Ask Jenna Anything: Building a Team


Ask Jenna Anything: Building a Team

Jenna Kutcher 

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Jenna answers all your burning questions on building a team on the Goal Digger Podcast and reviews who is on the JK team and how we work together.


Hey Goal Diggers! Another “Ask Jenna Anything” Episode all about building a team! I fielded your questions from both the Goal Digger Insiders FB group and the Goal Digger Instagram  (if you’re not hanging out there, you’re totally missing out!)

I was absolutely floored by the amount of responses I got from you guys, and I decided to group them by category! I am still letting you call the shots and am fully covering ALL the nitty gritty details.

Many of you know my story– a burnt out photographer, blogger, businesswoman juggling (and struggling) with all the balls in the air. BUT finally, I reached a breaking point, took a leap, and outsourced one job… then two.. Then hired a full-time member… and another… It’s been a whirlwind, but the BEST decision I’ve ever made, and today we are covering all the behind the scenes magic of how you can hire your own dream team! Let’s get started!



(Is your name mentioned on air?!)

Okay, first things first… so many of you asked!  What does your current team like?  What are their roles? Are they full-time or part-time? Is YOUR team in person or all online?

Morgan K:  Jenna! I need help with the struggle of taking my personal brand to hiring. I own a fitness studio, named as me and had so much growth this year. I wonder how to prepare clients I engage with face to face each day that someone else will soon be in front of them too!

Marie W: What I’m currently needing help with is HOW do you go about hiring your first employee? Where do you look? What do you look for? I really need someone to help manage my day to day tasks but I’m terrified of hiring someone who isn’t a good fit

Meagan J: How do you divide responsibilities during a project? And about communication, I know you communicate via slack, but being that your team members are mostly contractors and set their own schedules, are your communications ever lost in translation when someone isn’t logged in?

Another from Megan J: How do you set expectations when taking on a new team member?

Megan J (again! Love it!): Do you find it difficult to work remotely with your team at times?

Alyssa C: How do you budget for hourly workers? Are they paid a “set” number of hours per week? I loved your episode on hiring your team, but want to hear more about the hourly worker piece, especially with everyone working remotely.

Rebecca T: What is the best way to hire/create a great brand ambassador?

Molly G: How do you, Jenna Kutcher yourself, make time to reach out and offer guidance to everyone, given the huge volume of photographers and fans you have? How do you keep it personal and meaningful? What keeps you from delegating most of this to your support team?

Melissa (Instagram) Have y’all set up a Trello board or anything like that to communicate deadline, ideas, etc?

Blue salad (on Instagram) : How do you handle management of your company with employees and keeping your brand consistent?

Aida G: Hey Jenna, I would love to know how you handle all the projects that you have going on without being overwhelmed (I know you have people working for you – but, you also need to keep track of what they are doing – right?). I just want to learn how I can juggle different projects in the most efficient way. Thanks for all your amazing content:

Corinna-marie (Instagram) Hi Jenna!! My question is is in regards to your amazing team. How did you find them and what is your advice for someone who wants to be on a team like yours! Where can you find those opportunities and how can you best position yourself as a candidate to become a boss babe’s employee?



Wow, what an episode! Any and every hiring question you guys dreamed up about building a team! I cannot tell you how much hiring and outsourcing changed my life, and I hope this episode gave you the tools to pursue the leap!

And, as always, if you have questions for me, I am CONSTANTLY checking our Goal Digger Podcast Insiders FB group and Goal Digger Instagram account to make sure I am answering YOUR questions. I want to see your name in those groups!


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  1. Amanda says:

    I have recently found your podcast and I really like it. I’ve also discovered that I’m not great at being the boss. I actually like having someone give me goals or projects to accomplish and if I know they are counting on me to get them done, I’m much more motivated than if I try to set projects for myself. So I loved this podcast from the point of view of the team member. Now, I want to know how I become a virtual assistant and work to be a great team member. Does anyone have suggestions about how I begin this next step in my journey? I’m afraid of the answers I’ll get if I just use google!

    • Hey Amanda! SO glad it was helpful! My advice would be to get really clear on the type of business and person you want to work for and engage with and get to know their business. Then, get clear on what strengths you have to offer and what type of services you could provide that might match the needs of who you’d like to support. Then, get out there and introduce yourself! Best of luck!


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