Imposter syndrome: The silent struggle of leadership transitions

Cindy Silverman
Cindy Silverman
Oct 29 2024
5 min read
Imposter syndrome: The silent struggle of leadership transitions

Imposter syndrome is something many leaders experience, often in moments of career transition. In fact, a study by KPMG found that 75% of female executives reported experiencing imposter syndrome at some point in their careers, particularly during career transitions. Having worked closely with professionals at various stages of their careers, I’ve seen this self-doubt surface most frequently when individuals are promoted from individual contributor roles to management. This shift can be daunting, especially in a work culture where traditional in-office mentorship and support systems have weakened. Many leaders find themselves in new roles with high expectations but without a roadmap for success.

This challenge is particularly acute for women. According to the same KPMG study, 85% of women believe their imposter syndrome is driven by the need to meet the expectations set by societal and workplace norms. Women, more so than men, often report feeling unworthy of their new responsibilities. While men might not notice or acknowledge these feelings, many women are keenly aware of the challenges they face—being underestimated or “mansplained” in meetings or managing former peers who might question their authority. These dynamics fuel feelings of insecurity, leading many women to believe they don’t deserve their roles, even when they’ve earned them.

The Confidence Gap

When professionals take on new leadership roles, they often face a lack of external validation. Research from Gartner indicates that a full 49% of people promoted within their own companies are underperforming up to 18 months after those moves, and McKinsey reports that 27% to 46% of executives who transition are regarded as failures or disappointments two years later. This is particularly true for those working remotely or in hybrid settings, where opportunities to observe and emulate role models are scarce. In the past, aspiring leaders could watch their mentors in action during meetings, absorbing not just knowledge but confidence. Today, learning by osmosis is harder to achieve.

Without the visible feedback loops that come from shared office spaces, many newly promoted leaders feel disconnected, questioning their abilities and the decisions that led them to their new positions. Often, the absence of these experiences creates a crisis of confidence. Leaders begin to doubt whether their contributions are valuable or even heard. It’s not uncommon for clients I work with to believe that every misstep will be scrutinized, every decision second-guessed. According to a report from Gallup, only 21% of managers strongly agree that they receive meaningful feedback from their leadership.

Building Confidence: Where to Begin

One of the most important steps in addressing imposter syndrome is to start by taking stock of your strengths. During 1:1 skill development sessions, I help clients reflect on their past achievements. Together, we review moments when they excelled, faced challenges, and ultimately succeeded. This exercise helps them realize that they do bring value to the table, even if they’re feeling unsure in the moment.

Next, we focus on the perception gap: How do they perceive their skills versus how others see them? Often, there’s a significant mismatch. Research suggests that men tend to overestimate their abilities, while women often underestimate their performance, despite similar levels of competence. I encourage leaders to seek feedback not just from their direct supervisors but also from peers and those they manage. It’s essential to understand that colleagues are often too focused on their own work to spend much time critiquing others. By soliciting feedback, leaders can gain a more balanced view of their performance and learn that the fears they carry are often unfounded.

Managing the Inner Critic

Many professionals are their own harshest critics, replaying perceived missteps in meetings or overanalyzing every piece of feedback. A major part of my approach is helping clients quiet that inner critic. We work on reframing thoughts, focusing on what went well rather than obsessing over what could have gone wrong. It’s important to remind leaders that perfection is not the goal—progress is.

Preparedness can also play a huge role in overcoming imposter syndrome. When you walk into a meeting fully prepared, with a clear understanding of your goals, you project confidence. This isn’t just about having the right data but also about knowing what you want to achieve. When leaders feel prepared, they’re more willing to speak up, share their ideas, and even push back when necessary.

Pushing Beyond Your Comfort Zone

Ultimately, building confidence means pushing yourself beyond your comfort zone. This can be as simple as speaking up more often in meetings or as complex as presenting new ideas to a skeptical audience. I often remind clients that leadership development is a journey, and every uncomfortable experience is an opportunity to grow.

One of the best ways to accelerate growth is through targeted skill development. Working 1:1 with an expert allows leaders to focus on areas where they feel least confident—whether it’s leading meetings, managing teams, or making strategic decisions. Precision skill development offers a structured way to tackle imposter syndrome by addressing specific weaknesses and turning them into strengths over time.

Creating Networks of Support

Another critical piece in building leadership confidence is creating a network. Many professionals today are siloed, especially in remote work environments, and don’t have the benefit of casual feedback from peers. A LinkedIn Learning study found that 85% of employees believe they would feel more confident in their roles if they had stronger workplace networks. I advise leaders to actively seek out mentorship and peer support, both within and outside their organizations. Not only does this help them gain new perspectives, but it also reinforces that they’re not alone in their struggles.

Confidence doesn’t just appear overnight. It’s built through experience, feedback, and support from those around you. By focusing on skill development, taking stock of your strengths, and silencing the inner critic, leaders can not only overcome imposter syndrome but also thrive in their new roles and soft skills.

Cindy Silverman
Cindy Silverman
Cindy is a certified Leadership Coach with over 30 years of executive experience, including her role as Managing Director at Citigroup. Throughout her corporate career, she successfully led Consumer Banking businesses worldwide - earning a reputation as a collaborative leader adept at building and managing world class teams, driving business transformation, and navigating crises. As a recognized expert in leadership development, Cindy has played a pivotal role in creating training and mentorship programs designed to accelerate cultural change and enhance performance. Currently, she is focused on her portfolio career which includes a robust coaching practice as a PCC certified coach and consulting for various private and public companies as a trusted senior advisor. Over the years, her coaching practice has engaged with hundreds of clients across all sectors of the economy and management levels. Her extensive business experience and deep understanding of corporate culture and politics uniquely position her to connect with clients - facilitating their professional growth with empathy, insight, and unwavering support. In addition to her coaching and consulting work, Cindy serves as a Global Advisor for How Women Lead, is a limited partner at How Women Invest, and sits on several local nonprofit boards. She holds a BA in Economics from the University of Michigan, an MBA from NYU Stern School of Business, and a certificate in Executive Coaching from Georgetown University’s Leadership Institute.

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