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The WorkOps Podcast is your weekly conversation with HR leaders and People Ops practitioners doing the real work.
In every episode we dig into one story. A process that went sideways, a system that just didn't work, and what someone actually did about it. Packed with practical lessons you'll want to bring back to your team. Whether you're supporting 500 employees or 5,000, this is how the best People leaders are building for what comes next.
Chesney Woodall (00:00)
We had about 10 % of our workforce onshore with visas and we didn't know when they were expiring, who was in charge of you know, where were they in the green card process. It was all discombobulated and it didn't live within HR. It didn't even live within our legal department. It was managed by one guy.
who had done it from a legacy company and he left and it fell to me.
Jeet (00:23)
Hey everybody. Welcome to the WorkOps podcast. I am Jeet and today I'm joined by Chesney from Cedar Gate Every episode we dig into one story, a process that went sideways, a system that didn't work and what someone actually did about it. So Chesney, thank you so much for joining us today. Before we jump into things, can you tell us a little bit about yourself and how did you choose PeopleOps and HR?
Chesney Woodall (00:50)
Yeah, absolutely. Thanks so much for having me, Jeet. So like you mentioned, my name is Chesney Woodall and I got into HR kind of by accident. Like I think a lot of HR professionals do. When I went to college, I actually thought I wanted to be a psychologist or maybe a school counselor. So I knew I wanted to help people and I wanted to understand why people do what they do. But after a year or two realized I didn't want to get a master's degree, didn't want to be in school that long. So I pivoted and focused more on a business
career path and just happened to land in recruiting after graduation. So spent a couple years there and kind of thought to myself, recruiting is great, but I want to be on more than just.
more than just the first couple of weeks of an employee's hire, right? I wanna work with them throughout their entire life cycle. So I actually went and got a HR certification and got an opportunity to step into HR for a global company as a generalist and have worked my way up to a director level. So it's been a great ride so far.
Jeet (01:51)
quite a journey. ⁓ It's often that we actually hear that, hey, we've chosen to do HR because we want to help people and focus on some of the more human pieces of the role and help to enable them to do their best work. But then what we hear in reality is that often HR teams are kind of mired in that.
operational work and in the day-to-day repetitive admin that's kind of getting in the way of helping them do the work that they signed up to do. And that's what really we are here to talk about, which is a process or a system that was brought into a company and why it wasn't working and how you kind of flipped it around. So first of all, and you don't have to any names if you don't want to, but what kind of company was that ⁓ when
this process was implemented or system was implemented.
Chesney Woodall (02:41)
Yeah, so the particular process that I'm going to talk about was for a global healthcare data analytics company with about a thousand employees across the US and Asia. So we were in that, I would say like mid-size to large space and servicing, you know, our platform serviced over 60 million lives on it. So.
It's a large data company that I was stepping into and you would think all the processes are there and in place, but it was still a relatively new company in terms of how long it had been around. When I stepped in, the company had only been in place for about six years. And so we were still figuring everything out.
Jeet (03:06)
you
well.
Six years and a thousand people globally, that's quite the trajectory they've had. And what was the process or system that you want to talk about today?
Chesney Woodall (03:29)
Mm-hmm.
Yeah, so.
The biggest gap that we had was actually with our immigration process. Like I mentioned, we're a global company. Some of those people came from acquisitions and such. So how the company grew to that thousand employee footprint was through acquiring some other companies and building out a comprehensive platform. And so our benefits were pretty good. Our employee engagement was all right. Our onboarding was good, but immigration, which is a fundamental part of that business continuity and accomplishing the goals that we have with our clients.
was completely undocumented. There was no standardization. ⁓ We had about 10 % of our workforce onshore with visas and we didn't know when they were expiring, who was in charge of what, you know, where were they in the green card process. It was all discombobulated and it didn't live within HR. It didn't even live within our legal department. It was managed by one guy.
who had done it from a legacy company and he left and it fell to me.
Jeet (04:35)
no. no.
Isn't that funny? It's funny how long a company can go without a process just kind of being taken together and then not breaking until there's a single point of failure like a human being. And when they leave, then it completely breaks down. And interestingly, when these employee processes break down, it somehow invariably tends to come to HR.
Chesney Woodall (04:48)
Mm-hmm.
Jeet (04:59)
I'm not really sure why, but it always seems to land in HR's lap. Do you see this with other processes as well? Or was it just that specific one?
Chesney Woodall (05:06)
yeah. Yeah. mean, even payroll
is another good example, right? With most companies, payroll can either fall within its own department. It can live within finance or sometimes neither of them want to do it. And they say, HR can handle that. And that's even how we work, right? And we were only a three person HR team on the U S and then we had about four people in Nepal. So processes were different, but you know, I mean, there's certain
Jeet (05:20)
you
Chesney Woodall (05:32)
processes and procedures that no one else wants to own it. HR is going to own it.
Jeet (05:34)
Yeah.
Yeah, if it touches the employee then ⁓ it comes to HR. What I like about the change that's happened in HR now though is that it seems that other departments are more open to working together and they're just kind of seeing the employee experience as a whole. So HR is working much more closely with IT and with payroll. So hopefully things have improved, which we'll get to later on in the podcast. ⁓ But we'd love to dig into details now. So what was the process? What were the steps of the process? ⁓ And what was kind of failing in that process?
Chesney Woodall (06:07)
Yeah, absolutely. So we didn't have anything centralized. We didn't have any sort of system in place to track things. Everything was housed in emails, right? And we had an outside immigration council that we worked with. But again, everything was emails with a gentleman who left the company. So I couldn't even access like what documents were sent to him, where are things at? That ball dropped and I had to find a way to pick it up. So.
Really all we were doing was Excel spreadsheets, which as we know are not the most reliable, especially for change management, understanding why did this get changed? accidentally copy and paste into the wrong cell. It was just discombobulated and that was the best we could do at the time. And it left gaps, right? We didn't know who was responsible for what, were managers being responsive.
Jeet (06:40)
you
Chesney Woodall (06:58)
how close were we to someone's visa appointment? It was just kind of flying by the seat of our pants. And the biggest issue with that that kind of spearheaded us needing to put a process in place was we had about 25 cases going on simultaneously. And that in line with all of my other HR responsibilities was just too much to keep up with.
Jeet (07:19)
That is a lot. And you mentioned there's three of you and a few more folks in Nepal handling all HR processes, including employee relations, learning and development, recruitment, ⁓ HR, BP responsibility across a thousand people. No wonder things started to drop through the cracks. What was the most memorable reactions from employees and HR team members, like those 25 cases that you were managing at the same time or even members of your team?
you
Chesney Woodall (07:47)
Yeah, honestly, I would say there was a lot of fear from employees of, I going to lose my work authorization? Am I going to have to go back to my home country? When they come on shore, they uproot their life. They bring their family, they get their kids enrolled in school, they buy a house. And that uncertainty of, am I going to be able to stay in the United States?
caused a lot of anxiety, right? So from the employee perspective, that was really challenging. And then you also couple it in with executive leaders who are losing their minds over the potential of these people going back offshore. And the reason that's such a big deal for our company is we're in an industry where a lot of our data cannot be sent offshore. So there is a business necessity to have our top talent in the US.
Jeet (08:36)
Yeah, it's crazy, isn't it? We have all these kind of checklists and processes and spreadsheets and it's so easy to separate the humanity from a process, but really underpinning that process are real human emotions, fears, people changing jobs, changing countries, and their families to consider as well. So it's interesting. A lot of that is, I guess, extrapolated out when you just look at a spreadsheet on a Google or a Microsoft Excel sheet. But it's really great to
that that was the thing that kind of stuck out to you. It was the human emotions at the end of the day and the human work and the process was just something underneath it. And speaking of the process, when did you realize that something had to be done? Was it the 25 cases at that point?
Chesney Woodall (09:22)
Yeah, and that was about a year after immigration fell to me. So by that point, I had kind of accidentally become the immigration subject matter expert within our company, right? I sat there and Googled everything and was using Chad GPT to help me understand the different visa types, what the requirements are. ⁓ And so I had become the SME. And about a year in, I realized, okay, we're not doing things as efficiently as we can be.
nor do I think that we were doing things in the best interest of our company in terms of our image at like the embassies and stuff like that. I was like, man, there's more we can do. So it was about a year after immigration fell on my plate that I kind of went to my boss and I said, this is not sustainable. So what can we do to put a better platform in place?
Jeet (10:10)
I love that you're using chat GPT to inform that. That's great to hear. So you're already AI forward even at that point, is awesome to hear. And I guess what it meant was really that you weren't able to scale yourself or scale your time. Like after a year, it sounds like it's just so much that you wouldn't be able to do the other things that you might want to do. ⁓
Chesney Woodall (10:12)
yeah.
Mm-hmm.
Mm-hmm.
Jeet (10:33)
We're going to come into the attempted solution or the solution when you did speak with your boss and you wanted to change it. But I want to skip ahead a little bit and kind of find out when you did get that free time, when the solution was in place, what did you then redirect towards or what were you able to do with that? Or like, what was the impact that you saw from that?
Chesney Woodall (10:46)
Mm-hmm.
Yeah,
I mean, it opens you up for so much more strategic time, right? Like you mentioned at the beginning of the podcast, so many HR professionals are bogged down by repetitive administrative things, right? A solid chunk of your work week is either working on reports or updating profiles in your HRIS system or whatever it may be. And so when you can take something and automate it, you get to start thinking of...
Okay, hey, I know this certain team has had a lot of turnover lately. What can I do to work with the manager to make sure that they have the resources in place? Or, know, hey, I'm noticing that this other team, right, there's been some performance issues. Let me start proactively getting with the leaders on that team to talk about performance more than just the annual performance review cycle.
Let me start scheduling department overviews for our new hires and start thinking about that experience. So it just opens you up to really take a step back and look holistically at what's not necessarily broken anymore, but what can we still improve on, right? Because nothing's ever perfect. You can always make it better for that employee experience.
Jeet (11:59)
Yes, absolutely. I'm glad you said that. You're speaking like a product manager, which is music to my ears. It's just like, are the iterative improvements that we can make, which is great to hear. And a I guess, sidetrack on the questions. You mentioned ChatGPT. How are you using it these days? Or have you shifted to Claude? Or are you trying different models?
Chesney Woodall (12:14)
Mm-hmm.
Yeah. So I love AI. actually, my team and I named our Chat GPT Heather. So we always kind of make the joke of, yeah, Heather helped me with that. But yeah, mean, Chat GPT was the first AI that I used. And I would say I was using that for a couple of years. I've since started trying to use Co-Pilot a little bit more.
Jeet (12:22)
Hahaha
Chesney Woodall (12:37)
just because for our company, we've had some changes that I can tell you about a little bit later as well. But we've had some changes to our co-pilot is now the preferred system and it's encrypted within our company. So just from a business perspective, I'm using that more so, but I'm still using chat GPT for fun stuff on the side in my personal life as well, right? Creating graphics, helping me, you know.
Jeet (12:58)
Yeah.
Chesney Woodall (13:02)
do layouts in my house, helping me develop an organization list, whatever it may be. So people who aren't using AI yet, my gosh, it opens up a whole new world to you.
Jeet (13:12)
Yeah, it totally does. what's been interesting to see is, I was reading an article recently where they were saying that you have to kind of commit initially and there's a bit of a tax that you've got to pay upfront to learn it and to also train the AI to behave in the way that it does. I assume you were creating custom GPTs already and they're doing a lot of the generative AI work for you. How was that kind of learning curve for you when you were experimenting internally and what's been a learning curve with Copilot?
Chesney Woodall (13:41)
Yeah, I mean, I think like you mentioned, right, you develop as weirdly as it sounds almost a relationship with your AI. So, you know, and again, right, when you're using it for work stuff, can make sure, hey, you know, this is a work conversation, keep the tone professional. But then if you're trying to figure out something personally, I've hit mine up with, girl, help me with this, you know, so.
Jeet (13:48)
Hahaha, yeah.
Ha ha.
Chesney Woodall (14:04)
I think when you transition to a new one, like you said, setting those parameters for here's my expectations for you as an AI platform. If I put a prompt in and I say, hey, help me create a slide deck to present to our executive leadership team on why we need to do a corporate 5K, right? What the benefits are of that for both our medical benefits and ⁓ our employees' health, mental health, all of that, right?
Jeet (14:11)
Hmm.
Chesney Woodall (14:28)
When you're setting a prompt like that, though, you need to give guidelines and parameters to that AI and not everyone knows that. So, I mean, there's so much training out there and resources for how to work with it, how to develop those prompts the way that you want. And I think it's just about being a self-starter, but you can also, if you don't know where to start, you can literally ask the AI platform, where do I start? How do I use you effectively? And I think it's just all about taking that first step. ⁓
Jeet (14:50)
Yeah.
Chesney Woodall (14:57)
And being willing to kind of test it out, it's going to fail sometimes. It's not going to give you what you want. Also just a best practice, always verify the data that it gives you, right? Because it's computer, but it's not perfect.
Jeet (15:06)
Yeah.
Totally, totally. And you mentioned something really important there, which is that it's going to require a bit of testing, and it's not always going to be right. And we have to carve out time for that a little bit. How are you thinking about creating that time for your team to kind of experiment and use Copilot? Like, what does that look like from, let's say, a year ago to now?
Chesney Woodall (15:28)
Yeah, I would say our team has integrated it so much more into our daily lives. At first, there was a little bit of hesitation on what exactly can you use it for. And obviously being an HR, right, you work with a lot of personal data. You can't.
Jeet (15:44)
Yeah.
Chesney Woodall (15:44)
upload your spreadsheets and have people's security
numbers, right? You can't say, hey, run an analysis on who's enrolled and what benefits. So you have to be smart with it. And you have to make sure that you're still protecting your employees when you're using open AI, especially. And so I think for our team, we've really embraced it. Obviously that helps, right? We work for a tech company. So ⁓ even from the back end, our company really encourages us use AI, but use it in a smart manner.
Jeet (16:06)
Hmm.
Yes, like all tools, right, at end of the day. We've got to use it and we've got to point it to the right thing. I want to jump back a little bit to our initial conversation around the immigration workflow and some of the solutions that you might have tried. So, we'd love to hear how did you or your colleagues attempt to solve the problem and what worked and if anything, did work.
Chesney Woodall (16:16)
Good day.
Yeah,
absolutely. So with putting a new process into place, my first thought was, let me go talk to my project managers, right? We have internal project managers who are clients. So I walked down to one of them in the office and I said, Hey, help me out here. I need to build out something. Do we have any resources currently that our company uses so that I'm also not going to finance and asking you to spend more money? And she said, yeah, you know, we use JIRA and
you know, that's a great resource. You can build it out entirely independently. And so I started working with our project management team, our incident reliability team, and our IT team to really build out that system and, you know, utilize something that was already in place. The company is using it in other departments.
It can be siloed to where only the HR team sees this particular projects. ⁓ but we spent probably about two months building it out of what are all the fields that we need? What are the steps in the process? How do we create templates? And then how do we get all the employee data into here so that I can easily just go and look at this dashboard and see, you know, okay, of our seven renewals that are happening, what stuff is waiting on me? What stuff is waiting on the manager? What stuff is being filed? Does it need premium processing?
Jeet (17:45)
Hmm.
Chesney Woodall (17:50)
⁓ And so partnering with the teams that you have, you have to trust that the people you work with know something about what they're doing. Utilize that expertise and partner with them. That cross-functional collaboration, A, it's gonna set you apart in HR because they're not gonna be scared of HR if they know you. It helps you to create a really feasible solution that's gonna make your life easier.
Jeet (18:08)
haha
Yeah, it takes a village, right, to be able to solve the problems internally. So that's awesome to hear. And it's awesome to hear that you had that support and that partnership across the different departments, which I've got to say isn't always the case with competing priorities. So it's, it's really good. And it sounds like based on what you built out in Jira, it did work out pretty well. You were getting visibility. You were able to see what was landing ⁓ in your, in your plate. Was there anything that didn't work? Or is there any other learnings that you kind of uncovered as you continue to
of that process.
Chesney Woodall (18:46)
Yeah, I would say the downside to it is that it was still a little manual, right? So even though you're building out this platform, it's not pre-selecting things based on what you input, right? So if a manager puts in a ticket for a request, I still have to manually go in and assign the template of the checklist of things that need to happen or, you know, sending out the emails depending on what stage.
Jeet (18:52)
Hmm.
Chesney Woodall (19:10)
It'd be nice if it could be automated of, I've now selected that this has happened, automatically generate this next step. Maybe it has that capability and I just don't know about it, but you work with what you have and with the knowledge that you have. And again, that was my first time even using that platform. So gotta give yourself a little grace of it's better than it was, but this process still needs to evolve further.
Jeet (19:18)
Yeah
Yeah.
Totally, you gotta start somewhere, right? And then once you have a baseline, then only can we say, okay, what else can we improve on top of that? Sounds like some of the things that you're mentioning might be a job for the AI, which kind of brings us into the final few questions for today, which is, if you had to revisit the process today, how would you attempt to solve it with or without AI? Would it look different if you were to look at it today?
Chesney Woodall (20:00)
Yeah, I think there's definitely an opportunity to use AI to help train you on a system you don't know. So for our internal processes, I do still think Jiro is probably our best route of housing it. However, it'd be nice to go into Copilot or Claude or JotGPT or wherever and say, hey, here's what I'm trying to do. How can I automate it? What am I missing?
walk me through step by step how to make these changes, rather than me calling up my ⁓ incident reliability team and saying, hey, can you help me with this? It's more effective to teach yourself. And you're growing your skills. And that's going to help you now and in the future.
Jeet (20:33)
Yeah.
Yeah, totally. Is this something that you're going to then continue to improve or GFuel? This is now in good place and it's time to look at other processes. I see you nodding.
Chesney Woodall (20:47)
⁓ yeah. It's definitely going to continue to be
improved. So we've also, we've had some organizational changes in the last six months. So that's opened up a whole new, you know, of worms. So I definitely think there's more opportunity to improve it and expand upon it. It was kind of one of those of let's put this solution in place. It's not perfect, but let's put it in place so that we can do some of this other stuff. And now let's loop back and fine tune it.
Jeet (21:16)
Yeah, I gotcha. And I imagine this is one of many other processes that are being iterated on and improved on. And I guess in your role today, what are some of the processes that take up the most time or cause, I guess, the most trouble? Would you say that comes to mind?
Chesney Woodall (21:33)
Yeah, honestly, it's I'm kind in this weird phase right now where I don't have a clear answer for that. We've actually just been acquired into a much larger company. So a lot of what was bogging down on my plate is now housed with another centers of excellence. So right now I actually don't have a lot going on that is overwhelming that needs to be refined because I don't own all of it anymore. So pros and cons with that. You know, it's nice that there's
other people to help pick it up and run it forward. But the downside to that is when I do see a broken process, it's no longer necessarily something that I own or can fix. ⁓ So that's challenge. That's a mindset shift, right? When you go from owning it all to letting someone else have those reins, ⁓ you know, that's a whole different beast.
Jeet (22:09)
Yeah.
Yeah, and I guess you've got to work with a few more people, a few fresh ways of thinking, and the different cultures across different companies. Congrats on the acquisition. I hope the integration goes smoothly there. And I guess if we're talking, let's say, dream state or ideal state, now that there is AI, and agentic AI, not just generative AI.
If you were to kind of think about one process or one use case that you think is super ripe in your current company to use AER agents that isn't being currently optimized with, does anything come to mind right now?
Chesney Woodall (22:56)
I think the one thing that I've noticed that I think could be better is finding ways to help employees find information, especially with us integrating into this large company.
a repository of information that employees just can't find. And so even using AI from a simple aspect of where do I find this policy? How do I find these benefits, right? If I'm trying to do this, how can I get to that? So even just something as simple as that, which it sounds simple, but again, when you have a massive global company, that's a lot of undertaking even there.
Jeet (23:33)
Yeah.
Chesney Woodall (23:34)
not fully on the process side, but it's the employee experience and making their lives easier. It's great to have benefits and resources available, but it doesn't do you any good if your employees can't find it.
Jeet (23:44)
Totally, you've got to make the most out of the investments that you've already made. as you said, it's not just the process. And I'd say it's not even just a tool. There's a bit of change management of like, ⁓ let's ⁓ encourage people to self-serve. Because as you said earlier on, a lot of folks in HR join HR because they want to help folks. And it's so easy to just say, hey, just DM me, and I'll give you the answer.
And there's kind of that mindset shift, right? Of like, well, actually let's help me help you effectively to self serve, which I think we're seeing a lot with other HR leaders that we talk with. It's those little improvements that really drive that kind of business value and unlock time for everybody. ⁓ So thank you, Chesney, so much for joining us. Before we wrap up, any other final thoughts you'd want to leave someone with who's in the middle of kind of the process optimization in this new world of AI and
Chesney Woodall (24:13)
Yes.
Mm-hmm.
Jeet (24:37)
and AI agents.
Chesney Woodall (24:39)
Yeah, absolutely. I would say my best advice is don't be scared of it, right? It's okay that you don't know. It's okay that you don't have the answers. It's okay if you feel like you have a little bit of imposter syndrome, right? Go out and challenge yourself. And especially if you're in an organization where you have a seat at the table, that seat matters. Use your voice. Be part of the strategy moving forward. And if something's uncomfortable or uncertain,
There's resources out there, right? Use AI to your advantage to develop it. Ask, you know, mentors how they've managed it, but don't be afraid to step outside of what your norm is. It's going to be better for you. It's going to be better for the company, right? They hired you for a reason. They trust your expertise for a reason. So use that seat.
Jeet (25:27)
I love that. Yeah, it's so true. feels like everybody's kind of making it up as they go along in any case. So there's no harm in trying things out. And I love what you said there about actually, it sounds like AI can help HR be more strategic as opposed to become more operational tactical. So great to hear that. And Chesney, thank you so much again for joining us on the WorkOps Podcast. And where can people find you? Would that be LinkedIn?
Chesney Woodall (25:52)
Yes, LinkedIn is the best place. ⁓ Chesney Woodall is ⁓ what you'll search. I'm pretty sure I'm the only one with that name. Not a common name. So yeah, feel free to connect with me on there. Drop a note of how you found me ⁓ or even following, I guess is fine. But DM me on there. Like, let's talk. Let's have a conversation.
Jeet (26:00)
Hahaha
Awesome, thank you so much. And to everyone listening, we're gonna drop Fresney's profile in the podcast notes and we will catch you on the next one. Thanks everybody.
Chesney Woodall (26:23)
Bye.