You are a competent, strategic professional. You think clearly and deliver results. But there is one part of the job that almost no one prepares you for: managing a boss or colleague who is driven by insecurity.
This is more common than most organisations admit. Research suggests that around 36% of adults have an insecure attachment style. A 2024 Korn Ferry report found that 71% of U.S. CEOs and 65% of other senior executives experience impostor syndrome — a persistent fear of being exposed as incompetent. Even leaders who appear confident and charismatic can have unresolved fears that quietly distort their decision-making and undermine collaboration. They may micromanage, emotionally withdraw, resist feedback, or seek excessive praise. A 2023 Pew Research report found that more than a third of American workers describe their boss as 'dismissive' or 'unpredictable' — traits strongly linked to insecurity. The impact on teams is serious: higher stress, more burnout, and greater staff turnover.
The good news is that when insecurity is driving someone's behaviour, it is possible to 'manage up' — that is, to positively influence people who are senior to you. Drawing on peer-reviewed research into attachment dynamics and work with executives, experts have built a practical framework for working with insecure leaders or colleagues.
Researchers identify two common patterns of insecure leadership. The first is the anxious type. Anxious leaders crave constant affirmation and connection. They respond well to praise but spiral when they feel criticised or excluded. They may micromanage, change direction suddenly, or react strongly to an imagined slight. Their energy can be inspiring, but it can also drag a team into emotional turbulence. Katharine Graham, the late publisher of The Washington Post, showed anxious insecurity early in her leadership. After taking over the paper unexpectedly in 1963, she admitted to feeling terrified in meetings and hesitant to speak up. With the support of editor Ben Bradlee, she was eventually able to work through those anxieties.
The second pattern is the avoidant type. Avoidant leaders project calm and independence, but underneath they are uncomfortable with vulnerability. They pride themselves on self-reliance, shut down open dialogue, reject criticism, and rarely show uncertainty. Working with them can feel like working around a wall. Steve Jobs was sometimes described as displaying avoidant tendencies: emotional distance, quick withdrawal when challenged, and a strong need to maintain control. Few colleagues felt secure enough to fully connect with him — though some, such as designer Jony Ive, did manage to break through. A striking historical example of managing up successfully is Henry Kissinger, who spent much of his career working with the deeply insecure President Richard Nixon. Despite Nixon's distrust and constant need for reassurance, Kissinger helped steer him toward significant foreign policy achievements that might otherwise never have happened.
Experts also identify three common mistakes that people make when working with insecure leaders. The first is overaccommodation — easing the leader's anxiety by agreeing quickly, softening bad news, or shielding them from criticism. This may feel helpful in the moment, but it reinforces insecurities, blurs professional boundaries, and often leads to burnout and lost credibility for the person doing the accommodating.
The second mistake is withdrawal. When a boss is volatile or emotionally distant, the natural response is to pull back — communicating less, withholding feedback, and disengaging emotionally. But this creates a vacuum that reduces transparency and trust, and it can reinforce the leader's belief that they cannot rely on others.
The third pitfall is confrontation without calibration. Challenging an insecure leader's behaviour directly and without careful thought can easily backfire — even when the intention is good. The way you raise a concern matters as much as the concern itself.
