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Avoid These 3 Mistakes When Onboarding Freelancers

We all know it. Hiring and retaining talent (especially when it’s remote and not 100% loyal to your company) can be a pull-your-hair-out experience for most entrepreneurs.

Not only does it take an incredible amount of time to find good people in the first place, but if you don’t know how to onboard them the right way it can lead to misunderstanding and, ultimately, staff turnover.

Below you’ll find 3 big blunders when it comes to finding and onboarding freelancers for your agency.

If you onboard freelancers without these in mind, you’re bound to break things down sooner or later—and possibly blaming people for not performing (when the easy-fixes below could have easily solved the problem).

Failing to Update Training Documents or Not Matching Them With Skill Level

If everyone needs you for a piece of information it’ll be incredibly hard for you to grow beyond yourself without burning out.

Having the processes on your head won’t work for too long.

Clear processes and procedures for tasks are a must, but here’s where most people go wrong:

  • They either create a document and forget about it for years expecting people to use it.

  • Or they don’t provide instructions that correspond to the skill level they’re searching for.

Let me illustrate.

Say you’re looking for a Project Manager. You probably won’t need the same level of detail compared to someone who will manage your email and calendar.

One might have his or her own processes and only need direction. The other probably won’t. And when they don’t, it’s your responsibility to provide such training.

Since you’re a busy business owner, adding leverage and building a document (instead of doing one-on-one training forever) is really a no-brainer.

Having a thorough enough training allows you to:

  • Have freelancers start learning by themselves without taking time away from you or your team.

  • Get freelancers indoctrinated on your team’s culture and how things work in your business.

  • Make further training easier due to their already-learned material.

  • Make replacing people easier and faster.

If you don’t have these documents yet, go small first and grow from there.

Training documents could start off being literally a 1-page outline with a few bullet points or a set of screen shares with step-by-step tutorials.

Consider assigning the task of keeping these up-to-date to someone in your team if you can afford it. And don’t forget to evaluate the alignment between the depth of the training and the quality of the result you want (or the skill level of the position you’re trying to hire for).

From our experience, it’s worthwhile investing early on in a proper wiki-style knowledge base software. Internally, we use Outline. It even allows you to share part of your knowledge base to the public. We use this feature for our developer-focused tutorials.

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Unmet Expectations = Conflict

I’m sure you’ve seen this happen with clients. If there’s a problem, it probably comes as a result of high (or un-communicated) expectations.

Well, it can often happen with employees or contractors.

When things are not clear upfront and people start assuming due dates, compensations, or workload, things can get messy.

Here are just a few examples of how to avoid this. These can get you thinking and make sure you don’t shoot yourself in the foot:

  • If you’re working with people overseas, state clearly times and dates for communications and delivery (including the difference in timezones). Especially if we’re talking about client work.

  • Write things down on paper if you feel it’s necessary and make sure you both understand each other’s viewpoint.

  • If you’re paying them hourly, ask how many hours it will take them to complete their work. Things could easily take longer and the profitability of a certain project could be at risk.

  • If applicable, ask for days and hours of availability, or preferred method of communications.

This specificity should run through all of your communications with these people. The fact that they work with agencies doesn’t mean they know what to expect from you.

All agencies’ processes are different, so set your expectations upfront and prevent conflict.

Be specific. It’s crucial that you are always on the same page with the people in your agency, even if they’re working with you on a contract-basis.

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Going for one full-stack freelancer instead of diversifying

Everything that’s entirely built upon one leg is bound to fall down.

A business with one big client. A manufacturer with one primary supplier. An agency with only one full-stack freelancer.

Thinking that you can hire one person to do most of the things you need sounds great in theory. But especially with freelancers—where there’s really no explicit loyalty or commitment to your agency—you could end up having a hard time if they leave or are fully booked when you need them.

It’s always smart to have a few bullets in your pocket when it comes to talented contractors to outsource work to. 

Prevent having to postpone due dates or turn projects down by simply having (at the very least) two options for the primary skills you need to deliver a service.

This isn’t always possible, but if you have the opportunity to do it, go for it. It can be of great help when business starts booming. Trust me. You won’t regret it.

Which of These Are You Falling Into?

When there are so many things to keep up with and so many details you need to take into consideration in your agency, important details like these can be forgotten.

Did any of these mistakes pop an idea in your head to change something on your business right away?

Remember: Documentation, expectations and workload diversification. Three simple details that can be quickly fixed but can cost you thousands if ignored.

If you have these in place, congratulations. If you’re missing any, make sure to correct them—or apply them in the first place.

Ready to give it a try?

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