Your First Hires: Who to Bring On at Each Stage

I used to be the whole company.

Here's what I wish someone had told me then: for most small businesses, the first hire should be a part-time assistant who takes admin, scheduling and customer support off your plate. The right time is when you're turning work away, or spending more hours on tasks someone else could do than on the work only you can do. After that, every stage of your business calls for a different hire.

In the early days of Live Your Message, I wrote every email, every blog post and every customer support reply myself. I was the CEO, the marketer, the admin and the tech person, all before lunch.

And I couldn't grow past the hours I had.

Today we have an extraordinary team. It took a while to get here, and I don't mind admitting I made some serious hiring mistakes along the way (and paid for them). This is everything I've learned about who to hire first, who comes next and how to find people who are actually great at the job.

Five signs it's time to hire help

You don't need a certain revenue number to know you need help. You need to be honest about where your week is going.

1. You're stuck in low-value tasks

If your day is packed with answering emails, updating your website and handling customer questions, ask yourself: is this the best use of my time?

I used to spend hours writing blog posts. I love writing, but it was pulling me away from developing programs and building partnerships, which is the work that actually grew the business. Once I had help, I had time for the things that mattered.

So ask: what are the tasks only YOU can do? Everything else is a job description.

2. You're turning clients away

A full schedule is a great problem to have... until it isn't.

When you're maxed out, people who want to work with you hear "maybe in a few months." Some of them wait. Many of them don't.

I felt this most when we ran in-person events for small groups of high-level business owners. There was so much planning, logistics, support and design behind them that there was NO WAY I could have run them the way I wanted to without a team. I even flew in one of my longest-serving coaches to help support the participants. That support is why the events worked.

3. You're doing tasks you're not good at

There are things you're amazing at, and then there are things you just... aren't.

For me, that was systems and processes. I'm a creative at heart. I thrive on big ideas, not detailed workflows. Once I hired someone who excelled at systems, everything in our business ran more smoothly.

What's your weak spot? Instead of forcing it, hire someone who can do it better, faster and with a smile on their face.

4. You're always working in your business, never on it

Michael Gerber writes about this in The E-Myth Revisited. He tells the story of a baker who's so busy making pastries she has no time to think about growing the bakery.

Most business owners at this stage are that baker. Your team's job is to free you to think about strategy and growth, not to give you more people to micromanage.

5. You feel like you can't afford it

Here's a counterintuitive truth: if you feel like you can't afford help, it's probably the moment you need it.

Wearing every hat costs you time, energy and income. When you're stuck doing low-value tasks, you're capping what your business can earn. I'll show you the math further down.

Who to hire at each stage of your business

The right hire depends on where you are. Here's how I'd think about it, using the same stages we use in Momentum.

Start ($0 to $30K a year): no team yet

At this stage your job is to find out who you serve and get paying clients. Don't hire anyone to "build the business" for you.

Pay for help by the task instead. A freelancer to set up your website, a designer for a logo, a bookkeeper at tax time. Use tools for everything else. If you're here, the start a business page is where to begin.

Build ($30K to $100K a year): a part-time assistant

This is where most first hires happen. You have clients, you have income and your calendar is starting to strangle you.

Start with a part-time assistant, often a virtual assistant, for five to ten hours a week. Good first tasks:

• Inbox and calendar: sorting email, booking calls, sending reminders.
• Client onboarding: welcome emails, forms, contracts and invoices.
• Customer support: answering the questions that come up again and again.
• Social media scheduling: posting what you've already created.

A tech freelancer for website or email platform problems often comes next. And before you hire for any task, check whether software or AI can handle it. More on that in using AI to scale to 7 figures. For the rest of this stage, see how to grow your business from $30K to $100K a year.

Scale ($100K+ a year): operations, delivery and marketing help

Past $100K, the bottleneck shifts. It's no longer just your inbox. It's that every decision, every client and every project still runs through you.

The hires that usually come next:

• An operations or project manager who runs the day to day and keeps projects moving without you chasing them.
• Delivery help, like an associate coach, a community manager or a support lead, so clients get great service without you on every call.
• Marketing help for content, copy or ads, once you know what message and channel work.

Which one first? Whichever removes the biggest bottleneck. Firing yourself from low-value work is one of the core strategies in my guide to scaling a service business. I wrote more about this stage in how to scale a service business past $100K without burning out.

$1M+ a year: leaders, not helpers

At seven figures you're hiring people who hire and run teams of their own. Your job becomes vision, culture and the few decisions only you can make. That's a big identity shift, and I wrote about it in from 6 to 7 figures: how your role has to change.

Hire your weaknesses (and what you don't want to do)

"As soon as you can afford it, hire your weaknesses."

That's Sara Blakely's advice, the founder of Spanx. Hire people to do what you can't do or aren't good at.

I'd add one thing. Hire people to do the things you don't want to do. Work you dread drains far more energy than the hours it takes.

But here's the catch. For a lot of business owners, getting help makes everything worse, not better. It feels like jumping out of the frying pan and into the fire.

That's because hiring help isn't enough. You need to hire right. If you hire people whose values are very different from yours, or who don't have the personality and working style the role needs, you're setting yourself and them up for failure.

The way I see it, you have three options:

1. Do it all yourself with the "if I want it done right, I have to do it myself" mantra, and end up in Burnout City.
2. Shoot in the dark. Hire, fire and hire again until something works.
3. Learn from people who've already made the mistakes, so you don't have to.

I recommend option three. (I've collected more of my own expensive lessons in 7 mistakes I've made growing and scaling my business.) Here's the process we use at Live Your Message.

Hiring is like dating your co-workers

I think of my team as co-workers, not employees. And hiring them is a little like dating.

You don't rush it. And you don't get married right away.

The goal of a good hiring process is to meet the REAL person behind the polished, put-together job seeker. Everyone is on their best behavior in an interview. You want to see how they work on an ordinary Tuesday.

So for a first hire, don't commit to a long contract on day one. Start with a small paid project or a trial month with a clear brief. You'll both learn more in four weeks of real work than in four rounds of interviews.

Write a job post that does the filtering for you

Most job posts list duties and requirements. Ours describe the mission, the kind of person who thrives in the role and what the work actually looks like.

They also include our Awesomeness Test questions right in the post (more on those in a second). That means the people who apply have already seen what we care about and done some real thinking to get through the door.

It works. One candidate wrote in to congratulate whoever had written our job post, because it stopped them in their tracks.

A few things to put in yours:

• Why the role matters: who it helps and what changes when it's done well.
• A real week: the actual tasks, not "other duties as assigned."
• Who thrives here: the traits that matter more than the résumé.
• A small task to apply: something that shows how they think.

Test skills, not talk

First thing to know about hiring: lots of people are great when you talk to them.

They want the job. They need the job. And they know just what to say to get the job.

But I've found that some of the best talkers are the worst workers.

So test their skills, not their ability to talk their way into your heart (and your company). The best way I've found is a short test built around specific, role-related scenarios.

At LYM we call it the Awesomeness Test. Someone applying for customer support answers questions based on real customer situations we've had. Same for marketing, web development, office management and every other role.

If you're hiring an assistant, your version might ask:

• A client emails at 9pm saying they can't log in, and their call starts in 15 minutes. What do you do?
• Here are three emails from today's inbox. Which do you answer first, which do you pass to me and why?
• Rewrite this welcome email so it sounds warmer and clearer.

If you don't want to build a test from scratch, or want to add to it, look at the DISC assessment. It shows personality and behavioral style in four areas: dominance, influence, steadiness and conscientiousness. You'll learn a lot about how someone communicates, makes decisions and handles detail. You can find free versions online.

Adding the Awesomeness Test and DISC to our process changed everything. We can now see quickly and accurately whether someone has the skills to do a great job and whether they fit our values and culture.

Dig deep in the interview

I don't believe in traditional, surface-level interviews. "Tell me about your last job" tells you almost nothing.

What I do believe in is behavioral interviews: questions that show how someone actually behaves, how they see themselves at work and how they handle problems, pressure and responsibility.

Questions like:

• "Tell me about a time when you had more work than you could handle. What happened?"
• "What did you like least about your previous job, and why?"
• "Tell me about a mistake you made at work. What did you do next?"
• "Walk me through how you'd learn a tool you've never used before."

Their answers show you what's going on below the surface.

A red flag to watch for: people who go on and on about how hard their last job was, or can't stop putting down their previous boss. That's often the blame game, a "poor me" mindset that doesn't own its part.

If you notice that kind of unprocessed emotional energy in an interview, or at any point after, take it seriously. In my experience it eventually spills over and affects other people on the team, and sometimes the whole company.

Set your first hire up to win

A great hire with no handover will still struggle. Most first hires that fail, fail here.

Before your hire starts:

1. Record yourself doing the task. A quick screen recording while you talk it through is plenty. That becomes their training and your first written process.
2. Define what "done" looks like. "Answer support emails" is vague. "Every support email gets a reply within one business day, using these saved answers where they fit" is clear.
3. Hand off one area at a time. Inbox first, then calendar, then onboarding. Don't dump everything on day one.
4. Hold a short weekly check-in. Fifteen minutes to answer questions and give feedback while it's still small.
5. Let go of how. If the result is right, resist redoing it your way.

The "I can't afford it" math

Let's put numbers on it. These are made up, so swap in your own.

Say you bring on an assistant for 10 hours a week at $25 an hour. That's about $1,000 a month.

Those 10 hours probably cost you more like 15, because you do admin slower than someone who's good at it. That's around 60 hours a month back.

Now say one client is worth $2,000 to you. If you put even a few of those hours into sales conversations and sign one extra client a month, the hire has paid for itself twice. Everything else is time back for you.

The question isn't whether you can afford help. It's what the hours you're spending on admin are really costing you.

What the right team gives you

The techniques I've shared here are how we hire at LYM, and the results have been nothing short of amazing.

Every person on my team sees their role as more than a job. It's a mission, a purpose... a calling. They believe in what we're doing, and that belief, commitment, loyalty and expertise is a BIG part of how a business started by an artist whose father told her she had no marketable skills became a $57M company.

I swear they all want me to succeed... sometimes even more than I do.

That's what you're really hiring for. Not hands. People who care.

Where coaching fits

Knowing who to hire is often harder than finding them. Hire too early and you're paying for help you can't direct. Hire the wrong role and you've added cost without removing the bottleneck.

In Momentum, your Coach helps you look honestly at where your hours are going and decide which hire will free you up most at your stage. For business owners past $100K a year, Momentum Amplify adds monthly Masterminds with me and a senior Coach. You can see how it works on the scale your business page.

Whatever stage you're at, start with your two lists: the work only you can do and everything else. The second list is your first hire.