Fractional talent fails not because of the people but because leaders skip the basics: onboarding, expectation setting, and clear accountability checkpoints. Lia shares three keys that fix the most common freelancer and contractor breakdowns before they become expensive disasters. This episode is essential for founders, team leads, and anyone leaning on freelancers or agencies to scale right now.
This episode is part of the Hiring, Onboarding & New Team Members series. Browse all episodes →
Mic drop moments
“…hiring is expensive and time consuming. Did we know that it is a $1 trillion problem nationwide?”
“The expectations weren’t set from the beginning. And I share that example because it truly can happen in companies, big or small.”
“Someone’s never too senior to be able to shadow you if you need them to learn certain things about the business or the culture, about how you approach things.”
“…it costs between Gallup or LinkedIn reports, 50 % to 200 % of someone’s salary. So if you bring in a key, like a senior hire, 150, $200,000. that could be between $100,000 and $400,000 to replace that person.”
Episode highlights
The buyer’s remorse moment every leader dreads
You made the hire. They have the resume, the track record, the experience. A few weeks in, something feels off and you are second-guessing a major financial bet. Lia opens with exactly that moment and makes the case that this feeling is almost always a signal that a process broke down, not that the person is wrong. The good news: the process is fixable, and it starts well before day one.
Why the interview needs to go deeper than skills
Most interviews stay surface-level, covering role specifics and past experience. For senior or leadership hires, that is not enough. Lia pushes leaders to ask questions that reveal how a candidate thinks, how they solve problems, and how they approach driving strategy forward. In her Ops Playbook program, she builds interview questions that map directly to a company’s values so leaders can assess fit on what actually matters, not just credentials.
If you are not asking those questions in the interview, you have no right to be surprised later when you do not like the answers.
The expectations conversation most leaders skip entirely
The interview is also where expectation-setting belongs. Are they inheriting a system or building one from scratch? Do they have a team under them or are they doing the ground-level work themselves? Lia shares a story from her time at Google: a senior hire from McKinsey who was accomplished and seasoned, but walked into a role with no team beneath her after years of leading large teams. The mismatch was not her fault. The expectations were never set.
That same pattern plays out in small businesses constantly. A new director at a med spa or salon comes in ready to hold people accountable but has no tools, no reports, and no aligned goals to work from. Clear expectations in the interview prevent both sides from experiencing buyer’s remorse on week three.
What knowledge transfer actually looks like for a senior hire
Once someone is in the door, the temptation is to hand them the keys and assume their experience will carry them. Lia pushes back hard on that. A senior hire still needs to understand how you think, how you make decisions, and how you handle the unexpected situations specific to your business and culture. That is not months of hand-holding. She estimates a couple of weeks of intentional narration: walking through your thought process out loud so the new hire can build a baseline to operate from.
Someone is never too senior to shadow you if the goal is learning how your business actually runs. If a candidate resists that, that is a signal worth noting in the interview itself.
Getting aligned on what success looks like in the first 90 days
If you hired someone to run a function you do not fully understand, like marketing or operations, you may not know how to evaluate whether they are being effective. Lia’s fix: have an explicit conversation in the first weeks about what the next 90 days look like and how you will both know it is going well. Frame it as a partnership. Bring ambitious goals but give the senior hire room to help define the benchmarks, because they are the seasoned professional you hired for exactly that reason.
This alignment conversation is high leverage and does not take long. It is a matter of a few focused discussions.
The real cost of getting this wrong
Gallup reports that replacing an employee costs between 50 and 200 percent of their annual salary. For a senior hire at $150,000 to $200,000, that is a potential replacement cost of $100,000 to $400,000. Turnover costs U.S. businesses roughly a trillion dollars a year. Lia uses these numbers not to scare but to reframe: the process work she is describing is not overhead. It is the highest-leverage investment you can make in the first two weeks of a hire.
Doing these two things, sharpening the interview process and investing in knowledge transfer and alignment, gets you 80 to 90 percent of the way to a successful hire. The margin of error shrinks dramatically when the process is thoughtful.
Related episodes in this cluster
- Ep 219: Did you make a bad hire? How to know and what to do next. Most ‘bad hire’ situations are actually bad onboarding or missing feedback situations. Lia walks through a 30/60/90-day check-in framework that helps you assess a new team member clearly, without panic or dragging it out too long. This episode is especially useful for founders and small team leaders who are second-guessing a recent hire.
- Ep 191: The two onboarding mistakes that kill a new hire’s excitement before week one is over. Most onboarding failures come down to two problems: new hires left with nothing to do and no direction, or new hires who charge in too hard and alienate the team. Both happen because the leader never set clear expectations before day one. This episode walks through exactly what to fix, with Lia’s own story of a disastrous first day as the centerpiece.
- Ep 190: Three hiring mistakes that wreck your team (and what to do instead). The three most common hiring mistakes are moving too fast, underpaying, and bringing on a high-skill but low-collaboration person who poisons team culture. Lia walks through each mistake with real examples and shares how slowing down, paying fairly, and enforcing a no-jerk rule are your best protection against costly turnover. This episode is essential for founders, team leads, and new managers who have ever felt the pressure to fill a seat fast.
- Ep 188: How to manage contractors and freelancers without the headache. Fractional talent fails not because of the people but because leaders skip the basics: onboarding, expectation setting, and clear accountability checkpoints. Lia shares three keys that fix the most common freelancer and contractor breakdowns before they become expensive disasters. This episode is essential for founders, team leads, and anyone leaning on freelancers or agencies to scale right now.
Want to go deeper?
The Unstoppable Team. How to build a team that runs without you in the room.
Full transcript (click to expand)
Lia (00:00): You did it, you finally made that big hire and they were expensive, but they have a ton of experience and you know that this is going to take work off your plate. It’s gonna get you out of the weeds. And then the person starts and you’re super excited. You kind of give them the download of everything and you expect them to be off and running. And a couple of days later, weeks later, you’re like, this is what you came up with or why would that make sense? Or what is going on over here? This person is not doing this at all the way I imagined it.
And right away you get this feeling of buyer’s remorse. And I’ve been there. And I think all of us have been there that make this big hire. We take this huge leap. We take this financial risk. And then we’re looking around saying, I don’t think this is the right person. Well, today on the show, we are talking about this exact situation that I know so many of us have found ourselves in. Whether you are a business owner or a corporate leader that big hire, maybe finally hired someone that you’ve been
begging for that head count for, and now you’re like, I don’t know about this. For business owners, this is money out of your own pocket feeling like, my gosh, I don’t wanna take that risk ever again. We’re talking about how to avoid this by setting up the hiring process right from the beginning. And there are two things for me diving into, so you’re wanna listen to the end.
so on the show today, we are gonna be talking about the two things that ensure that when you bring someone on, they are set up as best as you can. Now there are no guarantees with hiring because we’re dealing with people and humans are complicated, but we can de-risk this so much by doing these two things that I’m gonna talk about today.
it comes to bringing in anybody on your team, junior role or senior role, we’re always taking a risk. We’re dealing with humans. Humans are complicated. They come with all different sorts of things. They might be great in an interview and not really be able to do the job that they said they could do. Or they might have fantastic experience somewhere else, but it just doesn’t translate to your team culture. So there are no guarantees, but we can definitely de-risk it by doing the two things that we’re gonna talk about on the show today. The first one is around the hiring and interviewing.
process and the second one is about really downloading that kind of knowledge transfer. And that’s a pretty corporatey way of saying like getting someone to be able to sort of reach your mind, which was the goal in the first place for these senior roles. You’re needing someone to really understand right away how to operate at your level so that they’re maintaining that expectation you have. Now let’s talk about the first piece, bringing in the right person.
And sometimes we rush it. Sometimes we bring in the first person that reaches out or sends a resume. They seem like a great fit. They check all the boxes. We want to try to interview and meet with a few different people because we want to understand, wait, how is this person relative to another person with maybe a different set of skills or a different background or, some sort of other composition of things that could be good for this role. So super low hanging fruit is to talk to at least three people for a role just so that you get that balanced perspective.
But this is not really about the recruiting process. I want to talk about the interviewing process because this is where so many of us fall short. We do an interview that’s just about the specifics of the role and we are not getting under the surface about what that person really needs to do from a bigger picture, a bigger thinker perspective. And a lot of, and this is so important for bigger roles, so important when you’re bringing someone on for a leadership role, which is what we’re talking about today. We need to understand
how this person thinks, how they solve problems, how they are going to take responsibility for helping grow the business or drive the strategy forward. And if we are not asking those kinds of questions, we can’t be surprised later if we don’t like how they handle those, because we actually had no idea and we never gave them an opportunity to explain that to us. Now, when I work with clients in my Ops Playbook program, I actually write out questions to ask in interviews that map to that company’s values.
because we wanna be able to really get at those specifics when we ask these questions. again, it’s not a guarantee, but we have a better sense of, okay, this is how they approach that thing that’s important to me because it’s in my company’s values. Do I agree with that? Is that going to bring a great perspective, something that I think will move the needle, or are we kind of out of alignment? These kinds of questions are really important. And that’s why it’s so helpful and critical to talk to a few different people.
because you’re gonna wanna see how some of these perspectives map to something else. Now, the interviewing process is also where you start to set expectations. And this is, think, again, one of the other pieces we overlook. We just talk about the role and not how we are as a leader, not the way that we wanna engage with this role, not what the first kind of few months looks like, not how we evaluate success. That all really has to be part of the interview.
And for our leaders, when they come in, we want someone to know, hey, you are gonna be building out the whole strategy here, or you’re gonna be taking an existing strategy that’s great and evolving it and running that. Totally different roles, totally different sets of responsibilities. Or for a senior person, hey, you’re gonna have this team under you to help execute, or you are going to have to do this from scratch, bring in the revenue to then build a team. I’ve seen that in companies big and small.
I was on a team at Google and we brought in a senior person to run some strategic work. And she had come from McKinsey where she had a whole team under her. And in this role, she didn’t have a team. She was very seasoned, very senior, but because she didn’t have a team, she felt like it was a total mismatch. Like, hey, I’m supposed to do all the strategic work and then do all the backend research. That’s not what she had been used to. She hadn’t done that level of
ground work for years and years in her career. And it just didn’t feel like a fit. The expectations weren’t set from the beginning. And I share that example because it truly can happen in companies, big or small. I see it all the time in small businesses as well. We bring in a manager, let’s say you run a med spa or a salon and you bring in a director you want to oversee the whole facility. And
they are supposed to be holding folks accountable, but then you haven’t given them any tools to do that, right? there’s not reports and there’s not expectation sets and people aren’t really supposed to be, hitting any goals like yet. And so when the person comes in and implements that, there’s a little bit of backlash. Now, if you want someone to set up that whole system, that needs to be clear to that person so they know what they’re signing up for, right? Is it new or am I inheriting something? That’s gonna be really key.
and all that expectation setting comes in the interview process. So the person knows like, do I wanna move forward with this or not? That is so critical because when someone starts and they were like, well, this isn’t what I signed up for and you’re thinking, yeah, it was, that’s where we start to get that buyer’s remorse on both sides. So now let’s move into, got the interview, we got folks in the door. Well, how do we do that knowledge transfer or like getting someone literally in your brain? This is something that’s difficult.
you brought in a senior person, you want them to already get it. You want them to already know how to do it. They have experience, they did this, they had a great track record somewhere else, right? Or they wouldn’t be coming in as a senior role. It can be very frustrating to have to do this step, but without this step, it’s very hard for someone to be successful. And that means they have to spend some time with you. You’ve got to put in a little bit of time. I’m not talking about years, I’m talking about days, okay? Maybe a couple of weeks, really.
hearing how you think, how you make decisions, how you approach certain tricky situations, what happens when this happens, what are some of the unexpected things that can come up. The more you talk through that and literally narrate your thought process as you’re going through that, that is going to help someone be able to think, okay, this is the way they would think about that. So I wanna use this as a baseline. That’s the expectation. Now I can add to that.
in some situations, maybe I can’t, maybe this is the process and the protocol we want to follow. In your conversations, that’s where you’re going be downloading.
someone’s never too senior to be able to shadow you if you need them to learn certain things about the business or the culture, about how you approach things.
incredibly valuable. And if you’re,
person you hire is like, don’t need to do that, then that’s where we want to put that back into the interview process and say, hey, here’s what the onboarding process looks like. we spend the first week or two together so we can really learn the ropes and start to get this shared brain state. That is important that someone’s up for that. Now, if you are bringing in someone and you have no understanding of that side of the business, okay, so you’re bringing in, you know, someone to run like you
a new department that you don’t have any background or context or really opinion about, then maybe you’re not telling them what to do for the role. But there is an amount of, hey, this is how we make decisions in this company. This is how the culture is. This is some of the things that, you know, are really important for me to be seeing. Let’s figure out together how we define success. You still want to be getting a line around how some how you know if someone’s being effective.
And because I think this is one of the trickier things. If we don’t have any idea, like, let’s say we brought in someone to run marketing because we have no idea how to do marketing. And we have no idea even how to know if it’s successful or not, besides like that we made more money. Or if someone to run operations and the stuff takes longer to really kind of see the fruits of its labor, right? Like saving time and optimizing people is a little bit of a longer tail. If we know nothing about that and we look like, hey, why this thing costs this amount of money?
we’re going to maybe misjudge that the person was or wasn’t effective. So in this early days is when you’re talking about, let’s look at what are the next 90 days, maybe what the first six months looks like and how we know it’s successful so that you get on the same page. And again, if you don’t really understand the kind of nuts and bolts of the work, which bringing in a senior person, maybe you don’t, like probably not potentially.
that’s where you want to talk about it as a dialogue and say, okay, here’s kind of what I’m thinking. Is this on track? Is this in line? You know, maybe you vet it with a couple other peers, right? A lot of times, or you bring in a coach or some of the consultants that kind of talk to you about. when I am working with my clients to figure out what some of these roles are, we talk about, what should the expectations be of that person, right? Because you also don’t want to hire someone that says, it’s going to take a year to see any results. And you’re like,
I think it could be 90 days, but you know, want to be able to get aligned, but this is a partnership. And I encourage you to not interview someone or not bring someone on and then have them be trying out for their job again. Like that’s not a good place to be. So you want to have them start with some degree of trust that like, hey, yeah, we were in this together. I trust that what you’re gonna come back with is…
is reasonable and maybe aggressive if we’re in a small business or a high pressure corporate team. We’ve got to have ambitious goals, but I am going to trust you to be setting those benchmarks because you are a seasoned leader. So these two pieces are critical. Really setting those expectations in the interview process and then making sure you’re super aligned if there’s a lot that you’re kind of brain dumping and getting them to really understand how you operate, how you make decisions, or
if it’s something that’s not work that you had any responsibility over before, getting a line on what success looks like. This is a number of conversations. It doesn’t take months and years to do this. These are critical, high leverage moments that are going to de-risk hiring because we all know it, hiring is expensive and time consuming. Did we know that it is a $1 trillion problem nationwide?
the cost of turnover costs businesses in the United States a trillion dollars a year worldwide. I think it’s like 10 trillion, something ridiculous. Okay. Maybe two trillion, whatever it is, trillion is a lot. That is the cost. They say it costs between Gallup or LinkedIn reports, 50 % to 200 % of someone’s salary. So if you bring in a key, like a senior hire, 150, $200,000.
that could be between $100,000 and $400,000 to replace that person. This is something you really wanna get right with your senior people. It is a pain in the butt to have to start from scratch and to feel that buyer’s remorse staring down at a $400,000 price tag for getting this wrong. And the way we reduce the risk, it’s not a guarantee, but the way we reduce the risk is by being thoughtful about the process.
meeting with more candidates so they can really evaluate it, having conversations around interview questions around the values fit, really setting expectations in the interview so that you make sure someone knows what they’re signing up for and you know that person knows what they’re signing up for, and then really making sure in the onboarding, you’re getting aligned on what success looks like. I think that gets us like 80, 90 % of the way there.
And then of course, there’s always margin of error. But on that price tag, how awesome would it be if we knew we had done everything we could? And that’s what we do. Those couple of things, matter of conversations. And we go from there. And if you are interested in support for your team on how to map this out, especially with those interview questions, reach out, liagarvon.com slash contact. We will have a quick conversation, talk about what you’re looking for, really how to structure.
the hiring process so that you are feeling like it’s very objective, it makes sense, you’re getting that full picture you need, and then building out that onboarding process. All right, liagarvin.com/contact See you next time.
Questions this episode answers
Why does my new hire seem great in the interview but not work out once they start?
Most of the time it comes down to two things: the interview didn't go deep enough, and the onboarding didn't set clear expectations. If you only asked about the specifics of the role and never explored how that person thinks, solves problems, or handles responsibility, you have no baseline to compare against once they start. And if you never told them what the first 90 days look like or how you define success, both of you are guessing. The hire didn't fail, the process did.
What interview questions should I ask when hiring a senior person or leader?
Go beyond the job description. Ask questions that reveal how this person thinks, how they approach problems, and how they take ownership of strategy or growth. Map your questions directly to your company's values so you can hear whether their instincts are in alignment with how you operate. You're not just screening for experience, you're screening for the way they'll show up when things get complicated. Talking to at least three candidates also helps because you can compare perspectives and see whose approach actually fits.
How do I onboard a senior hire who already has a lot of experience?
Even experienced hires need time inside your head. Spend a few days, maybe a couple of weeks, narrating how you think, how you make decisions, and how you handle tricky situations. This isn't micromanaging, it's giving them the baseline they need to operate at your level. If someone pushes back on that kind of onboarding, that's a signal to address early. Build it into the interview so candidates know what the first few weeks look like and can decide if they're genuinely up for it.
How do I set expectations with a new hire when I don't really understand their area of expertise?
If you brought someone in to run a department you have no background in, like marketing or operations, you still need to get aligned on what success looks like. Have a dialogue in the early days: share what you're thinking, ask if it's on track, and define the next 90 days and first six months together. Without that conversation, you risk misjudging whether the person is effective because you never agreed on the benchmarks in the first place. Define it as a partnership, not a performance review.
How much does it actually cost to replace a bad senior hire?
According to Gallup and LinkedIn data, replacing someone costs between 50 and 200 percent of their annual salary. For a senior hire earning $150,000 to $200,000, that's potentially $100,000 to $400,000 to start over. And that doesn't count the time lost, the team disruption, or the pressure it puts back on you as the founder or leader. Being more intentional about the interview and onboarding process won't eliminate all risk, but it gets you 80 to 90 percent of the way toward getting it right.