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How to Know When & What to Outsource: From the Experts

As you scale, you need to expand your team and start delegating tasks. That can be as daunting as it is exciting, especially as you start to hire new employees and get them trained up to work alongside you.

And eventually, you’ll scale to the point where you may need to outsource work even beyond your existing team, relying on agencies, consultants, or freelancers to help with everything from accounts payable to content and social media marketing.

Many businesses struggle to know when it’s time to outsource, and to determine which elements of their business would best be handled by an external team member instead of an internal one.

Good news: This is a challenge many business owners and department leaders have faced before. 

We talked to three business owners with extensive experience in the topic about their opinions on outsourcing, including when to get started and what to hand off, and today we’re going to share what they had to say.

How to Know When It’s Time to Outsource Key Tasks

Knowing when it’s time to find a third-party to come in and help with a select task is crucial. How do you know when your team needs the extra help when there are so many factors (including training, budget, and time) to consider?

Massimo Chieruzzi, who runs DivByZero, was a Co-Founder of AdEspresso, and is the Co-Founder and CPO at Breadcrumbs, said it’s all about opportunity cost.

Dave Shanley is the CEO of Content Camel and works as a growth advisor for businesses like Kosli after extensive entrepreneurial experience. He said that there are two areas of consideration when outsourcing tasks like marketing: getting more done, or specializing in skills that your internal team might not have.

Gaetano Nino diNardi, a growth advisor for brands like Wagepoint, Cognism, and Splash, strongly recommended that at least for marketing, businesses should be focused on the “moving faster” aspect that Dave commented on.

The Biggest Advantages of Working with Third-Party Vendors

When we asked our experts about the biggest advantages of working with third-party vendors, they all talked about that “moving faster” aspect discussed above. There’s no denying that outsourcing means you can pick up steam quickly.

So time aside: What are the advantages to working with freelancers and agencies for outsourced work?

Gaetano also stressed the financial benefits, noting that outsourcing to third-parties allowed for flexibility and scalability simultaneously, allowing you to keep full-time headcount low. And, as a plus, “businesses can write off fees from agencies and service providers.”

How to Prioritize What to Outsource With Limited Resources

Knowing what to outsource, obviously, is a massive part of the process. And our experts each had outstanding advice to share. 

Massimo, on the other hand, noted that he’d prioritize any tasks that required specialized knowledge to make a difference for the business.

And Dave noted that “right now” priorities should always be given consideration when choosing outsourcing options.

How to Find Quality Freelancers, Agencies, & Consultants to Outsource Work To

When it comes to choosing who to outsource to, the most common solution is the easiest one: Referrals.

Gaetano echoed this sentiment: 

Freelancers vs. Agencies: How to Choose

One common question that many businesses have when outsourcing any task is to choose between freelancers or agencies.

And his opinion on when to use agencies:

Gaetano noted the value of freelancers, stating “Freelancers are a great bet for many situations — especially highly specialized marketing roles such as link building, conversion rate optimization, or freelance SEO copywriting.”

Red Flags When Hiring Third-Parties for Outsourced Work

Okay, you’ve settled on the type of work you want to outsource, and you know you either want to work with an agency or a freelancer.

Now it’s time to actually select that third-party to outsource to… and it’s important to be able to watch for red flags in the process.

And one red flag is one you might not expect: Someone who claims to do too many things in supposedly-specialty services.

And sometimes, even a highly skilled agency or freelancer just isn’t the right fit. A lot of it comes down to the style of work.

When to Start the Outsourcing Process

Outsourcing isn’t as simple as delegating a task to someone on your internal team, who is already hired, trained up, and ready to go (even if they’re busy).

The best service providers may have a waiting period, and it takes time no matter what to find the right vendor, go through negotiations and onboarding, and actually get started.

So when should a business get started?

Gaetano recommends always trying to have at least a one-month cushion when outsourcing any projects.

Final Thoughts

Outsourcing may take a little trial and error. You may even go through a vendor or two while finding the right one— sometimes it just isn’t a fit, or you realize that you have other priorities elsewhere. That’s okay.

No matter what, remember that when it comes to outsourcing, always be crystal clear in your communication.

As Dave says:

So start with transparency and clear instructions regarding your goals, your expectations, and any vision you have. A great vendor will be able to build off that and get you the results you want.

Want to learn more about starting and managing your business? Check out our blog for more!

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