How to Hire Your First Assistant

woman at desk

Four key steps to help you hire your first assistant.

Hiring your first assistant can be a challenge especially if you’re in your first business.  You might resist hiring help because you aren’t making as much money as you’d like.

You might think, “I need to do it myself” or “how can I spend money when I’m not making enough money.”

Or you might feel guilty hiring someone to do a task that you could do yourself.

You may be limiting your ability to make money by doing everything yourself.

I know that this slowed me down the first two years in my current business.

Doing tasks that you don’t like doing or you aren’t good at doing will impede your progress long term. Click To Tweet

When I started Extraordinary Work Group in 1996 – my virtual boutique PR firm – I was a solopreneur. I had recently left my corporate job at a hospital where I had an assistant plus access to a large IT department that handled any computer issues.

I struggled with tasks that I didn’t enjoy doing yet I was in start up mode and thought that I couldn’t justify hiring someone.

That thought – I can’t justify hiring someone – actually slowed down my progress.

In both businesses, the biggest challenge I faced was technology. 

I’m not a detail person who likes data and organizing so anything administrative felt like drudgery for me to do.

My first assistant was the daughter of my accountant.  I hired her to help me a few hours each week.  This was a huge relief.  She did the filing, invoicing and things that I never seemed to have time to do.

As that business grew, I hired Casey who ended up working with me for 10 years as my assistant.  Casey’s skills grew with me and she learned how to handle many of the technology tasks that seemed to take me forever.

After I hired Casey, my next hire was Shelly who was a terrific PR person that I had worked with at a PR agency.  Then once we landed the Microsoft Healthcare Industry Group as an account through their main PR firm, I hired Jeff.

Both Jeff and Shelly worked with me for more than five years.

I began to be curious about the team’s strengths and talents and how we operated as a group.  I had each employee take the Strength Finder, Insights, and the Enneagram assessments.

What was a huge aha moment was that I had intuitively hired people who had strengths in areas where I had weaknesses (they weren’t my natural strengths).

I was not a detailed analyzing person but Shelly and Jeff were both analyzers who enjoyed doing research and working with details and spreadsheets.

My strength was in pitching the news media stories and getting our clients in top business publications.  This was not an area of strength for either of them.  They would rather dig ditches than pick up the phone and pitch a story to a business journalist.

I created an “A” Team by hiring people who had strengths opposite of mine.

Together we were a powerful team that excelled at our work.

Now in my second business, I have a superb team of two that assist me with this business.  Amber who does a remarkable job handling the backend technology and project manages our work.

Brandi is exceptional at customer service so her job is to interface with my clients and handle requests for speaking and logistics among other tasks.

Yesterday a client told me that Brandi is a remarkable extension of my brand.  She said, “You both are the most heart-centered people who really care about people.  Working with Brandi is like working with you.”

The top 4 Steps to Help You Hire a great person.

1.    Make a list of what you love doing and what you don’t like doing.

Don’t spend time doing tasks in your business that you don’t like or that you simply aren’t good at doing.  Why?  You’ll waste a huge amount of time that you could be spending getting new clients or selling your services.  Hint: this is what you want to delegate to someone who excels at doing these tasks.

2. Write a job description that outlines what you are looking for in a person.  

Be clear about the type of person you want to work with including the qualities you want them to possess such as “team player” or “has initiative.”  Don’t hire someone that has your strengths – go for someone who can shore up strengths in areas that are not in your zone of genius.

3.  Narrow down your choices and ask your top two candidates to take a personality/strength assessment.

Hire people who excel in the areas where you’re not as strong. Usually you won’t like doing tasks that aren’t in your strengths zone. I’m not an analyzing type so Excel, slogging through numbers and financials, and detail-oriented work is not something I want to do.

Consider asking your candidates to take one or more of these assessments.  

Kolbe A Assessment 

This is my top recommended assessment to use for hiring – the Assessment A.  This assessment measures how a person instinctively takes action (mode of operation).  It’s $49.95 and it’s my favorite tool for hiring someone.

Gallup Strengths Finder

Take this assessment to find out your top 5 strengths so that your dominant talents help you excel, and perform better at work.


You can take a free assessment to help you learn how you or your new hire experiences the world.  There are 9 types of personalities and you self-select your type by reading paragraphs about each.  This alone is one of my favorite personality assessment.  My favorite book on how to manage people at work using the Enneagram is The Nine Ways of Working that helps you learn to manage your team’s types at work and motivate them to excel.

Note: these assessments are a good thing to do with your existing team so that you can work collectively from a place of strength.  It’s important to keep people happy, motivated and working in their zone of genius – where they operate at their best.

4. Ask people you admire in business to recommend people who would be a great fit for your position.

This is how I found Amber, a project manager who handles all the technology for my business.  I respect my online friends who are running successful businesses so they are my go-to source of potential people to hire.

In both of my businesses, I’ve used this exact strategy to find the best people for my team.  I absolutely love the people who have worked for me in my first business and the two that are currently working with me.

Happy hiring!

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