‍‍Unlock Hidden Opportunities: How and When to Evaluate Your Executive Career

In today’s fast-paced executive landscape, career growth is rarely straightforward. Instead, the journey often involves a zigzag path of lateral moves, strategic shifts, and opportunities to step outside your role to gain new skills. One of the most effective tools for managing this journey is the Three-Year Career Checkup, a structured self-assessment that allows executives to stay aligned with their professional goals, industry trends, and the evolving job market.

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But why every three years? And why is it important to explore new opportunities even when you’re not actively looking to switch roles? Let’s delve into how regular career evaluations can set you up for long-term success.

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To help answer these questions, we sought insights from Brian Boomsma, an accomplished executive recruiter at GLC with over 20 years of experience helping professionals advance to their desired Roles. With a deep understanding of company requirements, market trends, and leadership demands, Brian has guided many executives through critical career transitions.

Why a Career Checkup is Essential—Even When You’re Not Looking to Switch

Brian Boomsma explains that career exploration shouldn’t be reserved for moments of dissatisfaction or active job hunting. “Even if you’re not thinking of leaving your role, it’s important to assess your position in the market,” he advises. "Exploring opportunities regularly, while you're working, is about staying informed—understanding your value and the trends shaping your industry.”

Here are the key reasons why a regular career checkup is essential:

Stay Ahead of Industry Trends

‍“Industries change quickly,” Brian notes. “For example, the role of a CFO has evolved to include not just financial oversight but also digital strategy and data analytics. If you’re not staying up to date with these shifts, you risk falling behind.”
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By conducting a career checkup every three years, you ensure that your skills and experience remain relevant, preparing you for both internal promotions and external     opportunities.

Maximize Your Market Value

‍“Many executives are surprised to learn that their compensation may no longer reflect their value,” says Brian. “Even if you're not planning to leave your current role, it’s important to know what your peers in similar roles are earning.”
Periodically benchmarking your compensation against the market can give you leverage in negotiations or prepare you for a future transition when the time is right.

Identify Growth Opportunities

‍Career growth is not always about moving up—it can involve lateral shifts or acquiring new skills that expand your expertise. “Some of the most successful executives I work with have taken on temporary assignments or pursued certifications outside of their regular responsibilities,” Brian explains. A career checkup helps you identify these opportunities for growth, even within your current role.

When to Start Exploring New Opportunities

So why three years? According to Brian, “three years gives you enough time to make an impact in your role, but it's short enough to avoid stagnation.” During your checkup, it’s critical to assess your situation with three key questions:

1. Am I fulfilled in my current role?

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“Fulfillment isn’t just about compensation—it’s about feeling engaged and excited by your work,” Brian says. If you find that you’re no longer challenged or inspired, it’s time to explore what else is out there.

2. Is my compensation aligned with market standards?

‍“The executive job market is competitive, and salary expectations can change quickly,” Brian notes.  Regularly comparing your compensation package to similar roles ensures that you're being fairly compensated and prepared to negotiate for better terms if needed.

3. Am I thriving in my current culture?

‍“Company cultures evolve, and what once felt like a perfect fit may no longer be the right environment for you,” Brian explains. If the culture is no longer supportive of your growth, it may be time to seek a role where your contributions will be more valued.

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If the answer to any of these questions is “no,” it’s time to start exploring new opportunities, even if you're not actively looking to switch roles.

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Proactively exploring opportunities while you’re employed gives you more control and time to make thoughtful career decisions rather than waiting until you're forced to make a change.

How to Explore Opportunities While Still Employed

Exploring new roles while employed offers significant advantages, but it needs to be done discreetly and strategically. Here’s Brian’s expert advice on how to approach this process:

Engage Trusted Executive Recruiters

‍“Having a relationship with a recruiter is invaluable,” Brian advises. “They provide you with insights into the market, potential roles, and emerging opportunities, all while maintaining confidentiality.” By connecting with a recruiter, you stay informed about what’s available without openly seeking a new role.

Invest in Continuous Development

‍Career growth isn’t limited to promotions. “Executives who pursue certifications, leadership programs, or special assignments are often better prepared for larger roles in the future,” Brian notes. “These opportunities to upskill can be pursued without leaving your current job, and they set you apart in the long run.”

Network with Purpose‍

“Networking is not just about building connections—it's about staying visible and relevant in your industry,” Brian explains. Attending industry events or maintaining     relationships within leadership circles can help you hear about roles before they’re publicly posted.

Confidentiality is Critical

‍When exploring opportunities, discretion is key.  “It’s important to ensure that any conversations with recruiters or potential employers remain confidential,” Brian warns. “You don’t want to risk jeopardizing your current role before you’re ready to make a move.”

The Zigzag Path to Executive Growth

Career growth for executives rarely follows a straight line. “The most successful leaders embrace a zigzag path, which often includes lateral moves, temporary projects, or even time spent gaining certifications,” Brian explains. “These experiences allow you to become a more well-rounded leader, ready to take on broader responsibilities.”

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For example, a CFO might step into a sustainability project or pursue data analytics certification, positioning themselves for roles that require deeper knowledge in these areas. These non-linear moves prepare you for the increasingly complex demands of modern executive leadership.

Key Takeaways

● A Career Checkup is Essential: Conducting a three-year career checkup ensures you're staying aligned with market trends, your compensation is competitive, and you’re fulfilled in your role.

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● Exploring Opportunities While Employed: It’s important to explore opportunities even when you're not actively looking to switch roles. Doing so provides leverage and helps you make thoughtful, proactive career decisions.

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● Growth is Non-Linear: Career paths aren’t always vertical. Pursuing lateral moves, certifications, or special projects can often lead to long-term success in leadership.

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● Work with Experts: Engaging trusted recruiters ensures you stay connected to hidden opportunities, helping you navigate the executive job market discreetly and strategically.

What’s Next?

In our next article, we’ll dive deeper into navigating a passive job search—exploring how you can keep your career options open without actively applying or signaling that you’re ready to move. We’ll also discuss how executive recruiters, like Brian Boomsma, can guide you through this process while ensuring absolute confidentiality.

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Explore Executive Career Opportunities and Stay tuned for expert tips on managing your career transitions discreetly and strategically, without disrupting your current role.

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