The unexpected mistakes that cost executives their next big role

If you dropped an executive from 2016 into today’s job market, they would hardly recognize it. In just a decade, artificial intelligence has transformed how leaders are sourced and assessed. Simultaneously, demand for proven leadership is so strong that some retired CEOs are being called back into the workforce. These factors have changed the executive search landscape so much that it makes how candidates position themselves throughout the search process critical in getting the opportunities they want.

In my work and discussions with candidates, I’ve identified five common mistakes that may get in the way of leaders’ securing their next role:

1. Treating executive search as transactional rather than relationship-driven

The quality of a leader’s network matters more than its size. The goal isn’t to know the most people; it’s to build meaningful relationships with people who can offer valuable perspectives. In Show Up to Win: How to Land the Leadership Role You Want, which I cowrote with Jeff Sanders, vice chair and co-managing partner at Heidrick & Struggles, we encourage executives to be intentional about who they connect with and why. Before reaching out, they should ask themselves: What am I hoping to learn, and who is best positioned to help me learn it? The most valuable conversations come from leaders who have worked in comparable roles or navigated similar industries. 

2. Ignoring the recruiter’s call because you’re happy where you are

Leaders often assume they need to engage with recruiters only when they’re looking for a new role. In reality, the best networking happens before a career move is on the horizon. Without that pressure, executives can have thoughtful conversations with recruiters who can offer perspective on their strengths and areas for development, while staying informed about emerging trends shaping the leadership market.

This also keeps executives top of mind for recruiters when nontraditional opportunities arise. For example, Heidrick & Struggles’s 2026 High-End Independent and Interim Talent report shows demand for interim C-suite leaders has increased 151% since 2021. This is important because career priorities often evolve as personal and professional circumstances change. An executive who is committed to a long-term role today may seek greater flexibility tomorrow, and an interim role would allow them to choose assignments that align more closely with their interests and expertise. If leaders engage with recruiters only when they’re ready to make a move, they risk missing opportunities that could match their evolving career priorities they would never know about. 

3. Looking at salary and company name instead of the opportunity

When a recruiter reaches out, executives must resist the urge to lead with two questions: How much does it pay? And which company is it? Those details matter, but they shouldn’t drive their decision. Salary indicates what a role pays, but not whether it’s worth taking. Instead, executives should ask about the bigger picture: Why was the role created? What business challenge is the organization trying to solve? The answers will reveal more about a role’s potential than salary range or brand recognition ever will.

4. Letting AI do the work on résumé and interview answers

Résumés have always mattered, but AI has made a polished résumé a baseline. Any candidate can generate a clean, well-structured résumé in minutes, which means a strong one no longer sets leaders apart. The same shift is happening in interview preparation.

Used thoughtfully, AI can help candidates brainstorm questions and organize thinking, but the problem starts when they let it do too much of the work. Too often, executives share answers that sound too polished and not authentic. Hiring committees are trying to look past scripted responses and aim to understand how leaders operate under pressure and within their operating environment.

5. Forgetting the interview goes both ways

If leaders treat the interview process as an audition they need to win, rather than a two-way assessment, they’re doing it wrong. As an organization evaluates whether an executive is the right fit, the executive should be conducting the same assessment of the organization.

Before committing to an interview, leaders should research the culture of the company, its reputation, and its leadership dynamics to determine if the role is right for them. As leadership demands rise and executive burnout becomes more common, it’s important for executives to assess whether they are prepared for the responsibilities and pace of the position. Doing so will help leaders avoid hearing only what they want to hear or allowing excitement about the job to cloud their judgment.

The more informed executives are, the better positioned they’ll be to ask meaningful questions about decision-making processes, board expectations, and the organization’s ability to support its leaders through periods of change. 

Ultimately, the goal isn’t simply to land the job, it’s to determine whether the role truly aligns with their strengths, career aspirations, and leadership style. Leaders shouldn’t view interviews as one-off, one-way interactions, and instead approach them with rigor and commitment that positions them to find the right opportunity—not just the next one. 

The most successful executives don’t wait until they need a new role to build relationships, strengthen their market position, or understand how leadership expectations are evolving. They stay connected and curious, positioning themselves for what’s next long before they need to.