Onboard Yourself Like a Leader - The Ultimate 30-day Checklist

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Hey, CS Psychos, Rachel Provan here. And on today's episode, we're going to be talking about how to onboard yourself so that you can make a great first impression in your next CS leadership role.

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We'll get into exactly what to focus on and when, the mistake most CS leaders make that screws them over for the rest of their time at the company, and how to set yourself up for long-term success while knocking out some quick wins. That's all coming up next right here on Psychology of Customer Success, stay tuned. Humans don't think or behave like computers.

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You can't just run a command and get them to do what you want them to do.

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So why are you still basing your CS strategy based solely on logic? I'm Rachel Provan, CS leadership coach, award-winning CS strategist, and certified psych nerd. I teach CS leaders how to build and scale world-class CS departments using a combination of strategy, leadership, and mindset, using my secret weapon, psychology. Come join me every Wednesday for Psychology of Customer Success, where we'll dive into why people do the things they do, what motivates them, and the effect that has on your CS strategy, team dynamics, and executive presence. Make sure to subscribe on Apple, Spotify, or wherever you listen to podcasts, and make sure to share it with your CS bestie. Talk soon, and here's to your success. Okay, welcome back. I don't know if this ever happens to any of you, but do you ever have this thing happen where you are working on the things you're supposed to be working on? You're plodding along. I have a number of new initiatives that I'm working on for things that I think are really going to help you guys. I'm jazzed about all of them, but they all take time. I'm working on them. Then something out of nowhere that you weren't even thinking of doing just bursts out of you. I had this idea for an onboarding checklist for CS leaders in a new position. Every time you start a new position, it's a little nerve-wracking, and you never really know how onboarding is going to go. I had all these plans of things I was going to work on, and then nope. In about three days, I wrote everything for this onboarding guide, which is really fast for me. I guess it just needed to be out in the universe because that's what happened. I'm not going to waste too much time making sure that it is absolutely perfect on the margins and things like that. I'm just going to make sure that I get the information into your hands because I think that's what's needed here. Onboarding, it's kind of a question mark. When you start a new job, you just don't know what it's going to be. I saw a thing the other day on Instagram, and it was very relatable. It said something like, startup job day one.

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We expect you to be able to perform this entire job yourself by the end of the day.

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Corporate job day one. A password tool is used to secure your computer from bad guys called hackers. Really, that is kind of the experience that I've had in both.

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Neither were what I would consider to be ideal, but more importantly, neither gave me what I needed in order to do the best job I could. No one really provided the information I would need or the right meetings to go to. It's just a really tricky thing to leave in someone else's hands.

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Most people just kind of expect the company to handle their onboarding. Look, maybe they will, depending on what level of company you're at, but most onboarding is non-specific at best.

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They don't know what you need to know to succeed in your role. Honestly, a lot of onboarding is created by HR. Sometimes you have the executive leader of that team creating it, but most often not. I found there aren't a whole lot of concrete guides on how to do this for yourself. I've also found that a lot of companies, especially startups, really expect and appreciate when you know how to come into a place, take the initiative, and go in search of what you need, ask questions, learn what you need to know, and then present it. When I've done that in previous roles, that was what really knocked people's socks off when I would come into a role and approach it this way. So I am sharing the magic with you all. What I created was a 30-day checklist for the first 30 days of your new role as a CS leader. It's almost day by day. It's definitely week by week, and certainly the first week I go day by day. I'm not going to get into every single thing on the checklist here because it exists for you to read. It's a checklist. It's not long.

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But we are going to get into some of them so I can dive a little bit deeper. I know that some people like me really like to hear about something rather than just read it. For me, it goes in my brain better that way. We need to remember first impressions matter. In your first month, you're not just getting onboarded. You are showing people what customer success is and what they can expect from the department. Even though you might be super excited to be getting started, and you want to show everyone they made the absolute perfect choice in hiring you and not know how they ever lived without you before, the best bet here is to actually suppress those natural instincts. Slow down, shut your mouth, and listen because you don't have context yet. What I'm going to do here is just kind of walk you through those first 30 days and give you a little bit of context. The 30 days actually starts before the first day. What I like to do to just start out on the right foot is just reach out to your manager a week before or a few days before and express excitement about starting and ask for any materials that they might have on hand that you could review so that you could hit the ground running. Most of the time, they won't really have much for you, but they'll appreciate the ask. If they do have something, read it.

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But this is why I like to do it a week in advance. It's not like, yeah, we have this 230-page SOP book you can get started on. You want to give yourself a little time to read whatever they provide you. Generally, that way, it's not just this awkward thing of like, you've been through the interview process, they've hired you, everyone's excited, and then just like radio silence until day one. It just helps buffer that time really well. Once you're actually in the job, everyone gets really nervous about their first day. Honestly, in most places, your first day is going to be spent filling out paperwork. Bring your passport because that's the best kind of ID for them to need or have a scan of it. Complete your HR paperwork. You're going to be making sure you have access to all the right software. Touch base with your boss. Ask to have like a 30-minute meeting with them that day. If they haven't already scheduled something, most bosses will.

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But in the meantime, the first thing you want to do is send an introduction email to your team, to your direct reports. Basically say, hi, I'm your new manager. I'm so excited to get to work with all of you. Here's a little bit about me, a little bit about your professional background, a small personal tidbit or two that's non-offensive. My favorite food is popcorn, and I like the Steelers. I don't even know what sport that is personally, but I know that's a team. When you talk to your boss that day, just discuss what you expect to focus on in the first week. Ask them what they'd like you to focus on. Let them know anything you're thinking about looking into. Explain what you've already set up and establish a check-in cadence for during your onboarding. How often are you going to talk to your boss? How would they like you to check in with them and give them info on what you've learned? Who should you go to for questions? Things like that. After that, you're at work now. You got your first day down where really nothing real happens. The first week is all about having open ears and taking lots of notes.

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You're going to identify all the important meetings that you want to be on and make sure you're invited. All-hands meeting. If you should be on a go-to-market meeting, hint, hint, you should. Maybe an executive team meeting. You want to make sure you have all the correct invites. Again, confirm with your boss. You want to schedule that first team meeting by the end of the first week. It's really weird to have a new boss whose face you haven't seen yet and who you haven't communicated with. I don't know about you, but whenever I've had a new boss, I want to get a sense of the vibe right away. They're not going to get that through email.

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They're only going to get it through seeing your face, hearing your voice, and seeing how you interact with other people. It doesn't have to be a big first meeting. Again, you're going to be asking a few questions, listening, and introducing yourself.

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That will put everybody at ease because whenever there's a new leader, everyone's first thoughts are, oh my god, are they going to hate me? Are they going to fire me and bring in all their own people? The sooner you can allay that fear, the better because they're going to be completely distracted until you do that. Whether or not you have fully taken the reins yet, work is going on.

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People are renewing, not renewing. Strategy is existing whether or not you are taking control of it. So you don't want them distracted and stressed. Let's see. You want to start having your first one-on-ones with direct reports that week and the next week where you really just get to know more about your direct reports, talk together about how each of you can work best with each other. For me, I prefer questions in Slack. If you want me to actually do something, review something, remove a blocker, send that to me by email. That's me. That's my personal preference of how I can track things best. You might want to ask your direct reports that. If you have a lot of them, that might be a lot to keep track of. But at least saying, hey, this is how I like to work and giving them a sense of that can be really useful. Asking them about their strengths, their weaknesses, what they want to do with their career. These are all nice things to do to start building a relationship. The number one question that I recommend that you ask them is, do you feel that your work is valued here? And check their facial reaction because they may or may not give you the true answer to that because their guard is still up. They don't trust you yet.

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But check their face. For a lot of people, that answer is no. And that's something that you want to change. Even if you can't give them a $30,000 raise, you always want to make sure that someone feels appreciated and that their work is valued. So you're asking that question tells them that you actually care about that. And again, you're there to listen, not to talk on and on about yourself. Find out their sense of the company. What are you guys doing well? Where could you use some improvement? What are some things that you've tried to fix things that haven't worked in the past there? That can be really useful in terms of, hey, now you know the history and you don't go trying to fix something in a way somebody did six months ago and everyone's kind of sitting around rolling their eyes, waiting for it to fail again. Because you can't assume like, aha, I have the perfect answer to that problem. You don't know yet. You don't know the nuances of the company. You don't know what factors are creating influence on the problems. You might think it's a simple problem and it might be much more complex and much more upstream. So again, this is why we're listening. This is why we're taking notes. As you meet with the direct reports, see if there are any themes that are coming up. Are they all saying you're really bad with upsells?

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The upsells aren't aligned to the customers. They're not interested. Or your retention is really bad because they never have a chance to talk to the customers again, except maybe once a year after onboarding or when they're asking them for a renewal. See if those things are coming up over and over or if it's a mixed bag. Because if they are coming up over and over, that's something that, okay, this really does sound like an issue. I'm going to dig deeper here. I'm going to want to sink my teeth into this. Keep your eye out. Don't commit to it yet. Keep your eye out on those things for quick wins because as you're there, you do want to score a few quick wins within your first month, not your first day, not your first week. No one is expecting that from you and it's something that can really shoot you in the foot if you try that too early.

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You're also going to want to send some emails to cross-functional leaders.

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Get meetings set up with them for weeks two and three, just one-on-ones. And it's going to be similar to what you're doing with your direct reports in that just getting to know them a little bit, understand how their department works, what's important to them, what their biggest focus is right now, and talk to them about how do you like to work with customer success.

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And then say, these are some things that have worked for me in the past with this kind of a team. And again, you can space those out. You don't want to be having six meetings a day if you can manage not to. And you're probably scheduling a lot of these, so you can manage not to. You want to retain some of this information and not be an absolute dishrag by the last meeting of the day. This is their first impression of you too. Your first impressions are getting needed out. It's not all at once, which is annoying, but it's something where marathon, not a sprint. So we have to account for that.

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You're going to want to get a high level overview of the product. That's probably something you want to do well before you get started. It's probably something you did in the interview phase, but just dig a little deeper, look at their homepage, Google them a little bit, see what use cases they have. I'm not suggesting you need to become a power user this week.

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I'm just saying know what the product does. If your aunt asked you, oh, tell me about this new company, you could tell them a reasonable facsimile of what they do. Not just like, it's something with managed services. I don't know. It's very techie, a lot of wires.

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That's what you want to avoid. You want to take that time to also define your specific role within the organization. Take some notes, figure out this is what the company needs in terms of customer success. Not how can I fill every single hole in the company? That is not what you're here for, and it's a huge trap, but really define what is customer success.

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How do we get our customers to their desired outcomes so that they will buy more, so that they will renew, so that they will tell other people? What are the things at this company that I will need to do? Who will I need to interact with? What software will I need access to?

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What in the past has been my role? What's worked well? How would that apply here?

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After saying, okay, I think this is what this company needs for me in terms of customer success, and that could be, I think we need to break up this customer base into a tiered model.

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I actually think I'm going to need someone to manage just the digital part of this, because it's going to be a lot different than the rest of the customers who are going to have a dedicated account manager. It really is going to depend on the company.

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The goal of what you do, the outcome, the getting those customers to their goals, to their results, that does not change. That is your role. It's the how that changes based on the company.

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So once you've got that basically written down, just meet with your boss, say, hey, I just wanted to align on expectations. This is what I see in terms of what this company needs from customer success. This is how I can best help you as a customer success leader. This is my specific role within the organization to increase retention, increase expansion, increase advocacy.

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That's week one. Now, before you start freaking out, it's okay if you don't get to every single one of these. It's okay if you take this 30-day checklist and you break it out into a 90-day checklist for yourself. Because let's be honest, in interviews, they have us do those 30, 60, 90 presentations. I understand it, but I almost have to laugh because I know that it is never going to go anything like whatever you present in there, because those are the best intentions and then things fall from the sky and you have to deal with them. So just be aware that if you don't follow this perfectly, it doesn't mean you're failing. It doesn't mean you're a bad leader. It doesn't mean you're doing anything wrong. It just means you live in reality. So in reality, know that these are things that are going to need to be done and try and keep them in this time frame. If it goes a little bit outside this time frame, just do not use this list as a tool to beat yourself up. Use it to help you. That is all. Because reality does intrude. Things are chaotic in CS almost always.

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Schedule time in your day in advance. Block off time in your calendar to get this work done.

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I talk about this all over the place, but you need to block out at least one hour of your day, I prefer more, so that you can get the strategic work done that you need to do for your CS department. Because otherwise, it's going to get filled up with emails and meetings.

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If you don't work on that strategic work, on those strategic initiatives, you are not doing the job that they are paying you for. Even if they're asking you to do something else in the moment, you have to remember what your job is there and give yourself time to do it.

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This is your strategic work right now. These are your strategic initiatives.

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You're not building the onboarding or redoing the onboarding framework yet. It's understanding what needs to be done, prioritizing, and making a plan. That's really what you're doing in your first 30 to 60 to 90, whatever you want to call it. You're ramping up time. You're really building relationships. You're getting to know the product and the data and making sense of that puzzle and the operations and processes. Then once you have that context, you're setting a plan and you're starting to take action on it. That's basically the high level of all of this.

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The reason I created this is because that's very easy to say and very hard to do without someone holding your hand and saying, go do this now. On to E2. Here, you want to make sure that you're confirming the corporate goals and OKRs. If you're not familiar with OKRs, it's just objectives and key results. Some companies call it big rocks. It's basically just what are we trying to accomplish in a set period of time as the entire company.

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There's a goal the company has and here's what each department can do in terms of doing its part to help meet that goal in a specific time frame. Maybe it's in a quarter, maybe it's in two, but that's what the executive leadership team is going to be looking at.

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They're going to be saying, how can we increase revenue and increase efficiency and reduce spend?

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Those are the main things that they are tasked with by their bosses, the board.

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They're going to be looking at all the operations, the budget, and saying, what are the projects we could do to make that happen? What's our best guess? Make sure you understand what those are right now. What is the number one thing that they want handled this quarter that would move the on NRR? Because that's really what they're asking for from you. Make sure that you understand what those goals are and that you don't just assume what they are. You want to ask to see the current financial metrics. You want to be able to determine the gross revenue retention, net revenue retention, and customer lifetime value. If they have a customer acquisition cost versus customer lifetime value, that's awesome and you want to know that, but often they don't have a lot of these.

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They should have GRR and maybe NRR. What's funny is most people want you to improve NRR, but if you ask them, okay, what is it now? They're a little hedgy about what exactly it is because sometimes they don't know. They're not sure how to do that calculation or they're doing it wrong.

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Those are also referred to as GRR, gross revenue retention, NRR, net revenue retention, and CLV, customer lifetime value. Those are your big three as a CS leader and you want to be tracking them at all times. They are unfortunately slow movers. They're lagging indicators, but they are what you're working towards. In this time, you're going to be continuing to attend your one-on-ones with your direct reports, having the one-on-ones with your cross-functional leaders, and explaining past collaborations with similar departments and understanding their current focuses and learning how they like to partner with CS. You're also going to start doing a thorough assessment of the current CS team. What are their strengths, what are their weaknesses, and where are your opportunities? Relationships, relationships, relationships. Your career depends on your relationship with these people. That does not mean act like a puppy dog and make sure they absolutely love you and do everything for them to make them like you. Your job is not to make them like you. Your job is to make them respect you. Now, there's nothing wrong with them liking you. There's nothing that says those two things have to be mutually exclusive, but make sure you're going for respect before likeability. That just means toning it down a little, not offering to do all their homework, listening, asking questions rather than, again, offering to take something off someone's plate or solve their problem. If they haven't asked you, do not give advice yet.

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It is not going to be as welcome as you think. I know you really want to show them how you can be useful to them. Right now, most people never get listened to enough.

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And most people, there aren't a lot of people interested in hearing about their job and their problems and their view on things. Be that for them. That is going to make them appreciate you so much more. And it's going to help you in your role because you're actually going to understand what's going on there. You're not going to just wait for that piece of information that you wanted to hear so that you can launch into whatever your spiel is on the topic. Week three, you're going to start looking into strategy, planning, data analysis. You're going to want to make sure that you've had some product training or getting some product training now. It's not enough to know what they do. You need to know how they do it. It is my personal belief that you do not need to know how to do every single thing in the product that a CSM does because that's not what you're going to be doing. You need to understand high level how the product works, the things they need to do, and how long that takes, how everything fits together. But you don't necessarily need to be able to do an entire demo because that should never be part of your job going forward. If you are someone who is going to be having customer accounts, you're going to be owning accounts, that might be a little bit different. But yes, product training is important, but it's not as important as understanding the big picture. So just keep it in line with that. Along with product training, you're also going to undergo systems trainings. If you have a CS tool, if there are HR tools, your CRM, et cetera, whatever tools they're currently using to run their business now, you're going to have to learn those too if you didn't know them before. Now is the time you're going to want to dig deeper into available data on the customers, not just the financial data, but how did we get there? What's at play? You're going to want to assess any sort of data health, any data information that you have, customer usage data, try and take a look at it, try to get somebody to chop it up for you, analyze it, ask them some questions about it. If you have customer health and data on adoption and usage, that's fantastic. If you don't, you're going to have to just ask questions and see what you can get. But without that information, you're going to be in a very reactive mode. There's only so much you can do when you're just taking emails and calls from customers, right? You need visualization into how they're using the product and what success looks like for your successful customers. So look at, okay, who are our most successful customers? What does their usage look like? What is their use case? What is their size? See if you can start to say, okay, well, for customers of this size with that use case, if they activate within the first 30 days and get this first value within the first 45, they tend to go on to adopt really well. If people don't get that result in the first 30 days, maybe we need to create some kind of alert for that, or at least just be aware of it, saying this is something that we're noticing, so we're going to want to put something into place to ensure they hit that value in the first 30 days. And make sure the customer knows it too. They want to succeed, so making sure that they understand that.

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You're also going to want to, and this is probably something you won't be able to avoid anyway, but start analyzing customer feedback. What is the feedback that you've been getting from customers? What are their key pain points with the product? What would they love to see? What do they love about the product? Don't just focus on pain points here. You need to know that the product is good. You need to know what people love about it so that you can encourage that in customers, so that you can encourage pointing that out to your CSMs, and so that you can talk to product without just being like, well, your product is garbage, and this is wrong, and this is wrong, and this is wrong. That's not a great way to make a first impression. Once you've analyzed the data, the customer feedback, and the financials, now you can probably start to create a strategic plan to align with those company goals. We have a better picture now. I do have a version of this. There's an upgraded version where there is every single template, email, agenda, question that you ask, metric you need to track in separate Google Docs for you. You just click on each one, and it'll take you there. It becomes basically just fill in the blanks for you because I understand that you don't have a lot of time. If you don't have to actually map out the template of what am I going to say to this person? What questions do I need to ask? It's a little bit easier.

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So my favorite thing about that upgrade is that there is a slide deck so that you can plug it into a professional-looking presentation that you can show to executive leadership and say, these are my insights from the first 30 days or 90 days. Again, however you're doing this, these are my insights. These are the quick wins, the low-hanging fruit. Here's our long-term strategy and roadmap. That is something that really tends to impress people. That's what's going to make them feel like, oh my God, we hired the right person. Not you're offering to handle every little initiative or be on some committee or raising your hand whenever they ask for people to do something. It's this kind of strategic work that really makes that impression.

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So you're just starting to work on that at this point. You're starting to get those key data points into those slides. Now, the final part of this, which would be week four, if you're doing it in the first 30 days, it's really execution, review, and planning ahead. You want to really understand the use cases and customer profiles. Look at the customer journey if there is one.

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I tend to think there should be more than one customer journey because if you have more than one use case, it's going to take different things to get them the result that they are looking for.

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I have a bunch of resources on the customer journey. I like to look at it as customer value realization maps. That's something that I teach in CS Leadership Academy, where it's not just like, oh, what touch points do we have with them, but really how do we get someone to that desired outcome of that use case? How do we get them those results? What do we have to do? What does the customer have to do? You want to review anything that you have already that gives you that information. You're going to identify and execute quick wins to build momentum.

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And I do have a list in the upgraded version of what are some that you can look for.

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They might be easy to identify at your company, but if you need some inspiration, these are things that have worked for me, have worked for other CS leaders I know that were like, okay, so these are some quick wins because CS is notoriously a slow growth process.

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So you want to show that you're more than all talk quickly. You're going to track those key metrics, measure success. And look, all anyone in a leadership position is doing, whether it's a manager of CS all the way up to the CEO. There is nothing particularly special about these people.

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Even if they've gone to business school, yeah, they might have some frameworks, but honestly, it's just a group of grownups in a room trying to make a plan to make something happen, to increase revenue, to increase the number of people using your product.

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They're just spitballing ideas and saying, this sounds like a good one.

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What do we have to do? Let's go for it. That's it. So you're going to try things. You're going to try strategies. You're going to see how they're working, and you're going to adjust based on the results. That's science. You have a hypothesis. You test it. You see how you do. You use that information to refine it. In science, we understand that your first try probably isn't going to be right. No one even expects that. They're like, all right, I'm going to start at this angle and just see where it takes me. The data is going to show me where to go, but I have to get started with something. This seems like our best bet. You are also going to be wanting to solicit feedback from your team because they have more context than you do. So if you're going in a way that has already been tried or something really pisses off another department and you don't happen to know about it, but they do, this is a great opportunity for them to tell you. This is a great time to hold a team meeting to discuss progress and areas for improvement. I would talk to your team about what the plan is going forward, your strategic vision before you talk to the executive leadership team and ask for their feedback. Ask for their thoughts. You don't have to take it, but it's a respect thing. Honestly, I've had people have really good ideas that I've used instead of my own. Believe me, I give full credit to them. I'm like, okay, so this person on our team actually came up with this because they had this insight. I give full credit to that in any meeting. Make sure you do the same. That goes so far with your team. Once you've discussed progress and areas of improvement, it's really just going to be from here reflecting back on this first 30 days. Don't skip this. So many people skip reflecting back. What do you wish had gone better? What would you do differently next time? What went really well? We are always forgetting to double down on what went well. So don't skip that. Don't miss it. Do more of what works.

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Then use that to say, all right, well, what's my next 60 days going to look like? Start to map that out. Finally, once you have all that together, go ahead and present your first 30 days of insights of the customer success strategy and roadmap to your leadership team. That's really it.

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You want to remember to stay flexible throughout this. Again, it is not set in stone. These are best practices. Think about how many of these things you would not have done if you didn't know to do them, if you didn't have this in front of you. Even if you don't get to every single one, yes, that's ideal. Yes, that will get you the best results. But you're still doing better than you would have without it. I just know I tend to be a little bit perfectionistic at times and feel like if I don't check every box that I failed, I really had to learn over time that, no, that's still seven boxes. It doesn't matter that they're seven out of 20. Those are seven boxes that I wouldn't have done on my own because I wouldn't have known. Again, you're just going to want to seek feedback throughout this, tailor this to your company. From there, it should give you a better map of what you're going to be doing throughout your tenure there. All of this will be in the free onboarding checklist, which will be in the notes. I'll have a link to that.

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You can download it. There's an upgrade version to make this as simple as possible for you.

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Every email template to send, agendas for meetings, what questions to ask each department head, what questions to ask your team, assessments, metrics, data. There's a lot, guys. When I say this thing just poured out of me, I don't believe it. There's a lot of useful resources there. There is that template as well for that presentation. When you do a presentation, whether you use this template or not, when you do a presentation, please don't treat it as a Word document. 20 font is the lowest you should go. It really should just be sentence fragments and pictures to show data. It should be a guide to keep you on track, but it should not be a place for you to read it word for word. That's what the notes section is for, the presenter notes.

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Use presenter mode. Use the notes for that. Keep your slides clean. You can just put one or two sentence fragments on there and then you say the rest to them so they're not bored out of their mind. I do have another podcast about presentations called The Language of the Executive Suite, which talks about how to give presentations and why it's really important to get good at this as you move into leadership because you're going to have to do more of them. It's just how the grown-ups share ideas. That is what I have for you today. I'm so excited to get this resource into your hands. You can go to provansuccess.com slash checklist to download it. It's free. There will be an option on there to upgrade it on the PDF itself. You don't have to. You can do a great job just with the checklist. That was really important to me. It's more, do you want this done for you or do you like to do things yourself? This also gives you a really good idea of what it's like to work with me inside the CS Leadership Academy, the kind of templates and guidance I provide, and the way I look at strategy. It's not everything in there in terms of the strategic models and strategy building because that takes a while to deliver to you and explain to you and to get you to think like a CS leader in that way, which is why there's a CS Leadership Academy versus just an onboarding guide. But this will give you a good sense of like, oh, this is the kind of resources this can provide me. I really do love helping you guys. Until next time, take care of yourself, get some rest, and make sure to share this with your CS bestie.

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Talk soon and here's to your success.