How to Know When It’s Time to Hire Help in Your Business

Kim Bernstein
Apr 28
2 min read

Running a business often means wearing a lot of hats—bookkeeper, marketer, customer service rep, CEO… you name it. And while hustle is part of the journey, doing everything yourself isn't sustainable forever.

So how do you know when it’s time to bring in help—whether that's a contractor, employee, bookkeeper, or virtual assistant?

Here are the biggest signs it might be time to make that first (or next) hire.

1. You’re Constantly Working IN the Business Instead of ON It

If you’re stuck doing admin tasks, answering emails, or chasing invoices—and never have time to work on big-picture growth—that’s a sign.

🔍 Ask yourself: Are you spending your time on tasks that someone else could do more efficiently, while you focus on strategy and revenue?

2. You’re Turning Down Opportunities

If you're saying no to new clients, bigger projects, or collaborations because you're simply maxed out—it’s time to expand your capacity.

✅ Help can allow you to say "yes" to more growth opportunities without burning out.

3. You’re Making Mistakes (or Cutting Corners)

When you're stretched too thin, errors creep in:

Missed client deadlines
Forgotten tax payments
Skipped follow-ups

Hiring help can protect your reputation, your cash flow, and your peace of mind.

4. You’re Stuck in Feast or Famine Cycles

If you’re constantly swinging between too much work and not enough work, it may be because you’re stuck doing everything during busy times—and neglecting marketing, networking, and planning for the future.

📈 Having the right support team can help even out your workload and your revenue.

5. You’ve Identified Clear, Repeatable Tasks

Hiring works best when you can hand off specific, consistent responsibilities like:

Bookkeeping and financial management
Customer service emails
Social media scheduling
Administrative tasks

✅ Clear processes make training easier and ensure a strong ROI on your first hire.

6. Financially, It Makes Sense

Before hiring, review your finances:

Do you have consistent revenue to support a contractor or employee?
Will freeing up your time allow you to bring in more revenue?

📈 Sometimes the cost of not hiring is bigger than the cost of hiring—especially if you’re leaving money on the table.

Final Thoughts

Hiring help isn’t just about working less—it’s about working smarter. It's a strategic move that can boost your growth, improve your client experience, and (most importantly) protect your health and energy for the long haul.

Not sure where to start? Begin with the tasks that drain you the most—and watch what happens when you have the right support in place.

KB2 Bookkeeping & Tax is here to help you lighten your load—so you can focus on growing your business, not just surviving it. Let’s build your dream team! 💼📈