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Season 1, Episode 12

Onboarding New Clients


Our panel dives into client onboarding — what it means, how we’ve approached it in our businesses, and how you can customize and improve your onboarding over time.


Onboarding new clients

Episode Summary

Our panel dives into client onboarding — what it means, how we’ve approached it in our businesses, and how you can customize and improve your onboarding over time.


  • Kai Davis
  • Meg Cumby
  • Erik Dietrich


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If you’re a freelancer, then you’re not just an expert in your field. You’re also a business owner, responsible for everything from bookkeeping to marketing to customer satisfaction to business development.

On the Business of Freelancing, our panel of experienced freelancers discuss the issues that they have encountered while building up their business — and give you practical, actionable advice to take your career to the next level. We also invite expert guests to provide their opinions and perspectives on how you can better succeed in your freelance career.

Episode Transcript

Kai: Hey, folks on today’s episode of the Business of Freelancing, we’re going to dive into Client Onboarding. What it means, what it means for each of us, how we’ve approached it in different ways over our businesses and clients and how you really customize, iterate, and improve onboarding over time. You’re going to love this episode.

Hey, folks, today on our panel, we have me, Kai Davis, we’re joined by Meg Cumby.

Meg: Hello.

Kai: And Erik Dietrich,

Erik: Hi, everybody.

Kai: So when it comes to Client Onboarding, how would you grade yourself like one to 10? What score do you give? Starting off just for me, I’d say I’m maybe a 4 or a 4.5. I definitely feel like I know what to do, but getting the implementation in place and moving right forward through it, there’s always stuff left to do and stuff left to iterate on and develop. How about you all?

Meg: That’s a hard question. For me, the projects are often let’s say, just for context, they’re smaller, they’re not often in the five or six figures. There’s a couple of five figures, but they’re usually in the four-figure range, and often not that big. So, for new clients, it’s often a smaller, smaller engagement. So in that context, maybe a 5 out of 10. I’ve got some, some processes in place, remembering to always rely on those processes is the key for everybody.

Erik: I might say, a six, silver business, Hit Subscribe. We have Erin who handles account management, so she does onboarding. So some of this it’s not directly me involved anymore. We have welcome collateral, like a welcome bouquet that we send to clients, and it lays out who their points of contact are, and a lot of different things. I have to give myself a fairly good score or our business a fairly good score, because not only is that down, and there’s collateral and things involved, but it’s repeatable, like Erin could train someone else to do it.

So there’s room for growth and improvement in that. I don’t know, if currently, it completely explains everything or clears up all the client’s questions or establishes everything, we think of it as a work in progress. But it is fairly sophisticated, there’s a clear procedure, and between that and a sales call, we’re establishing how we operate, how working with us goes, etc.

So yeah, if I think back two years ago, when I was just doing freelance app dev, or what have you, there was no onboarding, there was just you take on the work and have some kind of discovery call and then start going. So I feel like, conceptually, that’s come a long way, at least, with businesses, I preside over.

Kai: One thing you hit on there, I just want to echo. Starting to turn it into a process like documenting it somewhere, be it, on paper, in a Google Doc, in Notion, just someplace that says, okay, these are the four steps and we can improve and change them over time. But this is what we start with and what we always try to do. It can be such a huge step forward, it just makes it easier to remember and not, dig back in the memory banks, Oh, what did we do three months ago or a year ago last time we onboarded someone instead, but we captured some version of the process to iterate on?

How did you get started with capturing that process, Erik? Was it you writing it down, delegating it to someone else? How did you get that first version on paper?

Erik: It was the delegation. When we brought… In the early days of Hit Subscribe, I did everything that was client-facing. My wife and I partnered on the business, and she was kind of internal like managing. Well, the business started as just me writing blog posts and her editing them. But as we brought people on internally, she would handle the management of the author process and the editors and stuff that we’re creating the content, and I was doing everything external.

I knew our sales pitch, and I knew what we would do, but it was bringing on Erin, who we hired specifically to do account management, it was that at that point, like it almost had to get documented because she was going to be picking it up. So the documentation around that initially was rudimentary. As an improved, she drove a lot of that because she was recognizing I’m often answering the same questions.

So the creation of some of the collateral, the elaboration of the documentation was her but it was really kind of that moment of hiring that it happens. So if you are looking at getting better at Client Onboarding, the thing you might do is almost pretend that you were about to make a hire to do it, even if you weren’t, and document what that person would need to know.

Meg: Awesome way of looking at it.

Erik: Yeah, I wish I could say I discovered that other than accidentally, it wasn’t like I thought of that. It’s just retrospect.


Meg: That’s true of most, realizations in businesses. You just discovered along the way, oh, the design comes, after you’ve come across something by accident sometimes.

Kai: Meg, how about for you? Is your onboarding documented? Does it live in the brain? Since you’re a solo shop, what does that process look like?

Meg: Yeah, a combination of column A and column B, a little bit. Thinking about onboarding, what it actually encompasses? When it starts, for me, it would start, right before after the client and I agree to work together. So, because the process is pretty simple, there’s some documentation, and it’s pretty simple, where it’s after we agree to work with together, I send a welcome packet, which encompasses what some people would find in a proposal since it’s a productized service.

Here’s what we’ll do, what you get, confirmation of the price we’ve talked about. Then outline next steps, which are, I send an invoice they pay it, they connect me with the needed contact, and I send some background questions for them to answer which are pretty brief again.

That’s usually for a sub $2,000 service, that’s often, how else a new client want and what we’ll be working on. But most likely all those questions exist, the documentation, obviously, the welcome packet, I keep that pretty simple, and that exists. I’m sure I’ve had that written down, but it’s so ingrained in my memory now, just yep, here are the steps we go through.

Kai: Especially with a productized service,  it’s natural that the onboarding just becomes part of the service overall, since like, hey, they’re getting this experience, it isn’t a separate thing. It’s part of what they’re paying for, and it just flows forward.

Meg: Yeah, if I think about it, really, the onboarding is written in the welcome packet, because it has the next steps in there. So yeah, it’s written down for me and the client, so they know exactly what’s going to happen next.

Kai: As I was thinking about this topic, and this episode, one thing that came to mind is the difference between, say, a $500 project and the onboarding you do. The $500,000 project and the onboarding you do on one level, there is a bit of difference there. Like for a $500 project, I’m going to send them a PDF, they get an automated email, hello, thank you for working with me, share me on this, click here.

With a $500,000 project, me and my imaginary team of expert, consultants will fly out to their location, do an onboarding, do a kickoff, talk with them, have the celebratory beer and steak as every large project has. But maybe, within that, the details, the actions we’re taking, it’s kind of identical, I am setting expectations, I’m laying out boundaries, I’m sharing information and requesting information. I’m confirming the timeline of the next step and no matter the magnitude of a project, even like the $50 million project, it’s still those same beats, nothing really changes there. How about for you guys? In your own businesses, do you see something similar? Or does that resonate with you?

Erik: Yeah, for me, with Hit Subscribe our customer lifetime value tends to be usually in the six-figures, maybe sometimes, five-figure one-off engagements. For anyone listening out there, people in custom app dev, in particular, would understand this. But if you are doing a lot of lengthy custom projects, you’ll know intuitively that you’re going to have at least a call, if not an in-person meeting for something that’s in the five-figures, six-figures, plus, if it’s like three-figures or four-figures that might just all get done over email.

So there is this sense that the bigger the project, the more high touch the sales processes, but I think that there are elements that are common across that. For instance, almost without exception, because we’re in that middle area for Hit Subscribe. Our sales cycle is a series of emails, then one, maybe two phone calls, and then we work together.

If we were for some reason, negotiating, like an absolutely enormous like seven-figure content process, a lot of our onboarding would be the same we just might, as you mentioned, fly-out or have the steak dinner or what have you ahead of it. But it would largely be the same kind of activities, expectation setting, defining the rules of engagement, how you do and don’t work. All of that would go on regardless.

Meg: That’s true. What would be the definition of onboarding for people that may not have thought about this in the exact term?

Erik:  Actually to back up if I think about myself like in the early days of freelancing, just doing like freelance app dev or coaching, the kind of things I was doing. I might have thought of this of like, well, what do you mean onboarding? It’s like they have an RFP or whatever, and you answer the RFP, or you talk to someone and you discuss and maybe they hire you, or maybe they don’t, and then you do what they say.

So, it might be worth clarifying, what is onboarding for people that don’t have that experience. My take on it would be even if you don’t, aren’t aware of it, you’re doing some form of onboarding, it’s just probably what’s mostly happening is that it’s your client, defining how everything’s going to work rather than you. The thing is, that you might want to become aware of is that’s not inevitable. As you get more mature as you get a standard operating procedure in the business that you’re doing, you’ll start to have…

It might come initially in the form of rules, like, I don’t answer email on the weekends, but gradually, you build up a series of things that you do that are true of how you work with clients. Then it’s like, if nothing else, introducing clients to those rules, so to speak. So setting expectations, informing them how you work, etc.

So I’m surrounding it and defining it with examples more than like an actual definition. But that’s how of it like the rules of engagement if you will, and if you don’t define it, they will. So it’s better if you do.

Kai: Yeah, very much agreement for me. You’re right, Erik, it’s kind of is squishy, it could encompass a time, it could encompass just like that they have paid, I have requested access to GitHub, we are done, but you’re right. In my mind, onboarding is really intentional time to define the parameters, the boundaries, and the expectations on both sides within a working relationship. The dating metaphor always comes to mind if I’m onboarding, you go on your first or second date, you’re still saying like, Oh, no, I don’t text on the weekend, because it’s my personal time, or I love yoga, whatever it might be, hello, please date me.

But it’s exactly the same when it comes to onboarding a client. Here’s what it’s like to work with me. Here’s how to get in touch. These are common questions I have for clients, ask me the common questions you have. Here’s what other folks have asked me in the past, just to make sure you’re on that same floating, or on that same level when it comes to Okay, what is this multi-month or multi-year working relationship going to be?

Not to say it’s locked in stone with onboarding, but onboarding is at least an intentional time to say, hey, let’s have these important conversations. Let’s level set in terms of communication responsibilities, who should ask the dumb questions that come up, that always come up? Just so everybody’s on that same plane?

Erik: Yeah. So does it include the sales call? I think is a good…  I think yes, it’s almost to me, I think of onboarding is once for us, there’s a sales call, that’s when things are serious. So I conceptually, think of me getting ready for the sales call, the sales call itself, and then sending a proposal and some of the stuff we do, so everything from sales call through, Okay, now we’re working together,  I think of it as onboarding personally. Is that kind of the right timeline for both of you? Or does it start earlier?

Meg: Interesting. But what do you think, Kai? And then I will [inaudible].

Kai: I’m not opposed to sales overlapping or being part of onboarding. Since you’re absolutely right. It’s when you start to find like, Oh, no, we’re only available two days a week or we’re here, no matter what you need. We’re in Slack, ask us the question. So there definitely are onboarding elements that move into the sales process. What comes to my mind, though, is I often think of onboarding as extending into honestly, the second month of the engagement, since there’s going to be meetings, there’s going to be conversations. You’re going to realize three weeks in Oh, I did not tell them this very important thing, let’s have a call, have a DM, just catch them up to it.

So if we’re saying onboarding, can move into those initial conversations and sales calls, it also could spread out or some elements of it spread out to month to working together as you start to get everything moving forward, just because there always are parts that need to be explained or need to be synched upon.

Meg: Yeah, it’s interesting how it could be very much that moving target and people can define it for what makes sense to them. For me, I would probably do it after. But it depends on how you’re… Like if you’re thinking about onboarding as setting expectations and setting up a great experience for both parties, you could see it as starting with the sales call, for sure, and really even as far back as you’re setting an expectation, your website.

For me, I’ve always considered it more like if I’m thinking how I’m defining it and so there’s obviously fuzzy. It is more and more after maybe at the sales call point and then through to the point where I get that background information and the work is starting on. The official what they are paying for has started. That for me is because I’ve got a productized service that’s very defined deliverables. Let’s say it’s not a coaching arrangement or it’s not a custom, often not a custom arrangement. So that’s where I put the parameters but it could shift, by the way.

Kai: And discovery within a project also overlaps with onboarding, since you’re requesting information, sharing them on information. I think of my podcasts tour service where I get clients, booked on a dozen to two dozen podcasts that are looking to appear and there’s the audience. We start off me requesting information, me laying out the engagement of the next steps. But even at the start of the second month, we’re still saying, Okay, let’s run through a real pretend it’s live, podcast recording to make sure we could overcome unexpected things and smoke test these different topics. So there is an element of still leveling up that client to working with you that far into the engagement.

I’m just doing a reread of Kathy Sierra’s excellent book Badass. One thing that comes to mind through this conversation is really onboarding serves to help make the client badass at working with you. You’ve worked with dear listener as on this recording dozens of clients, but a client working with you, it’s the first time ever working with you. So onboarding helps say here’s how to work well with me, here’s how to make sure this is a great relationship.

If you’re not spelling out, I don’t work on Fridays, or submit through the forum, please don’t email me if you find a bug. It’s going to be a hard relationship to get started. But if you lay out these expectations, shared expectations, it becomes even easier just level that client up over time.

Meg: Yeah, I like that view because often when we’re talking about our onboarding, it’s about setting expectations of do not, this is the limits of what I’ll do. But like I said, that does help frame it more, it’s is like, okay, yes, it’s not just me putting up my boundaries, it’s making sure that we both have a great experience and that everything’s clear on how things will go so that everybody’s happy with or not happy, necessarily, but everybody’s not that the expectations are not mismatching, with the experience.

Erik: It’s paradoxical, but as part of onboarding, and why I conceptually think of it starting in around the sales call, is there’s also an element of disqualification there potentially, as in if you’re saying, I don’t answer calls on the weekends, or what have you. If that’s going to be a deal-breaker for that client, even though passing on businesses, though, is always a bummer, you want to surface that right away and say, this isn’t going to be a fit.

So as you’re establishing this is how you can best work with us. There’s also this element of assessing fit. Part of the onboarding process is going to be that it’s a lot better for both of you to learn now than six months from now that it’s not a fit. So I do think there is this element of like on the optimistic side, we’re ensuring it’s a fit, here’s how to work well with us. Here’s how we’re going to make sure this is a home run. But then on the flip side, or maybe we’re not the right solution for you, is an important part of the process.

Kai: Yeah, full and enthusiastic agreement for me on that point, in a sense of your onboarding a week or a month in returns, whoa, this is not a good relationship. I view that as a success for onboarding because if you didn’t surface it, then maybe it doesn’t surface until a month three months six, or when you could have collected testimonial.

They’re like, no, we pass because oh, we weren’t a good fit. We didn’t identify it, and a better onboarding process would have led us surface this or address it and eliminated, oh, I could compromise in this way. You’ll compromise in that way. Great. This is now a fit again. But if you are doing onboarding, you don’t really have that space to surface those objections or figure out how to problem-solve through them.

Meg: Yeah, in designing your onboarding process, you want to… It’s not only about making sure that you’re setting the boundaries that you need to set so that you can perform well and be able to be the best you can do for it. But like also, jus surfacing those early really does make sense too, so that people, like you’re really not causing problems later on.

Kai: Switching tracks for a second, if somebody in the audience is listening, they’re saying this onboarding thing sounds kind of good might have handed off a couple of those disaster clients in the past. I’m curious what each would recommend as like the minimal viable onboarding, just get started with this. You definitely don’t want to make it too fancy or overwrought or over-engineered at the start. But what are the essential elements that we each see as being both essential?

For me, the thing that I’ve always tried to short circuit or pull back from has been a kickoff call since sometimes it’s like, oh, I don’t want to get on yet another call but time and time again I’ve seen just getting on a video call spending 20 or 30 minutes talking with the other person, seeing their face, hearing their voice letting them see you are an actual person, not just an avatar and some flair based emojis in Slack, really helps develop a better relationship there.

So whenever I get that urge, maybe I’ll just skip the kickoff call this time, I’m starting to see that as a signal, oh, no, I’m having a little resistance to it. This is probably when I especially need that kickoff call. when we need to get on the line and just have a chat. How about for you guys similar experience or other things that come to mind as those onboarding essentials?

Meg: Agreed on that? Would you kickoff call and client qualification call? Would those be separate for you?

Kai: For me, they would. I think of that client qualification whole is more of that sales call, hey, let’s see if you are a good fit for this service and [inaudible]. Hey, now that you’ve paid, let’s talk through the nuts and bolts, what happens next, the timeline for this engagement and answering those questions.

Meg: It makes sense.

Erik: I’m trying to think through what I would consider in retrospect, our business is like minimum viable onboarding. I think that establishing the particulars around communication, so when and how you’re available, as a chat phone call. That’s a big one.  Laying out the next steps, okay, so we’re engaging, one, two, three, four, this is what’s going to happen.

Then another thing that comes to mind is getting an agreement on essentially the scope of the project. So one of the things that we do as Hit Subscribe, it’s relatively easy to build the custom packages that we do around creating content for clients. But to call out exactly what it is, we’re delivering this many blog posts a month, and maybe a white paper this often or whatever. Here is exactly what it is we’ve agreed and what some of the specifics around it are, and here is the price. So all of those things come together, what happens next, what the rules of engagement are, how we communicate, and what does the project look like in very well defined terms.

Kai: Mmhm, mmhm.

Meg: Yeah, agreed. For me, the kickoff call, definitely for anything. I used to do the background questions, I get the information I need for my productized service, rather than a kickoff call I get through there. But I 100% percent agree that you need to talk to the client. So I’ll talk to them.  I combined my qualification call and my kickoff call. Once I get a sense of if they’re good sense, then we’ll do a little bit of preliminary information on that call. So, I combined those two for a smaller service. That might make more sense. 

I don’t think I’d had much of communication. Certainly setting up expectations around if you haven’t done it in a proposal around when you’re getting paid and how you’re getting paid, that would be another one maybe to add in there. It’s actually a really good time during our onboarding to… I’d be remiss if I didn’t mention it, it’s a really good time to set the expectation that you’ll be asking for a testimonial or a case study.

Kai: Mmhm. Excellent, polite.

Meg: [laughs] As somebody who does social helps, people get social proof for a living. I don’t think I could miss that. It’s so much easier if you set that expectation at the very beginning to do that.

Erik: I’m really interested in that. Do you recommend that people kind of build in and say, hey, here’s the terms of success? If that goes well, I’d love to get a testimonial about it, something like that when there?

Meg: Yeah, sort of the line? I like the basic line, and again, this depends on the scale, like what scale of clients are you working for? What’s your service, but I’ve seen as complex as having it in the contract terms, that there’ll be a good fit of effort for asking to provide a testimonial. So, if you’re, at a certain level that might be great, but really, it can be as simple as in a welcome material saying near the end of our engagement, I’ll ask for feedback, and indicate how that will happen.

I like doing it on a wrap-up call. With your permission, I’ll use that feedback as part of a testimonial or case study that you can review. It’s just sort of setting up that expectation that you’ll be making the ask, assuming things go well, but certainly you’ll ask for feedback either way. Then saying that with your permission. We’ll use it as a testimonial that lets them know that they can say no later if they don’t want, but at least they’ll know that the ask it’s coming

Kai: I always avoid unexpected surprises too, it’s not like hello, we have three days left in this project. Please give me a testimonial. It’s, we’ve touched on this three or four times maybe just once or twice, but we’ve raised it and they might not remember but they at least know this has happened that you’ll be asking for a testimonial.

One thing I’ve often seen and recommended in the same approach is saying that oh, I’m going to ask for referrals to people that you’d love to see me work with, as this project wraps up, or if we hit these success metrics, just to again, plant that early seed and have it be a natural segue into it, as the project starts winding down or wrapping up.

Meg: Mmhm. Certainly it removes that awkwardness for you and them like so now at the expectation. I like saying like, you’ve almost made the commitment to get that stuff so now, you can’t ask for it because you’ve already told them you’re going to ask for it, it just removes the awkwardness. Maybe that’s a way to think about onboarding as just removing awkwardness for people and the opportunities for misunderstandings. That’s just in the interest of everybody.

Kai: I love that framing of it in a sense, that gives a nice natural way for a listener to iterate on their onboarding, like, document what you’re already doing, or what you want to be doing, run through it. As you go through that engagement, make a note to yourself, okay, what felt awkward Oh, when I sent them the invoice for the second leg, it felt a bit awkward. What can I do earlier on to outline how this is going to move forward, or at least address these potentially awkward points and just slowly smooth it over with time? It won’t ever be perfect with one iteration, but it’ll at least be heading in that direction.

Meg: How to deal with scope changes, there’s another thing to put in your onboarding. Like, what happens if the project deviates, the needs deviate from both of your expectations? How you’re going to handle scope changes?

Kai: Mmhm.

Meg: Definitely, yeah. Anytime noting where there’s friction during your projects and seeing if that could that have been solved with better expectations set at the beginning or a better process than at the beginning?

Erik: This is something that just struck me as interesting because it comes up with our business, but do you in your businesses ever see turnover in your client contact and then have to re-onboard a new person that’s coming up to speak as that is something that happens with us. On a somewhat regular basis that are our former sponsor leaves, and then a new person comes in, and we help them get up to speed and rerun our onboarding? Is that common? Do you both experience that?

Kai: I do not. I work with definitely smaller, more indie based businesses. Typically the point of contact for me is the decision-maker, is the sponsor. But what I do sometimes run into is we’ll start off on project A, project A raps off, and then they decide to move forward to project B, maybe it’s a one-off project into a recurring project. So there are elements of re-onboarding them or resetting these expectations. But it’s not as heavy as ellipta, as the first time is that it’s like, oh, we were doing A, B and C before now it’s C, D, and E, no more A and B, and just sort of level setting again with that same person. How about you, Meg?

Meg: Yeah, turnover? Not as much of an issue because usually, I am working with smaller indie companies. So usually, I’m working with the people that don’t turn over as much. So, that’s not so much of an issue. Again, like I said, what I end up doing is often having recurring, them come back, not for other engagements. So there’s a much smaller, it’s more like project onboarding, than it is Client Onboarding, we’ve already talked. Certainly, it’s good to have a sense of whether or not something’s changed since the last time you’ve worked with the person and do you need to re-onboard them with new expectations or things like that.

Kai: What’s the process like for you, and Hit Subscribe, Erik?

Erik: Typically, it’s as you were saying, it’s not as heavy a lift. Because often, if somebody that’s our main contact, transfers into a new role, or leaves the company or something, they’re backfill is usually coming up to speed. They’re leaning on us, educate me about the prior history of this arrangement, and you’re an incumbent, so you’re in there as a favorite vendor. So that tends to be easier, but we’ll typically maybe offer like, there is some precedent to get on and essentially rerun our sales call, like I have a deck that I run through with some information that’s specific to the client, and then some general information about how we work.

So sometimes we’ll actually get on a call and go through that or we’ll just send the collateral and agreements that we’ve sent in the past and do some explanation. So it’s the same process as sales and post-sales onboarding, except to almost by definition, a more receptive audience. If it’s something that comes up for anyone that’s where having documentation and things that you share with the client comes in really handy, because then it’s a no brainer, the new person emails you and says, hey, how do you work?

Oh, here you go, you can read all about it, let me know if you have any questions. Versus if you didn’t have that collateral, then it’s, oh, well, , let’s get on a phone call. Then that’s more improvisational conversation.

I remember this from a lot of years where, without a deck, for instance, I could do a pretty consistent sales call, but I might forget to cover a certain point or miss something. So when it’s documented, written down, and you have collateral, you don’t forget things. So, if re-onboarding is something that’s going to come up for you, having that stuff is super valuable.

Kai: A huge, yes for me. I have been doing consulting, freelancing, and contracting work for over a decade now. I’m only at the point where I’m like, Oh, nicely designed collateral, nicely designed resources. They provide so many benefits in terms of keeping me on script, making it easier, and not rewriting the same thing again, and again, and again, for the client or the lead. We could do an entire episode, we should do an entire episode on that sometime. But yeah, hugely [inaudible]. If anybody out there is saying, should I create these evergreen assets? One thousand percent, yes, it helps more than you think it well.

Meg: Yeah, the importance of good templates, too, and unlike just having templates. I remember, in earlier days, even though I used largely the same thing, just re-jigging a lot of not having to have too many fields that you have to re-customize because it can waste so much time on stuff. For example, one thing I took out of my onboarding because I found I changed it so much was that my hours of work.

Number one, it doesn’t really matter for the types of projects I do, whether I’m working from 8 to 4 my time, or 10 to 6, it doesn’t really matter. What I found was actually that was causing more friction than anything, because if I answered an email outside of those hours, then it looked like I was breaking, then those boundaries don’t matter. Yeah, it’s more important. So yeah, just keeping the customize of like, that’s something that changes too. But yeah, keeping those customizable, or those more of changing things, maybe somewhere, at least all in one place, so that you’re not constantly, rewriting things is huge.

Erik: Something that I’ll say too that it’s hard to overstate is if you have a documented and scripted process for sales, and then between sales and engagement, and through the beginning of engagement, not only does all of that help you and potentially help you in business, or at least make winning business more smooth, but it’s like very persuasive to clients. Because, if it’s you, and then some other people that are just coming in, in the sales call is almost them interviewing you, for those people. But you say this is how I work, it shows that you have experienced that you’ve encountered different scenarios in the past and that you are a pro at this, and you know exactly how to walk them through it.

Just from experience over the years, I can’t tell you how different that makes sales and post-sales go. Because it is the adage, I’ve heard a lot there is like somebody is going to define that call, somebody is going to get organized. The default for a lot of clients is it’ll be them. Then it’s almost like they’re giving you a job interview, but if you lead and you say this is how we work. Here are how we handle these various situations, etc. The client flips into a more passive mode and says, Oh, this person knows what they’re doing. I’m going to defer to you on these things.

You wouldn’t believe some people might think that this wouldn’t even work with the enterprise. It does. It works with like companies and people are companies of all sizes, people at all levels of the org chart. If you lead with that organization, and you demonstrate that you’re experienced and organized, they will naturally defer to how you were saying things should go.

Kai: It’s a strong self vote of confidence. I’m confident enough in my skills, my abilities, my sense of business to say, this is how I work best. Yes, we can customize the engagement or how we’re working together, depending on mutual agreement, but this is the starting spot. I always think of the dentist and the dental office as a good comparison for the type of business I want to run.

Not once I got into the dental office and been like, so tell me about how you work and they’re like, I don’t know, what do you need?


Kai: I want dental advise. I’m scared I want to run out of this dental office. But if they show up in there like we start with this, we do an inspection we do a cleaning da da da, if you have a cavity da da da data, and it shows like, Oh, they have done this 10 million times. I don’t have to even think they will ask me when I need to share input. It’s exactly the same for our clients. If somebody shows up and it’s like, how can you help? I don’t know. I need some marketing. It’s not an expert level look.

Meg: Agreed.

Erik: That’s a great analogy, by the way. I sometimes think of that in terms of like you’re picking among a couple, a few housing contractors or something like fixer leaky basement, if one shows up and is like, alright, this is what I do I run this inspection, it might be one of these two types of problems, and so on and so forth. Then another one shows up and is like, well, I don’t know, show me what’s going on? What do you want me to do?

They will inspire different levels of confidence. But like the dental metaphor, hits home a lot harder, because that’s like a visceral terror. The idea of you show up at the dentist, they’re like, oh, what do you want done? What do you think I should? I would run out very quickly.



Meg: I don’t want to go to the dentist’s office to begin with.


Meg:  Oh, dear.

Kai: One more advanced move that I’ve done in the past, I don’t do it currently, just because business model has shifted, but when I was doing when… When basically, the bread and butter, and the main thing I would sell is multi-month, typically three to nine-month marketing promotion, digital PR engagements.

I would intentionally set aside 33 to 50% of that first month’s payment and say, Okay, this is now my budget for gifts, onboarding expenses, or resources to send to the client. Because I also view onboarding as building a stronger or a stronger relationship with that client, and just being able to set aside and say, Okay, I got $500 in the bank here, oh, I saw a client tweeted about enjoying this author. Let me see if I could get like a signed copy of a book and send it to them.

Or, oh, we need to create this little asset or resource or, hey, let’s send them a bottle of wine, they just had an anniversary. It’s just small touches, you could do that help show a high level of polish and show attention. For me, at least, it was a lot easier to spend that money when I said, Oh, it’s already set aside, and not, do I really want to spend this money, it could be my profit, yada, yada.

So small things, definitely not an intro were a beginner move. But for people selling larger ongoing projects, it can be useful to both think of onboarding again in that larger, longer timeframe. Set aside some cash set aside a budget line item, just so you could spend on things that relate to onboarding, over that onboarding period.

Erik: That’s really interesting. Not something that would have occurred to me, but that is probably an unrivaled way to make a great impression on people is those types of touches.

Kai: Also helps move over any rough bits in the first month or two, like, Oh, communication on that call was a bit nasty, or I thought we were doing A and B, we’re doing B and C but that relationship is good. They sent us this thing, it feels positive and feels like a friendship or working friendship, then Oh, they are vendor number 347. Let’s get vendor 348 in here, we go do a better job.

Also how to referrals and referral asks just to strengthen that relationship early on. So when you move into testimonial ask or referral ask, it feels… I’m not what word to use, not like they owe you something, but it just feels easier for them to reciprocate in that way.

Meg: It generates the good feelings, the brand loyalty.


Kai: Moving into a wrap up here. One thing that stands out to me from our conversation here is there’s no absolutes when it comes to onboarding, it’s squishy both in terms of what you can do, where you can start and swishing in terms of well, where does it really start and end? For some of us, it starts within the sales call for others. For me, it extends, into that month, too.

So dear listener, if you’re saying, hey, where do I get started? Well,  just starting to document, what you’ve been doing, what that standard operating procedure looks like. Using that as that base template to iterate on, really is the easiest and most successful way to get started.

How about for you guys, what feels like the absolute essentials or the most important takeaways for our listener?

Erik: I would say, if you have no concept of how to do your onboarding process, the very first thing I might start with is write down what are non-negotiables or deal breakers for you. I wouldn’t have an onboarding process that’s just you telling a client what are deal breakers for you. But’s it’s a great way to get started, what are the things that would just blow up an engagement that would be terrible, and you write those out because those are probably the easiest thing to come up with.

Then once you’ve got that in place that might start you thinking about other aspects of getting to know the client and working together. So I’d say start with those because those will help you get in the spirit of what you’re thinking but then don’t actually make this your official process until there’s some positive stuff to go alongside and here’s how we don’t work. That’s how I don’t work but here’s how I do. Try to think of what would, it was Kai, you said like, make the customers awesome. I forget the name of the book.

Kai: Badass.

Erik: Yeah, okay. But balance that out. So here’s what I don’t do. But here’s what I do. Here are some of the nice things that I found valuable over the course of time and helping clarify things. I have my patented discovery call or whatever it is. So start with the non-negotiable bads and then balance those out with good. Then you’ve got… The beginning of a pretty solid onboarding process that’s just educating them about how to work with you.

Meg: Yeah, plus one to everything you both said. As a starting place, like writing down what you already do, at the beginning of a new engagement, and figuring out like I said, even just documenting that, or if you don’t have a regular process, figure out what might be commonalities and just try to put together a process.

Then I like the idea of starting with a welcome packet, which can literally just be a PDF, a couple pages of PDF, and just to put that in, like, here’s how dear client we’re going to start working together. That’s a good one on one level step.

There’s certain things that are going to happen anyway, the payment, communication, what you need from them to start working to get like, or  there’s something that happens that, was intentional or not, there are things that happen there. So just documenting those, how they happen, and maybe start doing those the same way each time and then letting the client know, even just a PDF, that’s a good way to start.

Kai: I like it. How about a picks? Anybody has top of mind picks resources, books, whatever you may have to share with the listeners to help them along on their business and freelancing journey.

I’ll start with one of mine, I referenced it already in the call but strong recommendation go out and buy a Badass by Kathy Sierra. It’s a book really about making users awesome. But it extends so much beyond like, hey, how do I make this program or make a customer awesome to, hey, how do you make a client? How do you make somebody who’s buying your services, truly awesome, changed them for the better? One of the most impactful books I’ve ever read? Definitely on the top five lists. So we have a link on show notes, strong recommendation for me. How about you, Erik?

Erik: I don’t have anything topical this week for onboarding per se. I’m trying to remember I’ve definitely read tidbits here and there about it. But I don’t know if I could give a concrete book recommendation that would be good. But just as a personal fun thing. I know a lot of people are probably familiar with the Expanse, the sci-fi series, and the books by pen named James S. A. Corey.

What I discovered recently is that James S. A. Corey is actually two people. I read a book series by one of them whose name is Daniel Abraham. It’s in the fantasy side of the fantasy sci-fi genre, but it was really enjoyable. So, to me, it’s almost like discovering this author, it’s a weird situation, but it’s like discovering that there’s this whole bunch of other books by this author that I like. So in case, anyone doesn’t know that I can give a link to his site. But Daniel Abraham is his name, and he’s written a bunch of other books besides the Expanse, and I definitely thought they were a fun read.

Kai: Oh, yeah. good tip, and good recommendation. I did not realize it was a Voltron team of authors.


Kai: About for you, Meg. Pack a goal, one non-topical.

Meg: For topical. I’m sure a lot of people have heard of Calendly before but for picking, getting helping people to offer times up for calls or meetings. Calendly, I don’t think there’s a day that I don’t use this. There’s a free plan for one type of event, a paid plan I can say worth its weight in it well worth what you pay for it. I think it’s $8 a month for the lower tier of the pay plan.

But just to be able to show people times available, you can set your availability, it syncs with your Google Calendar, probably a couple other calendars so that you won’t you won’t get double-booked. It just removes that whole dance of here’s three times I’m available. Are you available? No. That back and forth. I would not be able to live without that. So be very handy for those kickoffs and meetings and with the client.

Kai: I will chime in one thing I love using Calendly for especially when it comes to onboarding is just setting up like a different meeting type. So I have a normal like quick conversation one and I’ll just share that in Slack, share that on onboarding. But for this kickoff meeting, oh, if I maybe it’s a 90-minute meeting, maybe I’m asking specific questions in that Calendly forum, I’m like, hey, what are the top of mind questions? We have consultant experiences gone poorly on your site before just to start surfacing some questions or some comments or topics for me to work into my agenda.

So strong, enthusiastic plus one on Calendly. It’s a powerful resource and when you start using it for like, oh, what do I want to ask for this specific type of event, it truly leaps forward to an even better resource.

Meg: I like that a lot. I also like with the multiple day types, I can customize the availability so that the times are not bananas for the person’s time zone so I’ve got a Europe time and West Coast time, being on the East Coast, so I’m not offering times that are like four o’clock in the morning their time they’re just to help make that experience a little bit better.

Kai: Thank you, dear listener, for tuning in and listening to our Perspective On Client Onboarding. If you’ve got a question or you’ve got something you forgot, when it comes to onboarding, you want to make sure we hear it. Go ahead and take a look in the show notes, and shoot us an email, or shoot us a message.

We’re always delighted to hear from you all, but until next time, have a great one.