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How To Hire And Train Your Content Dream Team

Hailey Dale


I’m Hailey – content strategist and founder here at Your Content Empire where we help you create more profitable, purposeful and productive content — and hopefully enjoy yourself more while doing it too. Learn more about me here >>

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Content Systems
Content Strategy
Sales Funnels
How To Hire And Train Your Content Dream Team

I want to start by recognizing that it is hard to hire. It doesn't matter what stage of business you're at. Whether you're new and it's your very first hire or whether you have been hiring for a while, there are still struggles when it comes to finding and hiring the members of your content dream team. 

One of the biggest struggles of hiring is the perception that it's a huge time investment. What if you hire the wrong person. What if you spend all this time training somebody only for them not to work out.

I run an agency which means I must have a well-functioning Content and Sales Funnel Dream Team. Luckily, because I have another side of my business, My Content Empire, I get to benefit from those hires as well. I’ve also developed a knack for hiring and mentoring great people.

I want to share some of the tips that I have about how to hire, how to train and how to retain your content Dream Team.

There are plenty of positions that you can hire for. In this post, I'm going to focus on three of the team members who are going to help you. Those three people are your virtual assistant, you're a designer and your copywriter.

The Virtual Assistant

Your virtual assistant (VA) is probably going to be one of the first people that you bring onto your team. There is a lot of time-consuming parts of getting your content created and scheduled every week. A virtual assistant can help you to free up yourself a bit so that you can spend your time in the places where you are needed in your business. 

Generally speaking, you are probably ready to hire a virtual assistant between 6 to 12 months of starting your business.

A virtual assistant is going to help you with

  • scheduling your blog posts 
  • getting your social media up into your scheduler 
  • scheduling and formatting your email newsletters
  • doing a bit of customer service in your inbox
  • managing and scheduling out your Pinterest and other socials
  • doing a bit of community management, if you have a Facebook group, or want somebody to just kind of respond to people on Instagram who follow you.

When hiring a VA, always consider how comfortable you are with them and how comfortable you are teaching people. When you hire a VA, consider your areas of expertise. Hiring a junior level assistant may save you money in the beginning and if you provide detailed instructions, this individual could grow into the ideal team member. Alternately, if you don't necessarily feel comfortable with some aspects of your business, you're going to have to hire somebody who knows how to do it already. 

The Designer

A lot of people can get by without a designer, especially if they have some good brand templates added into a very user-friendly software like Canva. I know a lot of people who have their VA doing their design work as well. 

I think that it's worth having an actual designer on retainer so that you can have them do more complex projects. 

Designers will help you with anything branding and design. This could be any of the following:

  • Launches
  •  PDF freebies
  • Ebooks
  • Course materials
  • Templates
  • Blog post graphics
  • Social graphics 

When you find yourself creating a lot of these items in your business, that will be when you know you're ready to hire a designer. It is important to understand the benefits of outsourcing some of these tasks off your plate. Even though I have a background in design, I found it was more beneficial for my business to find a quality designer. 

A big consideration when hiring your designer is to make sure that you like their style. Also, look at their portfolio to see if they can work within a variety of design styles.

The Copywriter

Most online businesses require a huge amount of copy. Having a copywriter to share the load with you will probably be one of the things that you're going to value the most. Copywriting is one of those things that takes a big amount of focus and if you are spreading your focus over a ton of different things as the business owner, it's going to be worthwhile to have somebody who knows your voice and can help you create copy reliably.

These are just a few of the things that a copywriter is going to help you with:

  • social media copy
  • blog posts
  • email copywriting and email templates
  • promotional copy for launches and different campaigns 
  • Web copy 
  • Press releases

When you're hiring a copywriter, it is important to remember that most people can write but not everyone can write well. When you're hiring a copywriter I recommend doing a test assignment. 

Or The All-In-One Team …. 

Another option if you either don’t want to hire, train and manage individual contractors is to find an all-in-team. This can also be helpful to streamline all of your marketing and content to make sure it’s being approached as a cohesive strategy. 

This is the work that we do for our clients through the Content On-Demand package, where we handle everything from strategy, blog posts or podcasts, social media, graphics, paid ads, Pinterest and scheduling. Plus measurements and funnel optimization so you know exactly what your ROI is from your content and we can make sure it grows.

Behind The Scenes Of How The Content Dream Team Works In My Business

My dream team may be a little bit different than what you're building in your own business because we have the agency as well as The Content Empire. 

I want to give you a little bit of a sneak peek behind the scenes of how the team works here. There's me, I'm trying my best to stay in the CEO role to do more strategic planning. I do a lot of writing as a content creator. 

The next role that I have in my position is my online business manager. She is a lifesaver. She helps me with the day to day running of my business while I am being pulled in every direction. She's another me and has probably been the most successful hire in the past year because of how much time and work she's taken off of my plate.

The next position is our copywriters. We have two right now but we sometimes have three. We have a lot of copywriters because we have a lot of copy projects. They handle everything from opt-in pages to welcome emails. Next up we have a designer. We usually just have one designer, it isn't necessarily a demand that's big enough to warrant having two different designers on the team. I also use her over on the content side of my business.

And then finally we have a virtual assistant. Sometimes we have two! We usually have one dedicated to customer service and one of more of a tech VA. 

How To Hire: Posting The Job

When coming up with your job posting there are some things to consider. 

1.) Experience

How much experience do you need for this position? Do you need them to be completely self-sufficient or do you already have pretty detailed documentation or can pull that together so that you can hire somebody who can learn those things?

2.) Location

Do you need somebody local or is remote okay? If it's remote does timezone matter? If you are working on tight deadlines or have a customer base in a specific time zone, having remote workers in different time zones could be too much of a challenge.

3.) Responsibilities

I like to brainstorm the different things that I'm going to have them do. After I've brainstormed all of the tasks that I want to outsource I start grouping them into categories. 

4.) Qualities

What are the things that will not work for you? Hat kinds of qualities do you expect in your team? If you work on deadlines as we do, we need to hire people who can meet deadlines and have strong time management skills. 

5.) Values

Consider the type of person that you're bringing into your kind of work environment. Even if you're not working side by side with them, you are still working together and relying on each other. Is it important to you that your team has a positive attitude or understands the importance of communication? 

6.) Application method

Finally, you want to think about how you want them to apply. You want to have a detailed process for them to follow. Are there specific questions you need to be answered in a cover letter? 

Now that you know who you need to hire, sum this all up into a description. Think about dating ads. Seeking a sunny copywriter, who is skilled at writing social media copy and email newsletters. 

How to Hire: Interviewing

Before you start setting up interviews, you have to decide how you want to go through all of the applications you are sure to get from your great job description. I like to take all of this and create a spreadsheet with the scoring matrix. As I'm reviewing each candidate I make sure that they meet all my requirements and I will input them into my spreadsheet based on this with a score out of 10.

Once I identify my top choices, I can start setting up interviews. I have a few standard questions I like to ask. What is the last thing that you learned independently? How did you develop your skillset? What is your strongest characteristic as a writer or designer? What is your biggest area of improvement?

From the interview process, I'm able to identify my top two or three candidates and I send them a paid test assignment. 

How to Hire: Offering the job

Finally, we move on to hiring and onboarding someone. If they're interested in the job, your next step is having a contract. A contract lays out the agreement for anything from the rate of compensation to the start date and responsibilities for both you and for your new hire. 

How to hire: Training

The final step in hiring new staff is training. There are a bunch of different ways to train someone. This is going to depend on the level of experience that you required. If you hired somebody that you knew you needed to train, you're going to need a system for training. As Amber McCue calls it: your clone-yourself systems

Before I bombard any new hire with all the different things we have going on in the business I try to keep it to just one category of assignments. Think about the thing that is going to save you the most time and free you up the most.

I hope this behind the scenes look at hiring your dream team was helpful. Learning how to hire and train your content Dream Team members doesn’t have to be daunting. 

Want to hire your first Content VA? Use my free Content VA hiring spreadsheet ↓

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