Hiring your first support person might actually be more difficult than launching your business.
I know that might sound scary, but stay with me here. While everyone talks about how hard it is to start a business, this phase—bringing on your first team member—can be even more challenging. Why? Because now you’re learning a completely different set of skills while still running your business.
You’ve taken the leap and hired someone to help with administrative tasks. Great! But now what? How do you actually train them without spending more time teaching than you save by delegating?
When you launched, you were focused on one thing: getting clients and serving them well. Now you’re learning a completely different set of skills while still running the business.
Shifting Your Mindset
When I first started thinking about training someone, I felt a weird mix of guilt and fear. Guilt because these tasks seemed so simple, how could I justify paying someone else to do them? And fear because what if they didn’t do things exactly the way I wanted?
But I realized that by trying to do everything myself, I was actually holding my business back. Not just that—I was holding myself back from serving my clients in the best way possible.
Remember that feeling when you’re in a coaching session and everything just flows? When you’re completely present with your client, helping them transform their relationship with money? That is your zone of genius. That’s where you need to be spending more of your time.
Avoiding the Excellence Zone Trap
There’s this sneaky trap I call the “excellence zone.” These are tasks you’re actually pretty good at. You might even enjoy them a little. For me, it was organizing client financials into spreadsheets and setting up systems.
I could do these tasks well, but they didn’t light me up like coaching did. The trap is that because you’re good at it, it’s easy to keep doing it yourself. But every minute you spend there is a minute you’re not spending in your true zone of genius. And your zone of genius is where your business grows and thrives.
Practical Training Approach
Just like we create personalized money plans for our clients because everyone’s situation is different, we need to create a personalized training plan for our new team member.
I learned this lesson the hard way, in my own coaching practice. At first, I tried to train my initial hire while maintaining my full client load. Let me tell you, that was not my brightest idea! It’s like trying to build a house while also running a marathon.
Here’s what actually works: Block off about 20% of your usual client hours for the first few weeks that your new employee starts. Yes, I know that sounds crazy from a revenue perspective, but think about it like this—just as we tell our clients that sometimes we need to invest money to save money, sometimes you need to invest time to make more time.
Two Essential Tips for New Hires
The Rainy Day Project
Have a rainy day project ready. This is a task your new hire can work on when they’re waiting for answers from you. For me, this was organizing my client CRM. It was perfect because they could do it in chunks—5 minutes here, 20 minutes there—and it didn’t require constant oversight. So while they were waiting for feedback from me, they weren’t idle. They were consistently working on something while simultaneously learning more about the business.
Create a Growth Fund
From one financial coach to another, create a growth fund or new hire fund where you can save a little bit of money each month before you hire. This will help you absorb the loss of revenue or newly added expense until you’re able to drive your revenue again.
The Seven-Step Training Process
At the Financial Coach Academy®, we’ve developed a seven-step training process for our new hires and we share this with our Academy members. We created it because we kept seeing coaches try to train their team members the way they’d been trained in corporate jobs—very rigid and formal—but that wasn’t working for small personal businesses like ours.
1. Show and Tell
This first step is all about context. When training someone on client onboarding, for example, we share stories about why each step matters and how it connects to other steps so they see the bigger picture and understand the overall client experience.
2. Do It Together
This is where you work side by side, just like you would with a client learning to budget for the first time. Record yourself doing tasks before your new hire starts so they can review the videos between training sessions.
3. Watch Them Lead
Let them teach it back to you. I was shocked by how much I’d forgotten to explain and which parts they picked up naturally versus which they forgot.
Pro tip: Provide feedback only at the end of their demonstration. If they realize they skipped a step on their own, let them discover it. They’re more likely to remember it when they learn it themselves.
4. Independent Practice
This is when your team member does the task on their own while you work on other things. This is where your rainy day project becomes crucial.
5. Review Their Work
Too often, managers train someone once, then expect flawless execution. By following our process, you’ll catch errors early. Review their work, the steps they took, and check for accuracy and thoroughness.
6 & 7. Feedback and Refinement
These last steps are ongoing. Adjust and refine as you go. Repeat steps 4, 5, and 6 until no feedback is necessary.
By following this process, it takes more time up front, but you’re being proactive instead of reactionary. You’ll catch fewer errors on the back end and put out fewer fires. Plus, the working relationship builds on trust and open communication.
Effective Communication Systems
One mistake I learned early in supervising my new hire is that it’s not a good idea to be available all the time for questions. It meant I was constantly interrupted and couldn’t focus on my real work. It also meant team members didn’t think through problems on their own.
Here’s what we do now:
- We have specific check-in times for new hires throughout the day (9 a.m., noon, and 4 p.m., for example)
- If they’re stalled without an answer, they work on rainy day projects
- We use different channels for different types of communication:
- Urgent needs via Slack
- Questions for our next check-in in a Google Doc
- Ideas for improvement tracked by team members for all-team meetings
- Weekly planning in Asana with goals posted in Slack every Monday
We’re a fully remote team with members all over the world. While I wish I saw my staff more because they’re amazing people, I’m routinely in awe of how productive and communicative we all are while having total flexibility.
Maintaining the Long-Term View
Some of our biggest leaps forward happened after I learned to let go and trust my team. It’s like what we teach clients about money—sometimes the hardest part isn’t the practical steps, it’s the emotional journey.
Think about why you started your coaching business. It wasn’t just about making money; it was about making a difference. Adding someone to your team isn’t just about making your life easier (though that’s a great bonus); it’s about expanding your impact.
Imagine if all your time was spent just coaching clients. How would that feel? That is possible for you, maybe not tomorrow or even this year, but use that vision as your guiding light. The idea that you are working in your zone of genius, whatever that may be, and you’ve got other people working in theirs—that is your vision.
Just like we tell our clients, progress over perfection. Your first attempt at delegation won’t be perfect, and that’s okay. What matters is that you’re taking steps to grow your business in a way that serves more people while honoring your own energy and time.
Your Next Steps
Here are some things to get you started as you think about bringing on your first (or next) team member:
- Write down everything that lights you up in your business, those moments when time just flies by
- List three tasks that drain your energy but could easily be done by someone else
- Record yourself doing just one of those tasks, explaining it as if you were teaching a friend
Just like we tell our coaching clients, you don’t have to figure this out alone.