How to Manage an Insecure Leader

You’re a competent, strategic professional. You think clearly, execute well, and deliver results. But there’s one part of your job no one prepared you for: managing an insecure boss or colleague. This is a more common problem than organizations like to admit—even at senior levels of the hierarchy. Recent research suggests that about 36% of adults have an insecure attachment style. And a 2024 Korn Ferry report found that 71% of U.S. CEOs and 65% of other senior executives experience symptoms of impostor syndrome—the persistent fear of being exposed as incompetent. Leaders, including CEOs, other C-suite executives, and board chairs, may appear confident and charismatic, but under pressure their unresolved fears of inadequacy and rejection quietly distort decision-making and can undermine collaboration. They may micromanage, emotionally withdraw, resist feedback, or seek excessive praise. If you work for or with such individuals, you’re not alone. According to a 2023 report from Pew Research Center, more than a third of American workers describe their bosses as somewhat or extremely “dismissive” or “unpredictable”—traits often linked to insecurity. When teams are negatively impacted by those kinds of managers or colleagues, it can lead to pervasive stress, higher burnout, and increased turnover. However, when insecurity is driving the behavior of someone who is senior to you or more powerful, it is possible to “manage up.” Drawing on our peer-reviewed research into attachment dynamics in organizations and on our work with executives, we’ve created a practical framework for addressing two common forms of insecure leadership and building a more functional working relationship with any insecure manager, peer, or team member. Two Types of Insecurity Insecurity is fundamentally relational. It’s shaped by early life experiences and amplified under stress. Our research has explored two common insecure attachment patterns—anxious and avoidant—and how they show up in work relationships. Anxious leaders crave an affirming, constant, and often unrealistic connection, lighting up with praise but spiraling when they feel excluded or criticized. They may micromanage, overapologize, or change direction abruptly in reaction to the latest conversation or imagined slight. They pull teams close and then, when overwhelmed, push them away. Their energy can be infectious, even inspiring, but it can also be draining, as teams feel dragged into emotional turbulence. Katharine Graham, the late former publisher of The Washington Post, began her leadership journey with anxious insecurity. After her husband’s suicide, in 1963, she unexpectedly took control of the paper. She admitted to being terrified in meetings and hesitant to speak up. Her own account and biographies note that she was seen as an “insecure woman thrust into a man’s world” and made mistakes as a result, including mishandling the 1975 pressmen’s strike. However, in part because of her relationship with then-editor Ben Bradlee, she began to overcome those anxieties. One of us (Jeffrey) coached a senior finance executive whose challenge was not technical competence but visible anxiety anytime the CEO questioned his recommendations. This executive struggled to separate professional disagreements from personal rejection, another common problem. Avoidant leaders, by contrast, tend to appear calm and rational, projecting an image of control and independence. But beneath that surface is a discomfort with vulnerability that keeps them distant and hard to reach. They pride themselves on being self-reliant, shun open dialogue, reject criticism, and rarely show uncertainty. To work with them is to work around a wall built from a fear of needing others too much. They may shut down when challenged or become hypervigilant when the stakes are high. Steve Jobs, the late cofounder of Apple, was sometimes described as displaying avoidant tendencies: emotional distance, rapid withdrawal when challenged, and a strong need to preserve control. Reports suggest that few colleagues felt secure enough to fully connect with him because he rarely acknowledged his mistakes or showed emotional openness. However, some of his collaborators, such as designer Jony Ive, were able to break through. We can find good examples of subordinates working to counteract insecure leadership in the political realm, too. Consider Henry Kissinger, arguably the 20th century’s most influential American diplomat, who spent much of his career managing the brilliant but deeply insecure president Richard Nixon, a man known to be distrustful of many and in need of constant reassurance. Of course, Kissinger did not prevent Watergate, but he did push Nixon toward meaningful foreign policy successes, including the withdrawal of U.S. troops from Vietnam, the establishment of relations with China, and a détente with the Soviet Union, which otherwise might not have been achieved. Common Pitfalls to Avoid Many people who work with insecure leaders or colleagues respond in counterproductive ways. In our research we’ve identified three common traps that people fall into, thereby exacerbating the negative dynamics in their workplaces. Overaccommodation. When leaders feel uncertain, it’s natural to want to ease their anxiety by anticipating their needs, agreeing quickly, or glossing over bad news. When they are withdrawn or unpredictable, you might avoid bringing them in on issues, shield them from criticism, or limit their exposure to others. But overaccommodating often leads to blurred boundaries and unrealistic expectations. It reinforces the leader’s insecurities and, for you, can result in burnout, frustration, and diminished credibility. Consider a strategy director who, worried about an anxious chief executive’s reaction, quietly rewrites the investor deck himself after every minor comment and removes any data that might trigger concern. The CEO becomes even more dependent on him to “fix” things and increasingly intolerant of ambiguity, while the director burns out and loses respect with peers who see him as serving one person’s anxiety more than the organization’s needs. Withdrawal. Your instinctive response to neediness or volatility from a boss might be to pull back—disengaging emotionally, communicating only when necessary, withholding feedback, or tuning out altogether. This creates a vacuum, reducing transparency and trust, and may reinforce leaders’ beliefs that they can’t rely on others. We see this happen often with avoidant leader relationships. A regional sales head, for example, stops bringing tough pipeline issues to her distant SVP, reasoning, “He doesn’t want to engage anyway.” She sends short, cryptic emails instead of having real conversations. While this self-protection is understandable, it cuts the leader off from information and contact, undermining trust. Confrontation without calibration. Attempting to confront an insecure leader’s behavior head-on can backfire. Even well-intentioned advice can be perceived as a threat, leading to defensiveness, retaliation, or a further breakdown in communication. What matters is timing, tone, and strategic empathy. Addressing issues too bluntly or too soon can close doors rather than open dialogue. Mary Haasdyk Vooys Consider a scenario one of us (Dritjon) observed involving a talented operations manager and his avoidant VP. Frustrated by the VP’s lack of engagement and delayed decision-making, the manager confronted him during a tense project review: “Your unavailability is paralyzing the team, and we need clear direction from you now.” Though the feedback was accurate, the VP experienced it as a public challenge to his competence. He shut down, cut the conversation short, and then became even less accessible, gradually sidelining the manager from key decisions. What had been intended as a plea for collaboration was interpreted as a direct threat to authority. Now, let’s look at how you can operate more like Bradlee, Ive, and Kissinger to build more-productive relationships with and better manage both anxious and avoidant leaders. The 3R Process We teach people a three-step process—regulate, relate, reason—for managing the insecure behaviors of others. It’s based on a framework developed by Bruce Perry, a psychiatrist and neuroscientist specializing in attachment and brain development. This “3R” sequence recognizes that when people are under pressure—as most leaders often are—they revert to relying on their instincts, which can hinder logical thought. Before you can connect with and exert influence over insecure leaders, you must first help them regulate their nervous systems. After that, you can relate through connection and then, and only then, reason through the issue at hand. Here’s how the model works in practice. 1. Regulate. When people feel danger, no amount of logic or strategy will get through to them until their brains are calm. That is especially true for insecurely attached leaders, who may be more likely to perceive feedback or ambiguity as threats. An avoidant leader may need space and predictability. An anxious leader may need soothing nonverbal signals. With anxious leaders, your role is to anchor the conversation with steadiness. A grounded, confident tone and a clear message can ease their anxiety. Consider phrases like “We have time to address this.” Avoid mirroring their anxiety or dismissing their concerns. Instead, acknowledge the concerns and slow down the pace. With avoidant leaders, regulation involves minimizing perceived intrusion and emotion and emphasizing structure. Consider phrases like “I’ve analyzed the options and have a recommendation.” That signals clearheaded thinking rather than emotional turmoil and conveys respect for their space and authority while demonstrating competence. 2. Relate. Because insecure reactions are rooted in early attachment patterns and stem from a disrupted sense of belonging or worth, they require a relational response. This doesn’t mean becoming overly personal or indulgent. It simply being present, attuned, and trustworthy. Leaders who feel safe are more likely to listen, reflect, and grow. With anxious leaders, consistency matters. Check-ins, follow-through, and predictable behavior create the scaffolding they need. Use inclusive language (“Let’s explore this together”) and signal shared commitment. Be cautious with sudden changes or ambiguity, which they can read as abandonment. Being physically present is also important because it calms an anxious nervous system. Put away devices, maintain appropriate eye contact, and lean in slightly. Move away from your desk to sit beside the anxious person during difficult discussions. These proximity cues work at a preverbal level, signaling availability and engagement in ways that words alone cannot. With avoidant leaders, respect their preference for independence and predictable, emotionally undemanding relationships while creating subtle opportunities for connection. Instead of asking, “How do you feel about this?” try “What’s your take on this?” Before challenging their plans, first align with their intent: “I see how this supports the efficiency targets you set last quarter. I’ve been thinking about one potential side effect we might want to mitigate. The idea is to signal “I’m on your side,” which makes it more likely they will stay engaged when you eventually raise concerns. Relating also means respecting their preferred channels. Some avoidant leaders genuinely do better with written communication than with frequent meetings. Working side by side in a shared document or sending a brief update instead of insisting on another call can be a way of “being with” them that feels safe enough for them to stay available. 3. Reason. When leaders feel regulated and connected, they’re ready to engage their prefrontal cortex—the part of the brain responsible for executive function, reasoning, and planning. This is when you introduce feedback, strategy, or problem-solving. Frame your reasoning within the relationship you’ve built. Communicate clearly and ask for input. This not only invites collaboration but also strengthens the leader’s sense of agency. It’s key with both anxious and avoidant executives. With anxious leaders, frame problem-solving collaboratively: “Now that we’ve identified the concern, what options do we see?” Then think aloud: “I’m weighing three factors: the client’s history, the email content, and our relationship context.” This transparency reduces the uncertainty where anxiety flourishes. Document decisions to prevent post-meeting spirals. Send a simple follow-up email confirming agreement, which they can return to when doubt creeps in. With avoidant leaders, present information in a way that maximizes their autonomy: “I’ve identified two paths. Option A optimizes efficiency, whereas B maximizes stakeholder buy-in. I am leaning toward A…but what is your opinion?” This framing positions you as a thinking partner rather than someone seeking emotional or practical caretaking. Build arguments systematically and dispassionately. Clear logic and empirical evidence are key: “If our goal is market penetration, then consumer survey research shows that A is the way to go. If it’s margin improvement, then the financial data indicates that B makes sense.” This approach respects their need for intellectual control while opening doors for collaboration. Accounts indicate that Kissinger practiced the 3Rs in his interactions with Nixon. In the face of the president’s volatility, he offered calm, structured analysis. He would publicly reinforce Nixon’s sense of control and legitimacy, even when privately pushing for a different course of action. Ive also seems to have employed the 3Rs at Apple. Instead of pushing Jobs into open-ended conversations about feelings or team morale, he centered nearly every interaction on the work itself and invited Jobs into a highly structured design process, where visits to the studio revolved around concrete prototypes and clear product questions. That preserved Jobs’s sense of control while still giving Ive regular access to his judgment. Graham has described receiving similar support from Bradlee during The Post ’s coverage of the Pentagon Papers and Watergate: unwavering reassurance, regular detailed updates, and thoughtful discussions of his opinions as editor and her choices as publisher. The operations manager we mentioned earlier also received 3R guidance from a senior colleague who coached him to first give his VP space, interacting through structured emails, and then to build rapport by focusing on common interests and shared wins before finally proposing solutions in the form of clear options that preserved the VP’s autonomy. The 3R framework is adaptive. Some situations require rapid cycling through all three phases, while others may need an extended focus on regulation. In a hallway escalation with an insecure coworker, it is possible to move through all three steps in five minutes: first, a calming comment and steady tone (regulate), then a brief affirmation of partnership (relate), and finally, a choice between two options (reason). But when you’re trying to work toward a major strategic decision with an insecure boss, you might have to spend more time on each of the 3Rs. The point is not to apply a rigid script but to be conscious of which mode you are in and not to skip ahead. You must read your leader’s attachment cues and respond accordingly. Remember, too, that instinctive patterns intensify under stress. When feeling pressure, avoidant bosses can become even more distant and controlling, whereas anxious leaders need even more reassurance and are more easily thrown off course. In those moments, you need to resist being pulled into their pattern. If you can stay grounded enough to regulate first, relate second, and reason last, you are far more likely to achieve a constructive outcome. . . . Whether you’re managing up, down, or across, understanding the psychological roots of insecure behavior can transform how you relate to those displaying it. Instead of labeling a boss, peer, or employee as “difficult” or “emotional,” you can see dysregulation for what it is: a psychological state. Kissinger’s approach to Nixon, Ive’s partnership with Jobs, and Bradlee’s relationship with Graham all followed that logic. They calmed their leaders’ insecurities, invested in the relationship before pushing for change, and chose their moments for reasoning carefully. You may not be redesigning the iPhone or negotiating treaties alongside your insecure leader or colleague, but the same process applies. Regulate first. Relate next. Reason last. Over time that disciplined approach can protect your well-being, help your team stay steady, and channel a leader’s insecurity in ways that serve rather than undermine the common good.

How to Manage an Insecure Leader

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