EO30 Onboarding Meets Offboarding: Why the End Starts at the Beginning

Join Erin Rice from Process Street and Naomi Hattaway, a workplace transition expert and creator of the Leaving Well framework, as they explore how thoughtful onboarding and offboarding shape a stronger, more human-centered company culture.

In this episode, Naomi shares how intentional practices, like inclusive job postings, onboarding reading guides, and stay interviews, set the tone for an employee’s journey from day one to their final farewell. She unpacks the emotional and cultural weight of workplace transitions, highlighting the impact of small gestures, transparent communication, and personalized experiences.

Learn how to build a seamless transition strategy that boosts retention, nurtures employee connection, and turns former team members into lasting brand advocates.

Transcript

Erin Rice

Welcome to Process Street's employee onboarding podcast where we are unpacking great onboarding ideas and best practices from the world's top HR practitioners and thought leaders. At Process Street, that starts with our mission to make work fun, fast, and thoughtless for teams everywhere. My name is Erin Rice and I'm the people and operations specialist here at Process Street.

Today I'm joined by Naomi Hattaway. Naomi is an expert to organizations who are ready to do better when it comes to navigating workplace transitions. Through her Leaving Well framework, she offers clarity, tools, and practices that stick and guidance that supports a diverse client portfolio. Her deep understanding of professional health spans multiple industries and combines strategic visioning, organizational development, and community care.

She delivers a deep commitment to equitable practices, a willingness to have tough conversations, strong project management and facilitation skills, and compassion and generosity to every interaction and facet of her work. As a speaker, she delivered keynotes at Union Pacific's Law and Risk Conference and the Families in Global Transition Conference in both Washington, DC and the Netherlands.

She has spoken at conferences and presented workshops as well as speaking engagements with lots of different organizations, including NERSC, Nonprofit Association of the Midlands, Creative Mornings Omaha, and Creative Mornings Field Trips. After living across the US, her family moved to India, where they lived for three years, and she learned to thrive in the midst of chaos. Following one year in Singapore, they moved back to the US and have trapeze their way through Florida, Virginia, Ohio, Nebraska, Florida again, and currently building her dream home in the woods outside of Atlanta, Georgia. Naomi's love languages are accountability, tattoos, and really good playlists. Thanks for joining us today, Naomi. 

Naomi Hattaway

Thanks for having me on, Erin. Every time I have something read my bio, I'm like, that's way too long. But thank you for reading it.

Erin

Well, I love it. And it gives such a really good 360 view of your experiences and why I'm so excited to talk to you today.

Naomi

Yeah, I'm looking forward to it.

Erin
Before we dive in, I like to start with an icebreaker. And I love that you've lived in so many places. I'm similar. We have also trapeze our way through the United States, not so much outside, although if we got to move to Portugal, I think we would say yes. But I would love to hear if, you know, family, job, money, none of those were specific things that you had to consider. Where would you move back tomorrow? 

Naomi

That's a good question. So moving back where we have already lived before, I can't even answer that question with just one location. I loved when we lived in Singapore because we had access to so many amazing places and so much culture and so much rich, just things that we could do, activities, food, the religious practices, all the things that were there we loved. But I also really loved India, although that was chaotic. And I also know that a place that we lived in the past is not going to be the same if we moved back because of the place changing and also myself, you know, and our kids' ages and all that. So I don't know if I could answer that question, but probably somewhere in Asia. 

Erin

Yeah, that's awesome. I haven't had the opportunity to live outside the United States, but our space is Brooklyn, New York. I loved Brooklyn and we were there for a short time, but the impact was so dramatic. And it's probably like you, it's a little bit chaotic. It's everybody's on top of each other and you just build relationships so naturally, which was amazing. 

Naomi
I often think too that we did all of our moves with our kids being different ages, of course, but mostly when they were young and there's such an amazing built in community that happens when you have something like school. And so I often think about folks that have to navigate moves without children and how more important or maybe more challenging it is to find community. 

Erin

Yeah, I totally understand that. Well, what we really came here for employee onboarding. So I'd love for you to answer a little bit or define a little bit about what your thoughts on thoughtful onboarding is and how it's more than just a welcome checklist. 

Naomi

Yeah, I love that question. And I think so much about the workplace we've lost the thoughtfulness in it because we're busy, know, regardless of if you're a for-profit or a nonprofit or anywhere in between or social enterprise, we have work to do. And so the last thing that we think about often is onboarding. So when I think about doing it thoughtfully, it's really putting the human back into the process. So it starts for me with the job posting and the job description. And so thinking about ways that you can really be equitable in your job description. So that means looking for bias that might not be intentional around age or disability. And I think that there's ways that we can add inclusive language without making a big deal about it. One example that I always share is, how a lot of job descriptions say must be able to lift 50 pounds. Now, I mean, which jobs for the most part, I mean, there's obviously some that would need to have that, but a lot of people just put it in as a way to kind of cover their bases.

One example that you could choose instead to be more thoughtful would be that the person in this role regularly is asked to move equipment that weighs upwards of 50 pounds. That is a small, small shift, but it can go a long ways. The other thing that I think that we can do when it comes to thoughtful onboarding is when it comes to the actual hiring and interview process, I love to recommend that people use a hiring matrix. And part of that really is thoughtful because you know that the people that will be involved in the hiring are on the same.

So thinking about the competencies that you're looking for in a potential candidate, thinking about how you can weave in your organization's values into the hiring process. You can even ask a simple question to just say, one of our values, for example, is transparency. Can you tell me about a time that transparency won the day in the way that you navigated your work? Another example would be one of our values is compassion.

How does compassion show up for you in your daily work? That can just bring in a really beautiful level of thoughtfulness as well. I also think that thoughtful onboarding can start and this people tend to either agree or disagree with me on this. Sending those interview questions ahead of time, I think is really, really thoughtful. Some people don't like it because they think that it prepares people too much and that they will get canned answers. But I think it's actually to the contrary that you can end up with much more thoughtful answers if you give them the opportunity. There's also a quote that I love from Dr. Jaya John, and he says, fruitful organizations pay attention to your season of entry. They don't push you through a careless hiring and orientation process. They initiate you into the culture. And I think that's important because culture can start in so many different places, but if you're not thoughtful about your culture and how you're bringing someone into that intentionally during onboarding, I think it's a big miss.

Erin

Yeah, for sure. It's so interesting thinking about that branding, the thoughtful branding that goes into. I will share that I am transitioning out of my role at Process Street. And so I've been able to really reflect on how to transition this new person in and have been able to do some of the interviews preparing for the transition. And one of the feedbacks that we've gotten is job descriptions just really illustrate the vibe that they're expecting. And then my personality illustrates the vibe and the brand is all there. And it was really cool to sort of reflect on like the pride and what we've built since I've been here. Which brings me to my next sort of focus on how does thoughtful onboarding relate to thoughtful offboarding? 

Naomi

I love that. I love that we're drawing that connection because it's so important. And I think there's the phrase, know, think about, start with the end in mind. But we don't often correlate that with the workplace. I think that it's so important to realize and come to an agreement, everybody, that people leave. Like that is a reality. And so if we know that people leave and if we can say yes to that, then we can just make the time in between when they start and when they leave more intentional. I love the idea of having reading guides for people as they come and onboard.

That can be a simple one page document that just maybe it has a podcast that one of the team members has been on, or maybe it has articles that the organization has been referenced or talked about, or maybe it's just articles or a documentary that showcases the work that your organization does. That can go a long way in helping that person move from that interview process, like you said, Erin, where they're getting the vibe and they understand what the expectations are. That can help really get them really engaged.

I also love the idea and then I'll pivot to your question in just a minute. I also love the idea of swag. So you're wearing right now a teal turquoise Process Street shirt. I love the idea, especially for remote teams, send swag ahead of time once they've accepted the offer. Send a t-shirt, mug. It doesn't have to be something that's branded. It could be a book or something that just says, we're so excited that you're coming. The other thing that I think that comes into play when we think about thoughtful onboarding and offboarding is the idea of stay interviews. And I don't know if any of your other guests have talked about stay interviews, but often the exit interview is at the end of the person's time at the organization. Honestly, I feel like it's mostly a cover-your-rear end for the organization to see if there's anything that they should be aware of. But if you introduce stay interviews along the way, that's a really beautiful way for the manager and the employee to have a touch base.

It could be to talk about things that they thought were going to happen during that onboarding and what they thought the engagement was going to be about. And maybe there's a shift. Maybe they've got questions. Maybe they have capacity needs that they want to talk about. The other thing that's really brave in a stay interview is to ask your employee, are you happy? Are you looking? Is there anything I can do to make your experience here more fruitful or more thoughtful? When stay interviews are conducted in a really meaningful way, oftentimes people will raise the idea of, don't know if this is the right spot for me or I have another opportunity or my family's gonna be moving. What that does is instead of having it be something that we can't talk about, the reality that people leave, instead it becomes something that they can manage and be more intentional about how to navigate the fact that someone might be leaving. The other thing about stay interviews too is it just normalizes for the organization that we know people leave and if we know people leave, then let's plan for it.

So don't know, that's probably a little bit long and windy. Maybe you have another follow-up question or I can just kind of dive into off-boarding. 

Erin

Well, I'm just so curious why workplaces are so nervous about talking about it. Like it's truth. It's the reality of the world that we live in.

Naomi

 It is. But I think, and so going back to living overseas and in different places beyond the US, other cultures have a much more, I think, healthy relationship to endings.

The example would be death. There's a lot of countries that navigate death as a norm where most people in the US don't want to talk about it. We act as though it's not going to happen. So you find that families don't plan. They don't have a state planning. They don't have their wills. They don't talk about what they want their burial service or their cremation to look like. And if we can't do that in the US, then I don't know how we are able to talk about endings in the workplace either.

There's a lot more positive ending related composting and sun setting and all those things in Europe as an example for the workplace. And we're at the very forefront of it in the US. And I'm excited to see it shifting a little bit, more people talking about this as a reality. But just think about how different it would feel in your workplace if like right off the bat, it was even stated, we know people leave and we know that eventually you're going to leave.

None of us are in our first jobs. I don't know. I don't know anyone that's still in their first job. So I'm hopeful that over the coming years, coming decade, that we'll get better about it in the United States. Yeah. Yeah, that's a good point. We're nervous about talking about a lot of stuff. We are. We are. And I think that there's from an individual level, if you're listening to this and you're not a decision maker, not a manager, but you're on an individual level,

You can also help perpetuate that by just talking to your manager. I know it feels scary, but saying, you know, I don't know how long my tenure here will be, but I would love to talk about what it looks like when we start to think about leaving in this workplace. What do you do? What's your policies? How does your HR team handle that? That could be a good step as well. Yeah, for sure. So how do we sort of set ourselves up for success in those moments? What would be your pieces of advice? Yeah.

I think some things start really early on and really simply. A lot of times when you go into a new organization during onboarding, there's some kind of a welcome event. There's some kind of a meet your new team members. But how often do we actually ask the new team member how they like to celebrate or be welcomed? Maybe they don't want a big party. Maybe they don't want anything that's a big deal. Maybe they would just like to have lunch, join the rest of the team. So I think little things like that can go a long way in just setting the stage for how we treat people in the workplace. When it comes to also onboarding, there's one other thing I just want to share. 

Often we create this really robust onboarding schedule, which is great to give the person expectations of what to anticipate, but we don't give any time for the, as far as the ones I've seen, we don't give enough time for someone to just absorb what they're learning. So my favorite onboarding schedules include maybe morning time and then afternoons that are free to sit, absorb what you've learned, ask questions, keep a notepad of what questions you might have and let that be a two-week process. think we also rough rush through onboarding and we expect everyone to be ready to go right away. 

In terms of leaving well and off boarding, I think the most important thing to just date and you might be having some of these experiences too, Erin, once you know that you're going, it makes it hard to stay. And so having pivot points along the way where maybe you could offer the person, know, once you've given your notice, if you find that that notice was too long, we are here to adjust that if need be. The last thing you want is a completely unengaged, checked out person who's also trying to balance whatever's next for them. And so just keeping lines of communication open is really, really huge. 

The other thing I love doing, that's another simple example, is plan to have the person's last day be supportive and what they need and not chaotic, running around, butting up all the last things that need to be done. A really thoughtful idea is to give someone a DoorDash gift card and just say dinner's on us. We know you've got a lot going on as you depart. So there's just simple ways I think that we can do it. Now, I mean, we could get into knowledge transfer and cross training and all of that jazz, but at end of the day, it really matters how we treat people. 

Erin

Yeah, for sure. It's funny, I think because I've had leadership roles previously. As I was moving through and sort of building out my department over the last three years, I've done everything with the mind that this needs to not live in someone's brain. I mean, we're Process Street. It's a process management platform. It's supposed to function without intellectual property being mind shared. And so looking back and reflecting on that has been, made me really proud of past Erin because there isn't that much that has to happen. It's like in Process Street changing out my task assignments to me in my department now instead of just me. And it's a few things here and there that got missed in the shuffle, but there's so much of that knowledge that's all documented in these workflows and in these SOPs that I'm really grateful.

Naomi

I love that. And I love that you said like past like today, Erin is so grateful to past Erin. That's so important. Your eventual departure from the organization. Sometimes you also can hand a project over well ahead of you leaving and maybe that other person is better at it than you are, or maybe they have more capacity. I think a lot when I work with organizations and we do succession planning, which is the proactive version of being ready for the reality that people leave, the thing that trips people up all the time is realizing that they do more than they thought they did when they start to like write it all out or start to grab processes. And then they always say, I don't have a process for this. I don't know how to do it. And so there's, mean, you all have great things to offer with Process Street. There's also really simple ways that you can document the things that you do using something like Loom, where you just talk through what you do and turn it into an SOP. And so I think it's just important to be mindful of what the next person coming in will need from you. But it's never too early to start documenting what you do, how you do it, and where to find information that matches what you do. 

Erin

Yeah. It's funny, until I came across your profile and your company, I didn't really connect all of the thoughtfulness that was done in my onboarding and how it's impacting me now. But it definitely is. And everyone's going to be better because of it, including the legacy that I hopefully leave so that things are smooth.

Naomi

And I know that you are leaving one just because of the things that you're already doing. And that's another really important thing to talk about is the legacy, because that goes back to like the conversation about death and endings. Sometimes we are so afraid of not having a legacy that we don't look at what we are creating just intuitively and naturally. We are all leaving a legacy. And what that is, is really up to us.

It's also, there's a certain part of legacy that isn't up to us. It's what other people perceive of us. And so when you add in just little, small, thoughtful, simple things, that also trends towards the organization's legacy. And when you have people leaving, which is a reality, the best thing is when they can talk fondly about your organization in the future versus a really tenuous off-boarding process or when you haven't onboarded well or off-boarded well and people leave upset that doesn't lend itself well to your organization's legacy either. 

Erin

Yeah, for sure. I love that you brought that up. One of my best experiences was taking on a leadership role that I was very nervous because I had big shoes to fill. And on my very first day, when I opened my drawer to get a pin, there was a note from the previous director that had hired me and said, you can do this. And in it was basically like, you're going to be amazing. Like start this day on the right note and here it is. And like, I would go back and read that on any day that I was feeling disengaged or frustrated or anything. That is so, cool. And that legacy still lives with me today. Like I still think about that. And I've been thinking about that because, you know, I'm going on a new adventure. And so it's just so much. 

Naomi

Yeah, that's a really cool thing. And I think that reminds me, too, going back to the ask the people how they want to be celebrated.

There's something beautiful called, I don't know what it's actually called, but like a Post-It Waterfall, where if you're in person with your team, having everyone stick a Post-It note with just a word of advice on their first day and put it on their desk. If you're remote, that could just be done through whatever your chat mechanism is or through an email. Yeah, those little things really do add up, don't they? They really matter. They do. And I don't think that when we are making those intentional decisions that we realize the long lasting effect of those moments that carries on with that human long past this job, that job, the next job. You're kind of shaping somebody in a way. Yeah, you are. You're shaping the people and you're also continuing to support the culture. And I think we think often about culture as it's like a one and done or a set it and forget it. But every time you bring someone in, that energy and what they bring to the organization shifts culture again. And so it really is up to each of us to do our part to either impact it for the good or impact it for the negative. Yeah, which kind of makes onboarding and offboarding the most important thing that you could do in an HR role. It is. And I think that we make it harder than it needs to be. 

Also, the other thing that I love when organizations do is just admit that we also don't know everything. And so it's beautiful to think about HR professionals, HR teams, hiring managers, just being honest and saying, we actually don't know what your onboarding is gonna look like because maybe it's a new role or maybe there's a huge catalytic shift in the organization and the role is changing. So I think it's beautiful and very human centered to also just say, there's a lot we know about this and there's a lot we don't and we're gonna invite you into the process and ask us questions along the way. I think that's one of the most healthy cultures that I see in organizations are ones where it's okay to ask questions and one where it's okay to say we don't know. 

Erin

Yeah. Have you ever seen something that was kind of like a pivotal moment or a specific moment in the onboarding that directly correlated with like an offboarding that you can speak to? 

Naomi

That's a good question. I think the thing that comes to mind is around naming norms. So letting someone know ahead of time, you know, maybe it's maybe it's in onboarding materials, maybe it's on their first day, maybe it's in their first couple of weeks. But naming norms around how we decide is a huge one that impacts all the way through the life of an employee and can also help with offboarding. When we talk about transparently how we decide, maybe it's that the onboarding person doesn't have any role to play in decision making, and that's for other people on the team. Maybe feedback is requested from that person's role. It's important to let people know how their feedback will be used, how we can close a loop. Ultimately, I always recommend people create a decision-making matrix, letting people know where their role fits into the organization's decisions, not just the org chart and the hierarchy of who reports to who, but can the role that I'm coming into, can it actually influence change or am I here to be more of a cog in the wheel? That helps with, I think, employee satisfaction throughout the process, then it also helps them be more in control of what is theirs to control during off-boarding and that cross-training and knowledge transfer. So that's probably the thing that comes to mind right away, is naming things like that. It could also be as simple as naming meeting culture. When we have meetings, do you expect that people come with an agenda? Do you expect that people have an option to attend a meeting, whether they feel like they can contribute to the agenda or not?

Those kind of things also really contribute to employee satisfaction, just naming the reality of things. And then I think the other thing that's really beautiful that has a correlation between the two is what can that person offer in terms of recommended changes or speaking up and saying, this doesn't feel right or this might not be a mission value aligned. I think that can really help. The other thing I love about stay interviews, I forgot to say this earlier, is when you can also have an exercise and this works great as a team, have them bring their resumes. And a lot of people go, my gosh, why would we ask our employees to bring resumes to a meeting? But the beautiful thing about it is then you ask people to update their resume based on projects they recently completed or new skill sets or new training that they just had. Oftentimes we don't update our resumes until we need it in a pinch. And then we're not thinking clearly about all the wonderful things we've done.

When I've walked organizations through that, what the people have always said to their managers is, this was so thoughtful and this was so cool to think about like in the middle of my working here, you're encouraging me to make sure that everything that I'm learning here and everything that my skills that I'm bringing are represented in my resume. So there's just some, you know, interesting kind of quirky, funky things that can be considered. 

Erin

It's interesting that you bring that up because it makes me wonder why a hiring manager wouldn't want to do that. Without doing any research, my guess is we don't want them to leave us, right? Like they're likely good employees. They probably do well above and beyond what they're doing. I mean, they're still employed, so they must be. But it also makes me think that I would be more inclined to stay. 

Naomi

No, I know. And there's studies that show like 79 % of people are thinking about leaving, maybe not actively, maybe they're not actively looking.

But if that high of a percentage of your staff are pondering leaving, having a sit down and having people update their resumes, especially as a really fun group activity is not gonna make them any more likely to leave than they already were. The other thing that really comes out of a group meeting like that where you update your resumes is you can, it's a great capacity gap analysis. So if someone's talking about like, I'm gonna add this project, I'm so excited. Someone else may not even know that they were working on that project. They may have things to add. It's also an opportunity to say like, where did projects not get done? And then, you know, having the ability to talk amongst each other about where they could fill in the gaps. It's just, I've never seen anything negative happen from having those. 

Erin

It reminds me of like our family discussions at the dinner table where we're like, what was your rose today? What was your thorn? And, you know, celebrating those roses. And one of the questions we ask sometimes is like, what was really hard today and how'd you get through it? And then hearing the kids like, support each other and saying like, wow, you went through that today. Like, that's so cool. I'm so glad you shared that with us. I can only imagine in an adult setting that people would then be like, that project was so cool. You should be so proud of that. I can't believe you didn't add that already, you know, and there's a lot of like really positive accolades that would be team building. 

Naomi

The other thing too, Erin, you were talking about legacy. I think the beautiful thing that we don't think enough about, but is also a truth is that what we instill in people while we are working alongside them, they take to their next role. So the ripple effect of small, little integrations and implementations of really thoughtful policies, individuals can also take those to their next workplaces. So even if we think really tightly about like, we don't want our people to leave, there's such a bigger, broader world impact, honestly. I mean, that sounds really big to say, but there is a big world impact when we implement these strategies with the people that are working with us now, knowing that when they leave, they'll take some of that culture and that thoughtfulness into their next places as well. Yeah, and that would make it all worth it, right? Absolutely. And when a person leaves, happy. Now, there’s all sorts of scenarios where someone leaves and maybe you can't control the happiness factor.

But when someone leaves in a more thoughtful way because of what the organization has done to support them, they will go almost recruit for you or at least they won't talk negatively about your organization. And it's to me, that seems worth it too. Yeah. And if they're client-based, they'll probably keep talking about the amazing product or the service or whatever that is offered. Absolutely. There's another beautiful thing that kind of correlates, but not necessarily, but it's around, you if there's a reduction in force or mass layoffs that an organization is going through. I've loved watching the HR departments who really don't have a say in that, be willing to create a directory of sorts of the folks that are leaving, putting it out publicly and saying, we just lost a bunch of really good people who are really talented. Here's their names, here's our contact information and the favorite thing that we loved that they did while they were here.

Erin 

That's a really powerful way to also support people leaving well. Also, those of us who are in recruitment love to go to those directories and be like, hey, you want to come work at our establishment? I think they should start with thinking about their own experiences. When was the last time that they had a really powerful onboarding experience? And what was it about it that made it powerful or thoughtful or kind or generous or whatever it is? Same with offboarding.

When was the last time that you left? You know, I'm thinking about speaking to the HR manager. They've left also. Going back to what our own experiences have been is a really great way to then plan proactively for the experiences of others. I think the other beautiful thing to think about when you are wanting to re-envision your onboarding and offboarding is just talk to your people. Talk to them and ask them the same question. What would make our onboarding really, really powerful? What could we shift? What could we change? And what should we leave behind? 

Erin

That's so true. Well, thank you, Naomi. This has been such a pleasure. I have enjoyed chatting with you today and I will be signing off for the last time. Thanks, Process Street.