Most business owners reach the hiring question the same way. They are tired, the calendar is full, and somebody tells them to hire for whatever is causing the most stress. It sounds like relief. A lot of the time it turns into months of paying for help that never quite moves the business forward, and the owner ends up more frustrated with the team than with the decision that created it.

In this Double Kaufman episode of The Amanda Kaufman Show, co-host Rebecca Kaufman (Amanda's sister, who has also worked for her) puts Amanda in the hot seat on hiring: how to know it is the right time, and how to get the quickest return on the decision. Amanda, founder of Clairvenu, walks through the help she suggests getting first, the four categories most hires fall into, the worst and best hiring advice she ever received, the thinking behind hiring her own sister, and the reason a lot of team problems trace back to culture.

The First Help Most Business Owners Need Is a Mentor, an Accountant, and a Lawyer

Ask for help at the very beginning, before you start. Amanda's first suggested investment is mentorship and training, followed right away by an accountant and basic access to a business lawyer.

How It Matters: For this episode, Amanda keeps the definition of a hire simple: you are asking a human being to help you. One of her first mentors, Brendon Burchard, liked to say the best time to have a map is before you get into the woods. A mentor who has already taken the wrong turns saves an enormous amount of time. On the money side, too many entrepreneurs learn how to make money without learning how to manage it, and then the IRS shows up at the end of the year wanting its piece of money that was spent long ago.

How to Do It: Find a mentor who has been where you want to go. It does not have to be a $30,000 or $50,000 investment. It could be a couple thousand or five thousand, and Amanda points out that the value depends a lot on your willingness to learn and implement. For accounting and legal, services are a fine place to start. Amanda used services for her first business and moved to relationships with professionals as the business grew.

Common Mistake: Treating hiring as something that starts with a VA or a team. A lot of business owners skip the mentor and the accountant, then pay for those gaps later in wrong turns and tax surprises.

Most Hires Fall Into Four Categories: Admin, Delivery, Sales, and Marketing

Once the business is making money, the help most owners need sits in four areas. Each one gets evaluated a little differently.

How It Matters: In a service business, you make money by making promises and then keeping them. Admin support protects your time. Amanda borrows a line from Dan Martell: be super easy to find and very hard to reach, so you stay out of the pick-your-brain trap. Delivery and fulfillment help speeds up and standardizes what you deliver. Sales roles are typically commission-based. Marketing is where Amanda sees people overhire the most, because there is always another thing to do and another magnitude to take it to.

How to Do It: For admin, start with systems, automation, and very part-time support before thinking about a full-time assistant. For delivery, know what you are paid for each unit you sell and how much labor goes with that unit, and treat that as your budget. For sales, understand how the role gets compensated. Amanda hired Rebecca into sales on commission, which meant she could afford the hire because she was not carrying a salary, and when Rebecca was successful, she got paid. For marketing, know the return. The best business owners can tell you what they gain each time they post, how many leads come in each month, and how many convert.

Common Mistake: Hiring a salesperson on a decent salary with no tie to performance, or hiring a social media person without knowing what visibility is worth to the business. Amanda has talked with many entrepreneurs frustrated that a salaried salesperson is not producing, and her question is simple: what reason would they have to produce if there is no impact on their financial performance?

Hiring for Whatever Causes the Most Anxiety Leads to the Wrong Roles

The worst hiring advice Amanda ever received was to find the area of the business causing her the most anxiety or grief and hire for that first. It meant hiring on emotion, and it cost her.

How It Matters: Amanda paid quite a lot of money for that advice, then took it. It led her to spend tens of thousands of dollars over years with the wrong team, and she is clear that she means the wrong roles, not the wrong people. Entrepreneurs are usually more tired than they would like to be, and nobody makes their best decisions while feeling emotional and distraught.

How to Do It: Start from how the business actually runs. Every business performs activities on a rhythm, and those activities either add value or they do not. Amanda frames the whole game as input and output: if the output exceeds the input, things are good. If a lot of input produces a small trickle, something in that set of activities is broken, and that is where to look before hiring.

Common Mistake: Hiring from depletion. Amanda says a lot of people hire very emotionally, usually when they are exhausted, and even she was scared out of her wits the first time she hired Rebecca.

The Spreadsheet Test Shows When a Hire Will Pay for Itself

The best hiring advice Amanda got was to make a spreadsheet. List exactly what gets done in the business, exactly who does it, and exactly when, with time estimates, then put a cost on each activity.

How It Matters: Amanda calls herself a dreamer with a spreadsheet. Once you know who is doing each activity, you can assign a number to that person's time. For a solopreneur, that is you, and your hourly figure can come from your owner's draw. Amanda uses her own example: a high-quality email takes her about 20 minutes. Now there is a real cost to compare against less expensive labor that gets the same quality of outcome in a reasonable period of time.

How to Do It: Go through every activity, assign a cost, and ask the important question: can I make a trade? When Amanda hired an overseas team, she was specific about what they did: pushing buttons, exporting files, uploading files. That activity happens no matter what, so even if it takes someone five or ten times longer, a much lower cost of labor makes it a no-brainer hire. While you are mapping, ask one more question about each task: if I deleted this thing, how much money would I lose?

Common Mistake: Hiring the cheapest possible help and expecting the same output. Rebecca calls the quality of the outcome "the big caveat," and Amanda agrees. Someone at $3 an hour will happily take the work, and the output usually will not match unless there is training, process, and a mechanism to support it.

Get Comfortable With Firing Before You Hire

Before you hire anyone, you need to be at peace with the possibility of letting them go. If that idea feels unbearable, it is a sign the leadership and management skills need work first.

How It Matters: Rebecca points out that the odds of landing the perfect fit with perfect onboarding on the first try are super low. Amanda adds that when an owner is paying team members with no idea what their outcomes are or the quality of their output, her gentle suggestion is to end it as soon as possible and recalibrate. Without clarity on the activities that produce outcomes, it is too early to hire.

How to Do It: Amanda did this exact exercise before hiring Rebecca. Rebecca was not her first hire, but she was the first sister Amanda hired, and Amanda pictured it going catastrophically before she agreed. She weighed whether she could live with a rift in the relationship, decided the risk was worth taking, and says the benefit was incredible. She was transparent about what the business needed, where the gap was, and what it would take to afford the support. When the working relationship wound down, both of them describe it as the least dramatic conversation, because they already knew the terms of engagement. They are working together again now.

Common Mistake: Keeping the numbers secret until one day it is too much and a big, dramatic change follows. Amanda sees a lot of business owners do this, and sometimes they end up blaming the team member when there was never any calibration between the owner's effort and what it was producing.

Team Problems Usually Come From Culture, Not Individuals

Hiring does not eliminate problems. It trades them for different ones, and the biggest lever on how a team performs is the environment the owner builds.

How It Matters: Amanda is not a fan of the term "A players." She has been in environments where she was not an A player and environments where she was, so she does not see it as a fixed identity. You can cultivate an A environment, and the people in it will rise to the occasion because they do not want to see others fail. A strong culture also tends to push out the people who are looking for something else.

How to Do It: Look at the norms, standards, and behaviors that are actually accepted on the team. Ask whether you are ready to give quality instruction and expectations, and whether you have patience for the human life things that come up for the people who work with you.

Common Mistake: Blaming business problems on the individuals who were hired. "And that's a leadership problem, not a recruiting issue," Amanda says.

Conclusion

The path Amanda lays out is gradual. Get a mentor, an accountant, and a lawyer from the beginning. Know which of the four categories a hire belongs in and how that role should be measured. Skip the advice to hire for whatever hurts most, and run the spreadsheet test instead: map the activities, cost them out, and look for trades that make sense. Before hiring, make peace with the possibility of letting someone go, and remember that culture shapes how people perform. Amanda also suggests you do not have to jump into the deep end. Pay a premium for a freelancer or an agency to take one activity, learn what it is like to give work away and give feedback, and build from there. And if you are sitting in a tangle of past hiring decisions, she has been there too. There is very little that cannot be adjusted, and business really is about learning.

To hear the full conversation, listen to Episode 373 of The Amanda Kaufman Show on YouTube, Apple Podcasts, or Spotify.

Frequently Asked Questions

When is the right time to make your first hire?

Amanda's answer is to ask for help from the very beginning, starting with a mentor, an accountant, and basic access to a business lawyer. For operational hires, the right time is when you are clear about the activities that produce outcomes in your business and can put a cost on them. Without that clarity, Amanda says it is too early to hire for most.

What should a small business owner hire for first?

Amanda groups operational help into four categories: admin and managerial, delivery and fulfillment, sales, and marketing. The best first hire is an activity that happens no matter what and that someone else can do for much less than your time costs, with the same quality of outcome. Her own example was an overseas team handling exporting and uploading files.

How do I know if a hire will have a good return?

Map your activities in a spreadsheet with who does them, when, and how long they take, then assign a cost using your hourly figure from your owner's draw. Compare that to the cost of someone else doing it with comparable quality. Also ask of each task, if I deleted this, how much money would I lose?

Should I hire a freelancer or an employee first?

Amanda suggests starting small. Paying a premium for a freelancer or agency to handle one activity lets you test what happens when you give work to someone else, without a longer-term commitment. Employment carries real legal obligations that vary by location, so talk to an expert about whether a role should be an employee or an independent contractor.

Where can I get help building a business that can afford its team?

Amanda's free live training, How Serious Service Businesses Build High-Converting Funnels & Acquisition Systems That Run 24/7, walks through how the pieces of a service business fit together so growth is built on a system you can measure. Register at https://clairvenu.com/training. If you want an outside perspective on your specific situation, apply for a free Revenue Clarity Conversation at https://clairvenu.com.