673. Shift 3 — People Leave: Make Transition Readiness Part of Your Culture - Naomi Hattaway

Summary

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Episode Overview

Theme:
“People Leave: Make Transition Readiness Part of Your Culture”
In this thought-provoking episode of the We Are For Good Podcast (Episode 673), hosts Jon McCoy and Becky Endicott are joined by nonprofit leader and transition strategist Naomi Hattaway. Together, they tackle the rarely discussed—yet inevitable—reality of staff transition in nonprofits. The conversation dives deep into why embracing and preparing for staff departures must become integral to organizational culture and health, especially amidst sector-wide uncertainty.

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Key Discussion Points & Insights

1. Normalizing Turnover (00:00–03:50)

• Naomi Hattaway opens by addressing the elephant in the room: people leave, and organizations must face this truth head-on, not as an emergency but as an ongoing reality.
  • “There are people on your team, as you're listening to this, that are planning to leave, and you're listening to this, and you might be planning to leave also.” — Naomi [00:00]
• Jon echoes a recent LinkedIn post, reinforcing that departure is especially prevalent at the start of a new year—when reflection leads to change.

2. Building Organizational Health Amidst Uncertainty (03:50–07:05)

• Naomi draws a parallel between dental and organizational health:
  • “If we don't tend to the reality that people leave, what does the rest of it even matter?” — Naomi [03:51]
• The social impact sector is experiencing scrutiny and instability—funding cuts, leadership churn, and pressure around equity—making transition readiness more essential than ever.

3. Practical Tools for Transition Readiness (07:05–12:32)

• Reserve Policies:
  • Health includes organizational reserves for navigating departures and succession planning—not just financial emergencies.
  • “Uncertainty to me always looks like change happens to us. Transition is what we can do about it.” — Naomi [05:26]
• Four Core Practices:
  1. Honest infrastructure (documentation)
  2. Endings literacy
  3. Financial truth-telling
  4. Distributed knowledge
• Documentation is Key:
  • Start with relationship maps, brain dumps, and memos of transition work.
  • “How would you ever want to leave your legacy or the mission of your organization without documenting what's in your head?” — Naomi [08:14]
• Scrappy, informal documentation (“scribbles on a napkin over nothing”) is often more useful than polished, unused playbooks.

4. Developing Endings Literacy: Embracing and Learning from Departures (12:32–16:07)

• Culturally, discomfort with endings means poor handling of staff departures, leading to avoidable disruption.
  • “Ending's literacy starts when you can name the thing.” — Naomi [12:52]
• Start with non-threatening discussions, like board term completions, to open up conversations about endings.
• Recognize that individuals' reactions to endings are deeply personal and influenced by individual histories.

5. Financial Truth-Telling & Planning for Transition Costs (16:07–19:23)

• Acknowledges the real costs—both hard (search, agency fees, stipends) and soft (lost capacity, morale)—of staff transitions.
• Encourages organizations to plan for these costs up-front, including interim roles and stipends for internal candidates.

6. Distributed Responsibility for Transition Readiness (19:23–20:21)

• Everyone, regardless of role, can contribute—through small acts like documentation or by initiating culture shifts in team meetings.
• Leaving a legacy doesn’t require formal authority: “You can leave crumbs, you can leave back-on-napkin stuff, you can leave a Loom video for your team.” — Naomi [19:23]

7. Tending to the Emotional Side: Grief, Loss, and Honoring What Came Before (20:21–25:39)

• Naomi shares her interim leadership experience—where often she arrives after a sudden departure or even a death.
• Key rhythms introduced:
  • Space for grief and the naming of loss
  • “Katie's Way”: Retaining and celebrating positive elements from departing leaders
  • Regular team “temp checks” to provide support tailored to different coping styles

8. Succession Planning: Beyond the Check-the-Box Approach (25:39–27:33)

• Succession planning must not remain a closed-door activity or a static document; it needs to be “taken off the shelf” and woven into day-to-day culture and conversations.

• Organizations where succession is lived (not just planned) foster more trust and resilience.

  • “Healthy systems don't stop people from leaving. They make it possible for people to leave well.” — Jon quoting Naomi [27:54]

9. Leaving Well: Individual, Organizational, and Community Impact (27:54–31:01)

• For individuals: Honest exit conversations, transparency about reasons for leaving, and authentic expression.
• For organizations: Budgeting for transition, enabling offboarding conversations, and communicating with those served—removing shame from the process.

10. Human-Centered Change Under Stress (31:01–33:37)

• Naomi emphasizes dignity in departures, transparency, and small but meaningful gestures (like a DoorDash card during layoffs) as examples of care.

• She encourages extending support—EAP benefits, therapy, practical resources—to those going through transition.

  • “Truth tell with compassion. It beats false reassurance every time.” — Naomi [31:01]

11. Practical Homework & Closing Wisdom (34:13–39:27)

• Naomi’s “one good thing”:
  • Pick one key task in your current role and document it, as if someone needed to do it tomorrow.
  • Share this with a teammate to spread the culture of readiness.
  • “Your someday of someone leaving is today.” — Naomi [34:45]
• She urges organizations to include “strategic sunset scenario planning” on board agendas to reduce harm to staff and communities if closure becomes necessary.
• Colleen Hacker (sports psychologist) is quoted: “Do good now.”

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Notable Quotes

• “There are people on your team, as you're listening to this, that are planning to leave, and you're listening to this, and you might be planning to leave also.”
  — Naomi Hattaway [00:00]

• “If we don't tend to the reality that people leave, what does the rest of it even matter?”
  — Naomi Hattaway [03:51]

• “Uncertainty to me always looks like change happens to us. Transition is what we can do about it.”
  — Naomi Hattaway [05:26]

• “Ending's literacy starts when you can name the thing.”
  — Naomi Hattaway [12:52]

• “Healthy systems don't stop people from leaving. They make it possible for people to leave well.”
  — Jon quoting Naomi [27:54]

• “Your someday of someone leaving is today.”
  — Naomi Hattaway [34:45]

• “Do good now.”
  — Colleen Hacker, via Naomi Hattaway [36:51]

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Timestamps for Important Segments

| Timestamp | Segment Description | |-----------|---------------------------------------------| | 00:00 | Opening truth: People leave | | 03:51 | Dental health analogy & tending to turnover| | 07:30 | Four must-haves for healthy transitions | | 08:14 | Practical documentation advice | | 12:32 | Endings literacy and talking about loss | | 16:20 | Accounting for the real cost of departures | | 19:23 | Distributed responsibility & personal legacy| | 20:51 | Grief & honoring departures as interim | | 27:54 | "Leaving well" defined, mic drop moment | | 31:01 | Human-centered transition under stress | | 34:45 | "One good thing" homework assignment | | 36:51 | “Do good now.” - closing wisdom |

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Memorable Moments

• “Katie’s Way” — Memorializing the best of a departed leader while preparing the team for what’s next. [20:51]
• USB drawer story — Naomi finds an office with mysterious drives and keys, underscoring why documentation matters. [24:19]
• Practical takeaway: Document one function of your job today as if someone else needs it tomorrow. [34:45]

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Tone & Language

• The conversation is direct, candid, and deeply human, balancing practical advice with empathy and realism. Naomi and Jon model vulnerability, humor (“go to the dentist!”), and hope, making difficult topics accessible and actionable for mission-driven listeners.

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Resources & Connect

• Naomi Hattaway: naomihattaway.com
  • Transition archetype quiz for teams
  • Board development, transition coaching, interim leadership
  • LinkedIn: Naomi Hattaway
  • Instagram: @naomihattaway

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This episode is essential listening for nonprofit leaders and teams ready to stop fearing turnover—and start building cultures where every transition strengthens the mission and the people behind it.

Transcript

[Naomi Hadaway]

Foreign. I think that that's the first thing that we just have to really start to get really, really settled with is that people leave. There are people on your team, as you're listening to this, that are planning to leave and you're listening to this and you might be planning to leave also.

[John]

Hi, friends. Welcome back to our 12 shifts in 2026 series. And I don't know about y', all, but I love that these are a balance of not just new ideas to to try. They're like shifts that compound and lead us to a better way of moving through this world. And today's is so important and I'm going to call it out that it's not traditional. You're not seeing this on a lot of trends lists. So I just want to put a flag on the ground that we want to normalize that because today's shift is called Building for Health. We're talking about people and systems and how can we do that through uncertainty? We're already going to tell you that 2026 is going to bring more uncertainty and we just want to lean into that and have some open conversations. And honestly, I can't think of somebody more gifted in our community to come in, take our hand and walk us through today's discussion. I want to introduce you to Naomi Hadaway. She's probably not new to you if you've listened to the podcast. She's also been part of the Gather at the well series with Lindsey Fuller. She has really seen what it looks like to protect teams during change. And friend, don't you feel like we need that conversation? Naomi, so good to have you in this house. Thanks for being here.

[Naomi Hadaway]

I'm so glad to be here, John. And I love talking about the topics that don't end up on the trends lists because those are usually the ones that aren't as sexy or savvy or easy to talk about. So I'm glad to be having this conversation.

[John]

I want to just like lift. I saw our friend Christina Martin Kinney shared a post yesterday on LinkedIn that I thought was really timely because she said, hey, people are planning to leave your team right now. Like it's the new year. There's a lot of goodwill in the sector that people probably push through when it was not easy, when it was lots of toxic things happening. But now that the New Year's here, we should be planning that people are gonna make a change, you know, and I think I love that truth selling happening on that platform. And so I kind of wanna lead in asking you about what does that look like? What does building for health through uncertainty in this year mean to you? And why do you think it's so urgent we lean into it right now?

[Naomi Hadaway]

Well, first of all, I love that Christina posted that because it is so true. There are people on your team, as you're listening to this, that are planning to leave, and you're listening to this, and you might be planning to leave also. I think that that's, like, the first thing that we just start to get really, really settled with is that people leave. None of us are in our first jobs. And what I see a lot with leadership, too, and leadership, you know, it doesn't matter your title. We are all leaders in our space. But I think that we have this weird thing that we pretend that we're always going to stay forever at our current jobs. And I think what I've seen is kind of some trends is like, going into Covid. People said, I can't leave my team now. I have to stay. I can't leave them now in the middle of this. Then we kind of had that little. The downward hump of, like, not through Covid, but things are feeling a little bit better. And so then we had some resurgence of, oh, I could stay, this isn't bad, or that's when people left. There's these ups and downs. And I think you're right that 2026, I mean, everything feels on fire. Literally, 2025 brought fire to a lot of parts across the country. We are under the microscope in social impact, in nonprofit organizations, in ways that we, I don't think have ever had happened before around initiatives and how we prioritize diversity and equity and all of those things. And it also feels like funding is just has. There's a whole lot of organizations that are on, like, the brink of closure and transition. Yeah. And I think that one of the other things that I would encourage folks to think about is it all doesn't have to be a disaster. It feels that way. But health can either be looked at as, like, you only have this much time left, or it can be, what will you do at this time? I literally just went to the dentist earlier this week. I hate the dentist.

[John]

Oh, my gosh. I still hate the dentist.

[Naomi Hadaway]

Yes, the dentist. And she says to me with a little bit of, like, judgment, how long has it been since the last time you were at the dentist? And I was like, I don't know. And I really don't honestly know. And she's like, you realize that your mouth health and your gum Health and your teeth health impacts the rest of your body. And I'm like, I know, but. I know, but I was doing other things. I was working on my blood pressure and. And she said, if you don't tend to your health in your mouth, you are not able to tend to any of the rest of it. And so I think that some of the things we're talking about is kind of similar of like, if we don't tend to the reality that people leave, what does the rest of it even matter? So it's messy and it's hard. And I also think that what's really hard for a lot of organizations is when you're actually tending to the community's needs and you're watching what happens when their infrastructure and all of that, the bottom falls out. We feel even more drawn to make sure that we are protecting them, but we have to also protect the infrastructure of our people and the reality that people leave.

[John]

Yeah. I mean, how empowering to think about this conversation. Not as reactive, but proactive and what kind of shift that that has? Because there is some ways that we can point to all the signs that we don't feel well or that we feel overwhelmed or that we feel so low. This is like getting to some of the root issues of, like, things that we maybe are in. Under our control that we can lean into. Probably not everything. But I'd love for your take on that, too, of like, naming the things that we can control in this new year.

[Naomi Hadaway]

Yeah, well, and I. So a lot of times when I'm working with clients, I will say to them, I'll ask them, what's their reserve policy for on a financial level, And I usually get kind of a like, ugh, face of we don't.

[John]

Did you go to the dentist Question?

[Naomi Hadaway]

Like, it's a, you know, and it's not said with any judgment, but it's just. It's to try and normalize the fact that you might feel like your funding is at risk this year. And also you should navigate what it looks like to hold reserves or at least to start somewhere. When you have a reserves account started, that means you also have to have a reserves policy, which means you have to go to your board. And there's just some things that feel really scary. But when you can start with, say, a reserve account, and you can start with, say, a reserves policy with your board, then that opens up some more, I think, awareness to be able to say, okay, what would we use these reserves for? And then you start to get to the real meat of it, which is, could we use part of our reserves to protect our organization from the reality that people leave? And what does that look like? Does it look like we can pay for succession planning? Does that look like being able to navigate having a professional interim come in? Does it look like having a stipend for an acting executive director should someone internal step into that role? So I think uncertainty to me always looks like change happens to us. Transition is what we can do about it. And we won't have control over everything. But there are certain small pieces. And Health for nonprofits in my book also looks like having a reserves policy. So that's one like really practical thing. It might sound scary to listening, but you can literally start with I don't know what banks require for a reserves account, but you can start small and you can let that be in a high yield savings account. You can have it be in a money market, something that helps to. To grow. But you have to first be willing to have the conversation with your teams about what does stability look like for your organization.

[John]

I love that. I mean these are the conversations to be had because it's going to open up so much more. I think of what that does even in like personal finance, if you have a safety net, if you have an emergency fund, like how that kind of shifts your mentality and like your peace, I would even say at a deeper level. So as you think of other ways, practical ways that organizations can kind of lean in to be healthy this year, what are some of the other must haves that you've got?

[Naomi Hadaway]

Yeah, so I've got four for you. I think that there's honesty. I'll start by naming the four and then we can dig into them. So one of them is really honest infrastructure. And that looks like documentation. So we'll talk a little bit about that. I think ending's literacy is so important. It's something we don't have.

[John]

Endings literacy. This is so good. I've never heard anybody talk about this.

[Naomi Hadaway]

Well, and I know we don't talk about it.

[John]

And it's.

[Naomi Hadaway]

It goes to our feelings about death and dying too. So if we don't have a culture in our country in the United States that that knows how to navigate death and dying, we sure as heck don't know how to do it in our workplace. Wow. We've talked about truth telling. So financial truth telling is a piece of it. And then distributed knowledge. Distributed knowledge. So let's. You want to just start at the top.

[John]

Let's do infrastructure. I've been there yeah.

[Naomi Hadaway]

Okay, so infrastructure looks like documentation in my book. And people always freak out a little bit about knowledge transfer and they're like, how would I ever possibly get everything that's in my head out onto paper? And my question back is, how would you ever want to leave your legacy or the mission of your organization without documenting what's in your head? You have to start somewhere and you can start super easily. So there's all sorts of tools now that aren't necessarily AI supported. So if you don't want to do AI, you don't have to. One way is to just record yourself doing an activity that will either help you prompt in your brain what's not clear, what steps did you miss, what needs to be documented and written down. If you do want to use AI or use a supported tool, they can turn it into SOPs or step by step documentation for you. There's also something I shared recently on social media, which is the three pieces that I think are really crucial. And you can literally start with a Google Doc, or If you're a SharePoint user, a Microsoft Word, whatever, you can start with three documents. So one is a relationship map. And just starting to. You could write it on an napkin for all I care. Who matters why? What's the contact info? What's the context? What are some external blocks? Those kind of things. Also a brain dump. Oh yeah, go ahead.

[John]

I just, I feel like you're illuminating something to me because I'm a branding wired human, so I always love everything to look neat and nice and all this, but this is scrappy. This is like opening up loom and recording how to actually do the thing.

[Naomi Hadaway]

100% or sticky notes or notes app. Like it doesn't have to be perfect and beautiful. And I'll be truthful too. When you have a beautifully put together, perfect knowledge transfer set of documents, the person who you're handing it to will probably only use a small portion of it. So you're also not needing to get every single thing out. What you're doing is creating stability in them, knowing that there are processes or that there are things written down. And I think then when you think about brain dumps, it's like, where are the accounts held? Is it at this bank or is it at this bank? It's also trying to take away guesswork for the person that's coming in. They're already trying to learn a new role, a new culture, Anything too around key contacts and quirks. Like just this person loves when you just schedule the meeting and send the agenda 24 hours ahead of time. This person really likes to go to lunch and talk about it in person instead of doing a meeting. Like those are also really, really helpful things. So it doesn't also have to be at a really high level that feels stressful. It can be little small things. The other thing that I always recommend is kind of a memo of transition work. So thinking about like wins from the last year, what went really, really well and where did you get stuck? Another thing I recommend is go to your drafts folder and if you've got emails that you haven't sent, that's a.

[John]

Good thing that you should get out on paper.

[Naomi Hadaway]

It's so obvious, right? But. And if you're not a drafts person, what is sitting in the proverbial drafts folder? What have you wanted to get pushed through and haven't been able to? What's been tried but failed and then pending decisions is another really great thing to start documenting. And again, John, it doesn't have to be perfect. You could have a beautiful branded document that that goes through a flow, especially if you start introducing this to your teams. But it's better to just have scribbles on a napkin over nothing.

[John]

I. Some people may think that we're being very simplistic here. And I'm saying this stuff matters because even when our small team at we are for good, one of us steps out. This is the kind of stuff that not doesn't allow you to have a sick day, actually be sick and not be texted. I don't know how to get into this. I don't know where this landed. I think this is such good hygiene type things. It is opens up the door to everything else. So this is like core level. I love this so much.

[Naomi Hadaway]

It goes back to the dentist with the hygiene.

[John]

I hope that's your one good thing that you're just priming for us today.

[Naomi Hadaway]

It is go to the dentist. Call your dentist. The one thing I will say is that I have been an interim at organizations where say the executive director died. Now, there is not knowledge transfer. What I will say is that we figure it out. You know, we are scrappy, we are smart people. And so I don't want to insinuate that there has to be all of this pressure to do this in order to leave a good legacy. You don't have to, but it sure doesn't hurt to start thinking about this and we're not thinking about it. So anything that you do is one more layer deeper that you can get around that literacy.

[John]

You're kind of teeing me up to talk about literacy. I was geeked out when you said endings literacy. I just relate that our culture alone just kind of avoids the topic of it. I met someone in our community who is a death doula, and it was like, so awesome because her passion is walking through end of life with people, and it's something we don't even think about. So take us there of what your thoughts around that are.

[Naomi Hadaway]

Yeah, I love the idea of the death doulas because regardless of what you think happens to us after death, I have not met anyone who doesn't think that we die. Like, everyone's in agreement that that is the natural to our physical body's life, and yet we still don't talk about it. I've talked to so many people in different countries who they honor and prepare for and walk their community through death and dying. And in the US we just really suck at it. And I think the beautiful way to start with endings literacy is to talk about something that doesn't feel so close to home. So I often recommend that we start at the board level. And I'll say something like, you'll have board terms, right? And they'll say, yeah, we can serve three terms of two years each. And I'm like, cool. So then at the sixth year, someone leaves. Well, yeah, well, what's your process around that? And then everyone starts to get real fidgety and real antsy, and you're like, I mean, some people have left their term early anyway. Ending's literacy starts when you can name the thing. And so if it's more comfortable to start at a board level, that's great. The other way you can talk and start to bring in endings literacy to your work is talk about the last person who left. I'm not saying talk about them as a human. But what did we get right when Sally Jo left? What did we get wrong when Ernie left? What did we do well, as a team to come together? Because there's also the reality of the stairs, the people who stay behind, not stairs that you climb up or down. So if we aren't protecting the person who leaves in a way, and if we're not prioritizing the people who stay, there's so much opportunity there to start somewhere. And I think about all of those what do they call, like, the best place to work awards that everyone gets. I would love for one of the categories of how someone gets to be a best place to work and be around how they handle endings. Like, how amazing would it be to go to a new organization and know that they're going to treat you well on the way out and support your leaving. I. It just, it gives me goosebumps every time I think about that because it just be really. It'd be really amazing.

[John]

Can I just say to that, I will say we've interviewed so many people over the years and that is one thing that stuck out to me. When you hear a leader talk about their enthusiasm, their excitement for just the humans and what is going to happen in their next step. Like to me, that's like leadership and infinite game of like, you know, zooming out bigger to understand that we're all connected, we all need each other, we all have different seasons of life. I'm with you. I think that's not celebrated enough for sure. And so I love that you're putting a flag on that.

[Naomi Hadaway]

I think there's something else too around what's our own relationship to endings? We'll probably talk about this a little later in more depth, but we are not coming to the workplace with the same reaction to endings and transition that our neighbors are. And that's all based on our childhoods. It's based on how our relationships have ended. It's honestly based on how many times we've moved homes, how many cultural differences we've experienced, based on places we've lived or places we've worked. And so I think it's really important too, as you listen to this, to realize how someone reacts to an ending is much deeper than just they gave two weeks notice or it's much deeper than whether that was their manager and they're sad to see that or happy to see them leave. It goes into a much bigger piece of reality with our, our pasts.

[John]

Such a good call out and that's for so many elements, but specifically this one, I think it definitely is going to rear its head more. You've talked about financial truth telling a little bit. Is there something that you would lead us into beyond the reserves?

[Naomi Hadaway]

Yeah, just knowing that it costs money to have a transition in your workplace. I think that's the other thing that people are surprised about. They're like, oh, this costs money. It costs money to run a search. Even if you have a great HR team, it costs them capacity to shift away from their day to day and to go into launching a search. If you bring in an executive search firm, my gosh, those are real expensive. If you have not budgeted for, like I said before, stipends for acting folks that step into roles. I really, really strongly encourage folks to consider stipends for internal candidates if you have not budgeted for. If you need an interim as a professional. And a lot of folks will say, well, if we need an interim, it's because we're not paying an executive director. Right? Like if someone's left and we bring in an interim, that makes sense. But it's not equal. Because if you've used an agency, there's usually more costs. Maybe you're paying out a severance or a leaving package. So it's not equal for equal. So you need to plan accordingly. You also need to plan for what happens if there's any delays in the search and whether you need to bring in additional folks to help keep the organization floating. So I just think it's really important to think about it's financial and the practical work of knowledge transfer that needs to be prioritized.

[John]

I think where you're, you know, leading this conversation that's so good is that it's not a single point of failure. Like, this is a team, we are a team. We have to think about the impacts that are just bigger than one human. And that's part of how all this is shared responsibility, you know. So is there something you'd add to that?

[Naomi Hadaway]

Yeah, I think it's really easy to point our fingers to someone else and say, well, I think they're supposed to be the ones dealing with this. If you're a board member listening, you can bring it up to your board and I promise you it's going to feel so much better if you bring it up as a sustainability, long term resiliency thing instead of the ED freaking out saying, why are we talking about this? If you're not a board member and you're in an executive leadership team role, you can bring it up vice versa, you can bring it up to the board and say, I'm not going anywhere yet. But I think it's important that we talk about this. If you're not in a decision making role and your frontline staff or outreach workers or what have you, you can start by documenting your knowledge without even having anyone that makes a decision or controls a budget line item. And so I think it's really important to just think, what can I do to make our organization healthier when it comes to transitions and leaving and we can each take a small part. It doesn't have to be always, you know, it's someone else's job. There's of course ways that you can then make the circle bigger. You know, if you're not a decision maker you can bring it to your, your team during the team meeting and say, you know, I've been really led to start documenting. I would love if y' all would want to help or take a look at what I documented. What am I missing that can slowly just start to feed by naming it so much beautiful or culture shift.

[John]

Okay. That is like a hack for becoming the most valuable human, you know, in your work. So I think a lot of times we hear people will say, you know, I can't make this change of the organization. I don't have the decision power. Anybody can do this. This is all for the benefit of the organization. And it gives you momentum. It gives something that's replicable. And I agree. You model it and people want to do that, you know, or see the power of it.

[Naomi Hadaway]

The other thing too. And I'll own this a little bit. So I wrote a book about leaving. Well, and it's this wonderful little air, an airport book, because you could read it on the airplane. But what I missed in that was I directed it towards a decision maker. And so I got feedback saying, like, okay, but I don't control the budget. Like, I can't save money for the things that you're recommending. What do I do? And so I heard that and realized, like, oh my gosh, like there, there are ways for someone who's not in a decision making role to have impact. It also then comes back to legacy. I've detached myself from my reputation because I don't have a whole lot to say about what other people think about me. But I do feel strongly about legacy. And if I can do my part to leave an organization better than I found it, to me, that is something that doesn't need to have a leader stamp of approval. You can leave crumbs, you can leave back on napkin stuff, you can leave a document, you can leave a loom video for your team. And that goes a lot towards your legacy and impact that you had at that organization.

[John]

All right, you're passing chills over here. That's what this is about. This is so good, my friend. The way you think about this, the way that it connects to something bigger. Like, this is the heart of why we're doing this. I know we kind of let in this episode talking about uncertainty, and I loved your framing for it. You've also navigated so many interim leadership roles where you're dropping into different organizations. What's a rhythm that you've noticed that you can introduce early that changes how people walk into and experience uncertainty?

[Naomi Hadaway]

Yeah. So from my perspective, often I am brought in when someone literally has died or has resigned or has been terminated. So there's a lot of interim leaders that will support sabbaticals when the person's coming back. I really prioritize someone has gone and it has been pretty sudden. And so one of the first kind of rhythms that I introduce is holding space for grief and holding space to talk about loss. And that is usually something that people are so uncomfortable with because it's not something that's normal in our workplaces. It's easier when I can say Katie died. And so let's talk about Katie. Let's talk about what we want to have Katie's legacy still live. And here's a small example that someone could use. We did at an organization, her name literally was Katie. And. And we had everyone kind of elevate the top two or three things that they loved about how Katie led that organization. And then we all voted. What are the two things that we want to call Katie's way that we keep. What are the things then that we need to hold open for the next leader after I left to do on their own to bring in and build their way. And that was an awesome way for them to honor Katie, keep some stability in how things had been done, but also let them start to realize it can't be Katie's way or the highway going forward. It has to be whoever's coming next. And so that's one rhythm I would recommend. I also recommend team checks, like where there's just. Or temp checks, I'm sorry, where you can just hold space to be like, how are we doing this week? And I know that sounds super obvious and super basic, but talking about how each team member approaches this situation, some people might not seem bothered or impacted by it. It doesn't mean they aren't. It just means they handle it differently. Some might be visibly and like reacting to it. That doesn't mean they're shattered. You know, like just being able to name the fact that we all approach things differently is really important too, as a rhythm.

[John]

Hey, friend. Taking a quick pause to share about some of our amazing partners. Meet GiveButter, RKD Group Whiteboard and so on. These aren't just amazing partners for we are for good. They're value aligned allies who are fueling and growing the impact uprising. And so of course we want you to know them. So if you are looking for a new CRM or a fundraising or marketing partner, maybe an impact strategist or a creative team, we'd love to make a warm introduction for you to one of our trusted partners. They happen to be powered by amazing humans, too. You can check them [e-mail] Rex that's weareforgood.com RECS. I am obsessed with how you navigated that. Like, I just. It feels so aligned that you're honoring someone's legacy. You're carrying it forward. You're helping shepherd a team forward. Like, what a beautiful example. And I'm also thinking about your life. If you get a phone call and you just drop what you're doing to drop into these teams, what a gift that you could be of that mindset to drop in and shepherd teams. So I just love the way you kind of relate to that.

[Naomi Hadaway]

Yeah. Using that same example, what. What I dropped into was an office that had one drawer full of. What are they called when you have. They're old school. Like, we don't use them anymore. But like, where there's data, disk, disk.

[John]

Oh, like a floppy disk, USB drives. USB disk. I was like 20 years before that.

[Naomi Hadaway]

Okay, yeah. So I literally opened one drawer and there was USB drives. And I'm like, okay, we'll figure this out. Another drawer was full of keys. And so that has been such a driver for me of do not have a drawer full of USB drives and a drawer full of unidentified keys. We figured it out. We walked through and took keys to each door. We figured it out. But it doesn't have to be that way. And so there's a lot of examples from my time as interim leader that really fueled the work that I do. And there's also a way, I think, that each organization can choose based on your culture and based on your values to really name how your organization wants to navigate through loss and uncertainty and transition. Go through your values list, go through the competencies that you hire for. What pieces can you pull from that to say, okay, if we value stability, what does that mean then? When we have uncertainty, bring those up in your meetings, bring them up in your one on ones. I'm also a huge fan of stay interviews, talking to your team when it's not rocky, when it's not chaos about what are your plans? We know you're going to leave someday. You know, maybe that's tomorrow, maybe that's in six months. What do we need to give you between now and then? What professional development could we offer to support you? What are you not getting done because you're over capacity? Like, there's just so many. I could talk about this all day long, John.

[John]

I mean, because you're a gift, like understanding it and especially like navigating the human alongside it. What about those orgs that you know, do have more of a plan? I mean, succession planning is talked about a lot and some organizations are more ahead of that. How does that change things when an organization's really set up for the transition? And what's the vibe difference? I guess.

[Naomi Hadaway]

Yeah, I think that there is when an organization's set up for transition, whether it's known or not known. So that's. There's two different spheres. An org could be set up for transition because they've done it at an executive level behind closed doors and that's. And there's also the way that they could be set up because they've brought the whole team along in the latter. There's trust. And when there's trust, you kind of have this feeling of like superhero, like you can weather any storm because you know who you're walking through it with. I think that also the chaos and scramble of uncertainty feels less of a disruption to the work. It feels like something you've already navigated yourself through because you've prepped for transition. I think it's really important to think about any kind of planning has to be taken off the shelf. It can't be a dusty binder. I mean, we joke about strat plans, strategic plans being done, and then they're putting a binder on a shelf. And it's the same with succession planning. So I guess I would encourage folks, even if you think you've planned, how are you bringing it into the day to day? How are you bringing it into your team culture, your meetings, your conversations? And how are you, I don't like the word empowerment, but how are you encouraging your teams to model it and bring it into their day to day as well? And not just have it be at a hierarchical organizational level. It has to be part of your culture. It cannot be a one and done. So most people listening, if they're like, yeah, we've got that covered, what that means is you've just checked a box and you've done, done the, the needful, so to speak, you have to pull it into your day to day and make it part of your lexicon. And how you talk about your organization.

[John]

Isn'T just life funny. Like that's just a good, It's a true hack for everything in life. When we're checking the box, it's never, it's not usually connected, you know, at a deeper level. So can I quote you to you. Is that okay? Because you've said something that we think is just so incredible that healthy systems don't stop people from leaving. They make it possible for people to leave well.

[Naomi Hadaway]

Yeah.

[John]

Mic drop, TED Talk moment. What does leaving well look like for you? For you and kind of in the work that you've done, where have you ended up with that?

[Naomi Hadaway]

Yeah, I think it can take a bunch of different paths. For people that are in systems or organizations where leaving is not discussed, I think that leaving well can look like saying your piece in a way that is authentic to yourself. So an example of my, my first leaving well experience was I had been named the deputy director and successor to the executive director. It came very clear, very quickly that she had no intention of leaving. That was in 2019. And she's still there, which is great. She's an incredible leader. But it's. It was an example of how it was just a plan. It was just to check the box. So when I left later, I shared with a couple of board members my concern about the organizational resiliency and stability because they weren't going beyond just having the succession plan done and checkboxed. So for me, my leaving well version was to be able to speak truth to what I was seeing and why I was leaving. I think that in real life, it also looks like we've talked about having that organizational budget that supports leaving, whatever that needs to look like. I think leaving well also looks like not having to perform your exit. And so if it's hard, if it's sad, if it's messy, if it's fraught with all sorts of feelings, being able to have space to speak openly with your team, like, can you imagine being able to say, I'm giving my two weeks notice and I'd like to have an honest conversation with my team about what this means for me and what this means for you, but we don't allow that. We shuffle everyone through HR and through this system and this process that doesn't actually serve our humanity. I think leaving well also allows us to be honest with the communities that we serve about the why, especially if you've got a lot of turnover, that's sticky. And I know people are like, we're not going to talk out loud about publicly about our retention issues. Nonprofit transitions are not Talked about on LinkedIn. Like, no one's raising their hand and being like, it's Thursday. And I'm happy to share that we have really terrible. You're right.

[John]

But it's celebrated when you get to the new spot.

[Naomi Hadaway]

Right. And so I think that's the other piece of leaving well is being a model. If you have a great onboarding, offboarding an exit plan for your board, talk about it with your peers so that they can see the modeled behavior. If you, when you have layoffs, if you create a dashboard or a spreadsheet to say, here's all the people we had to lay off because of financial situations, but here's how amazing they are. Here's their contact information. Please reach out to them. Share that with other peer colleagues. Share that with your funders, Let them know how you're navigating transitions. Because this all happens in a vacuum and it happens quietly because we're, we have so much shame around how we navigate endings and transitions. That's another thing we could talk about all day long. But I'll stop there.

[John]

Well, I know you and Lindsay also have had such good, rich conversation of just like human centered policies. And so I'm wondering from your standpoint, what does human centered change look like when stress is already high? And I'm assuming, if you're listening, it's probably high right now between some of the factors we've talked about, but certainly the social, economic, political climate we're in as well.

[Naomi Hadaway]

I don't think that there's any way to make leaving easier or cleaner or less painful. I think that I would be fooling myself and everyone that I talk with if I tried to say, like, there's this magic wand that you could wave and have it all go really beautifully. But I think there are some ways that you can protect things and you can insert blank mission, reputation, values, humanity, policies like hr, honestly, is often there to protect the organization and not the people. And I think when you truth tell with compassion, it beats false reassurance every time. So as much as you can push yourselves to just speak openly and transparently about what's going on, that's one thing. I think protecting people's dignity during cuts is another thing. If it's a layoff, a redundancy, those kind of things that are outside of the control of the organization. This sounds so simple, and it might sound a little tacky. You know, if you bring someone into your office and you're like, we're having layoffs. And also here's a doordash card. But if you provide something that just says, we know this is hard and we don't want you to also have to think about what's on the dinner table tonight with the doordash card or something, that helps support their family in that, whether it means making sure that you extend your EAP benefits or making sure that you look at your COBRA policy for making sure that health insurance is still provided during layoffs. I think there are small things that you can do that helps a little bit with human centered work. I also think that it's so important to remind folks not just about, for example, eap, but have a list of maybe trusted therapists or bodywork professionals in your community that you can say like, hey, here's some, some actual practical ways that you might want to work yourself through this massive change. Any, any little thing that can go beyond just lip service, I think is helpful.

[John]

I think just thinking bigger about it is a powerful unlock because so many of these systems and processes to your point are not designed for the human. And when you zoom out and you think about the human and how you could support them and it not just be the whammy showing the humanity in that, I think that is beautiful care. It goes back to the values that are on your wall that you say that you're subscribed to. And it opens up a bigger, better conversation of just because we've always done it one way does not make it.

[Naomi Hadaway]

100%, you know, 100%. And there's always levels of elevation too. If, if the one question you asked yourself after listening to this is how did it go the last time someone left at our organization? That opens up everything that you need to know to then go forward. If it went great, what's one level greater that you could be the next time? If it went poorly, then you've got low hanging fruit, my friend, to find.

[John]

Yeah.

[Naomi Hadaway]

To start. And no one that's listening to this can say, well, we haven't had anyone leave recently because that's just the reality that people leave. And so it's a great kind of starter of getting your brain kind of primed to think like how could we do this better? How could we take this one level up? The other thing I will say is there are people in your organization who are primed to talk about endings and loss and death and dying and leaving. Find those people, maybe have an ad hoc committee that you pull together, people that just are excited about talking about this, that can help your organization kind of grow your sea legs, so to speak, in this topic.

[John]

I mean, it all connects just as you had talked about finding that interim leadership, sometimes internally thinking differently, like not always just going back to the same playbook that was maybe passed down. So friend, okay, we've Already planned at least three spinoff podcasts about this, which is great. I'm still holding out for your hot takes, but I want to, like, lead us in with today's theme with this shift, this idea that we're really centering and building for health this year. How would you round this out with a one good thing. I don't know if you want to give us some homework or if you want to just give us some mantra. What you got for me?

[Naomi Hadaway]

I think that what I would say for the. For a one good thing homework side of things is go back to what we talked about earlier. Take one function of your role today. And I'm literally saying, when you're listening to this and after this episode's over, stop listening to podcasts and then go to your document, your notebook, your whatever, and pick one function of your work and start to just line out what someone else would need to know if they were given that role to do the next day. If I win the lottery tomorrow and I find a beautiful island that I want to go to, how do I want to leave my work to someone else? The bonus of that homework is if you then share that with someone else and say, hey, I heard this podcast. You should listen to it, and then let's do it together. I think that just starts a beautiful ripple, and it's not too hard. I'm not a huge fan of, like, here's five steps that you need to take, and they're all going to take you forever. And you can start very simply with one document. I think the other thing that I would say as one good thing is your someday of someone leaving is today. Prioritizing in the future. Thinking about leaving and transitions is not going to serve you well. I recommend that people put things like strategic sunset scenario planning on your board agendas, and everyone freaks out about that. But it doesn't mean that you're planning to close. It just means that you have the wherewithal and the authenticity of knowing that these things happen to organizations. We're seeing organizations close at record speed right now, and sunsetting and closing usually harms the community in addition to the staff and the mission. And so thinking about that ahead of time and planning as much as you can around what does it look like if we end or when we end can really help you make honest decisions about today and about your present. There is a quote that I heard from a sports psychologist, and she said, do good now. Like, don't think about the next game or the next big the Olympics. What can you do today that is good for your organization, good for the community you serve, and good for your team. And I think starting to document your what lives in your brain is a one good thing that you could start.

[John]

Now, this conversation, I hope everyone listening just feels like truly like the exhale. Like, you know, we are walking in probably to a lot of uncertainty, but this is the kind of stuff that gives us grounding. It gives us roots to hold onto when things are going to come at us. And you've given so much practical takeaway. I just love the way you walk through this world. I'm so grateful this community connected us and how all the ways that you've poured in. How can folks listening connect with you if they don't know you already? And tell us a little bit about the work that you do so people can hire you and lean into the work that you're doing. All the things.

[Naomi Hadaway]

So first I have to go back because I normally don't like quoting people without attribution. And I had a blank. Her name is Colleen Hacker, and she is a sports psychologist that supported the women's soccer team to their win in the Olympics. I don't remember which year, but she's incredible. She's not on social media, so you'll have to do a little digging, but she is a brilliant soul. My website is naomihadaway.com you can also take a quiz which helps you understand your transition archetype, which I think then leads to really beautiful teamwork. So that's Naomi Hataway. What I recommend is that people have their teams take this. It's like nine silly questions, and you end up with one of four archetypes. And then just like you would say with CliftonStrengths, put that on a grid. Understand where your team lives in terms of their reaction to transitions and endings. And the work that I do is proactive. I do board development work around leaving. I also support teams to get more comfortable with transition leaving and loss. And then I do reactive work, which is the interim work of, okay, you have a leadership gap. You need someone to come in. I do that for six to nine months at a time. And then we're also launching an online community around professional development for the middle managers and people who don't have decision making. All right.

[John]

Community is everything. Yes.

[Naomi Hadaway]

Work on that.

[John]

Oh, my word. Naomi, I mean, thank you. Thank you for the clarity you bring, the calm in your voice, the words that you're saying over us. It's just been such a rich conversation. And we'll link up that link in our show Notes. Is there a place to follow you? Best online? Is LinkedIn the best place to connect?

[Naomi Hadaway]

LinkedIn is great. I'm also on Instagram. Aomihadaway. I'm struggling with Instagram, but I'm trying my hardest. My executive assistant's like, you need to be there. You need to share the word and the work and the impact. So I'm like, okay, fine. And I just want to thank you, John, Becky, and Julie for the work that you put out into the world and the impact one conversation at a time. I've learned so much from your other guests and from your willingness to allow folks to bring truth and new ideas and ways to shore up our organizational health. So thank you for having me.

[John]

Thank you, friend. So good to see you.