Onboarding with Courtney Ebersole

Guest: Courtney Ebersole, Learning and Development Manager, JumpCloud

Episode description

When a new employee joins an organization, the IT and HR teams need to work together to ensure that the new hire is able to be up and running on their first day. In this episode, Courtney Ebersole, Manager of Learning and Development at JumpCloud, talks about the overlap of HR and IT during the onboarding process and what IT admins can do to streamline the process. 

The following is a transcription of an episode of our podcast, Where’s The Any Key? Feel free to reach out with any questions you may have in response to this recording. You can find our show on Apple Podcasts, Spotify, and wherever podcasts are available.

Ryan Bacon: Welcome to Where’s the Any Key? the podcast where we talk about anything IT related and even some topics that are IT adjacent. I’m your host Ryan Bacon, the IT Support Engineer at JumpCloud®.

Introducing Courtney Ebersole

Ryan: So, I’m here talking to Courtney Ebersole, she is the Learning and Development Manager here at JumpCloud. And I just wanted to chat with her and get kind of a non-technical view on team building, and especially when it comes to culture and workplace dynamics, which she has done a great job developing that here at JumpCloud and that’s kind of her forte. So, welcome, Courtney.

Courtney Ebersole: Thanks Ryan. Yeah. So I come from a long line of learning and development opportunities. In my current role, I’m the manager of learning and development. However, my past has jumped all over the L&D scene. I started out, actually, heavily into the master data scene with SAP and really learned that what I love doing is the training process of people and I could care less about data. So, that was a long path to get where I was going in, really, the L&D scene and started out really in those enterprise companies learning what “best practices” looks like. I don’t always agree with those today. They don’t stay up to date. But I learned from that that I wanted to bring a more progressive, beautiful, experimental educational experiment to the companies that I’ll be working with in the future.

So I think what led me to JumpCloud was I’ve gotten those enterprise best practices along the way to where I am now at creating what I think can be a very immersive, inclusive educational experience. And part of that is how you onboard employees. So yeah, when I first came to JumpCloud, it was pretty apparent, and I think you would agree, that we had a lot of work to do with onboarding, especially in making the processes more streamlined and efficient. And along those lines, you were already doing some of the onboarding already. So I don’t know how you feel, but I think, together, we’ve turned it around to a very collaborative process, especially with IT processes.

Ryan: Yeah, I agree. When I started, they would have a little mini orientation session that maybe lasted 15 minutes. And then I would walk in and say, “Here’s your computer. Have fun.”

Courtney Ebersole: Yeah.

Ryan: And then, after a while, I’m like, “We should really do a more formal IT orientation.” And then, of course, once you started, your first big push was a full, immersive “Welcome to JumpCloud” orientation. And I think that was a move in the right direction.

Onboarding Seamlessly

Courtney Ebersole: Yeah. And then, using previous experiences, I know how important it is to keep that IT portion in there. It’s got to be solid. It’s got to be enough time as well. People have to be comfortable. Once you, Ryan, and Noah leave the room, things have to be running pretty smoothly on their computers or the rest of onboarding just goes terribly. So, I think coming from the stage one experience or phase one, if you will, where I got to experience what the current state was, was really helpful because I missed a lot of the nuggets of information along the way.

So that during phase two, I knew exactly where in the pockets, what we were missing and how to make your piece really cohesive with the HR piece so that people, when they come in, they’re all excited. They want to give the right documents, they have the I-9s ready, and they really want their laptop. And that’s important to them. As soon as they see laptop on the agenda, that’s the piece that they’re really looking forward to because it’s ingrained in us to… We want to get started. I want to start producing. I want to read my emails. I want to know what’s going on this week.

So, I know that already going in. And because I know that, well, I wanted to make sure it was part of morning one, and that you guys were the meat of morning one. And I think you would agree that now we have a good chunk of time and we’re working on the process, it’s not complete yet. But I think that they’re getting what they need so that when you leave the room, we know what to do.

Ryan: Yeah. I feel a lot better about the whole process now than I did initially.

Courtney Ebersole: Yeah. What was that like before? Once you left the room, before I was here, were you just getting flooded with Slack requests?

Ryan: Yes. And that was very much that people really didn’t have any idea what to do next. And because they pretty much went back to their team, and their team members were really good about getting them set in the right spots for the role specific stuff. But the general JumpCloud stuff seemed to be what was lacking. And I mean, other than the, “Here’s your parking pass. Here’s your equipment checkout for…” That sort of the logistical stuff, but the actual general information, I don’t know if we should call it fluff or whatever, was kind of-

Courtney Ebersole: Ouch and ouch. But you’re right. You’re right. The softer part has to come with time. And I’m glad that you said that too, because thinking back on what previous people onboarding at JumpCloud were doing, it sounded like there was a collection of eight to 10 engineers setting up a laptop before you even got here.

Ryan: Oh yeah.

Courtney Ebersole: And then, once the IT team was established, I think you took that process, correct me if I’m wrong, off of their plate and made it into the one-stop shop. You’ll at least set up the laptop so that it’s not being passed between eight people for two weeks, and hopefully it’s ready.

Ryan: Yeah. I mean, since the day I started, the number one priority that I was given was “streamline the onboarding process.” And so, that was front and center. It started from taking the roles, taking what all these different engineers were doing and putting them on my plate. And then, what took a longer time was figuring out what other stuff was being done that IT could do like what other resources did they need access to? Who gets GitHub access? What kind of GitHub access? AWS stuff. Everything like that took a while to gather that information into one place so that we can document it and improve it, and-

Courtney Ebersole: Which I think is the first part of… When you’re thinking about streamlining onboarding, you have to start with at least the permission-based role access. If that’s not there, the rest of the L&D team, learning and development team, they will be, in no better word, screwed because the rest of the time, those employees, all they’re going to think about is, “I don’t have access to this. I don’t have this.” So you’re working on phase one.

And then when I got here, phase two really started. It was like, “How do we make sure the flow of when IT hits in that new hires’ day is correct?” So they don’t want their laptop handed to them at 9:00 AM when they get here. That would be chaotic. They want to know where the bathrooms are, where to get coffee and the basics of here’s my I-9 documents, all of those things, to the point where I get them comfortable enough with each other so that they are comfortable. When you walk in the door, they’re okay asking questions. They start to perk up and they understand like, “Okay, these are the types of things I should expect out of the IT team giving me my laptop and what this time is used for. Then once that’s all done, they’re ready to learn other things, if you will, they’ve gotten the basics out of the way. So I feel like we’re pretty much complete from a phase two perspective.

Onboarding People in Technical Roles

Ryan: Yeah. That makes sense. Now what I would like to get your feeling on is when it comes to onboarding, doing the orientation for IT people specifically, which, since you’ve been here, we’ve only done one person, that was Noah… And how I did that, I don’t think I really consulted with you how I wanted to do Noah’s onboarding. I just went in with a list of demands like, “I don’t want him to start on a day that everybody else starts. I’m not going to have anything ready for him because I want him to go through and experience the setup process.” How do you feel about that? Do you feel like it’s more of a benefit, that it’s a good way? Or do you see any kind of detriment to not having them be in the normal onboarding process?

Courtney Ebersole: So, yes and no to the detriment question. And Noah, if you’ll remember, I think he started right before the class that I had officially started the real onboarding program. So, he got the same onboarding, I think, that everybody else up until that point got. And I don’t think there is anything we could have done better at that point.

However, going forward, there’s two things I really think about when it comes to engineers and technical hires, people that are highly technical, especially with IT processes, is that you can’t break it down so much that they’re getting a completely different feeling on day one and day two. So in that sense, I would bring Noah in with a regular class. In the background, there’s things I would change. I would give him the ability to play around in systems ahead of time. He doesn’t need to be in the watered down version of what everybody else gets in IT because what we give to the normal JumpCloudian walking in, that’s the standard stuff they need to know. What I would do for an IT hire if you were growing out your team is give them access to the laptop ahead of time. Let them play around. You give them that more dedicated experience upfront with the IT resources so they can build out their systems early because we’re not going to baby them when they get here, they need to be able to do that ahead of time, and they’re ready to roll.

I do think there’s benefit in someone in the future that’s joining your team attending the regular two-day session. But as soon as that two-day session is done, they’re moving straight into functional training. Whereas, other teams, I would ease them into more of their functional training. So I’ll give you an example. For somebody like Noah, on day two, when he goes off to lunch with you, I would expect that you and he would dive immediately into the weeds and really start to look at processes. And he’s prepared for that because he already has his computer. Things are set up, he’s ready to get his feet wet and his hands dirty. That’s most IT professionals that I know they don’t want to mess around with all the other processes. So what I can do for them is get the HR people processes speakers out of the way so that it’s a clear path that you can take with him at that point.

Ryan: And that’s actually a very good point because when I started, being that I was the first dedicated IT person here at the company, there was no plan for me really when I started. And I had to be very proactive about going to my manager and saying, “I need stuff to do.” It’s like, “Yes, you have given me some time to ramp up, but there’s ramping up and then there’s sitting on my hands, well, waiting for stuff to happen.” So, it was a very interesting process. And I do agree with you that having that structure and having that preparation ready for when they hit the floor is very important.

Now, circling back to what we were talking about. What about have them go through that normal onboarding process, and you were saying, kind of beforehand, give them access to their systems and some stuff so they have a little bit of preparation prior to the orientation that all the other new hires go to? Would you suggest that kind of a very short… not even a half day, but just like a pre-orientation setup. Where you have them start… Maybe come in for a couple hours in the morning like since we do our onboardings on Monday, our orientations on Monday, have them come in on that Friday before and do some stuff or come in earlier on the day that they start, like, how would-

Courtney Ebersole: Yeah. I see what you’re saying here. I can tell you that it’s something all managers want. It’s not unique to IT. A lot of them will tell me that they want to have a half day beforehand, at a certain level, and at a certain technical expertise.

I fully believe in making sure an employee has a great day one. You have to be careful about that. I’m not saying there’s situations where that doesn’t work. You just have to be really careful with the first touch experience. You don’t want to overwhelm them ahead of time. And you want to keep that first day pretty sacred as far as what they think about the company. So when it makes sense, I will say if you’re a very fast growing under 50-person team, that probably makes sense. You can bring them in early. I think, the larger you get, you need to keep that experience the same, consistent, inclusive.

I will say, for more technical hires, on day two and on day one, they get out of onboarding early because I don’t like to overwhelm them with too much information all the way up until 5:00 PM. I usually try to stop around two or three. That’s a good time to say, “Hey, you’re unique in this. And I want you to make sure that you understand what your role in our company and what your role in the technical side really is.” In those situations that we’ve had at JumpCloud, I do let them stay with their manager and attend meetings on day one. I do, on day two, encourage them that they’re already diving into a project and that their manager has that project ready because not having the project ready week one or their 30-60-90 plan ready week one is so critical to these highly technical roles. They know what they’re doing, they’re ready to do it. Once you’ve given them that white glove experience, if you will, make sure you’re giving them as much timely projects that first week as possible.

Ryan: I can agree with that. I feel that one of the worst things you can do, especially to a technical person, is have them start and immediately become bored.

Courtney Ebersole: Right. Yeah. I think that you can hear that echoed in engineering as well and certain areas, especially… I talk about this a lot, when you get to the VP and C-suite level, you can’t onboard the same because their drivers and their motivations are completely different. And IT is no different. Everybody’s role is like that. But usually I err on the side of easing in and not overwhelming. With IT, it’s a different personality that you’re hiring for and you want that technical, ready, eager person that’s like, “I want to start coding today. I want to start fixing processes today.” whether it’s engineering, IT, whatever the department is. So, yes, being prepared for week one and making sure they know exactly what their first project is, super critical.

Ryan: That is some really good advice. So, to sum it up, don’t segregate them from the standard orientation and onboarding process too much.

Courtney Ebersole: Right.

Ryan: Maybe do some additional stuff at the tail end of their first day and second day experience. And then, be ready for when they come to sit at their desk and start working to have them just go and start working and doing something productive and meaningful from the very beginning.

Courtney Ebersole: Right. I would say minute one after lunch is done, they’re not looking to chill out at their desk. I think a lot of teams are wanting to ease in, but yes, I think to sum it all up, make sure that minute one is just as impactful as they thought it was going to be in the interview. And that is very, very critical, very critical. Yeah.

Introducing an IT Team to an Organization

Ryan: All right. I can get behind that. All right. So here’s another question for you. So, with JumpCloud and with a lot of other organizations who start small and are growing and growing and get to that point where they realize that a dedicated IT team is needed, whether it’s one person, multiple people, or growing as where you are now, how do you feel that culture shift with introducing an IT team and the processes that come with it? How do you feel introducing that monkey wrench into a company’s culture can best be handled?

Courtney Ebersole: Yeah. I don’t think there’s a best way at this point, but I can tell you what I see and the shift and the change that people have to embrace. So on one hand, you’re going from a place where you might have six engineers setting up a laptop for a new hire. And that’s very clunky, but it just gets done. You just get it done. And you’re scrappy and you bring in every resource you can think of. Right? So there’s a different pace to it. However, the processes might not be streamlined to be making that the correct, most efficient way of doing it. Right.

But I think in that previous state people are very much leaning on random resources to make sure they have their technical person is what I’m trying to say. They’ve got that go-to that they really, really rely on. And they can download apps whenever they want. They can add extensions that they’re… Most companies will just, “Yeah, download whatever. We’ve got 10 administrators, go for it.” What happens when you bring the IT team on or the IT professional on is it’s kind of that culture shock for a bit, for lack of a better term, there is a culture shock. In certain ways, selfishly speaking, in HR and the people team, it’s a blessing because you’re not asking eight people to do a process that really should just be one team.

The other side of it too, from a security and IT perspective, is we have awareness of what apps are out there, what people are downloading. Can we leverage licenses? Holy crap, we’ve got 10 Salesforce administrators, heaven forbid. So I think from that selfish perspective, it’s a great cultural moment to know that you’re getting into that next phase as a company, you’re becoming a more mature startup or growth company.

But the other thing I will admit to is that that’s pretty hard for some people that like to go quick, be scrappy and they don’t care what the process is like. Right. They’re just getting what they need done and that’s all they see. I think what the IT team has the opportunity to do, if they do it correctly, is say, “Look at this process I built, this is going to cut down time for you in so many ways.” And that’s the part that I think IT teams need to do a better job advertising is that, “Here’s the time-saver. I’m not here to slow your day down, I’m here to make it quicker.” And I think you and Noah do a really good job of that. So kudos to you guys for taking that approach.

Ryan: Yeah, that was actually one of the big drivers of us switching the ticketing platform, going to a Slack driven platform and where we can tell people, “You know what? You don’t have to worry about if something needs a ticket or not. Just Slack us. Send us a message, tell us what you want, ask us the question that you have, whatever. And then, we’ll make that determination and just do it all on the backend and you don’t have to worry about it.”

Courtney Ebersole: Right. And I think that comes with your experience, right? You’re not clinging to processes that are clunky, or old, or we’re just doing it because it’s the way you do it, or this is the product we use. You and Noah keep that very customer service focused mindset. And I think that’s something that most IT teams can learn from. I don’t think we’re there yet as an IT community. But I think you guys know the benefit too of really saying, “We don’t need all this clunk, we’ll take care of that in the background so that it feels seamless for you as a customer.” And that, I think, is the beauty of the IT cultural shift. People see that eventually, but I don’t know if you would agree, but I feel like it takes six months to a year if you’ve got a solid team up starting out up and running.

Ryan: Mm-hmm (affirmative). And to go along with that, I think that that’s something you need to keep in mind when building your team. If you’re going for this more customer service driven department and these customer service driven processes, you need to make sure that the people that you’re bringing on board and adding to the team have that kind of personality to fit with it. Because it does require someone to have soft skills. And I know introducing soft skills into IT is scary. But I feel that it really does make your job easier because it’s a better experience for your end user, it builds a better relationship between the end user and the IT department. And I think that’s a really important part of both building and maintaining a good environment and culture within an organization.

Courtney Ebersole: Yeah. I think the fact that you and Noah, taking this learning approach, and, “Oh, I’m not mad that you downloaded that or you found this other system.” It’s like, “What does the system do? I’m very curious to learn something I haven’t seen before.” That speaks volumes to your customers, which are all of my customers, all the fellow JumpCloudians is that people don’t feel like they’re stuck with IT, and that they’re in it like a cog in a wheel, and “My ticket’s one of millions. And they’ll get to it when they get to it. And I’m not high on their priority list.” Even if there is a background behind the scenes, “We’ve got to get this done first.” we don’t feel that. So that’s really important. And I think, to your point, looking for people that can just ignore those traditional processes of this is the way we use ServiceNow or whatever it might be, and this is the process, and the IT team’s kind of running from you and hiding from you all of the time, that’s key to find in a person.

Ryan: Yeah, I agree. And that’s been my goal here at JumpCloud from day one is to have that more personable IT experience so I’m glad to hear that it’s working to some extent.

Courtney Ebersole: It has paid off, for sure.

Closing Remarks

Ryan: Well, thank you very much for coming and chatting, Courtney.

Courtney Ebersole: Thank you, Ryan, as always. And I’m sure we’ll continue to improve our processes along the way too.

Ryan: Always. Processes are never, never set in stone.

Courtney Ebersole: Not concrete. Agreed.

Ryan: Thank you for listening to Where’s the Any Key? If you like what you heard, please feel free to subscribe. Again, my name is Ryan Bacon and I work for JumpCloud Directory Platform, where the team here is building a cloud-based platform for system and identity management. You can learn more and even set up a free account today.

So until next time, keep looking for that any key. If you find it, please let us know. 

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