Strategic Outsourcing Tips to Get Your Schedule Back

blog business tips for entrepreneurs Feb 20, 2023
Holly Haynes business strategist sharing strategic outsouring tips
I get so much feedback from my clients behind the scenes, I thought it would be fun to share one of the hot topics we covered at our recent Collective Mastermind Retreat.
As a business coach for female entrepreneurs, twice a year I host what I think is a pretty epic retreat for mastermind clients, which is anyone that is new to the program or has been in the program in the past. This year we headed to Clearwater Beach, Florida, and held most of our sessions outside. Let me tell you, talking about how to grow and scale your business by the pool is pretty magical. I wanted to bottle it up and take it with me, so this is the best way I could think of.
Being a business strategist and always looking for business productivity tips, I wanted to share one of the lessons I taught which is building your dream team. And how to know when to outsource.

Knowing When to Outsource

The very first thing I do when I start to feel overwhelmed or get the nudge that it is time to hire someone to help is to make a list of every activity I do in a week. And then I categorize them:
  • What is a priority? (Absolutely has to be done).
  • What can be delegated?
  • What can be deleted?
The deletion part is key because my guess is there are activities on your list that you really don't need to do.
The last question I ask before making a decision is what do I like doing? Because the worst thing you can do in business is hiring someone to do something that fuels you.

The key to the equation is to make your job easier so that you have more time to focus on what you love.

And to create the capacity to dream bigger. Going back to that whitespace rule I have, your calendar has to have it, too. Now you have this list and you have prioritized what's important and what you like doing. Now what?

How to know who to hire

My mantra on this is either to have your house in order so that there are clear systems to follow OR your first hire is to get someone to get it in order. See how we just made the decision so simple? Either you love systems like me and you are ready to have someone just take over the things you don't prefer to do, OR your first hire is to get the systems in order.

The other key piece to outsourcing is this: every great leader or mentor has a team.

They have a support system, someone that is helping them. If you want to scale, the bigger picture has to be more than just you. Period. No one in history has ever done it alone. Ever.
 Do you love these tips? Take the Productivity Personality Quiz to get a Netflix-style binge-worthy resource list to help you find your focus and is customized to you! Take the quiz here.  

What Should I Outsource First?

I see so many of my clients get stuck on hiring their first hire or outsourcing a task. But the capacity that it opens up is going to allow you to get to your goal SO much faster. Here's an example. For years, I did my own website. Because I can. I have a technical background and even did coding in college. But as our business grew, website updates were taking ALOT of time and are not my area of expertise, so I hired a creative agency Studio Classica to take over. They can get done in literally 10 minutes what would take me two days. How's the ROI on that? What is your time worth? Because now I can spend more time developing new programs, helping you, and doing what I would call "aligned" growth activities in my business. See how that works?
Outsourcing can be everything from hiring a website designer to a virtual assistant to a copywriter to a babysitter.

The ultimate end goal is to create capacity for you.

Because the creative time, dreaming about your business and next steps, can't be outsourced.
When outsourcing, the ROI is not always monetary, and if it is, it is not always right away. But I would argue that creating the capacity to work on your business and not in your business is the best strategy.
Not sure how to hire first? Or have questions about figuring out what those big ROI tasks are? Want more strategic outsourcing tips? Shoot me a DM and ask away. I am an open book and will happily share our outsourcing strategy with you.
Looking for more on this topic and your High-Level Action items? Check out the Strategy Lab in the Crush the Rush Club!


Are you bursting with ideas and wondering how the heck you are going to find time to make it happen?

Imagine your time management fairy god-mother coming in to wave her magic wand and show you a better way! And actually, see results. we combine productivity best practices, business strategy, and community support to help you get to the next level without burnout.


Holly Marie Haynes is a business strategy coach, podcaster, mom of twins, and founder of the Crush the Rush brand. She helps women create simple scaleable offers and systems to grow to multiple 6-figures.

Holly Marie Haynes is a business strategy coach, podcaster, mom of twins, and founder of the Crush the Rush brand. She helps women create simple scaleable offers and systems to grow to multiple 6-figures.

© 2022 Holly Marie Haynes, LLC |