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
“Stop making a sunk cost of having spent all this time hiring and all this time interviewing on keeping someone that’s not a fit.”
“…nine times out of 10, this is real talk, you didn’t give the feedback. You noticed you didn’t like something and you’re like, this is what they thought was okay.”
“…compassion is figuring that out so that person can save face and everyone just kind of comes out in a better place.”
“…we can quiet our overthinking by thinking about it much more methodically.”
Episode highlights
The two mistakes leaders make after hiring someone
Most leaders fall into one of two traps: they decide within the first week that a new hire is not working out, or they wait far too long and let resentment quietly build for months. Both extremes create bigger problems than the original concern. The goal is a clear-eyed, methodical assessment that gives the person a fair shot while protecting the team.
Onboarding is almost always the missing piece
Before you decide someone is not a fit, Lia asks one question first: did you actually onboard them? If the new team member was never told what success looks like in week one or week four, what your decision-making style is, or where you want to be looped in, you have no real data yet. Poor onboarding and a bad hire look identical from the outside. You cannot skip this step and then blame the person.
The feedback you never gave is the problem nine times out of ten
Lia is direct: most performance concerns come down to feedback that was noticed but never shared. She describes a client whose new team member spent her first day on an airplane, unreachable. The client was furious but said nothing because she did not want to seem like the bad guy. When she finally had the conversation, the team member was mortified, apologized, and never did it again. She became a standout performer. The pattern Lia sees constantly is leaders keeping a mental running score of small offenses while the team member has no idea anything is wrong.
Use the 30/60/90-day framework to remove guesswork
Lia recommends structured check-ins at 30, 60, and 90 days. These are not formal reviews so much as honest gut checks. Are you seeing what you hoped to see? Is onboarding on track? Is the person getting enough context to do the job? These checkpoints create natural moments to course-correct early instead of waking up at six months with a vague uneasy feeling and no clear data.
How to evaluate performance at the six-month mark
By six months, the onboarding grace period is mostly over. Now you are measuring against the actual job. Lia recommends treating the role description like a rubric: what were the stated expectations, what KPIs or goals were set, and is this person meeting them? The catch is that this only works if those expectations were spelled out clearly. If anything on the list was implied rather than said out loud, you have to reset the clock on that item and have the conversation before holding it against anyone.
Red flags that are harder to coach through
Some things are coachable and some are not. Lia identifies the harder ones: lying or telling different stories to you and to teammates, deliberately stirring up negativity or an us-versus-them dynamic with the team, and a consistent inability to work collaboratively. These are not skill gaps. They are patterns of behavior that rarely shift with feedback alone. A mismatch in working style, like someone who came from a large corporate environment struggling to adapt to a scrappy startup pace, is harder to fix but worth naming honestly.
Stop making a sunk cost out of a bad fit
If you are 12 months in and realizing you knew something was off at month three, Lia’s message is blunt: what are you waiting for? Holding on because you spent so much time hiring is sunk cost thinking, and it hurts everyone including the team member who is probably also struggling. The compassionate move is to address it clearly and fairly so everyone can move forward. And if you give the feedback and this person rises to meet it, that happens just as often as not.
Related episodes in this cluster
- Ep 235: Why your new hire is not working out (and how to fix it before it costs you). When a new hire is not working out, it is almost never a people problem. It is a process problem caused by two gaps: an interview that skips values and expectations, and an onboarding that skips knowledge transfer. Lia walks through both gaps with a real example from Google and gives you the fixes to de-risk your next senior 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)
But I’m going to say this, if you get to 12 months and you are thinking, I’ve known all this stuff since three months in, I did the 30 day review, I did the 60, I did the 90. At six months, I wasn’t sure. What are you doing at 12 months? Like, what are you doing? Welcome to Leading Small Teams, a Real Talk podcast tackling the ins and outs of leading teams in the modern workplace. I’m Leah Garvin, your host, with a decade of experience driving team operations in companies like Google, Apple, and Microsoft, bringing you insider strategies to make you a more confident and effective leader.
From delegating to feedback to avoiding micromanaging and more, this podcast gives you the tools to empower your team, scale yourself as a leader, and grow your business. Whether you are managing a team of one or 100, everyone is welcome to hang out with Leading Small Teams. Hiring people is one of the most important things you can do, and it is one of the biggest pain in the neck activities you can do, because it is time consuming.
You don’t have time, otherwise you wouldn’t be hiring someone if you weren’t spread too thin, right? It is hard to know if someone is legit or not, if you’re asking the right questions, and you got to loop a lot of times your other team members involved, so it’s taken away from their work. It is a whole thing. So the worst possible outcome when we hire is to think to ourselves, oh, this person’s not a fit. After all of that, I made a mistake.
It’s devastating. But I see so many leaders making the mistake of not evaluating if this person’s a fit or not until way later, after a lot of damage has been done, or deciding within five seconds. Okay, so on one of the extremes, and that is what we’re going to talk about today, is answering the question, did I make a bad hire? How do I know, and what do I do? If you’ve asked that question before, then you’re like 100% of us leaders out there that have wondered that.
And so let’s say like, how would we even be thinking about this in the first place? So somebody starts, and maybe after a week or two, you start to think, gosh, are they a fit? Are they getting along with folks? Are they taking enough work on? Are they really owning something? If they’re in a more senior position, are they driving strategy? Are they just doing busy work? Or if they’re in more of a tactical position, are they getting enough done?
Are they actually worth what I’m paying them? We start asking all sorts of questions. It’s kind of like when you buy something really expensive, and you’re super excited in the store, and then you get back home, and you’re like, what? Did I need that? I’ve had that buyer’s remorse a lot. This is like my inner dialogue. I have to fight so hard and say to myself, you wanted this thing. You evaluated all the different options. You made this choice.
You went in there going into confident. Stop overthinking it. And when it comes to a hire, because it’s a person, and things are complex, and it could not be what you thought, the little wheel of overthinking can turn so fast and so hard. So let’s say you’re on the side that decides in five seconds, oh my god, this was a mistake. This person’s not a fit. Get them out of here. Well, the question to ask ourselves is, did we do onboarding?
Did we give this person insight into what they need to be doing, how they’re successful, what they should be working on, how other people do things successfully here, insight into your work style, the way you make decisions, what success looks like to you, what a good job looks like, where do you want to be looped in, what they should be doing by the end of week one, by the end of week two, by the end of week four.
This is all the stuff we talk about in my Ops Playbook program, because if you don’t have a good onboarding process, you have no idea if that person’s a good fit or not. So when we start, if we’re really early on thinking, I don’t think this person’s a fit, they’re out of here, it’s bad. That’s where we got to look back and say, what was the onboarding? What expectations did I make? And I’m going to tell you right now, so you don’t get to be the other side of this, where you waited six months and then you realize the person’s not a fit.
We should be checking in with ourselves after about 30 days. I encourage everyone that I work with to have check-ins at 30, 60, and 90 days, so that you can be thinking, okay, are we on track with onboarding? Are we seeing what we want to be seeing? You want actual opportunities to be seeing this in course correcting. So we want to be checking in, but we don’t want to make the decision, right? Unless something egregious happened, but that’s what we’re talking about here, right?
We’re saying, I’m not sure, I’m not quite positive, but is it just that the person approaches work in a different way? Maybe we hired someone from a different industry or work experience because we wanted a different sort of way of working on it. Now that they’re doing it differently, we’re like, I don’t know about that. So this is on us, right? We got to think about, okay, am I holding a reasonable standard? Am I giving this person opportunity?
What feedback have I shared? And I’m going to tell you nine times out of 10, this is real talk, you didn’t give the feedback. You noticed you didn’t like something and you’re like, this is what they thought was okay. Then you’re texting me. I got my voice notes from my clients, 15 minute long talking about all this stuff their team member didn’t do. And I’m like, okay, well, what feedback have you shared with them? And it’s crickets.
If you’re anything like me, you’ve had those nights where you wake up at three in the morning wondering, gosh, are people working on the right things? Or what’s the status of that project? And obviously, you can’t email folks at that time. But the tools you’re using ClickUp or Asana or Slack, it’s just too detailed. You need a bird’s eye view. Enter the snippets template. At the end of each week, your team member fills out the highlights from the week, any places they’re stuck in the top parties for next week.
So you’re never wondering, are folks working on the right things? Are there things that they haven’t brought up that really should be on my radar? And most importantly, what wins can we celebrate as a team? Grab your copy at leahgarver.com slash snippets. So we’ve got to give the feedback. We got to give this person the benefit of the doubt. I had a client and the team member started and she right away was unavailable, like was on a flight instead of being in the office that day.
So they were working from home, but in office would be at home. And she was not available. And she said, well, I thought I’d get Wi-Fi in the flight. I can get everything on my computer. I didn’t have any meetings. I was just going to be working on the computer that day. And my client told me this. And I said, well, what feedback have you given this team member? She’s like, well, she’s new. I don’t want to be the bad guy.
I don’t want her to feel like she messed up or get upset. And I was like, hey, but you’re really upset about this. And this is a pretty big deal breaker for you. So it’s a conversation you’ve got to have. And she brought it up with the team member and she said, hey, I realize you thought you’d be on Wi-Fi, but, you know, it’s unpredictable on the airplane and you weren’t able to have it. And, you know, you were out the whole day and we weren’t able to get a hold of you.
And there was really important stuff we had to decide. And the team member said, oh my gosh, you’re so right. I’m so embarrassed that I did that. I’m new. I’m still trying to prove myself. I don’t know what I was thinking. And she apologized and she has never done that again. She’s been a stellar A player, 10 Xer who made a mistake, who had an oversight. And because her boss said something to her, she was able to fix it.
Now, what I see a lot of times, we don’t have that conversation. And so we just start adding that up. Okay. There was that airplane thing. Now the second thing she wasn’t, she went to a dentist appointment. She mentioned that like now there’s this thing. And so you’re at, you’re keeping score and you’ve never given the person the opportunity. Now as the boss, you might think like who, who thinks like just being on an airplane on your wifi is okay.
I get it. That’s my opinion. But if you don’t tell the team member and you don’t give an opportunity, you can’t let them fix it. Yeah, it was a mistake, but she fixed it and she never did that again. Okay. So that’s what we want to do with the early little grumblings of this is not a fit. Now what happens if you get down and it’s six months later and you’re like, ah, I, I don’t know.
I mean, are they a fit or not? Or are they getting along with the team members? I don’t really know. And is this, do I even need this hire? You’re, you’re all over the place. Okay. And you’re thinking probably I’m paying this person and I want to make sure I’m getting my money’s worth, right? Yeah, natural. We’d all be thinking that. So again, it goes to a little bit of the onboarding. Like what were the expectations?
What feedback have we given that or that principle for the, for the deciding to quickly, it still applies, but then we want to get really clear. Okay. We’re six months in. How is this person performing? What are the expectations of their job? What are we measuring in terms of key performance indicators, KPIs, metrics, goals? Is this person delivering? Have they had sufficient time to learn the ropes? Probably after six months they have. And so now you’re evaluating against the criteria of the role, kind of almost treating it like a rubric, like, okay, here’s what was spelled out for them to do.
Are they meeting these expectations? And you decide if they’re meeting them by first having set the expectations. So if you look at that and you’re like, well, did they know that was their job or would they have known? Then you, then you’re kind of starting the clock over. If anything on that rubric on that, what was the job description and what were they supposed to be focusing on? If it’s things that you really never talked about, but they were implied that stuff that we’ve got to reset with conversations and for all of it, like nothing can be implied anymore.
I’m just telling you that like nothing these days in the work. I have heard it every single day. Every single business owner I work with has all sorts of implied expectations of their team members, and they don’t know. They’re not reading. They can’t read your mind. I wish they could be way easier for all of us, but they can’t. Right. So we’ve got to spell that out. Now there’s things that I think are way more difficult to, to repair things that I would say are red flags to me when I’m working with a team.
And one of those is someone lying, like telling you one story and telling team members other stories, misrepresentation, lying, right? They’re kind of playing both sides, someone that is negative and sort of spinning up negativity, kind of like us versus them with the boss. And they’re telling you maybe, Hey, I’m, I’m trying to, you know, keep, keep the peace, but they’re actually just stirring stuff up. That is a intentional action. So I don’t think that’s a good, a good thing at all.
Again, negativity, I mentioned someone that really can’t get along with other people. You’re in, you’re on a team, a team has to be cooperative and collaborative. That is by definition, what, what’s required to be a team. So that’s something that’s much more difficult to, to teach and coach through and upskill someone. So I’m kind of identifying some of the things that are not really expectations, but are just, this person is probably not the right choice. And sadly, I get it.
Sometimes we don’t see that until we’ve had a really hard situation or there was a project was at risk. We saw someone’s true colors or someone was out of town and they had a cover and then you see these sides of people. Sometimes it takes a good amount of time, but I don’t think we need to wait till six or even 12 months to figure that out. If we’ve had signals earlier on, and if someone’s on a fit, it’s in both of your best interest to figure that out.
That person is probably not happy. They’re struggling to figure out, you know, how do I be successful here? Especially if it’s a skills gap and they really, you know, it’s not the right job for them. Maybe the, what was required of the job took a little bit of a different shape and they’re like, I thought I could do this, but I really don’t know if I can. Maybe it’s that, you know, they’re used to working one way and it’s really hard for them to shake that.
Like if you, let’s say you have a startup kind of scrappier business and someone comes from corporate and they are really used to the bureaucratic and the more rigid structures and sort of they, at that pace, it’s going to be hard for them if they didn’t want that scrappiness and they didn’t want, like, they might always be, well, in this company it was like this and this company was like, all right, we get it. Like, that’s not where we are anymore.
That can be really hard on the team, right? So you’re starting to look at what are things that are coachable, teachable? Can they be, can you develop them through or is it really not a fit? But I’m going to say this, if you get to 12 months and you are thinking, I’ve known all this stuff since three months in, I did the 30 day review, I did the 60, I did the 90, it’s 12, it’s six months, I wasn’t sure.
What are you doing at 12 months? Like, what are you doing? Stop making a sunk cost of having spent all this time hiring and all this time interviewing on keeping someone that’s not a fit. If they’re not happy or they’re not adding value or they’re actually bringing down the team, this is something that we want to figure out. And I am saying to figure out and exit compassionately, fairly, equitably, all those things. This is not a conversation about firing.
I’m saying, how are you assessing, right? So you’re not jumping to conclusions and you’re giving someone an opportunity. Now, a lot of work that I do with teams is performance coaching. And I’ve seen just as many people turn it around as folks that have said, I don’t think this is for me or not, not turn it around. Essentially when someone gets hard feedback, it’s not the end. Sometimes folks just say, okay, wow, like this was, I didn’t realize how big of an issue this was, or gosh, I really need to get it together.
And I encourage you to take those steps because sometimes a lot of the times I’d say just as often as not people get back into gear and they, it can be repaired. So it’s not a lost cause, but what creates a lost cause is the resentment and being like, I just don’t give that person any responsibilities. So you’re overloading other team members and everyone’s just kind of like figuring it out until you deal with the situation.
Compassion is figuring that out so that person can save face and everyone just kind of comes out in a better place, right? So we might be on two sides of this. Is this a fit or not? It might be within two seconds and I’d give some more time and it might be way past the time you could have figured that out. Both of those are mitigated and rectified by expectation setting, onboarding, giving feedback and continuing to say, hey, what are the things that are coachable, can be developed?
What are the things that are just not a fit? We’re dealing with people here. There are no guarantees. I have been asked so many times, like how do I hire someone to guarantee they’ll work out? Like that’s not the way it works. Your best person ever could love your company. They could live for it. And then they get a job in a dream city or for a company that’s offering them two, three times as much pay.
And they’re like, gosh, I don’t want to leave, but I can’t pass it up. So it’s like we can’t control anything. These are humans, my friends, but we can quiet our overthinking by thinking about it much more methodically. And that’s what we talked about today. See you next time. Thanks for tuning in. And I hope this podcast makes leading your team feel just a little bit easier. If you liked this episode, check out my most popular tool for staying in the know of what your team’s working on without having to micromanage at leahgarvin.com slash snippets.
And if you’re looking for more support for yourself as a leader or for the team you’re managing, don’t hesitate to reach out at leahgarvin.com. See you next time.
Questions this episode answers
How do I know if I made a bad hire or just need to give them more time?
Ask yourself whether you actually did the work of onboarding. Did you set clear expectations for week one, week two, week four? Did you tell them what success looks like, how you make decisions, where you want to be looped in? If the answer is no, you cannot know yet if the person is a bad fit. The missing system is almost always the problem before the person is. Do 30, 60, and 90 day check-ins so you can course correct early instead of waiting until resentment has built up on both sides.
What are the red flags that mean someone is truly not a good fit versus just needing feedback?
There is a difference between coachable gaps and character issues. Coachable gaps include things like not knowing your expectations or coming from a different work culture. The harder problems are things like lying, telling you one story and telling the team another, intentionally stirring up negativity or an us-versus-them attitude, and a genuine inability to work collaboratively with others. Those behaviors are much harder to coach through, and if you are seeing them consistently, it is worth asking honestly whether this role is the right fit for that person.
Should I fire someone who made a big mistake in their first few weeks?
Not necessarily. Before you decide anything, ask whether you gave that person clear feedback about the mistake. Most of the time, the feedback conversation never actually happens. In one example, a new team member was unreachable while traveling on day one. Her leader wanted to let her go, but instead gave direct feedback. The team member was mortified, apologized, and never repeated it. She went on to be a top performer. If you skip the feedback step, you are not giving the person a fair chance to fix it, and you may lose someone great over a single oversight.
What should I do at the 6-month mark if I am still not sure whether my hire is working out?
At six months, treat it like a rubric. Go back to the job description and the expectations you set. Ask whether this person was actually told what was required or whether those expectations were implied. If things were implied and never stated clearly, you need to reset the conversation before drawing conclusions. If expectations were clear and the person still is not delivering, that is meaningful data. Either way, staying stuck in uncertainty at six months, without giving direct feedback or making a decision, is what creates the most damage for your team.
How long is too long to wait before deciding a hire is not working out?
If you are at 12 months and you have known since month three that something was off, that is too long. Waiting does not protect anyone. The person who is struggling is probably not happy either, and the rest of your team is likely picking up the slack. Letting a situation drag on because you feel guilty about the time and money spent on hiring is a sunk cost trap. The more compassionate move for everyone is to assess honestly, give direct feedback, and resolve the situation fairly rather than let resentment quietly build for months.