Read Time: 5 minutes
By: Heather Wentler
Succession isn’t just about who takes over. It’s about the legacy you leave behind. My final reflections on guiding Doyenne through a thoughtful transition.
Since my announcement in November about my transition out of Doyenne, our public-facing platforms have been quieter than usual. There’s been minimal social media activity, few newsletters, and fewer emails than normal. This isn’t disengagement — it’s what happens behind the scenes during a founder transition. Between the dozens of lists running through my head, the post-its plastered across my workspace, notebooks with lists that are basically attached to me at all times, and our digital tracking systems; the operational load has been overwhelming. Add on starting a my new role part-time outside of Doyenne, the holiday season, and working closely with the Board to recruit and hire the new Executive Director, my brain has been on overdrive.
If you’ve read past posts, you know I’ve been open about the ups and downs of leading Doyenne, the difference between being a founder versus a “new hire,” and the importance of thoughtful succession planning, which we did a lot of in 2020 in the aftermath of Amy’s death. Even as I sat down to write this post, I wondered what new insight I could offer. But what’s always mattered is sharing the real, sometimes messy, experiences of running any company — from internal feedback to community interactions, and personal events filtered through a professional lens.
Transitions are often framed around the exit itself. The point at which someone leaves. At Doyenne, we focus instead on reflection during all stages of running a business. While looking forward is important, looking backward is just as essential. Understanding how past experiences shape our reactions to new situations helps both founders and companies thrive in change.
When I announced my departure to the Board and our community, the response was overwhelmingly supportive. No one was really surprised, and the excitement for what’s ahead for me was palpable. Throughout the candidate search — from 19 initial interviews to the final two, and even as the new Executive Director started her first days — I never doubted my decision. This is what needs to happen, both for Doyenne and for me.
Where I did have that “Oh, shit. This is really happening” moment was when the transition became tangible: changing my email signature to remove “Executive Director” (while knowing no one can take away co-founder), removing my administrative access on platforms, attending what would likely be my last meetings with certain people, and handing over keys. Each action signaled a shift in leadership responsibility while also highlighting the continuity of the mission we built together.
Having served on boards or seeing staff transitions elsewhere, I’ve rarely experienced anything like the intentional handover we’ve created. Staying for the first month of the new Executive Director’s tenure has been a privilege in many ways. It’s allowed me to explore the gaps my various lists missed, gradually hand over operations, and witness the organization in motion under new leadership. This is possible because of the values and principles Doyenne is built on — intentional, thoughtful, and always rooted in community.
Many of you have shared with me the sayings, analogies, or advice I’ve offered over the years that have stuck with you. Thank you for holding them close and sharing back.
My top ideas for transitioning out of your company:
- You’re going to forget something. Trust your team and business professionals to fill gaps and support the incoming leader.
- Even the best transition plan will have hiccups. Have a plan, and be ready to pivot.
- Whatever happens after you exit or the organization closes, it is what it is.
- If the organization thrives after you leave — celebrate it instead of feeling negative about it. Success beyond your tenure is success for the mission.
- Feel your feelings. All of them. Move through them.
These are the things I carry with me every day — and hope you’ll carry with you:
- You deserve to be in ALL the rooms and at the tables
- Listen and learn from others openly, and leave behind what you don’t want to carry forward
- Apologize and hold yourself accountable when you make mistakes
- People’s reactions are rarely based on the current situation
- “Every rain cloud runs out of rain” — Maya Angelou
- Find your communities of support
- Be kinder than you feel
- Be Audacious
- You Got This!
- “Tits Out” — Amy Gannon
These reflections simultaneously act as leadership guides, personal affirmations, guidance for you, and the values that have shaped Doyenne’s culture.
Doyenne will continue shaking up narratives, testing boundaries, and pushing for change within the Wisconsin entrepreneurial ecosystem. The voice may sound different, but it’s still there. I’m still here, too — always just a message away.
Founder Blog: Reflections on Transition: Passing the Torch, Keeping the Legacy