I Need Help... With What? | How to Know When It's Time to Hire and Grow Your Business
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At some point, every entrepreneur says the same thing:
"I need help."
But help with what?
That's where most business owners get stuck.
In this episode of The MindShare Podcast, David Greenspan shares a conversation from the gym that sparked a much bigger discussion about hiring, delegation, leadership, and building a business that doesn't rely on you doing everything yourself.
Too many entrepreneurs hire because they're overwhelmed—not because they have a clear plan.
They bring someone on board, then spend weeks trying to figure out what that person should actually be doing.
Sound familiar?
David breaks down why that's backwards, how to identify exactly where you need help, and why your next hire shouldn't begin with a job title—it should begin with understanding how you spend your own time.
He also shares one of the simplest yet most effective exercises he uses with coaching clients to determine what should stay on your plate and what should come off.
Plus...
Once you hire someone, how do you know if it's actually working?
If your answer is simply, "I feel less stressed," you may be measuring the wrong thing.
This episode will help you think differently about delegation, accountability, leadership, and creating measurable results inside your business.
Whether you're a Realtor, entrepreneur, small business owner, or leader building a team, this conversation will help you stop hiring reactively and start building intentionally.
What You'll Learn
- Why most entrepreneurs hire too late—and for the wrong reasons
- The biggest mistake business owners make before hiring an admin
- How to identify exactly where you need help
- The four-box exercise to define your next hire
- Why awareness always comes before delegation
- The difference between assigning tasks and creating ownership
- How to measure whether an employee is actually improving your business
- Why tracking data beats relying on feelings
- How hiring changes your role as a business owner
- Why systems and communication matter just as much as people
Episode Breakdown
[00:00] "I Need Help"
- The gym conversation that inspired this episode
- Why feeling overwhelmed isn't a hiring strategy
- The question every business owner should answer first
[09:00] Before You Hire Anyone...
- Understanding where your time actually goes
- Why awareness is the first step toward delegation
- The exercise that reveals your next hire
[18:00] The Four-Box Framework
- What you're good at
- What you enjoy doing
- What you're bad at
- What you hate doing
- How these answers shape your business
[27:00] Commercial Break
[29:00] Stop Assigning Tasks—Start Creating Ownership
- Why ownership creates accountability
- Moving from busy work to meaningful contribution
- Building roles that grow with your business
[38:00] How Do You Know It's Working?
- Measuring success with tangible data
- Defining expectations before hiring
- Why business should be measured the same way elite athletes measure performance
[48:00] Hiring Doesn't Fix Broken Businesses
- Why people amplify your systems
- The importance of communication and leadership
- Preparing your business before expanding your team
[55:00] Your Action Plan
- Track everything you do for one week
- Complete the four-box exercise
- Identify where another person could create the greatest impact
- Build your next role with intention
Key Takeaway
Hiring isn't about removing work.
It's about putting the right work in the hands of the right people.
Before you bring someone into your business, get clear on what success looks like, what should be delegated, and how you'll measure whether it's actually making a difference.
The businesses that grow intentionally don't just add people.
They create clarity, ownership, accountability, and measurable outcomes.