• Skip to primary navigation
  • Skip to main content
Spinnaker Trust

Spinnaker Trust

Log In
  • Our Firm
  • Wealth Management
  • Trustee Services
  • ESOP Trustee Services
  • Real Estate Services
  • Our Insights
  • Media & Press
  • Contact Us

insights

How to Navigate a Leadership Transition

About the author:
Drew Oestreicher, CEPA
Principal, Senior Vice President, Senior Client Advisor

Drew loves working with families and small businesses to simplify their financial complexities and help them live their goals. As a Certified Exit Planning Advisor and part of a team of investment, tax, trust and estate planning experts, he enjoys being actively engaged with clients, helping them work through the challenges of succession and plan for the future.


: How to Navigate a Leadership Transition

About the author:
Laura Pfeiffenberger, ASA
Senior Vice President, ESOP Client Advisor

Laura enjoys working with business owners to find solutions to complex valuation issues. As part of Spinnaker’s ESOP team, she draws on more than 15 years of experience valuing privately held companies to help clients navigate their unique challenges and strengthen the services we provide to ESOP clients and their employee-owners.


: How to Navigate a Leadership Transition

Stepping away from leadership can be challenging, even when you have a solid succession plan. Here are four ways to make the transition smoother for you, your successor, and your organization.

1. Identify a new role for yourself.

If you plan to stay involved after your successor takes over, establish a role that allows you to contribute without remaining in control.

A board position or advisory role can let you share institutional knowledge, open doors through industry relationships, and stay connected — while giving new leadership room to lead.

2. Create a clear exit timeline.

Work with your team to establish a timeline for scaling down your responsibilities and transferring them to others.

Clear milestones create shared expectations, give emerging leaders confidence, and prevent a transition from dragging on longer than it should.

3. Think beyond the office walls.

For many business owners, work becomes a major part of their identity. Stepping away means thinking about what will give the next chapter purpose.

Professional associations, industry groups, nonprofits, and community organizations can provide meaningful opportunities to put decades of leadership experience to work in new ways.

4. Prepare for more than a business transition.

A successful succession plan isn’t only about preparing the organization. It’s also about preparing yourself.

Consider how you want to spend your time, rebuild relationships, pursue interests, and prioritize your health, leisure, and personal goals.


A successful exit takes planning on both sides. A thoughtful leadership transition prepares the next generation to take the reins while giving outgoing leaders a meaningful path forward.

Define your new role.
Set a timeline.
Plan for what comes next.

Keeping You Up-to-Date

More News

  • October 2, 2026

    How to Navigate a Leadership Transition

    Stepping away from leadership can be challenging, even when you have a solid succession plan.

    Read More

  • September 17, 2026

    Wealth Advisor or Trust Company?

    Five questions to help Maine families determine whether a traditional wealth management advisor or trust company best fits their financial needs.

    Read More

A sailboat in a cove

Start your journey.

Whether you are looking for top-tier wealth management or hoping to identify local trustee services, our team is standing by.

Contact Us

Subscribe to Our Newsletter

Select list(s) to subscribe to


Spinnaker Trust

Email

[email protected]

Mail

Post Office Box 7160
Portland, ME 04112

Office

207-553-7160

Toll-Free

888-449-3512

Fax

207-553-7162

Copyright © 2026 Spinnaker Trust Developed by Brassbound Privacy Policy