The Best Hire You Can Make This Year

Jenna Kutcher 

posted by:

Previous Post




May 16, 2018


If I had a dollar for every time I got the question “Where do I find a Caitlyn or Kate or Danielle”, I’d be permanently retired on a beach in Hawaii. Having just taken 6 weeks off while these ladies ran my business for me, I can wholeheartedly say that investing in my team was one of the best decisions I’ve ever made and is at the top of my list in terms of priorities again for this year.

So, today I want to share a step by step guide to help those of you thinking about adding to your team this year, how to identify what role would fit your business best, pick the best person and then what you can do to prepare to hand things over for a smooth transition. And before you think this might not be for you and leave me in this episode, let me challenge you to say that even starting small will make a huge impact and I believe anyone in business can benefit from what I’m going to share today.

5 questions that will help shed light on how to add to your team:

Where are you currently dropping balls?

The first step is to get really honest about what is not going well in your business. What balls are continuously being dropped? Maybe the answer to this question is not tasks in your business, but your home life instead. Are you making sacrifices there as a result of being overextended in your work?

Here’s what I want you to do. Over the next 5 working days, jot down in your calendar what did not get accomplished. Examples could be: emails unanswered, blog post not written, ordered take-out when you wanted to cook a nutritious meal for your family, etc. Is your business draining your energy or are you inspired to get to work each day? Another way to ask this question: are you working ON your business, instead of IN it? What do I mean by that? And how do you know the answer to that question?

What are your weaknesses and limitations? Own them.

I’ve told the story many times about how I was white knuckling my business before releasing control and asking for help in my business. Here’s the thing: You cannot do everything. Even as an action taker, hard working, love what you do business woman – trust me when I say balls are getting dropped, things could be done better or you’re missing out on life.

Why is this important? If you are going to release control and let go of some aspects of your business, it’s so important to realize that even though you are capable of some of the tasks on the list, you can’t do them ALL. If you hire someone on your team to help but are constantly thinking “I could do that”, your relationship will suffer. Instead, you need to have the mindset shift to “I can’t do this and do the important things on my list well”.

What excites you about your business?

The hard work is done, now on to the fun part. Awareness of what you love to do most in your business is important because these are the things that should not be outsourced. You might read advice or even hear about what I personally outsource in my business and be tempted to emulate those decisions. But, if you love editing or blogging and decide to outsource those things because that’s what others are doing, you won’t be happy with the results of someone else doing it because you’ll have higher expectations for these tasks that are important to you. Make sense? So I would challenge you to dig deeper than the big picture creative aspects of your business and tune into all of the tasks that you enjoy and keep those on your plate!

What are your biggest hopes and dreams?

What are the things you dream about but something has gotten in the way of you working towards making them a reality whether it’s lack of time, resources, knowledge or fear? Keeping this list in mind will help you release control on the other things in your business to free you up to focus on accomplishing these goals. It will also allow you to more clearly communicate the direction of your business to new team members so you will all be working towards the same goals and priorities.

Moving on to the next step:

Look through the answers to these questions, they should start to shed a clear light on the areas that make sense for your unique business and skillset to outsource and get help. Do you see trends among the things that you procrastinate, the balls getting dropped and your weaknesses and limitations? For me, the answers to these questions were: inbox, accountant, meal prep, and the list goes on.

Similarly, the things that excite you and fill you up in your business are the things that you and only you should be doing for a couple reasons – this is when you are working in your genius zone and will both make you fulfilled and happy in your business AND catapult your success at the same time. Why? Because I believe these gifts are what we’re meant to do in this world, our passions and what excites us is exactly where we should be spending our time.


So now that you have an idea on the type of tasks you’re looking to fill in your business, you might be thinking – ok, but how do I find them and how do I know what to look for?

  • My advice here would be first and foremost to find someone you just plain like. This is going to be someone you spend a lot of time with and through a simple piece of advice – one of the most important!
  • Don’t be afraid to ask hard questions and have uncomfortable conversations. It will save you trouble in the long run and may identify areas that need to be addressed up front or clue in to a potential red flag of someone not being a good fit.
  • Looking for a more tactical or scientific way to identify the right person? Take advantage of skill or personality tests like the Enneagram, Skill Finder, Myers Briggs, etc. It can be scarily accurate and so helpful in identifying the right fit for you and your business.
  • To be entirely honest, my first hire – Caitlyn, found me. And I believe this goes back to the saying “your vibe attracts your tribe”. Putting yourself and your story out there online will not only help you in your business and attracting the right customers to you, but also the right team who will be great cheerleaders and love your business as their own.
  • Look inside your own audience and customer base. If they’ve worked with you, chances are they are on board with your mission and values as a business. This is how I found my community manager Alex, and associate shooter Courtney who were students in my courses.
  • Start small: maybe getting help looks like someone helping clean your home, a meal delivery service, a short-term project or a site like upwork or Fiverr. Outsourcing will get easier with practice and start small before adding a more permanent team member is a good place to start.

(Psssst: Wondering what to do ONCE you hire someone? Tune in to hear my best advice!)

My mastermind girls have been asking how I grow such a devoted team and the simple answer is that I consistently ask them what’s going well, what could go better, what they’re excited about, what’s dragging them down and then take action on their answers. Both Caitlyn and Danielle’s roles are 100% different than when they first started me because of this. You can tune in to hear them talk about this in episodes 120 and 106.
There you have it, Goal Diggers, a step by step guide to hire help, what to expect, how to pick the right person and how to prepare and hand things over!

Don’t miss my free workbook “So, you think you want to outsource – 5 questions to ask yourself first” to walk you through this episode!




Leave a Reply

Your email address will not be published. Required fields are marked *

  1. Beth says:

    I am so inspired, Jenna. I am 50 years old, starting a new business and although my vision is clear, there is no way I can get there on my own. All of your freebies, insiders page, courses are helping me sort through all the “things,” find the right people to help me, and gain the confidence to go forward. Girl, you are awesome!


The Latest From the Goal Digger Podcast

BINGE listens


Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

hey there!


What do you want to read today?

Except instead of a video game, this is you IRL. Let’s get laser focused on setting your goals for this month, year, and beyond so I can hand over resources specific to how YOU want to grow!

Take The Quiz!



free downloads show


Free downloads to elevate your game.

FREE challenge



Screw the junk mail, I'm bringing "real" right to your inbox. Deep encouragement, tough questions, needle-moving challenges, and smart strategies to help you make your dream work. You in?

great idea alert!

Hey, Let's Be Pen Pals!

    © JENNA KUTCHER 2024


    |    SITE CREDIT

    |    GET IN TOUCH

    |    Legal