How to Attract, Hire and Manage Your Business Dream Team - Jenna Kutcher

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How to Attract, Hire and Manage Your Business Dream Team

Jenna Kutcher 

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Here on the Goal Digger Podcast, we love having conversations based on the conversations all of you are having inside of our Goal Digger Podcast Facebook Insiders Group, which is hopping. We love looking for trends to figure out what it is that you’re wondering or questioning or working on, and so this conversation comes directly from the group and it’s all about hiring. 

When Kylie and I get together for these Kylie and Jenna chats on the podcast, we spend almost as much time catching up between sessions as we do recording the actual episodes and that might have something to do with the boss-employee relationship and team dynamic I try to foster with every person I hire. 

I do hiring and team building a little differently than most, and I think it’s why I’ve been able to attract and keep individuals who thrive in their roles and do such a great job supporting this business. With that, let’s dive into the topic of hiring, managing, and developing a strong team to support your biz, shall we?

Contractors vs. Employees

Nearly everyone on our team has started as a contractor, meaning they’re likely using their skillset for multiple clients. Maybe they have a retainer or a certain amount of hours that they’re giving us each week. Some of those contractors have evolved into an employee – someone on payroll that is working solely in and for our business. 

Contractors are amazing because you can hire them on a needs basis. Maybe you have a launch coming up, or you just have a certain time frame that you need this help, you can hire them for an ongoing retainer when you’re not necessarily ready to support them full-time or to have an actual employee. 

I think, too, it’s really smart to start as a contractor to make sure it’s the right fit because when you start getting employees, there’s a lot of paperwork and a lot of legalities that come into play and there are some expenses. When you start with a contractor it’s a mutually beneficial relationship that allows for the level of freedom and maybe not the level of commitment that an employee requires before you go through all the steps to make someone an employee. 

My Intuition-Based Hiring

I’ve got to admit, I hire way more based on a feeling and that’s not always something I can put into a step-by-step strategy. However, there are pieces of my hiring process that I’ve identified as repeatable that would be helpful for anyone looking to add the right contractor or employee to their team.

When I look at a resume or cover letter or LinkedIn profile, I want to see what value you could bring specifically to my business and I want to know that you’re aware enough to see those gaps. You don’t just want a “butt in a seat”. You want somebody that understands the vision, but that wants to protect and carry that vision forward and is ready for whatever evolution comes next. This means you have to look past the skillset. 

With Kylie, for example, she had a background in radio, she understood audio engineering and audio editing, and had previous roles in video production, which isn’t necessarily being utilized in her role day to day, but it has been throughout her time with me in different circumstances. Kylie was also clear in her interview that she likes to work independently and get stuff done on her own time, while allowing for time to work on her own projects and side-hustle. 

That mix of skills made sense for a podcast producer and brought value to the team, even though she didn’t have a background in podcast production. And I love working with ambitious people and almost every single member of our team has a side hustle or serves other clients, or has other passions that they’re pursuing while they’re pursuing what I want to do. I love that because I think that when you’re passionate about your life, you’re passionate about your work. 

The Workday Format

No surprise here, I also have a different view of what a workday and “typical” work schedule looks like for my team… AKA there’s nothing typical about it from person to person who works in my business. I don’t care when the work gets done, just as long as it gets done and done well. Very few of my contractors and employees adhere to a Monday through Friday 9-5 schedule. 

We’re a bunch of creatives who find our flow states at different times of day or who need a 4 day work schedule so that 5th weekday can be dedicated to different projects or simply life! I, myself, am experiencing this in real time where I used to have very black and white boundaries but my goal is to invite areas of gray, because it’s honestly necessary in the season of life I find myself in as a mom of two and trying to figure out when is the work going to get done and where is my time best spent? I’m literally making that decision hour by hour, each day. 

I genuinely don’t care when the work gets done and I want to honor that everyone has different flow states and different seasons of their lives. I just need to be kept in the loop about that work and be able to trust that it’s going to get done, and it’s going to get done on time and up to the standards of the brand.

More from this Episode

What clues is your business giving you that it’s time to hire support? How do I approach managing a team? What is it like to be a boss of 10+ people when I started as a solopreneur? These topics and more are all inside this jam-packed chat about hiring. Hit play wherever you get your podcasts.


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  1. Casey Smith says:

    thank you for this!

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