Podcast: Onboarding Best Practices from a Digital Nomad CEO

digital onboarding best practices

Ever wondered if your new hire’s first ‘hello’ could be from a chatbot? Or if that glowing quarterly review could someday be delivered by an AI?

Tune in to our latest episode of Process Street’s Employee Onboarding Podcast, where Erin and Max Sher pull back the curtain on the future of employee onboarding, training, and those all-important ‘wow’ moments.

Discover why some traditions are worth keeping and where technology could step in to elevate the experience!

This episode covers:

  • Sher Agency structure & dynamics (as a globally distributed web design team)
  • How Max scaled up from a solo entrepreneur to a global team
  • How to improve digital onboarding efficiency
  • Important lessons Max learned about digital onboarding
  • How culture plays into good onboarding (especially remote)
  • The quest for the employee “wow” moment
  • Thoughts on the future of employee onboarding (including the role of AI)

You can listen on AppleSpotifyGooglePodchaserPodcast AddictDeezer, & all your favorite podcast platforms!

Introducing Max Sher: Digital Nomad & Web Design Agency CEO

Erin Rice: Welcome to the Employee Onboarding Podcast, where we’re 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 recurring work fun, fast, and faultless for teams everywhere. My name is Erin Rice, and I’m the People & Operations Coordinator here at Process Street.

Today, I’m joined by Max Sher. Max is the founder and CEO of the Sher Agency. He started his agency as a freshman in college.

At first, he provided any imaginable marketing services to every imaginable customer set until he realized the value of specialization about three years into the process. At that point, his business became completely unsustainable. So he started over from mostly scratch.

Since then, he’s been dedicated solely to creating awesome websites that move the needle in his clients’ businesses.

When he’s not making websites with his team, he is a design and business TikToker, a digital nomad hopping from city to city with his girlfriend and an amateur guitar player. Thank you so much for joining us today, Max!

Max Sher: Thanks, Erin. Happy to be here.

Breaking the Ice: Digital Nomad Lifestyle and Essential Items 

Erin: So before we dive in, I really like this idea of digital nomadism, if you will. I’m very curious about your answer to our sort of icebreaker question. Is there one item or one thing that you just simply can’t get rid of?

Max: Like a physical item?

Erin: Like a physical item. I would imagine being a digital nomad, you don’t have a lot of stuff.

Max: My biggest, most inefficient thing that I bring with me everywhere is music equipment, like guitars and amplifiers are definitely the thing that I am questioning whether or not I really need to be bringing with me to every location. But the answer has 10 out of 10 times been yes, unfortunately.

The Emotional Connection to Music and Hobbies 

Erin: Yeah. And I guess that goes with your new love of playing guitar.

Max: Yeah, it’s not that new. I’ve been playing since I was a kid.

Erin: Oh, okay. So you just call yourself an amateur because you’re not that good yet.

Max: And maybe never will be. It’s just a hobby, really – a good way to kill time and relieve stress.

Let’s Talk About Employee Onboarding 

Erin: Yeah, that’s great. Time for what we really came here for – employee onboarding! 

So Max, why don’t you tell me a little bit about the dynamic of your company, how many people you have, how you’re distributed, that kind of thing.

Inside the Sher Agency: Team Structure and Distribution 

Max: Yeah, so we’re a globally distributed company. I think there’s currently something in the neighborhood of 25 people involved. So not a huge company, but definitely bigger than I’ve ever managed before. Um, we’re a hundred percent remote. No two of us have ever met in person. 

Um, I think we’re on every continent except for Antarctica. I think that’s probably the gist of the distribution of the team. Almost everybody is involved in the creation or management of websites in some way. 

We’ve got a little bit of support on the marketing side as well. Management of the team, we’ve got a couple of people who do that, but really that’s the bread and butter of the company is the fulfillment side.

The Entrepreneurial Journey: From Coffee Shop to CEO 

Erin: Okay, great. And tell me a little bit about how you ended up starting your own business.

The Complexity of Launching a Business at 18 

Max: So I was 18 years old and I was at a coffee shop, hookah lounge kind of hybrid thing. And the owner knew me, I had been there quite a bit when I was a high school student and I was just about to leave for college. 

I grew up in Las Vegas, so this all takes place in Vegas. And he comes up to me and he’s like, hey, you’re a computer guy, right? He sees me on a computer doing homework all the time. I’m like, yeah, I’m a computer guy. 

He says, “I’m starting a grocery store and I need a website built for that grocery store that does delivery and all this. Can you do that?” In my head, I’d never touched a website before. I didn’t know anything about it, but I thought, you know, there’s got to be templates. There’s got to be some way to do it. I’m sure I can help this guy. It can’t be that hard. So I said, sure, screw it. I’ll take a stab at it. 

One thing led to the next and I decided that in order to write a contract, I had to be a company. Little did I know as an 18-year-old, I could have just done this freelance. 

I started just doing other things for other businesses. And I had some design knowledge from high school because I had kind of an emphasis on that in high school. And throughout that time, I learned how to cold call, how to cold DM, all these things that I was trying to do to build my business. And I kind of got good at acquiring clients and that kind of grew into an agency.

Transitioning from Solo to Team-Based Operations 

Erin: And so then you get to this point where you’re ready to now hire legitimate employees.

Max: Yes, legitimate is the emphasis on this. People who know what they’re doing.

Erin: Right. Exactly. And then they’re probably qualified to do the job.

Max: Yeah, yeah. And no shade on that developer that I hired way back then. I don’t remember her name, unfortunately, but it’s not your fault. You knew more than I did.

Learning Curves in Employee Onboarding 

Erin: So tell me a little bit about what that experience was like going from an owner of a self-employed business to hiring employees. How did you tackle that?

Max: I was winging it for sure. Common thread here in all of my stories, I was winging it and I figured, you know, I’ve got these specific tasks that are taking more time than I think that they’re worth for me. So I’m gonna hire someone to do them for me. But what was really challenging at the start was I didn’t really know, there was no standardization in my business. 

One client would come to us for social media management, one would come to us for web design, one would come to us for logo design. So I kinda needed to just hire some jack of all trades. 

Thankfully, I just got super lucky and I hired this really smart guy. His name was Andrew. And he, we ended up just kind of becoming this two person team that was really just cranking out all this stuff and we were learning together and all that, but the hiring process was more or less, I think I posted a job on LinkedIn. We didn’t interview. I’m like, sure, let’s do it. That was pretty much how it went.

Erin: Sounds like you’re kind of going with your gut guy.

Max: Less so now, but yeah, when I was 18, you bet.

Shifting from Ad-Hoc Work to Process-Oriented Structure 

Erin: Awesome. And so what sort of led you to the point of going from like one-off projects, one-off kind of employee onboarding to turning it into a process and making more like of a recurrent situation?

Max: So that didn’t happen until several years later when I read this great book called Built to Sell. And that really taught me the root of all my problems was, which was the lack of standardization and a lack of processes. And I couldn’t write processes because I was doing a different thing for every person. 

And once I got to the point where I kind of restarted my business, as you said in the intro, about three years in, and really built it from scratch around one service. 

From there I got to the point where I had five team members, six team members, and we were constantly bringing on freelancers to assist with individual projects, then I was like, okay, we’re teaching the same set of lessons over and over again, as we go in like a role specific context, like whenever we bring in a new freelancer to help us. 

And I’m not talking about my core team at this point, just, just freelancers and contractors.

Streamlining Onboarding with Checklists 

We’re spending an inordinate amount of time teaching people how to find our Google Drive, how to find our Slack. So it was really a selfish thing at the start. 

It was like “I am spending too much time on this. I’m going to write it in a checklist.” And this is before I knew about great tools like Process Street. But I think I did it in like a spreadsheet or a Google Doc with the check boxes. And it was just like, “Hey, before you start work tomorrow, go through this”. 

And that was, that was kind of the gist. We had one for developers and we had one for everybody else.

Balancing Efficiency and Company Culture 

Erin: And what did you feel like that was missing? Do you feel like there was a disconnect between your mission as a company and that individual employee coming on?

Max: I don’t think I was sophisticated enough at that time to put, not that I’m very sophisticated now, but I definitely wasn’t when I was 20 years old to be able to say, you know, I feel like we’re not mission-oriented, we’re not teaching the values that we espouse as a company. I think at that point, we were hanging on by the seam of our pants. We were really just trying to get by and meet those deadlines.

We’re giving you exactly what we can and as efficiently as possible. And if you need more than that, it’s gonna be one-on-one communication.

The Importance of an In-Depth Onboarding Experience

Erin: Yeah. So what would you say a great employee onboarding experience looks like?

Max: You know, I would never go so far as to claim that I’m an expert on that subject. But what I would tell you is what works for me, what’s worked for my business and what people who are onboarded have been really impressed by is to really over deliver on the onboarding experience. 

For us, we now use Process Street for this. Our onboarding checklist is I think like 17 or 18 tasks. Just you have to read this and confirm, like read this and confirm and like set up your account and it’s almost an overload, but it’s not because it also gives them a place to go get the information later.

Fostering Cultural Alignment from Day One

And that’s really what I think the purpose of the exercise is. it’s not, I expect you to retain all of this information immediately. It’s okay. I now know that I can come back and find out how to find the files that I need in Google Drive or how to view my pay stubs and things like that. 

What’s really been beneficial to us going forward and what I noticed is a measurable difference in how we start by having people watch some recordings of all hands meetings. 

Like, Hey, here’s the all hands meeting where we discuss, you know, company shout-outs based on our core values.

Expectations and Boundaries in a Remote Work Environment

Another thing that I’d say we do a good job of teaching quickly is. Kind of our standards for remote work. What that means and like what kind of time tracking are you paid based on and what’s more for like client billable. 

So it’s like things to the effect of, hey, we expect x, y, and z hours from you per day, and you need to track them here. 

And it’s things like that, if you’re not used to a remote environment, it kind of helps get you acclimated quite quickly to how that works.

Empowering Employees Through Defined Boundaries

And then the third thing is it kind of gives them permission to set boundaries in their work. So like I mentioned at the beginning here, we have people all over the world sending messages to each other. And the time zones don’t always line up, in Nigeria sending messages to someone in Los Angeles, that they’re going to be getting messages in the middle of the night. So one of the things that I have them do is I have them click a box that says, hey, I confirm that I understand that I am not required to respond to messages that come in the middle of the night. I have working hours and I understand that I have authority to enforce and set those boundaries. And I think that’s been a source of positive culture for our company.

The Role of Automation and Settings in Work-Life Balance

Erin: Oh, I bet. Because it’s so annoying when those Slack messages come in while you’re trying to like get your kids settled or during dinner and you’re like, how important is this?

Max: Yeah, yeah, I think I haven’t seen it, but someone told me that someone went into that process and added something that says like, here’s how you set your notifications to snooze during your off hours so they don’t bug you. It’s, it’s helpful.

Erin: Yeah, you can also integrate your Google calendar with your working hours into your Slack so it does it for you automatically, which is really so fancy. I love good automation.

Specifics of Role-Based Onboarding

Max: Me too, that’s cool. 

Erin: So tell me a little bit about how you approach new hires and their onboarding process in order to get them up to speed and contributing quickly.

Max: Yeah, so there’s that big checklist that I just talked about that we go through. Then people have a role specific checklist that they go through. So this is for positions that we’re hiring regularly, like new designers, new developers, new account managers, things that scale with our fulfillment.

Addressing Employee Anxiety Through Defined Success Metrics

Um, for those types of people, we have a role specific process street that they go through and it’s like, okay, here are, um, here’s what success looks like in your job. 

We give them like a literal rubric, for what A level, B level and C level performance looks like. Here’s what you, where you go to get your daily tasks. Here’s all the stuff, really what we’re trying to do here is reduce anxiety and in my opinion, one of my beliefs as a business owner is that anxiety primarily comes from ambiguity. 

And if you can limit ambiguity in someone’s role and how they’re going to be evaluated and how they can succeed. You’re off to a good start. 

Even if you’re overwhelming them a little bit with information. The common feedback we get is that we do overwhelm people a little bit. They’re not stressed out in the sense that they don’t know what to do – I don’t get that feedback super often. 

Another thing that is absolutely critical is direct one-on-one communication with somebody. So oftentimes when we’re onboarding someone, I’ll message someone who’s either in a role very similar to theirs in another department or in the same role. and have them message them and kind of be their onboarding buddy. Not, we don’t have a formal system for this, but it’s, it’s something we, we just tend to do. 

If we hire a new developer, we’ll get the next most recent developer, the one who’s been there for six months, maybe and say, Hey, go have a conversation with this person, make sure they feel welcome, ask them about their day. 

Like, you know, check in on them and make sure that they’re finding what they need. I’ll typically ask someone. I try to ask the friendlier, more agreeable people to go make. to make that introduction and make people feel welcome.

Hierarchical Structures and Their Role in Onboarding

Erin: Yeah, that’s great. Buddies are awesome. And I imagine at the size of your company, are you managing all the employees and doing one on ones with them? Or do you have a hierarchy in place now?

Max: We have a hierarchy in place. I have an operations director who really oversees all team and fulfillment of the company.

Erin: Okay, cool. And so I would imagine having, well, I know having an onboarding buddy that’s not your direct manager is often very helpful because we can say all day that questions aren’t stupid, but we believe they are anyway.

Max: Yeah, exactly. I think it also helps to alleviate some of that anxiety to have a person to ask.

Mission Statements and Guiding Principles

Erin: Yeah, that’s great. So tell me, we talked a little bit about guiding principles and missions earlier. Tell me, do you have a set sort of mission that you share with the team and how do you help them sort of buy into that?

Max: I wouldn’t say we have a mission statement type of thing. What we do have is guiding principles that we use to guide our behavior in the way that we work with clients. 

We’ve just basically got these six pillars that are, we kind of try to do shout outs for people based on their adherence to them or being good examples of them. 

And that’s really how we enforce the kind of behaviors that we wanna see in the company. In terms of a mission, nah, I don’t have anything. I got nothing, but that’s sorry.

Strategies for New Employee Onboarding

Erin: Yeah, no, that’s okay. What advice would you give somebody on their first day to sort of help them absorb all the information, not get overwhelmed, ignore the ambiguity, that kind of thing?

Max: More so than memorizing exactly what everything says, just to kind of remember where you found everything and maybe bookmark the documents and just kind of come back to it over time. It’s something that you’ll be exposed to once and then you’ll remember where you saw it and you’ll come back and you’ll get it again. 

You know, I always tell people that the best onboarding is to start the job really like you learn the most by doing and we try and give you all this information up front but I really don’t believe that there’s any cure for learning other than doing that. I don’t think there’s a solution to learning other than doing.

Onboarding Timelines and Process Structuring

Erin: How long would you say it takes a new person to fully ramp up and complete their onboarding?

Max: We don’t let them start actual work until usually about the third day. Usually the first two days are, you know, for day one, you’re going through kind of company specific processes and all that stuff. 

Day two, you’re doing role specific processes, things that are more about, about your job, specifically meeting with your manager, meeting with colleagues, things like that. 

And then day three, you’re actually implementing it and you start under a supervised capacity, actually contributing.

Erin: Okay, so you mentioned you all use Process Street workflows for your onboarding. How do you have it organized? Is it organized by day one? Is it just to get through this over the first two days?

Max: Yeah, it’s really only two Process Street workflows that they’ll go through. One is the general, two is the role specific and it’s organized into tasks based on just the topic is really all that it is.

Future of Employee Onboarding

Erin: Okay, cool, that’s awesome. So looking to the future, I’m sure your intention is to grow your company.

Max: Yes.

Erin: Do you see the processes that you have in place as scalable that you would be able to then hire, you know, 10 web developers at once?

Max: Yeah, I do. I think they’re pretty scalable. We don’t really change them super often. It’s only when we adopt a new software or something like that. It could be a little overwhelming on the lead developer to manage 10 onboarding processes and give the support and one-on-one care that is needed to succeed there. 

But from a process standpoint, I do think we’re there. I think we would just need a little bit more.

Role of Technology in Onboarding

Erin: Yeah, okay. And so then I have to ask, what do you see as the future of employee onboarding?

Max: That’s a tough question to answer. My gut tells me to go with the probably cliche answer of you’re probably going to have like an AI chatbot that helps you understand what your role is and kind of grades kind of does a quiz and grading quiz type of interaction. 

So I can imagine. training a customer service rep like, hey, what would you say if a client says this and kind of doing role play scenarios with an AI bot? I could see things like that for training purposes, for onboarding. 

I don’t know if anybody would really feel great about having an AI coach come in and tell them they’re doing a great job. I think you kind of still need a person. 

For now, at least maybe our beliefs on this will change over time. That’s really the only future projection I see, is just an implementation of AI, because that just seems to be implemented in everything today.

Human Element Versus AI in Company Onboarding

Erin: Yeah, absolutely. And now I think you can like to do AI videos where they take like a replica of your face and they make you talk and we talk a little bit about that and is that the future of like training and it’s like, well, I sure hope not. I still want to have a real conversation with every person that joins our company, you know.

Max: Right. And I’m also not sure that that’s better than the current situation, right? 

Like, our processes are full of Loom videos for me and other people on the team. I don’t know that an AI, if I typed the script, rather than saying it would really save me that much time. 

Maybe if I needed to reshoot something, it would save me a few minutes to edit the script, but I don’t know. My loom videos are usually like 10 minutes or fewer, so I can just re-record it.

The Quest for the Employee “Wow” Moment

Erin: Yeah, that’s cool. Awesome, so I don’t wanna take up too much of your time, but last question, what do you feel, and this doesn’t necessarily have to be related to your company, but what do you feel is something that companies can do to create that “wow” moment to help employees get buy-in early?

Max: I think the “wow” that employees are looking for when they join a company is not so much, wow, I’m impressed. I think that’s what you want from your customers maybe. 

But I think from employees, my mentality has always been this, wow, I really understand what I need to be doing here. I thought I was joining this small company. 

I thought I’d be winging it more than I actually have to. There’s a system in place and I can follow it. And that’s the degree to which I try to impress new hires. I’d like them to. just really feel secure and understanding exactly what they want, what they need to do and what success looks like for them.

Erin: Great, that’s awesome. Well, thank you so much, Max. I really appreciate you joining us today. This has been so great. I wrote lots of notes of things that I wanna share with my team. So yeah, I hope you have a great rest of the day.

Max: Thanks, Erin.

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Oliver Peterson

Oliver Peterson is a content writer for Process Street with an interest in systems and processes, attempting to use them as tools for taking apart problems and gaining insight into building robust, lasting solutions.

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