Onboarding a New Leader & Setting Up Your Big Hire to Succeed

Sei-Wook Kim (00:05.984) On today's episode, we're talking about what happens after you land that big leadership hire. The resume is strong, the interviews went well, the offer is signed. Now what? We're walking through how to set this person up to succeed inside your agency and how to know early if they won't. Peter Kang (00:23.152) All right, Sei-Wook. One of the biggest pivotal points for an agency is when they start to make key leadership hires. It's a really high stakes moment because if you make a hire that doesn't go well — a bad senior hire — the cost is way more than just the high salaries you might be paying out, right? There's the recruiter fee you might have paid if you used a recruiter. There's also the team's trust, because you've asked the team to believe in this new hire, introduce them to all the different folks, as well as making this promise that, hey, with this hire we're gonna go to new places. And then there's the client relationships. If this is a client-facing leadership hire, you've likely introduced them to the clients and now you're really hoping that it works. But sometimes these things go wrong, and with a poor hire you're talking about anywhere between six to twelve months that could be lost if it goes sideways. This is a really important topic for us to dive into. Sei-Wook Kim (01:34.526) Yeah. And the funny thing is that if you think about agencies, they usually put a lot of real effort into onboarding for the more junior hires, assuming that there's more you need to cover with them. And then if it's a more senior hire, you've gone through this process and you assume that because they're senior, they're gonna figure it out on their own. Peter Kang (01:56.641) Yeah. It's that temptation — as an agency founder you're already busy, so you go, okay, the senior hire is smart, they're experienced, I could probably go hands off and empower them to get the job done. And I think this mindset is often what backfires in the end. Sei-Wook Kim (02:19.04) Yeah. In the past we probably thought that the hard part was the recruiting, and now that we got them through the door, our job was done — like we'd crossed that threshold. But that's not the case. Peter Kang (02:29.8) Yeah. And let's put out that there are exceptions, of course. Every now and then you get somebody exceptional who, for whatever reason, maybe they're this super high-agency person coming in who basically onboards themselves. They won't take no for an answer. They come with their version of a ninety-day plan. They go, hey, I need to talk to these people, I gotta do this — and they're practically exactly what you would want. But the truth is not everyone is at that level or has those characteristics. They could still be a great hire. They just might not have those behaviors. So this is why having a system of some sort is gonna ensure that you're at least setting everyone up properly for success as a baseline. Sei-Wook Kim (03:25.255) All right, so the six areas we're gonna cover — a quick rundown: culture, goals and expectations, communication, checking cadence, skills check, and then this concept of trust but verify. Peter Kang (03:39.027) Yeah. This is the system I'm talking about that we need to establish, and it's comprised of these six parts. Sei-Wook Kim (03:45.501) Yep. All right. So let's start with the first, and that's setting up the culture conversations. If you think about someone who's new to the organization, the values and standards that you have at your company don't transfer automatically on their own, especially at many agencies that aren't in person or don't have the ability to have these organic conversations. So it's really about making it intentional — booking a lot of these conversations, especially in the early days. Like the first two weeks, have conversations with the founders of the company if that's you, key leads, key people, or people that have been around for quite some time and have some tenure in different verticals and functions at your company. Peter Kang (04:40.539) Yeah. And as you dive into these conversations, it's really important to hit points like: how do we work as an agency? What are the things that we tolerate? What are some of the things that we celebrate? And then of course it's great to get this person exposed to the texture of the agency, and they come in the form of stories — like, hey, this is how we came to run project management like this, or this is how we developed some of our creative processes, or this is how our engineering team or our marketing team operates. Those kinds of things really give more context and this institutional flavor for the new hire. So it's very important for these conversations to have these elements. And to some degree, before you set these things up with the new hire and the people on your team, you do want to give your team a heads up — hey, make sure you cover some of these areas with the new hire. Sei-Wook Kim (05:40.314) Yeah. And it actually goes both ways for the team as well. It's also an opportunity for the team to get onboarded to the leader too. They need to know what this person will do, why they were hired, and why they're gonna be really instrumental to the future of this business and what we're all working towards. So it's a two-way conversation — it's not just the new hire learning from the team, but vice versa as well. Peter Kang (06:08.995) Yeah. And this is all in service of building trust and familiarity, because the worst case scenario here is you hire this leader, you don't properly introduce them to the team, so this person continues to be a bit of a stranger to everyone. The team is also unclear about what they're here to do, so the team continues to go to the founder or whoever else they were going to before. And then this new leader who you've invested so much in never gains the authority and credibility to do their job well. Sei-Wook Kim (06:47.172) Cool. All right. So the next thing to cover is really spelling out the goals for this person and what great looks like. Goals go at all different levels. Start with what's the mission and vision of the company, what's the three-year plan, what's the vision and plan for this year and then this quarter — really breaking it down from broad to very specific. And then into the role itself: what are the metrics that define performance for this person and what are the goals you want them to hit so they know whether they're being successful or not. Peter Kang (07:26.628) Yeah. And the important part is that you might have covered this in the recruiting process — as you're negotiating comp, you might have talked about, yeah, if you hit XYZ KPIs or metrics, you're gonna unlock XYZ bonuses. But that was pre-signing. It's very important to reiterate and make sure you're on the same page again. This is worth being repetitive about. Carrying it through beyond the recruiting and hiring process shows that you were serious about it and this is gonna be a big part of how you're evaluating performance. Sei-Wook Kim (08:07.319) Yeah. The repetition is key. You can't just assume that someone will remember a conversation you had even a month ago or a week ago. So the plan is really getting granular with the first ninety days. You have the goal — then how does that break down month by month? And how do you break that down even further? Like, by the end of month one, this is what great looks like, by the end of month two and month three. How do you paint a picture for them to know that they're fully ramped up and successful in this role? Peter Kang (08:44.972) Yeah, definitely. So once we've got the goals and what great looks like spelled out, the next area of the system you really want to go over is agreeing on how you'll communicate. Communication underpins everything, especially with a senior hire, a leader that you've brought in. The number one thing to get clear on is how you as the founder are gonna communicate with this leader back and forth. Response time has always been important to us, and in a fast-paced setting like an agency, response time is everything — whether it's team members needing something, clients needing stuff, decisions need to be made and things need to get done. First and foremost, there needs to be clarity on what the SLA is on how quickly someone should respond to emails or Slack messages, et cetera. Sei-Wook Kim (09:56.948) Yeah. And along those lines, what is the right channel you're gonna use to communicate? Everyone has a different preference and tolerance. Like, some leaders are cool with, hey, just text me — everything moves quicker that way, I get notified on my phone. But other people want a boundary: nothing to my phone, that's off limits. You just need to have that conversation and settle it now, not many months later when you realize, hey, why aren't they responding to my text? Resolve it first and have that conversation versus assuming the method. Peter Kang (10:38.611) Yeah. Nothing is too small to lay on the table and just align on, because you never know the things that, left unsaid, could create a lot of resentment later on. And just along the communications line — not only the channels and the speed and response times, but also the ways of communicating, the behaviors you want to see with regard to communication. Being clear on those things as well. Part of it is also maybe a written style in an email — like, hey, maybe my preference is clear bullets and no huge blocks of text, please. It sounds very minute or in the weeds, but this is the mode of value creation between leadership. You gotta be clear on what we expect. And then of course the substance of the communication. It's almost like, hey, as a leader, I expect you to bring me solutions and options that I can react to and say yes or no to, instead of open-ended questions or unformed, unstructured brain dumps. You can specify that. Or maybe you do like the brain dumps — maybe that is what you prefer. But it's very important to get into the weeds of those details, because that way you're on the same page and once the communication starts to flow, there's no room for wondering, why is this person communicating with me like this? Sei-Wook Kim (12:20.765) Yeah. And it's really important to do this early on, because you could easily be three or four months in and if you're misaligned on something that's perceivably this small, it could feel really personal at that point — like, is it a dig on me and how I communicate? Versus it was never clear to begin with. So yeah, get it done first and have that conversation. Just align. Peter Kang (12:48.018) Yeah. Look, you have every right to define this — it's your agency. Sei-Wook Kim (12:51.024) Yeah. All right. The next point is setting the checking cadence. Before, we talked about more ad hoc communication and style, but this is the structure of how you'll check in with the leader. Usually that might take the form of a weekly check-in where you sit down for sixty minutes, an hour and a half, and then you might spend a deeper session every month or every quarter to go deeper into different topics. Every business does it slightly differently. Some people might use EOS as the system for meetings, and if that's the case then definitely plug this person into that process. But if not, all you need is just to define that rhythm — every Monday we're gonna meet for an hour, we're gonna talk about these types of things. Have that structure versus just winging it and saying, yeah, we'll meet when we need to. That never works. Peter Kang (13:46.073) Yeah. Just not having a cadence — you're honestly setting up for some kind of big-reveal failure later on. You wanna avoid that situation. And if we're digging into what you're getting out of these check-ins and what you should expect from them, it's worth being very clear on this as well. One thing you're gonna quickly see is what is this person's documentation habit. How good are they about taking notes, translating conversations into action items and to-dos, following up on those, and coming back the following week or the following quarter with true follow-ups and closing the loops. You get a real window into their habits there. And then you get visibility into progress, because if you've done what we talked about earlier — setting the goals, the metrics, and everything — the check-in is a time to say, hey, let's look at the numbers together, let's look at some of these KPIs together, where are you on this, has this progressed, or are we not where we want to be and why? And the other piece is that this isn't just an interrogation. This is a two-way conversation — an opportunity to give feedback and also receive feedback. Maybe this leader is trying to work on some initiative but there are blockers, and maybe you as a founder are one of them. So you need to do something differently, or maybe there are other blockages that you can use your influence to help move out of the way for this person. It's so important to have this space where someone feels comfortable bringing these things up and can trust you to help them do their job. Sei-Wook Kim (16:05.462) Yeah. That last part about it being an opportunity for them to ask for help is really important. There might be something unclear, or there might be feedback for you on how you're working together — it's just that space for them to talk about it. And having this ongoing cadence makes it really possible for you to hold this person accountable to different goals, metrics, and making progress, without you having to hover in every single Slack channel or be CC'd on every email. You're taking a step back, you're not micromanaging, but you're still holding them accountable to their goals. Peter Kang (16:44.639) Yeah, absolutely. All right. So the cadence is super important. Now let's get a little bit more nitty-gritty about verifying the actual skills. No matter what level folks are, it's still important to get a sense of the skill sets this person has to do their job. In an interview you might have had some tests or given them a little project that tested some of that stuff, but it's very different from then seeing them day to day. You don't want to automatically assume that these skills are fully verified beyond the interview. This could be anything from — let's say the job requires a lot of analysis with numbers, so spreadsheets are something that not everyone has skills in, and for this role it might be important to verify that they actually can use them. Maybe it's putting together decks and being able to tell a story, putting presentations together in a coherent way that's actually compelling. And then other things — like, are they using AI? But what are they actually doing with AI? Can you verify that? Is it just copy editing and asking ChatGPT, or is it something a bit more advanced where they're pulling in different data sources and really synthesizing things in an interesting way? You want to know all those things, because not knowing and being surprised a couple of months in — you ask them to analyze something and they make no movement or they're procrastinating, and then you realize, my God, they don't really know their way around a spreadsheet. You don't want to be in that situation. Sei-Wook Kim (18:54.695) Yeah. Try to identify it as early as possible. In the first couple of weeks, surface it. Just because they said they could do it in an interview doesn't mean they actually can, and you can only learn that through observation. And the fact that they don't know it, or maybe their skills aren't at the level you expected, isn't necessarily a deal breaker for them. The real challenge is if you don't identify it and you ignore it. If you identify it early, you can help them — give them resources, like hey, take this course on something, read through these articles, maybe meet this other person on the team who's an expert in this area and can walk you through it. If there's a tool, maybe you yourself can be the person to walk them through it. It's really about thinking about how you bridge that gap for them, but step one is identifying what the gaps are. Peter Kang (19:57.613) Yeah. And look, if you've hired a good person with a growth mindset who's genuinely talented in some regard, closing these gaps shouldn't really be an issue. It's just about, here are the resources to close those gaps. Sei-Wook Kim (20:19.909) Yeah. And a lot of these things — a lot of the concepts, the context on your business, your clients, your team, the tools, everything — just takes repetition. Just because you said it once in the day-one orientation doesn't mean they've retained it after they started. So just do it over and over again, and at a certain point hopefully it sticks. Don't be afraid to repeat yourself. Peter Kang (20:48.071) Yeah. All right. So we're now at our final piece. And if there's anything you take away from today's episode, it's probably these three words that we really think are the key to the senior hires you make, any leader you hire: trust but verify. By this, it's basically knowing how your leader is performing — and understanding that that's very different from micromanagement. Micromanaging somebody is dictating the how, redoing their work, being in their deliverables, saying, hey, that's not how you should be doing a presentation, here's how you should do it, moving around the pieces. That's micromanaging. When it comes to verifying, it's more about knowing how they're performing against the goals you've agreed to and spelled out clearly, and of course the cadence you've set up. Very, very important concept: trust but verify. Sei-Wook Kim (21:51.61) Yeah. And the worst situation is the opposite of this — where you think you've fully delegated your work. You're like, all right, you've taken this on, and as a founder you're like, I don't need to pay attention to it anymore. And oftentimes you might say, I'm just empowering them to own this area, I don't need to be in any of it, I don't really need to know what's going on because that's now their job. But the reality is that's not empowerment, that's just checking out. That's the challenge. Peter Kang (22:26.159) Yeah. And part of this situation you're talking about — this abdication, this delegating without paying attention — I think some of that sometimes comes from a lot of these agency founders who maybe started their agency young and have limited professional experience being managers or having worked in big companies. So when they bring someone on who's worked at a bigger company, worked with bigger brands, managed more people, you bring this person on and you have this dynamic where it's like, this person is so much more qualified than me, I need to be deferential to them, I should probably have no say in how they're working because I just run this small agency. There's a little bit of an inferiority complex — you're a little insecure about your own capabilities. So you treat this person as if they're gonna come in and do what's right for the company. I think that mindset is something to totally myth bust, because that's where it gets dangerous — all of a sudden there's no accountability on this person you've brought in. Sei-Wook Kim (23:50.668) Yeah. And oftentimes when you're making this big hire, you have so much on your plate and you're so busy, and you bring this person on and you're like, wow, finally someone else can take this over. It's almost like a relief to not have to think about this part of the business because you've hired this key leader. But yeah, that's not leadership. Peter Kang (24:17.204) Yeah, exactly. And this is what I say — you can't hold a leader accountable to results you're not tracking. The founder's job first and foremost is to hold folks accountable. Just because someone's super senior doesn't mean that accountability goes away. Sei-Wook Kim (24:34.283) Yeah. The key here is especially early on, keep a close eye on how things are going. You might be a little bit more in the weeds on what they're doing. But then as they master certain tasks or responsibilities, it's less about how they're doing the work and more about what are the key numbers, what are the key goals, are they hitting the metrics that matter to the business. And when you take a look back and manage from a goals and metrics standpoint, just be honest with the results. If goals are slipping, understand why. If the goals were wrong, you may need to adjust them. Or maybe it is a performance thing where the person isn't performing against the goals. Peter Kang (25:28.06) Yeah. And as you continue to trust but verify — verify, verify — you do want to make sure you don't get caught in a sunk cost trap. How many times over our careers have we tried to make things work out because, hey, we already paid the recruiter fee, we did all this onboarding, and my God, we told everybody we know that we hired this awesome person. To admit that it was a hire that didn't work out — it's such a big ego hit too. So there's all this sunk cost you're trying to deal with that makes it hard to ultimately make the right call, which might be, hey, we need to cut our losses and move on from this person. Sei-Wook Kim (26:27.069) Yeah. Because the most expensive cost isn't the recruiter fee and all that. It's the six months or twelve months where you just keep going, tolerating the underperformance, and the team is watching you tolerate it. And you start to get into this habit of tolerating underperformance, and that almost becomes your new standard. Then if the person does anything incrementally better, you're like, all right, maybe it's working out, maybe they're actually doing well. But you've lost perspective on what the goals are or what great can actually look like. It's really easy to get trapped in this cycle of believing that someone is working out. Peter Kang (27:14.973) Yeah. And at the end of the day, culture is simply what you tolerate or don't tolerate in terms of the standards across the agency. When you make a mistake with a hire and don't do anything about it, you're letting your culture basically go to crap. Sei-Wook Kim (27:40.357) All right. So to wrap things up, some homework for everybody to think about. If you have a senior hire starting in the next quarter, or one that started recently, go through and write a one-pager — go through the ninety-day plan, what are the key milestones, break it down by month, and cover all the things we talked about today. What are the communication expectations that you have? What's the cadence of check-ins you'll have? And what are the three to five metrics that define great performance for this role? It'll probably take you some time — if it takes an hour to write, maybe more than that. You can't assume that these people will know what you're thinking by the time they start. Peter Kang (28:26.884) Yeah. All right. In closing, the takeaway here is that the job isn't done when a senior hire signs, and it's also not done when you've handed over the responsibilities. It's all about knowing how they're performing the entire way and holding them accountable. And like we said: trust but verify. Thanks for tuning in, hopefully this was helpful. Till next time, we'll see ya. Sei-Wook Kim (28:56.614) Thanks.