How to manage contractors and freelancers without the headache

Your freelancer blew a big deadline, your contract didn’t show up the way that you thought they would, and maybe your agency that everybody recommended, they kind of blew it. And you’re sitting here thinking, I hired some kind of fractional support to make my life easier, and it made it way harder. This is what I am seeing every single day, whether it’s on the teams I work with at Google, or small business owners and founders, that we’re in a moment where we have to scale quickly up and down, and we’re leaning on fractional talent, and it’s not always working out.

But it’s not the talent in and of themselves, right? It’s not the people that don’t really care, it’s how we are leading them. And that’s what I’m going to talk about today. I’m Leah Garvin, and this is The New Manager Playbook, where I talk about problems big and small related to how to make managing your team the easiest part of your job. Because dealing with people is hard enough. And it’s especially hard in this moment where we have to do more with less.

So for a lot of us, whether it’s in the corporate world or in the small business space, we’re not able to hire as much full-time talent as we were before. So we’re in this little bit of a challenge of, well, I need to be able to have more people solving these problems. But if I can’t hire more full-time folks where I kind of know I have a little bit more accountability there, we’re really struggling. And so that’s the reality, right?

We’re having to tap into this talent pool where maybe folks have multiple jobs, right? Probably they do if they’re a freelancer or a contractor. They don’t feel maybe necessarily bought into our company. They’re not getting benefits, they’re not getting bonus structures, right? They’re not feeling that culture like a full-timer would feel. And so we don’t have the same incentives as we might if someone was on full-time. But it doesn’t mean that we can’t get that person really bought in.

And so again, that’s what I’m going to talk about today. And in this moment right now where we’re having to lean on these folks more than ever, it’s not a moment to think, well, I wasn’t supposed to have to manage this. And this is what I’m hearing all the time. How do I motivate a contractor or freelancer? What should I be paying someone, right? And what do I do? How do I know if they’re good or not?

If they made a mistake, how do I know if I keep them or not? And so stay with me because that is what I’m going to talk about today. My three keys to making sure when you hire someone fractionally that it works out. So I’m going to share that with you. But I really want to talk first about these kind of horror stories we’re all working through because I don’t want you to feel alone. And I want you to recognize really which tool to deploy when and how to know that it’s going to really solve this problem.

So I have a friend and she is launching a new tech product. It’s like a software service platform and she’s been working on the MVP. So this is like the initial prototype for the project. So she hired a developer team and she hired a UI designer, right, to do the visuals. And the developer team has been awesome. So that’s the contracted workforce and they’re going really well. But the UI designer has blown deadline after deadline after deadline.

And all of a sudden, this UI designer said, hey, you know, we had said this would be the rate and I was going to finish this by then. But in order for me to hit that deadline, the next one coming up, because they had missed so many, I need you to pay me twice as much. And my friend said, well, I don’t have budget for that. This thing’s already gone on longer than it was supposed to.

I’ve been paying him. Now he’s kind of like extorting me for the rest of it so that we finish this MVP. And she felt really stuck. And that’s something I’m seeing all the time is we get to this place with folks that we’re relying on, but they’re not an employee and the terms were a little bit confusing and we didn’t really set expectations. So we’re kind of stuck and we’re out of options. I have another colleague that runs a marketing agency and they hired a freelance that was supposed to take over a huge, huge part of their content creation.

But this freelancer had another job going on and that job happened to be paying a little bit more. And so all the content production and the deadlines that fell to the wayside and the person said, well, hey, sorry, I have two things going on and I had to prioritize this other one. And that left that person high and dry. And so this is challenges we’re all wrestling with because there’s a limited number of hours in the day and we’re having to rely on folks that, again, they don’t just have the one job.

They don’t feel super connected to the job necessarily. They’re not part of that culture. And we’re struggling to find accountability. The next big one is really folks making mistakes and missing things. We bring someone on really, really quickly. We want to ramp them up and this happened for me. I brought on a freelancer to really help kind of get my social media content organized. I had a Canva template for some of my things. I said, hey, look at my Instagram, look at my LinkedIn and just go from there and you’ve got this.

And she started on it. And right away, I saw like nothing really matched the template and nothing really made sense and it wasn’t what I wanted. And I just got so frustrated and I would fix little things and be like nitpicking and giving more clarity and all these. And I thought to myself, well, this definitely isn’t faster than doing it myself. And I said, I don’t think this is working now. And so I learned firsthand that, hey, something could have been done differently, but at the moment, I didn’t really know what that was.

And so I reflect on this and that’s where these three keys come into the picture. I said, well, what did I do that where it didn’t go that well? What did my friend that was running the design agency, where could he have gone better? And this other that had this UI person that was extorting them to be able to finish the thing. And that’s where these three keys come together. The first one is having some kind of onboarding or clarity around SOPs, right?

Your standard operating procedures, really how things get done. Now, if you’re thinking, well, onboarding, yeah, that’s for full timers. It sure is. And it’s for anybody that works with your team, anybody. Because how the hell are they supposed to know what you want something to look like or how you want it done? You’ve got to take a step back. And I know we’re hiring this talent because they can ramp up quickly. And maybe you say, hey, I want you to start today.

And by tomorrow end of day, I want this whole project done. Maybe that’s how fast we need people ramped up. That is all the more reason why we need some of these onboarding materials. And so in the background, you can be getting this stuff organized. How do you make decisions? When do you look at emails? How do you want to approve things? What are your brand guidelines and templates? What is your voice? Where do people store files?

Where do they check in code? How do they open the door in your physical location? What are the opening and closing procedures? Whatever it is that they have to understand right away, you got to have that easy to pick up, right? And that’s why the onboarding is such a key piece of my Ops Playbook program as part of my 90-day CEO, where I come into a company and really figure out all these things around priorities and working norms and create your own really company Bible or playbook.

That’s why onboarding is first, because we need to be able to give someone a tool consistently and say, hey, here’s the playbook, here’s the Bible, go run with it. So I create that for folks so that everybody on the same page understands what you’re working from. And you can do this by thinking about, well, if I’m hiring even just a freelancer, how do I want them to send me information? Do I want to use Google Drive or Dropbox?

How are we doing these little nuts and bolts that get in the way and slow you down and just cause you to say, nah, forget it, I’m going to do it myself. So onboarding and having something thought through, this is going to be so, so key. And again, if you’re thinking, hey, I need that Bible, hit me up, hello at legarver.com, because this is something that’s going to help onboarding full-timers and freelancers, contractors so much easier.

Now, the next piece is setting expectations, another brass tap management skill. Setting expectations is your biggest superpower and is the biggest place we miss as leaders. When we don’t set expectations, we’re assuming someone can read our mind or we think, well, they’re good at this skill. They were a great designer, they were a great engineer, they were a great customer service person or front desk person. They seemed good, they nailed the interview. Why aren’t they doing that well for me?

Well, because maybe we weren’t clear about what we were looking for. Again, our brand voice, some of these things that maybe showed up in the onboarding. And we weren’t that clear on what success looks like. We weren’t clear on, hey, if they’re doing content creation for you, how many posts, what templates to use, how you’re measuring success. If they’re doing development work, maybe we’re not clear on the deadlines or how the reviews happen or the checkpoints.

We assume so many things so often, especially if our other team members got ramped up and understood it really quickly. Then when we see someone else that’s not quite getting it, we think, well, they’re the problem. Whenever someone isn’t hitting the mark, got to ask ourselves, what expectations have I set? How can I be more clear? The answer to those questions is going to be so enlightening. And frankly, we can always be a little bit more clear.

So there’s always a little bit something. I didn’t say, am I clear? It’s not a yes or no. It’s an open-ended question. How can I be more clear? And even if you feel like you’re being super clear, then you can ask the person, hey, how can I be more clear? What else do you need to understand to be successful here? Sometimes they won’t know the answer to that because they’re just getting to know you. And then you might say, okay, well, let’s kind of check back in a few days once you get this thing going and let me know.

A lot of times you’ve hired someone, but somebody else is managing the work. Then check in with that person and say, hey, it’s going to be really important to set expectations here so that we see the outcome that we wanted. So when you’re not getting what you want, when you’re feeling like, well, this person’s not delivering and they’re not motivated, is it because I’m paying them too little or is it not clear? These questions you’re asking yourselves, ask them.

Now, okay. I wouldn’t maybe say, am I paying you too little? Because you want to have figured that out firsthand so that you’re competitive because I’ve said it before, and I will say it again. If you are paying people too little, they’re already looking for their next job. So that’s the topic for a whole other day. Okay. But you got to ask yourself one more point on this. When you are paying someone, you want to think to yourself, would I do a good job if I was being paid this?

And if the answer is no, you got a problem. Then you got to adjust it. So that brings me to the third point. The third key to really being able to successfully work with a fractional staff, whether that is a freelancer or a contractor at an agency, is to really be clear on when something goes wrong, how do they handle it? Now, in my friend’s example that I shared with you, when she had that UI designer and they missed the deadline again and then all of a sudden decided, well, I got to charge you double, that was such a big indication that this person, they’re not really operating in integrity.

Because the truth is when someone miscalculates a service, it really is on them and they’ve got to take responsibility. Now, sometimes we misjudge something that actually happens all the time. That’s human nature. It’s how we bring it up. Now, if that UI designer had said to her, hey, listen, I know I estimated this scope for the project, but when I got to this stage, I found that this, this, and this was more complicated. Now, this is what I originally proposed and it’s looking like it might take this much longer.

Is there a way we can meet in the middle? Do we want to reduce the scope? How can we kind of find a path forward through this? If they made it into a dialogue, it would have been a very different situation. And that’s where you really want to assess, hey, is this person just like, sorry, take it or leave it? If they really don’t care, they’re not a fit. And we don’t want to be in a situation where you feel completely beholden to our person that’s not doing a good job.

And this is true if it’s a full-time employee or a fractional or an agency. And the way that we don’t become so beholden, especially to a fractional support, is we check in more frequently. So we can find, hey, did we get too far along? And now we do feel stuck. We have no other options. We’ve burned through our whole budget. They have all the files on their end, having conversations around, you know, all the data and IP has to be stored on your end when they have to be delivering that, having clear checkpoints for review that’s more frequently as you’re building trust.

All of that is going to show you, okay, is this person, you know, someone that we want to move forward with so that you don’t feel like your work’s being held hostage? So these are my keys to navigating this fractional workforce to be able to really feeling successful. And the first two, frankly, all of it is really the brass tacks manager skills because we don’t bring on a fractional talent and think, well, phew, I don’t have to do anything now.

They’re just going to figure it out. Nobody figures stuff out on their own. You know, if it’s super straightforward, then that means you’ve had some kind of, you know, training system there already, the onboarding or whatever has been clear. Something has to be said to people in order to be able to figure out what to do. So if you have a clear onboarding system, sure, that may set some expectations up front. But really making sure you’ve checked in around you or again, the team managing this person has checked in around, you know, the deliverables, the outcomes, what success looks like, a big one, how long things should take.

That’s one of the biggest discrepancy, right? With us and fractional talent again, or, you know, full-time is we think something should take five hours. They think it should take 25 hours. And we’re like, what the hell are they working on all day? That’s the conversation of expectation setting saying, hey, okay, I felt like this was a five-hour task. This is why, here’s what went into that. What are you, you know, what is your estimate based on?

And then maybe it’s like, oh, wait, we had a different scope in mind. Or you might say, ooh, this person’s a little bit more junior than I thought. They’re actually needing a lot more support. And you can decide, do I want to pay 25 hours for that or not? Right? So these questions and these conversations allow you to really make sure you have sussed out, is this going to work for you? Because again, this utilizing fractional talent, this is supposed to allow you to move faster, to be able to do more with less, be able to scale up quickly, scale down quickly.

And so if you haven’t done these things, that’s probably why you’re encountering some of these headaches. Now, one last thing around this expectation setting piece, because it is the biggest, is we need to have some way to know like where things are at. And sometimes we’re not quite sure if we want to onboard this person into our task tracking system, right? Because maybe they’re just working on a couple of things. Well, my snippets template is like everybody’s favorite tool because it works for full-time employees, contractors, freelancers, even agencies.

And this is a literal Google doc where you have folks enter at the end of each week, top accomplishments for the week, top priorities for next week, and any places they’re feeling stuck or need support. Now, that last one is awesome because usually people won’t tell you when they’re stuck or need support and you just have to figure it out eventually because something didn’t happen. But this snippets template and sharing this with your contractors and freelancers and saying, hey, I just want to make sure we’re on the same page.

If at the end of the week, you can just share an update of where things are at, what are your key priorities for next week? And what are any places you need to talk about next week? That’s going to be game-changing. It’s going to give you so much visibility. It pairs with a task tracking system if you’re using an Asana or a Slack. But it also can stand really, really clearly on your own. So that’s at leahgarvin.com slash snippets.

And as I said, it’s literally people’s favorite tool because it works in any environment. It’s developed from when I worked at Google and was doing program management scale across products like Daydream and YouTube Shorts and all sorts of things. This is a product that can… A template, I mean, that can scale. And it’s also something that my clients with only two or three employees are really, really finding. It gives them so much visibility. So leahgarvin.com slash snippets.

That’s going to be your lifesaver for all of this stuff and more. All right. This is something that it can feel like a challenge, this whole fractional thing, until we get our stride. But once we do, it actually can be a great way to supplement your workforce. It can be a great way to have someone do a few projects and see, hey, yeah, this would be a great long-term fit to convert to full-time and so much more.

All right. You got this. See you next time.