’re doing OK,” says Nathanael Fast. “People don’t like the idea that it’s an employee’s job to manage their boss’s ego. But it does give you a sense of influence.” In one of Fast’s studies, he saw that when an employee said, “Thank you so much. I’m grateful,” it positively influenced an insecure manager’s evaluation of their employee’s performance.14 So consider thanking your manager for giving you a chance to work on a high-profile project or for introducing you to colleagues in another division. Doing this in private is great, but it may have more of an impact if you appreciate them in front of people whose opinions they care about. Not only will this put them at ease, but by bringing attention to some of their strengths, you’ll help them build confidence.

Buttering up your boss may be the last thing you want to do if they’re making life hard for you. But hopefully it’s a small price to pay for reduced stress and brighter career prospects.

It’s a bargain Nia was willing to strike with her boss, Tamara. Tamara was the kind of person who changed her mind easily, depending on who she had spoken to most recently. This gave Nia and her teammates whiplash, as Tamara would repeatedly change course on a decision. Nia’s solution was to become Tamara’s trusted adviser, the person Tamara turned to when she started to doubt whether they were headed in the right direction. “I had to constantly be on guard about who was whispering in her ear and be available to counter any concerns she developed that might take us off track,” Nia told me. “If I took an unflappable approach with her and gave her the dignity she craved, she could find her way. I felt a bit like she needed me to be her Rock of Gibraltar.” Although this required artful juggling by Nia, she felt it was worth it. She had her pick of plum projects and helped to run the department more smoothly.

Nia’s efforts changed the power dynamic between her and Tamara—a tactic that research has shown to decrease mistreatment from abusive bosses.15 If you can gain leverage with your manager—perhaps by developing skills that your supervisor will rely on or by becoming a trusted adviser—it might stop some of their problematic behaviors and even motivate your boss to treat you better.

Restore their sense of control

Insecure managers who have trouble trusting others often resort to micromanaging. You can interrupt some of their meddling by helping them feel like they’re in charge. You might say things like “What we do is ultimately up to you” or “I trust you to make the right decision” and then make suggestions about how to proceed.

Sharing information is another way to reinforce their sense of control. Many insecure managers are terrified of being out of the loop. Keep them updated as much as possible, and be transparent about what you’re working on and who you’re talking with, especially in other parts of the company. Schedule regular check-ins where you can share progress on projects your boss cares about and make them feel included in the process. While annoying to do in the moment, oversharing may save you the effort of defending yourself later.

Research shows that asking questions instead of providing answers in a conversation can also boost feelings of control in the other person. Pose questions that start with “What if …” or “Could we . .” that invite your manager to share their thoughts.16

Keep a compliments folder

When you’re working with an insecure boss, you need to find ways to bolster your own confidence so you don’t fall into the trap of self-doubt as Aiko did. This could mean keeping a list of your strengths on hand and reviewing them after a particularly tough interaction with your manager or spending time with people in your organization (or outside it) who reflect your best self back to you.

One of the best pieces of advice I’ve gotten in my career was to keep a compliments folder in my inbox. This is a place where I save any notes that congratulate me on a job well done, praise my work, or point out the impact my efforts have had on coworkers, clients, or readers. I don’t look in the folder nearly as often I thought I would when I first created it, but just knowing it’s there improves my confidence.

Create a folder in your email now and whenever you receive a compliment from someone—even if it’s minor—put it in there. When you need a boost, especially after interacting with your insecure manager, praise is just a click away.

• • •

Unfortunately, no matter how strategic you are, it’s unlikely that you will be able to cure your manager of their insecurity. Nor is that your responsibility. While the tactics in this chapter should help smooth out your interactions, don’t go overboard. If you become entirely focused on managing your boss, you risk not doing your job well or alienating people in the organization who wonder why you are so intent on making your undeserving boss look good. If progress feels elusive, refer to chapter 12 for a few last-ditch things you can try before throwing in the towel.

Despite Aiko’s questioning of herself, she was able to focus her energy on altering the dynamic between her and her manager by emphasizing that they had a shared agenda. She always went to great pains to include Cora in meetings and keep her informed. At the end of each week, before signing off for the weekend, Aiko would send Cora an email listing any developments on their projects or important conversations she’d had that week. These notes did double duty—they helped ease Cora’s anxieties, but they also documented the good work Aiko was doing. In the back of her mind, Aiko always knew that Cora’s insecurity might result in her trying to take down Aiko in front of others. And she was glad to have a record of the progress she was making to defend herself if this happened. Luckily it didn’t come to that. Eventually, Aiko left the company, but she reported to Cora for five years.

Looking back, she thinks she might’ve handled the situation better, especially if she hadn’t taken Cora’s behavior personally. Of course, this isn’t easy to do. When you have a manager who is always looking over your shoulder, questioning your work, or trying to inflate their own ego at the expense of others’, it can feel like a personal attack. But aim for some emotional distance from the situation. Perhaps imagine yourself as a cute, fluffy squirrel.

TACTICS TO REMEMBER

The Insecure Boss

DO:

• Remember that your insecure boss is human. Demonizing them won’t help anyone.
• Position yourself as an ally, not a rival.
• Pay your boss genuine compliments, or express gratitude and appreciation—in private, but also in front of others whose opinions they value.
• Start sentences with “we” as much as possible.
• Keep them updated and be transparent about what you’re working on and who you’re talking with, especially in other parts of the company.
• Schedule regular check-ins where you can share progress on projects your boss cares about and make them feel included in your work.

DON’T:

• Assume you know what pressures your manager is under or what’s causing their insecurity.
• Retaliate. If your self-doubting manager senses that you can’t be trusted or that you have disdain for them, their anxieties are likely to ramp up.
• Forget to share the spotlight when you succeed.