Should I Stay or Should I Go? Navigating Leadership Transitions


Welcome to Loden’s Leadership Conversations! Today, Let’s Explore: Should I Stay or Should I Go? Navigating Leadership Transitions

Gather Around, Growth Alliance Members,

Have you ever felt torn between staying loyal to your current organization and exploring the pull of new opportunities? Leadership transitions are among leaders’ most challenging—and transformative—decisions.

At Loden Leadership, we understand the complexities of these moments. Leadership roles often come with a deep emotional connection, much like a boat owner’s bond with their vessel. The journey begins with excitement and ambition, and the end can be both daunting and bittersweet. Yet, every leadership role has a “shelf life,” and recognizing when it’s time to adapt or move on is key to sustained growth and impact.

So, how do you decide whether to stay or explore new horizons? Let’s dive into the factors that matter most.

When Staying Is the Right Move

Sometimes, staying in your current role is the best decision—especially if you see room for growth and alignment with the organization’s future. Here are actionable steps to help you thrive where you are:

1. Address Skill Gaps

Evaluate your leadership profile and identify areas for improvement. Building new skills or refining existing ones can reinvigorate your passion and leadership impact.

2. Adapt to Changes

Organizational dynamics often shift with new boards, evolving community expectations, or internal developments. Take time to realign with these changes and demonstrate your ability to adapt.

3. Strengthen the Culture

Reinvest in your team and the organizational culture. Fostering a positive and thriving workplace can reignite your passion and inspire those you lead.

Signs It Might Be Time to Move On

In other cases, transitioning to a new opportunity is the best path forward. Consider moving on if:

You’ve Achieved Your Goals

It might be time to seek new challenges if you’ve accomplished everything you set out to do.

The Fit Has Changed

Organizational shifts, new leadership, or evolving goals may signal that your values and vision no longer align with the role.

You’re Ready for Growth

Transitioning to a larger organization, exploring a different sector, or seeking new challenges could provide the personal and professional growth you crave.

The Risks of Staying Too Long

While loyalty and perseverance are admirable, staying in a role beyond its “shelf life” can lead to stagnation, burnout, or misalignment for you and your organization. 

The Importance of Transition Planning

Whether you decide to stay or move on, a thoughtful plan is essential for success for you, your current organization and your new organization. Here’s how to prepare:

Evaluate Opportunities

Research potential roles and organizations to ensure they align with your values and aspirations.

Enhance Your Profile

Address gaps in your leadership experience to position yourself as a standout candidate.

Create a Transition Roadmap

Outline clear steps to leave your current organization in a good position and better than you found it  and also to set the stage for a smooth and effective transition to your new endeavour.

Reflect on Your Goals

Revisit your vision and long-term objectives. Align your next step with your aspirations for impact and growth.

How Loden Leadership Can Help

At Loden Leadership, we specialize in supporting leaders through these pivotal moments. Whether you’re deciding to stay or preparing for a transition, we provide:

Leadership Profile Evaluations

We’ll assess your strengths and identify areas for growth to ensure you’re ready for the next phase of your journey.

Transition Planning

From evaluating new opportunities to refining your interview approach, we guide you every step of the way.

Take the First Step

Leadership transitions aren’t easy—but they can be transformative. Whether you’re wrestling with the question of staying or moving on, remember that you don’t have to navigate this journey alone.

May your leadership journey be rich with purpose, relationships, resilience, and discovery. I look forward to exploring new insights together in our next post.

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