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.

This episode is part of the Hiring, Onboarding & New Team Members series. Browse all episodes →

Mic drop moments

“Recognizing that people bring a different context is the first thing. Now we wanna understand what value from that other context can we actually bring to make our organization better.”

“…this is how we actually innovate more. This is how we get better as a team by recognizing new backgrounds and experiences and things that aren’t the way that we were operating before.”

“We are not doing them a favor, we are actually prolonging the inevitable that they’re probably gonna be struggling.”

Episode highlights

The invisible force shaping your team’s friction

When someone joins your team, they do not arrive as a blank slate. They bring an entire operating system built from their previous environment, whether that was a chain-of-command healthcare organization, a fail-fast tech startup, or a high-stakes litigation firm. Lia’s central argument: if you are hitting unexplained sticking points with a team member, the most overlooked cause is a mismatch between their previous context and how your organization actually works.

This is not about capability. It is about the unspoken rules someone internalized over years of working somewhere else.

What context mismatch actually looks like

Lia walks through three concrete examples of where this breaks down.

Someone from a military or healthcare background, where orders come from the top and you execute without debate, joins a tech company that runs on bottom-up input and open iteration. The result is confusion on both sides: the new hire waits for marching orders that never come, and the leader wonders why this person never brings ideas.

Someone from a fail-fast tech culture joins a law firm where a single mistake can end a career or a case. The mindset does not transfer, and the person feels blindsided when psychological safety does not work the same way.

Someone accustomed to open, two-way feedback joins an organization where feedback to leadership simply does not happen. They push back once, get shut down, and spend the rest of their tenure confused about how influence actually works there.

Step one: recognize the context

The first move is to actually ask. When you bring someone onto your team, find out how decisions were made in their last role, how disagreement was handled, how information flowed. Do not assume. Someone who spent a decade in one industry has a deeply ingrained operating model, and just telling them “here is how we do things” is not enough. They will nod and then default right back to what they know.

Step two: mine that context for what makes your team better

Here is where most leaders stop short. Instead of treating someone’s previous context as baggage to overcome, ask what is genuinely worth borrowing. A hire who brings structured experimentation frameworks from tech can help a traditional organization pilot ideas more safely. Someone who comes from a culture of disagree-and-commit can help a consensus-heavy team stop reopening decisions that are already made.

This is how real innovation happens. Not from pretending everyone starts from scratch, but from deliberately pulling the best from each person’s background and letting it raise the floor for the whole team.

Step three: coach the person into your organization’s reality

Lia shares a story from a design team she observed. A designer who had come from a very top-down company had never presented his own work because leadership always did it for him. He joined a team where designers were expected to present, get feedback, and defend their decisions. His manager, instead of naming the expectation clearly and coaching him toward it, quietly worked around him. That designer never built the skill. If he had changed roles again, he would have been just as stuck.

Not coaching someone into the way your organization actually works is not kindness. It is prolonging their struggle.

It always comes back to expectations

Lia ties the whole framework back to one of her core principles: when expectations are unclear, people default to their old patterns because they have nothing else to anchor to. Setting clear expectations about how decisions get made, how priorities get communicated, and what success looks like gives a new team member the certainty they need to stop running their old playbook and start building a new one.

In a smaller organization especially, you do not have the runway to let someone figure this out over six months. Move fast on all three steps and you set everyone up to win.

Related episodes in this cluster


Want to go deeper?

The Unstoppable Team. How to build a team that runs without you in the room.

Learn more

Available on Amazon →


Full transcript (click to expand)

This is how we actually innovate more. This is how we get better as a team by recognizing new backgrounds and experiences and things that aren’t the way that we were operating before, and using those to elevate and make better what we’re doing. So if someone brings a process or an experience, because that’s how their previous job work, and it’s awesome. We don’t wanna say no, that’s not gonna apply here. We wanna say, Ooh, let’s learn from that.

Welcome to the Managing Made Simple podcast, where I bring a decade of experience working in some of the most influential companies in tech to help you navigate the ins and outs of being a people manager from conflicts to feedback, to delegating and more. We will leave no stone unturned when it comes to what makes us love managing, kind of hate it and everything in between. Doesn’t matter if you’re a new manager looking for some tips or a seasoned manager looking up their game.

Everyone is welcome to hang out with Managing Made Simple. Let’s go. Let’s go. Let’s go, let’s go. I know you’re here because you want to be a better manager, but I also know it’s often easier than done. That’s why I put together a scorecard of 20 things that you can do this month and every month to show up better for your team as a manager. From positive feedback to recognition to honoring those working norms that we know we gotta do, but sometimes forget.

This scorecard serves as a checklist and accountability buddy to remind you of all those things you gotta do to be a great manager. Download your copy today at lia garvin.com/scorecard. Welcome back to the show. I’ve been reflecting a lot lately on some of my experiences working in bigger corporations or in in tech and things that I am applying to smaller businesses or smaller companies so that they either don’t make the same mistakes or apply some of the principles that really helped folks move faster in scale.

And one theme that kept standing out over and over and over is what I’m gonna talk about today, and that is one big thing that you may not be thinking about that is getting in your way from having an effective teen. Because if you miss this thing, you are not fully understanding how your teams are coming together, why there are sticking points, why things aren’t going as smoothly as they could be. All right. So drumroll please.

I will unleash – what is this thing? This big thing that you may be overlooking is the context in which someone came from before joining your team. And when I say context, I mean what job were they in before? What sort of environments were they in before? Because this is likely going to dictate how they show up in your company and in your team. Whether you are a small business owner with just a few folks, or in a startup maybe with a few hundred people or in a huge corporation, whatever the situation is, whoever you are managing the context that person came from, this is going to dictate so much about how they approach work.

Because whether we like it or not, even if we join a new company, we think, okay, I’m just gonna like start over fully. I get it. I’m gonna do the onboarding. I’m gonna fully integrate into this situation. I got this. I’m good. We bring all that stuff that worked for us before or didn’t work, but we observed it. And when you think about this and you recognize where people are showing up from, you are so much further ahead to getting people aligned because you can tune right into that context.

So, let me give you an example of what I mean. There are different sort of hierarchy structures and different kinds of companies, right? So if you have someone in that comes from a medical or a healthcare background where it’s very chain of command or a military background where you know orders are given from the top, differences given to the highest person in the company or in the organization, that when an order comes forward, you do it.

You don’t really disagree, you don’t ask about it. You just kind of go forward. Think about if that person comes with that context. And they join a startup or a tech company where it’s, it tends to be more of a bottoms up where if someone makes a decision, it’s kind of like, yeah, well, what about this? What about that? There’s a lot of brainstorming, iteration, ideation, problem solving that can happen. This can be very, very confusing for this person now, especially if you come in as a leader who worked in the healthcare space or in government or in military, and people are like, no, I don’t really agree with that.

There’s gonna be a huge tension right off the bat. But then for the employees, the same thing that if the person is used to getting specific directions, Hey, here’s my marching orders, I’m waiting for that, and you’re saying, come to me with solutions and ideas, and we’ll kind of vet them. That’s confusing for that person. They don’t really actually know how to operate and be successful. Let’s think about another example. You know, working in, in law firms, if you come from a tech background and you are used to the concept of fail, fast, iterate, it’s okay if you make mistakes, we wanna just learn.

And you bring that mentality to a, you know, high stakes litigation law firm. Well, fail fast is not a philosophy that folks subscribe to. No. Failing fast could cause someone, uh, their life. It could cause someone their financial livelihood. It could cause the firm’s reputation. So if you bring this context, you may be like, wait a second. I thought it was okay to make mistakes. And now I know law firms are working on ways to bring more psychological safety and, and learning from mistakes.

But this mentality, in the same way as it’s applied to tech doesn’t show up the same way. And so this can be very confusing. You know, same thing with. If you come from a company where feedback is a two-way street, we can have open debate, open dialogue, we challenge authority, we ask questions, we say, Hey, I don’t think that was quite right. This open feedback, it shows up in firms like McKenzie. Obviously Bridgewater, if you join a company where that’s not the case, you are going to be for a rude awakening.

When you share feedback and a manager’s like, mm, no, you don’t share feedback to leadership. That’s not how it works here. And again, while I think I would argue we should always have feedback as a two-way street. If that’s not the context in that organization, you are going to have so many disconnects. So what do we do about this? Well, we first have to recognize every single person on our teams brings with them that context of the previous role or previous experiences they’ve had.

Okay? That’s the first thing to understand. And if someone has been in that world for a really long time, So let’s say you hire an employee and they worked in, they worked in healthcare for 10 years, or they come from the military, or they worked in finance or, or a law firm, or in construction, right? Whatever it is, and they worked in that field for a long time. You’re gonna really have to understand, you know, well, how, how did things go in that organization?

How were decisions made? How, how did people share disagreement or, or give. Give opinions or, or give feedback, right? You wanna actually understand what are the working dynamics of this person’s context, if they’re not the same as they are in your company. Because just telling someone, Hey, here’s how it is here. Come on, you got it? Like, go with the flow. The person is gonna nod and say, okay, cool. But they’re just gonna bring that same context.

Recognizing that people bring a different context is the first thing. Now we wanna understand what value from that other context can we actually bring to make our organization better. For example, if you brought someone in that worked in tech and they had a lot of patterns and ideas around experimentation and piloting and, and MVPs and and iteration, and they have these little tools for being able to make failure safer, that’s where we can bring that in and we can elevate an organization.

This is how we actually innovate more. This is how we get better as a team. By recognizing new backgrounds and experiences and things that aren’t the way that we were operating before, and using those to elevate and make better what we’re doing. So if someone brings a process or an experience, because that’s how their previous job worked, and it’s awesome, we don’t wanna say, no, that’s not gonna apply here. We wanna say, Ooh, let’s learn from that.

Let’s borrow from that. Let’s use something there. Because that’s how you really innovate is you say, oh, there are pieces about all different types of work, all different types of ways of operating that are going to make this better. Same with companies that had a decide and commit or disagree and commit mentality, spinning on decisions and having too much, you know, belief of consensus based. But really someone’s deciding and really, like we reopen things forever. There’s some patterns that can get companies stuck when they’re trying to be collaborative.

And yet they don’t have but on the line for making a decision. This is something I’ve seen so many times, especially in bigger companies. Well, if someone comes with a context of, Hey, we make a decision once we make the call, it’s a agree and commit or disagree and commit, and here is the only situations in which we open that decision, a, B, C, we’ve spelled ’em out, everybody’s agreeing on it, and then we go, well, this may not have been the way you were working before, but it sure as hell’s gonna make things easier to move forward if you felt that you were getting stuck or own decision.

That’s why understanding, well, what’s the value of this context that we can bring in and improve the way our company’s operating? This is going to be huge, both for showing someone we don’t water down all your experience when you’ve joined. We really value that and we wanna make sure that we’re leveraging the things that are great. Third thing about this context is helping coach that person into understanding, you know, yes, you bring this awesome context and we’re leveraging a lot from it.

And here are some things about the way that things work in this team. This is a big one. This can be really hard if you are a manager and or a leader and you have recently joined a company or an organization or started a business and the employees that you’re working with or the stakeholders you have to influence come from a very different context than you. This is a learning curve. It it absolutely is. And if you are managing folks or you’ve hired people that come from a very different context, This is going to be a learning curve for them.

I’ve been in this situation and I’ve seen it. I was on a team in a tech company that had a lot of folks from the healthcare and, and government agencies, and they brought a very different context than, than folks that worked in engineering and product management. And I saw a lot of breakdowns in communication because the healthcare professionals and clinicians and, and, and folks from government were communicating in the way that they were used to. They were operating within a tech company where the way you make decisions, the way you share information, the way you influence others, just looks very, very different.

And so I kept seeing the same issues happening. It wasn’t because folks didn’t have the same goal and didn’t both have the same passions and interest in, in, in whatever the product ideas were about. It was that they were missing each other on the context. And what would’ve been so helpful. For the folks that came to this company from very different context would be to stop and say, okay, yes, I bring this context. I am very passionate about the way that I’m working about these different things, but let me stop and think about how are you effective in this particular organization?

How can I be effective in an engineering company? How can I influence product leaders who think about things in this way? Because it is the, the, the way the kind of whole company operates, it is your responsibility to get on board with that. And yes, we said in, in like step two o obviously ideally there is a integration of the way that you worked and ideas and everything. Yes. And it’s gotta be a two-way street. We have to remember that.

It’s our responsibility to say, okay, I’m gonna leave some of that and I’m going to figure out how to work within this company. Same thing I was, I was working on a team and uh, it was a design team in a big company and a designer came from a company that was very, very tops down. Where only the leadership presented ideas. So he was a designer and he wasn’t used to showing his work because someone else presented it for him.

And he joined this team and it was very different. And designers, they presented their work all the time. They were sharing feedback and they were asking things and this person was not prepared for that. And unfortunately, his manager sort of let him flounder a bit by not stopping and saying, Hey, this is actually the expectation. We present our work. We give feedback, we talk about it. The leads don’t present the work for designers. Let me figure out what you need to build comfort and confidence in doing that.

Maybe some coaching, maybe some, some support, and then holding that person to that same expectation because he thought, oh, this person brings a different context. They’re not gonna be able to do this. Let me just sort of like figure out a workaround that didn’t help that person be successful. Because if that person changed roles, they would never have this skill. That’s an expectation company wide. So you see when, when we’re not helping someone integrate that context into, well, what is the reality in this company?

We are not doing them a favor, we are actually prolonging the inevitable that they’re probably gonna be struggling. If they don’t realize, oh, okay, here’s some things that worked before and here’s some things that I have to now adopt that I’m in a new company, and this is critical if you’re in a smaller company, because you don’t have a ton of time to wait and have someone learn and figure out the ropes, you need someone to hit the ground running.

And it doesn’t mean saying again, shake everything you had before. It’s not good. Get outta here. We’re in, we’re in this world now. No, it’s about doing this very quickly, recognizing the context, saying, Ooh, here’s some great things about what, how you did, and we’d love to integrate those here. And then here’s the way that we work. Here’s how we make decisions. You know, we’ll, obviously we’re open to fine tune, but this is the way things go in this company so that the person understands expectation.

It always comes back to expectations. This is something you will hear again and again. I talk about feedback all the time, and I talk about expectations all the time because when we are clear on expectations, when we know how to be successful, when we know how decisions are made, how priorities are communicated, what success looks like when we know all those things, Well, now we, we understand, oh, okay, this is how it works here. This is how it doesn’t, and I’m totally clear without expectations.

That’s really where we default to our old patterns because, well, what else are we gonna base it on? Right? We have to lean on something. We need certainty. So if you set clear expectations, that’s how you give that person that certainty, and that’s how you move forward. And with that, you have one of my biggest learnings from working in the corporate world. One of my biggest things that I said, ah, if I could only share this with folks that are hiring or managing this, is it not to ignore that context and to follow these three steps.

See you next time. That’s all I have for today. Thank you so much for tuning in to the Managing Made Simple Podcast where my goal is to demystify the job of people management so that together we can make the workplace somewhere everyone can thrive. I always love to hear from you, so please reach out at liagarvin.com or message me on LinkedIn. See you next time.

Questions this episode answers

Why does my new employee keep defaulting to old habits even after onboarding?

Because telling someone how things work here and actually helping them internalize it are two different things. Every person carries the context of where they worked before, and if they spent years in a top-down environment, a highly collaborative team will feel disorienting no matter how thorough the onboarding was. When expectations in the new role are not made crystal clear, people naturally fall back on what gave them certainty before. The fix is not to shake off their past, it is to explicitly name how decisions get made, how feedback flows, and what success looks like in your specific organization.

How does a previous job affect how someone performs on my team?

It shapes almost everything, from how they handle disagreement to whether they wait for directions or bring solutions on their own. Someone from a chain-of-command background like healthcare, military, or government may hesitate to push back on decisions, while someone from a tech or consulting firm may expect open debate. Neither is wrong, but if their previous context clashes with how your team operates and no one addresses it directly, you end up with communication breakdowns and confusion that has nothing to do with skill or motivation.

Should I ask a new hire about their previous work environment during onboarding?

Yes, and do it early. Understanding how decisions were made, how feedback was shared, and how disagreement was handled in their last role tells you a lot about what they will find natural versus confusing on your team. If someone worked somewhere that only let leadership present ideas, they may struggle to share their own work without coaching and explicit encouragement. Getting ahead of that gap instead of waiting for problems to surface is one of the fastest ways to help someone hit the ground running, especially in a smaller company where you cannot afford a long ramp-up.

How do I get the best out of someone who comes from a completely different industry?

Start by recognizing the value in what they bring, not dismissing it because it does not match how your team already works. Someone from a tech background may have tools for safer experimentation that could genuinely improve how your team operates. Someone from a more structured environment may bring decision-making discipline that helps you stop re-opening closed conversations. The goal is a two-way exchange: you borrow what is useful from their experience and they learn how to be effective inside your specific organization. That combination is where real innovation and alignment happen.

What happens if I let a team member skip learning the norms of my company because their background is different?

You are not doing them a favor, you are setting them up to keep struggling. One example from the episode is a designer who came from a top-down company where leads presented all the work, so he never developed the habit of sharing and discussing his own designs. His leader created workarounds instead of coaching him to meet the actual expectation. That meant when he eventually moved to another role, he still lacked a skill the whole company required. Protecting someone from a company norm does not remove the norm, it just delays the reckoning and slows the person's growth.