8 Questions to Ask Yourself Before You Start Outsourcing

8 Questions to Ask Yourself Before You Start Outsourcing

We entrepreneurs are busy, ambitious, innovative, and energetic. Which means we’ve often got far more ideas and work than we have time and energy to execute on them.

As most of you already know, I frequently and strongly recommend outsourcing and delegation to my entrepreneurial soul sisters because sharing the workload makes it so much easier to find balance and continued success.

BUT! I would never want anyone to start hiring contractors without a plan in place!

I would kick myself if any of you dove into outsourcing without first setting some goals and ground rules!

Yes, outsourcing can be a game-changer for overwhelmed entrepreneurs, but only if you approach it with a clear head.

So, with that in mind, here are 8 essential questions to consider before you start outsourcing to freelancers:

Outsourcing Question 1: Are You Feeling Pressured?

Do you really need help right now, or are you just feeling the pressure to hire because everyone else is doing it?

Don’t feel badly if it’s more about “keeping up with the Joneses” than managing your workload!

That’s totally normal, especially if you rub elbows with entrepreneurs who’ve been scaling their businesses actively for ages.

However, it’s important to get a read on YOUR specific needs before outsourcing and decide if you truly need the support. If you don’t, hiring contractors will be a waste of your hard-earned money.

Outsourcing Question 2: How’s Your Cash Flow?

Do you have more money than time

In other words, are you so busy with work and serving clients that you’re making great money, but you don’t have any time left over to build a life outside of your business?

If this is the case, you’re definitely ready to outsource!

Hiring a team of freelancers to take tasks off your plate will cost money, yes, but it will also create more free time for you. That tradeoff is well worth the investment. (If, on the other hand, you have more time than money, consider waiting until that shifts before outsourcing any work.)

Outsourcing Question 3: What Will You Outsource?

Do you know exactly what you’re going to outsource or do you just assume your contractors will figure that out for you?

You don’t want to be thinking up tasks on the fly to keep your team members busy AFTER you’ve hired them!

You want to make sure freelancers and VAs are working on tasks that are going to grow your business and help you make more money.

So before you consider outsourcing and start making hires, create a workload distribution plan. Decide which tasks will be handled by contractors and outline why they should be outsourced.

Making these choices in advance will also help you outsource to the right people, allowing you to select freelancers with the specific skills and experience you need to handle the work you want covered.

Outsourcing Question 4: Are You Ready to Invest?

Do you have a manageable budget set up for outsourcing, or does the idea of spending the money just stress you out?

Now that you know exactly what you are going to outsource, and you’ve got a good idea of how long it takes to complete those tasks, what will it cost you? Do you have a sense of how much virtual assistants and remote contractors charge for the work you need done?

While it’s true that a good VA can charge as little as $25-$30 an hour, experienced specialists are often more expensive. (For instance, a web designer may charge in the $50-$75 an hour range. So if you need web work done, you’ll need to be prepared to spend more.)

Knowing the cost ahead of time helps you to feel more confident about where your money is going, and helps you see outsourcing as an investment instead of an expense.

And jumping into outsourcing before you’ve run the numbers means setting yourself up for a nasty shock when the invoices roll in at month’s end! Calculate your outsourcing budget, then start seeking new team members.

Outsourcing Question 5: How Will You Train New Team Members?

Do you have a plan in place for onboarding and training your new assistant or writer or designer … or will you be winging it after you hire them all?

It’s tempting to believe that experienced freelancers will be fast learners and pick up your procedures quickly, and some of them certainly will do just that! But failing to train your team properly is a costly mistake.

Imagine you hire a VA and set her to work without walking her through your business basics, preferences, and rules. You’ll waste time going behind her back to fix things she’s (innocently) done wrong, and scrambling to re-do work she was supposed to take off your plate. This dynamic will drive you and your assistant crazy, leading to a bad experience for everyone. She may quit, and you’ll end up going back to doing everything yourself.

Instead, create a set of standard operating procedures before you outsource. Then use those to train and onboard your new team members. Everything will run more smoothly if you do!

Outsourcing Question 6: Do You Have the Right Tools?

Do you have a system set up to help your virtual assistant and other team members work within your business successfully? Are you organized enough to run a team, and will they have access to the tools they need to support you?

I strongly recommend a project management system like Basecamp to help organize and schedule tasks and projects.

A remote team needs to have a central place for communication, file-sharing, and scheduling. There are dozens of tools available to entrepreneurs – both free and paid – that can help keep an outsourced team on-track and aligned

Even if you decide to create your own organizational guidelines and filing systems from scratch, make sure they’re in place before you outsource any tasks.

Outsourcing Question 7: Are You Ready to Trust Your Team?

If you’ve been going it alone for years, handing over work to a contractor can feel downright scary.

Are you ready to relinquish control over certain tasks and projects within your business?

Can you outsource work without becoming an irritating micromanager?

This is a tough one, lovelies. Outsourcing will backfire spectacularly if you’re not emotionally ready to share the tasks that fuel your business. You can’t hire a VA to handle your emails and scheduling, then blow up at her if she makes a minor error.

Naturally, some of this comes down to hiring the RIGHT freelancers; seasoned writers and virtual assistants and social media experts who don’t need tons of oversight.

But it also comes down to knowing yourself, and recognizing how ready you are to trust team members.

Outsourcing Question 8: Do You Know How to Be a Team Leader?

Are you ready to manage and lead other people? Have you ever done it before? If not, what can you do to prepare yourself to oversee work done by people who aren’t even in the same room as you?

Outsourcing means learning to lead a remote team, which can be challenging even to entrepreneurs who have experience managing in-person teams!

Managing expectations, facilitating communication, knowing when to push and when to step back…these responsibilities feel slightly different when all communication and work is done online. I’ve got tons of resources in my blog archive to help you get ready, so read through those in advance of hiring new team members.

Don’t get me wrong, I am a HUGE fan of outsourcing! Hiring a stellar team of freelancers has saved my business and my sanity over and over again.

But it’s not a decision to be taken lightly.

So if you haven’t taken the plunge yet and are considering hiring a VA or contractor to support you, ask yourself these 8 questions and be brutally honest in your answers. Doing so will help prepare you to outsource wisely, grow your business, and carve out more precious free time in your life!



PS. I Can’t Make Your To-Do List Go Away…But My Business Templates Library Will Help You Avoid Project Overwhelm So You Can Build Your Business, Free Up Your Time, and Put More Money in Your Pocket!

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