Take The Leap
Take the Leap is the podcast where we get real about the rollercoaster that is entrepreneurship and life.
Sure, some folks make running a business look like a walk in the park, but let's be honest – it's more like a wild ride through a theme park with unexpected twists and turns!
Join us your co-hosts, Victoria & Ashlan, as we spill the beans on our own real-life experiences and shine a spotlight on some amazing guests. From the highs of success stories to the lows of epic failures, and hey, we'll even throw in some cringe-worthy, laugh-out-loud embarrassing moments for good measure!
So buckle up and tune in every week for a dose of raw, unfiltered truth about what it's really like to chase your dreams and build a business. Whether you're a seasoned entrepreneur or just dipping your toes into the startup world, we've got something for everyone. Even if it's just to make you think, "I'm so glad I didn't do what they did!"
Take The Leap
#129: The Realities of Workplace Transitions, Succession Planning, and Normalizing People Leaving
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In this conversation, Naomi Hattaway returns to talk about what it really means to design your work, your leadership, and your life with intention. From building a home meant for aging in place to preparing organizations for sabbaticals, leadership transitions, mergers, and meaningful goodbyes, Naomi brings a deeply human lens to what can often feel like operational or uncomfortable topics.
This episode is especially valuable for nonprofit leaders, founders, and business owners who know that people leaving is inevitable, but want to handle those transitions with more care, clarity, and humanity. Naomi reminds us that succession planning is not a sign of failure or departure. It is a way to protect the work, honor relationships, and build organizations that can keep moving forward.
Key Takeaways
- Succession planning is not just for CEOs. Every role holds knowledge, relationships, and context that matter. Planning for people to leave helps protect the mission and the team.
- Two weeks’ notice is rarely enough for meaningful transition. Naomi challenges the default exit timeline and invites leaders to think more intentionally about what people, relationships, and projects need before someone leaves.
- Good departures are part of healthy workplace culture. How an organization handles exits says a lot about how it values people and not just their productivity.
- Sabbaticals require reentry planning, not just departure planning. When someone steps away, the organization changes, and so does the person returning.
- Nonprofits need to normalize mergers, sunsets, and strategic endings. Closing or combining organizations does not have to mean failure. It can be a thoughtful way to protect impact.
- Leaders should ask better questions before joining an organization. One powerful interview question Naomi recommends: “What is your process when someone leaves?”
- Knowledge transfer does not have to mean creating the perfect binder. Sometimes the most helpful thing is documenting why decisions were made, not just how tasks are completed.
- Funders have a role to play in protecting organizational continuity. Foundations can support succession planning as part of protecting their investment in nonprofit missions.
- Leaving well starts with communication. Whether at work, in business, or around the kitchen table, we can all help normalize conversations about change, departure, and transition.
Guest & Host Information:
- Guest, Naomi Hattaway, Founder of 8th & Home
- Co-Host, Ashlan Glazier-Anderson, Owner of AshbeanPDX Marketing
- Co-Host, Victoria (Tory) Proppe, Owner of Imagine Marketing Strategies
Connect with Naomi:
- Take the Quiz to find your Transition Readiness Archetype: https://www.naomihattaway.com/assessment
- On Instagram: @naomihattaway: https://instagram.com/naomihattaway
- On LinkedIn: https://linkedin.com/in/naomihattaway
- Visit Naomi’s website: https://www.naomihattaway.com/
- Read Naomi’s book on Leaving Well: https://www.naomihattaway.com/book
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