Best Employee Onboarding Process for Small Businesses

Peter from ProcessDriven walks through his remote company's onboarding system, with HR experts Sarah Skeranski and Kate Steinke weighing in on automation, compliance, and culture. They cover practical tools like Gusto and ClickUp, and how to structure onboarding so new hires actually stick around.
All right, so you've finally done it. You've gone through a full hiring process, maybe like the one I talked about in this video. And now you have gone ahead and found your perfect new candidate, this human who's going to solve all the problems that the role has and is going to be a great contributing member to your team. There's only one problem. You're not quite sure how to get this stranger off the Internet and turn them into a contributing team member. What does that journey look like? Maybe if you're watching this video, you kind of know that that journey is called employee onboarding. Not the same as knowing how to do it in a way that you're proud of. Maybe like me hiring in the early days, you felt really nervous that you were going to make a bad first impression or that you were going to miss one of those compliance steps or that you were going to do something that isn't allowed in some law that you've never heard of. And then everything's going to start crashing apart. If you are not sure how to make employee onboarding reflect your brand and know what to include, this video might be helpful to you. Because in this video, what I'm going to be going through is my full and complete employee onboarding process. You can see what it looks like here. And on this process map, I'm going to go through each step that we do when onboarding a new hire here at ProcessDriven. But here's the thing. Even though I've been running ProcessDriven here for six and a half years, I'm not saying that my employee onboarding process is perfect. I'm not an HR expert or guru you should emulate without question. Please don't trust anything you find on the Internet because of that. And to make sure that this is super valuable for you, I'm not just going to be going through my map today. I'm also going to be enlisting the help of some seasoned operators. And I know that kind of sounds like you're eating computer parts, but what I'm referring to by that are people who've been around the operations block, they've hired before, they've experienced onboarding from multiple angles, and I've pulling them in throughout this video and they're going to give us some tips and tricks on how to make my onboarding process even better. With that, let's dig into the first leg of this onboarding process map, which is the candidate responding. Yes. To the offer. Awesome moment, right? Well, yes, except it's not official until you get it in writing. So once you get the unofficial and yes, we need to make sure we have all of the required information that we need for that person. So for me, that's looking for things like their address, their full name, that kind of stuff. If we don't have it, we'll need to email and track down that information. Once we have that information, that's when we pull in the big guns. In this case, Gusto. Gusto is how I do my employee onboarding here. It's a payroll and HR provider. There are many alternatives out there, but if I can be biased because I've used Gusto for years, Gusto is the best one out there for the small to mid sized teams like I am and maybe many of you are. I'm not sponsored by Gusto, but as it suggests here, it's the one platform that really makes people management possible. I swear, I don't think I ever would have hired employees if it wasn't for Gusto. And so Gusto's onboarding wizard is what I employ at this step. I type in the information I gathered back here and Gusto does all the rest. It collects the tax information and this and that. I barely even know what happens because it happens so automatically. And one thing that I do set up in the Gusto process process is a little message that you're able to custom type in. That message says, can't wait to see on your first day. Our first meeting will be at, you know, 10:00am Eastern on this date, whatever it is. That then leads me into the next step of our process, which is scheduling. Just a call on Google Calendar with the manager, the new hire and the CEO, which is myself. If we're doing a really fast onboarding, like someone's going to be starting in two days or three days, I might also invite the new hire's personal email address just so that they can make sure they get into that call with no access issues. From there, we've got just one more task in this initial leg, which is the create a human task in ClickUp. Now, ClickUp is a work management software. It's similar to SmartSuite, Notion Monday, Trello Asana, those tools that you might be familiar with. So if you don't use ClickUp, you can still emulate this in your tool of choice. But what we do is we create a human directory inside our work management tool. And you can see mine right here. Basic information about them, what people are in their life, and then personality types and other information about how to best work with this human. This human task is like someone's profile to the company. So we create this on someone's behalf to help introduce them to the team. But we also want to have it there so people can fill it in themselves once they actually start. From there, we make a little post in our team's chat room and just say, hey, new hire starting. Here's the date, here's the info. Just do a little, you know, exciting announcement. Because up until this point, the internal team doesn't really know a lot about the hiring other than we're working on it. We don't really disclose candidates or anything else. So this is our first chunk of the process. But when I took this process and I actually brought it to our Indie Apps members, our community for seasoned operators, and I asked for feedback, I got some feedback of some ways we could make this better. So let's actually cut to that right now.
So when you have somebody who sends, who says that they've accepted, and. And I'm assuming that's like a formal offer letter or something that goes out to the candidate at that point, do you then have a process or a checklist of all of the information that you need outside of Gusto? Because I know Gusto gathers a number of bits of information that. That you can use for most things, including i9s and W4s. But the. What other information is it that you're gathering? And is that something that can go out in a pre email once they hit say yes to be able to say, okay, great, we're excited to have you here, here, you know, now that you're here and we can actually ask you these things because legally you can't ask some things until they're hired. These are the things that we want to ask and get information so that we're ready for your first day.
Ooh, I love it. So what I'm hearing is we might have a missing step in terms of Sarah's view that we might be able to add something in here that kind of warms up that first impression and collects some of that information. Sarah, if I can pick your brain just a moment, is there an example of maybe one piece of information that you find that people might miss at this step that you would. You. If you were writing this email, you would make sure to include.
Well, I think again, depending on the system that you're using. So some systems like Gusto will ask for basic things. If you're using a more robust system, it might ask. You might be able to ask for. For specific things like do you like coffee or tea? Or do you like, you know, like some of those, those warm things of like, hey, we're so excited to see you. We're so excited to have you join here. You know, as, as part of this. We want to really get to know you and understand your likes. And, and here are some things, you know, like what's your t shirt size? What's your, you know, your drink preference? Are you a morning or an evening person? Are you, you know, some of those kind of warmups. Questions that aren't necessarily asked as part of the gusto process, but might be asked in some other systems like rippling where you can add custom onboarding questions.
I was starting doing some AI prompts to actually ask all these questions about the soft things. So you could actually do that. I was also considering how are all of this actually happening? I mean create human task and click up. Who's going to do that? Is that something that is actually triggered by the yes that you have in the start? Because then you can actually start that out as an automation. Yeah, you could do checklist and ClickUp or something like that. I mean you could have templates for it, but you could have it automated so it's actually done, done for you. Right, so, so that was some of what I came to think about.
Could you tell me a little bit more? I want to make sure I got this. You mentioned AI. Was that for the prompts here, for the email that Sarah. Okay, perfect. I want to make sure I got that in the right.
You can actually do a little bot. I think so you could have like an in house, an in house bot for you team. Invite the new, the new staff. I mean even though that they haven't started, if they want, they can join you. That's okay, I guess even in the U.S. and then they could have a talk with the butt nice and easy and trying to figure out the new staff. I mean, even though that they haven't started, if they want they can join you. That's okay, I guess even in the U.S. and then they could have a talk with the bot nice and easy and trying to figure out the company and get information. I mean in their own pace.
Yeah, yeah. Oh, that gives me so many ideas because we love our bots here at ProcessDriven and we love putting silly jokes and sassy answers in them. And now I'm thinking, wow, that would be a great way to set the tone.
Because I mean before you even have the new employee in house.
If.
You have any chance to start building the culture and showing the culture and all of that. That's a huge step, I think, to have a perfect onboarding.
Oh, I love that. I also like your highlight here because I think one of the things we always try to do with process improvement is figure out how can we have parallel processing, how can we have multiple things happening at the same time? And if we're able to move the human tasks in this case, or introducing the team, perhaps both of these to be happening simultaneously, where it's happening by an automation all firing at the same time. I mean, that's brilliant. Good tip. So I'm definitely missing an email or so here, and we're going to add that in as I improve this process. But let's move on to the next few steps. The next chunk of this journey is creating an onboarding list inside our work management software with a bunch of tasks in it and embarrassingly, manually adjusting those due dates. So right off the bat, I know when we pull in our panel, they're probably going to have a bone to pick with that. So this is a bit of a time waster. We should probably automate this. But we don't onboard that often, so we're a little bit lazy. Then we actually work on the list of onboarding tasks. You can see the full list of tasks right here. At the same time, the new hire is doing onboarding information through gusto. Again, all automated, just happening, you know, behind the scenes. But they've got some homework to do as well, of filling in direct deposit info and all that stuff. Then there's just this delay where we wait until the person's first day and then we have that meeting we scheduled earlier on with the manager, the CEO and the new hire. By the way, if you'd like to see the full list of onboarding tasks that I'm referencing here, there's many more that are cut off. You can watch this video where I go through the entire onboarding process, all of the tasks that are involved, so you can steal them for yourself now. Full disclaimer. I knew bringing this part of the process to our panel of IndieOps Network experts that I was going to get ripped apart a little bit. Like, I knew this process was crummy and they were going to let me have it. But even I was surprised by the arguments that came up around automation in this section. So listen closely as we get into this clip for how we can improve this section of onboarding.
I would say quite a lot of this could actually be automated. I mean, you can create all the accounts or most of them actually via API. So I would go for that even for smaller teams because if you can do the onboarding automatically, then you can do the offboarding automatically as well. And, and that's quite important because I mean now, now and then somebody leaves you or you kick them and you might not want to have a door open like after they leave.
Yeah.
And I know that have been kind of issue for. Yeah. A lot of companies back in time. Not from now naturally, because everybody is doing automations. Right. But before now everybody have tried it that they forgot to remove a mail or something like that and then somebody abused it and that's not fun.
I'm so glad you shared that because I think I know many small teams I don't want to name my name, that don't have any offboarding process at all. And I think that's actually a question we have later on that might be need to be one of our next pips is just making sure we all lock that down as well. Huh?
That's just as important as onboarding, to Peter's point of you have to turn everything off, you have to make sure that they have an experience offboarding, whether they're getting kicked from the team, as Peter said, or it's by their choice. You want to create an experience for them where it's like, okay, this company is still handling it gracefully and professionally.
And it's actually not just for the company, it's also for the person leaving. Because if you haven't kind of removed everything and something happens and you figure out, oh, this dude have had access for the last two years, maybe he did it, then you have all of that to go on. I mean, so it's actually for everybody's sake.
I have a question for the good of the order. How transparent are you all? Or would you suggest as we look at this process here at this stage. So a lot of this stuff, what we're seeing is, are things that are happening with the new hire at this point. Would you keep most of these conversations with the new hire? Say the onboarding list, the series of tasks, how transparent would you be with the rest of the team on the onboarding journey? Is that something that you would keep private with that person? Would you be reporting back to the team? How does the rest of the team function during this period?
You know, just like Sarah, you. You want the team to know where they are. You know, they want, you want them to have at least a high level look at the list of what they've accomplished so they don't go up and start talking about something and have them completely have no idea what you're talking about. Do you know what I mean? So, like, just something where they can check, oh, if they talked about how to do this, this or that, and then they can go have a conversation. You don't want to ever make them feel. Make the onboarding employee completely overwhelmed.
They're.
They're already overwhelmed. You know what I mean? So, you know, just make sure everybody's on the same page as to where they're at. It's not. It's not a big deal. Do you know what I mean? Like, no matter where they're stuck on it, just empowers everybody else to pitch in.
Let's. Let's keep moving on here. And I have kind of one last question before we go into the next leg here. At this step, there's this big delay, and I know generally in process spaces or if this was client onboarding, we'd say, oh, my gosh, you have a giant delay in the process. That's where buyer's remorse will set in. That's where people will be paralyzed. From the employee onboarding perspective, I kind of think the same thing. And I don't know how to solve it, though. So looking to all of you here, all of this stuff that we just talked about could be finished two weeks, three weeks, you know, at minimum a week earlier. And so there's this quiet in onboarding where there's just this. Let's just wait until the first day arrives and then we have that meeting. What do you all suggest? Or how could we fix this so that way there's not, you know, the employee equivalent of buyer's remorse or, oh, God, what did I just sign up for? How could we make this a little bit better? Because I think, honestly, you know, this is something that we do. It. It's. It's not a great experience.
Well, I mean, it's their decision whether they want to actually have a lot of talk with you and a lot of information from you before they start. So it's their choice if you kind of get too pushy from your side and want to kind of share everything with them before they even start. Some might like it, some might not. But, I mean, the easiest way to figure that out is actually asking, would you like to be in our internal Slack channel already? Now, it's just an offer.
It's. It's a simple bandwidth question. You know what I mean? Like, just ask them, how much time do you have to deal with this? Before your first start date, you know, and, and the question is always, you know, at what point have they signed any kind of non disclosure or anything like that? You know, legal stuff aside.
You could.
Go all the way from just making a list that they can go and check on their time. You could have your project leads, maybe write up a top level summary of the current projects that are going on just so they can kind of start getting into it. You could point them to a couple of tutorials for software they might not be aware of, you know, just put it on them to engage as much as they feel they can at the time. Do you know what I mean? So, and with, with all knowing that it's not a big, it's not a deal breaker if, if they can engage in with this or not. You know, it's just opportunities.
I love that. So everything being an option, I'm put on my.
Yeah, I'm gonna put on my, my. Please do, please do your thing. My hat. My HR hat. Red flags.
Exactly.
My compliance hat is the word I was looking for. So you have to be careful when you have somebody coming on that if you are asking them to do work, quote, unquote, any kind of work prior to their first day, you would have to pay them for that, especially an hourly employee, a non exempt employee. So usually I actually steer away from that. I might send them emails that they can read, but having them engage too much may actually create problems. And it's one of those things where it's like, oh no, this is a great person. And they would never go, they would never go to somebody and say that, you know, they were working and didn't get paid. But if something happens down the road or somebody else says something, you know, you just, it's, it's that gray area, it's that fine line. It's like just you know, kind of steer clear of that. But a lot of times people are super excited and they want, they want to get involved, they want to get started. So like sending them something about some articles or, or like, you know, for you get, for process driven, like here's some YouTubes that, you know, here's some things that you can watch if you, if you want to. Here's some things that you know, kind of understand that. But, but then throughout the process, so all of the process that we have, I don't do that all as soon as they sign the offer letter that's actually broken up between the time they sign the offer letter until the actual hire date. So they do have interaction with us over that period, over that two weeks that they've given their resignation from the previous employer, they're getting some things of like, hey, watch out for this email. Or hey, you need to fill out this form or hey, there's this going on. And every one of them is like, hey, we're so excited that you're coming. Here's one more step that we need you to do. Or here's one more thing we need you to do so that when they come and sort of like, hey, here's what the plan is for your first day so that they know that they're being thought about without them having to take action. Because this is also could be a really stressful time for them if their previous employer is like, wait, you have to finish all these projects before you leave. Or maybe it was, you know, the employer is trying to get them to stay and so you just want to kind of keep that engagement and let them know you're excited without overwhelming them with like more stuff they have to do kind of thing.
Oh, that's great. And this is a good time for me to put a quick reminder in here. Sorry Peter, just one second. Sarah is an expert. She is not your expert. Nothing we are talking about here is legal, financial, any other kind of advice? Don't trust any of us, all right? Trust no one, especially the four of us on this call. Get your own legal advice.
It's really early for me guys. I'm still on my first cup of coffee, so.
Sorry Peter, didn't mean to cut you off there.
No, that's fine, that's fine. No, I just thought about a soft way to actually do it. Offer, offer the. The new employee a way to, to, to connect is I guess simply by sharing the company social calendar or something like that. So I mean they can see what's going on and they can jump in or they can all up to them. No pressure. We expect it naturally, but no pressure.
I love that idea. And also I'll just add two little ideas that I kind of popped up based on what y' all have said. Here is if we're going to share the social calendar, let's also share our some of the team members social profiles. So hey, here's who you're going to be working with. Here's their LinkedIn share teams. LinkedIn. Because we often have that information from the new hire but it would be nice to kind of make that two way. Almost like here's my, here's who I am. We're not.
You could even, you could even ask the current employees to actually hook up with a new employee.
Yeah. Connect with them on LinkedIn.
I think that could be good also for like the cultural part of it, so that the new employee actually experience that you guys is actually reaching out and welcoming.
I love that.
And don't just, don't just send the really quick, you know, here I want to connect, but actually put a message in there that says, hey, we're super excited we get to work with you and make that more, more personal so that again, they're making, they're feeling. They're feeling connected to the group.
And I'm going to put one more idea in here because Sam is not on this call, but I think he would. I would be in trouble if I didn't mention it because he's been wanting to do this for a long time. But an idea that Sam has said a few times is sending out swag of some kind. Maybe he just like swag, but as a nice way to fill this interim period. I'm just calling him out here. But having that in here sounds like it could also be a nice way to engage without necessarily requiring work or any other funky things. Oop, there goes my screen share. I'm going to add that swag in here as well. Anyone else have anything to share on this piece before we keep moving on our journey?
No, but I love the swag. I do that for my staff. I have our mugs, I have notepads, I have all the home office things. And they're super excited. I always get a text message from them. It's like, I got my stuff today. So they. They do. It is something that kind of makes them feel like, like, oh, I'm part of a team.
That was a lot. Now, don't go away. We're not done with the process map yet. We've got another leg of the journey of what happens once they start on their first day. But I want to take a moment here to geek out around what you just saw. That right there, that feedback is the power of process in real life. Just a little aside because, you know, I'm a process geek here. By taking the time to write the way we're doing onboarding visually like this in a process map using process diagramming practices, which is literally just some shapes and arrows. Learn more about that up here if you want to start practicing it. All of a sudden, I was able to take this part of my business that I had never really shared with anybody other than my internal team and the new hire themselves and I was able to get feedback from people who have done it dozens, if not hundreds, if not thousands of times before getting creative perspectives, getting, you know, a new appreciation for the security of a fast off boarding. And that is really what, you know, ProcessDrive is all about. It's becoming aware of how you do things and then being able to communicate that with people in your mastermind, people in your family, people who have a different perspective. Because all of a sudden we're able to then reinvent how we work to be more intentional just by discussing it. And by the way, if this kind of conversation is something you'd like to see the full edition of, if this was fun to you, if you're like, oh my gosh, I want you to do that for my process, consider joining us inside IndieOps Network. Every single month we are doing process map reviews and roasts and improvements like this and this map here. All this feedback you just heard so far and we're not done yet. Don't, don't go away. We're going to be turning this into a revised process map with revised templates and revised equipment, different ways to make the process easier. And we're going to be publishing all of this to the Indie Apps Network community. So that way all of us can not only learn a better way to onboard, we can steal the fully ready to install method for onboarding so that we can all benefit from it. That's one of the cool things of the Indie Apps Network that we run here at ProcessDriven. Link for that is in the description below. It's a new program and I'm kind of nerding out about it. All right, let's get back to the actual process map and finish this out with the new hires. First day. Once the first day is here, we have a series of meetings happening inside our onboarding flow. Here we've got a meeting with the manager and CEO. We've got manager check ins that repeat an onboardy onboardy onboardy bitty onboarding buddy. Check in. There we go one to three times a week and then we have a series of other meetings that we just go through to really fill up the first three weeks of someone being here with lots of conversation. Now when I brought this to our panel of experts, they actually had quite a few suggestions on how we can increase and change this frequency, but I don't have time for that in this video. If you're an ion member, you can watch the full video inside the network but leave it to say this is kind of how we do this. As a remote team here, we are incorporating new technologies and such to make this even easier. More on that later on. But if you are physically, you know, in the same spot office, you might be able to take a more loose approach to these kinds of meetings. But in between all of these meetings, the new hire also has a list of information that they are getting. You know, things they should read, watch, learn, observe, whatever. And that is a full list of tasks that they get to work on at their own pace. Just like the administration tasks. These new hire onboarding tasks can be found in the other video that I will link in the description or maybe up above so you can reference it later. We'll have the blog version down there too, which is just really convenient for skimming in case you want to see exactly what these new hire tasks are. From there we have a peer feedback call. So along the onboarding journey, we'll have a call with the people that work with this new hire. This is particularly important for managers because we've had issues where managers are bullying and we didn't know. So what we do now is we gather everyone together and we just say, hey, how's this new person doing? Are they a good culture fit? Is there any concerns that you have about this new person that we might want to address at the 30 day mark? This peer feedback call happens during the first 30 days. Then it's a lot of wash, rinse and repeat. We wait for 30 days. We have a meeting to review progress. We wait again, we have a meeting to review progress. This just repeats until the 90 day onboarding process is ended. For each of these 30, 60 and 90 meetings, all we're doing is comparing the stuff that we already gave them in the job hiring process and revisiting it every 30 days. So in the hiring process we'll have a list of Kras. Here's what you should accomplish in 30 days if you were to get this role. All we're doing here is revisiting it. Here's where you're supposed to be at 30 days. Here's where you are, here's how we can bridge the difference. That's all we're doing in these calls and we just keep repeating it until we either realize the person's a terrible fit and needs to go, or we successfully finish onboarding. If you'd like to learn more about those Kras, you can actually watch this video up here where I go through Layla Hermozi's hiring process. She's a famous operator, if you've heard of her before. Her process for defining the role is not identical to what we do here, but it's a pretty good overview that would help you get started on the KRA side of things if you're an IndieOps network member. However, we do have our full KRA template inside the IndieOps network that you are welcome to steal. I just to want added in there the day before I'm filming this video so it's there and waiting for you. Once we have our 90 day meeting and we are like yep, this person's still an amazing fit. We officially rename our onboarding list to be the person's name and just a role growth list. So Layla's role growth and that just is repurposed as a learning and training list that is individual to that person moving into the future. And that is how we onboard employees here at ProcessDriven as a small remote company who wants to keep our budget and our time spent in an efficient way. All of the feedback you heard from our special guest here is something I'm still going to be incorporating throughout the month. We're going to have our team working on that while I'm out of the office here for a few weeks and as they do, we'll be sharing the revised map inside that Indie Ops network. I've mentioned a few times in this video and if you're not sure if Indie Ops is the right choice for you, one great way to understand the value of this community is to get to know the members in it, because that's really the superpower. So before we round out this video, I'm going to play a quick clip to allow each of our special guests to introduce themselves so you can stay in touch with them, understand their perspectives that they shared in this video and hopefully get inspired to maybe join us in the future.
I'm an integration, automation and AI nerd. Been doing this for like I don't know, 10 years, 20 years. Working in it for like yeah, close to 40 years. So that's why I'm here. Still trying to learn stumble into you Laila at some point because we wanted to look into ClickUp and learn it. So yeah, that's why I'm here.
Well, you're the only nerd here, clearly. No, I'm kidding. Kate, would you mind introducing yourself next? Sure.
So I'm Kate Steinke and I do operations management for fiber arts businesses and associations. So started out the career as a mechanical engineer and then life happens and turned into a crochet designer and more life happened. And so now I help small Businesses and associations get their stuff together and try to streamline it so it's not a hassle, but it's something to lean back on. And my focus is making it as clean and lean as possible so that it's not a struggle, it's a lifeline.
Oh, I love that. Are you a copywriter as well?
No.
Sarah, let's transition over to you, see if you could top that. No, please introduce yourself. We'd love to hear a little bit more about you.
No pressure there. Sarah Skeranski with EOS Human Resources Consulting. And we offer HR outsourcing and consulting for small businesses. We focus on companies that have less than 25 employees and also help people who are getting ready to hire their first employees set up those processes and set up their onboarding and offboarding and all of the things that you need for compliance and actually teach people how to manage their employees effectively. So I've been doing that consulting for about 10 years and before that was in HR, but also have some technology background and are looking out for ways to integrate technology for small businesses and be able to offer that as a solution as well.
Thank you so much, Peter, Kate and Sarah. And if you watching this video would like to go further on your own journey besides just following these wonderful operators, be sure to check out the video here on the end screen to continue learning along with us. And until next time, remember to enjoy the process.










