A Cheat Sheet To Hiring An Ace Freelance Team

Photo by  Shane Rounce

Photo by Shane Rounce

One of the most common advice threads for growing businesses is to hire help as soon as you can. Whether you’re a one-person shop or a business that intends to scale to a large team, getting from today to tomorrow requires additional hands that you don’t (and shouldn’t) have.

Rather than DIY startup building, your goal should be to work smart and export the tasks that aren’t in your zone of genius to others who will hit it out of the park. 

The fastest and most affordable way to go about this is to hire independent contractors and agencies who are happy to join your team on a project basis to complete everything from design, bookkeeping, research, copywriting, to consulting work. With the connectivity the internet provides, you can now hire support from anywhere around the world, so your talent pool options are incredible.

I absolutely love this model because it allows any business to receive injections of genius so that the business can shine from every angle. You can fake being buttoned-up this way and accelerate the maturity of your business. Fake it till you make it is incredibly feasible nowadays for the small business owner, which is awesome.

Finding solid, freelance talent isn’t easy though. Hiring well in this department requires its own manual and experience to get it right. I’ve learned a couple of hacks over the years that have helped me quickly create a list of top 3 contenders so that hiring someone for a project is quick, painless, and a right fit. Here are those hacks distilled in 4 easy steps — 


Human First, Resume Second

I’m able to ax out 90% of applications based on someone’s cover letter and style of outreach to me. If the candidate does not write their cover letter or present themselves in a manner that I vibe with, I do not need to engage with them.

So you will never see me hire someone who:

  1. Completely ignores who I am and what my business is about and doesn’t take the time to create a bridge between me and them. The person needs to give me the opportunity to know who they are.

  2. Has a communication style that’s completely opposite from mine.

  3. Sends me a cold email, LinkedIn message, or asks to hop on a phone with me without having a human conversation with me first (I’m a human being, not a robot).

  4. Has a business-first rather than human-first lens.


When you’re hiring for a remote role, that person’s soft skills have to align completely with yours. With a remote team, you won’t have the opportunity to clear things up in-person, and so, you have to be vigilant in hiring someone who aligns with your communication style right away.

For example, have you ever been on a call with your bank or an airline and had the customer service representative on the other end not address your question directly, skirt around your issue, or not provide any helpful solutions after being on hold for 30 minutes? It’s terrible right? 

Now imagine having to deal with that on a daily basis with a remote freelancer whose communication style doesn’t align with yours. It incites stress you don’t need, and overall makes you feel terrible over a minuscule conversation about font color. What a waste of time and energy!

I personally don’t want to work with that customer service representative on a project that has my name on it and you shouldn’t have to either. Misaligned communication has been at the base of every unpleasant project I’ve ever worked on, and this is why I look at the human first and resume second when scouting for a new team member.

I want to work with someone who’s mature enough to handle stressful situations and mistakes with respect and grace so that we never spend more than 5 minutes festering in that space. If someone has an opposing style where they would love to add a “0” to the end of that number, then we will not be compatible team members. 

To apply this for yourself and your business, create a list of 3–5 non-negotiables that are completely based on the candidate’s soft skills, actions, and approach. Look at this list every time you’re about to hire for a project and strive to remove 80–90% of applicants according to the rules of this list. If your business has more than one founder, create a list of non-negotiables that align with the values of the company.


Two-Week Rule

For everything that’s not covered under the human first rule, my two-week rule usually covers it. 

If the candidate’s resume looks great, but you’re not 100% sure what their work ethic, speed, ability to problem solve, and decision-making initiative is like, the two-week rule helps answers a lot of these questions.

Whenever I hire someone new, I let them know that I’d like to trial working together for two weeks to make sure that we’re both a good fit for each other. I put an alarm on my calendar for the two-week mark and when it’s time, send over my thoughts via email on whether I’d like to continue working with that person.

During those two weeks, I send harder assignments that may require the candidate to ask me questions, problem-solve, meet deadlines, or communicate. What I seek to understand is how the candidate thinks, solves problems, and follows up — things you usually don’t find out till a few months in, you’re able to understand within two weeks under this method. 

To apply this for yourself and your business, gather some thoughts on what’s important to you and your business as far as how someone on your team handles discomfort. What responses do you want to see from the candidate?


Get That Job Post Out 

If you’ve never hired someone to help you with your business before, taking the first step may feel overwhelming. However, once you get the job post out, everything else in the process will flow seamlessly, but absolutely nothing will happen unless you get the job post out, so start there ASAP. 

Here’s what I recommend to make the first steps of putting together your needs as painless as possible:

  1. Complete your personal assessment of the prompts in Human First, Resume Second and Two-Week Rule sections above.

  2. Look for job postings on Indeed, LinkedIn, and other job posting sites that align with the role you’re looking to hire for. Get some inspiration based on these postings on how to structure your own job posting.

  3. Draft a short paragraph or two that details what you’re looking for and include a link to your job posting. You can now use this post to share it with your network and job posting sites. For freelancers, I recommend sharing this with:

  • Your network, ask for referrals! Posting your job on LinkedIn is a great place to broadcast your need.

  • Post on private Facebook groups like Freelancing Females to find candidates.

  • Post on LinkedIn ProFinder and Upwork.


If you don’t find someone during the first round, list your job again! It’s all about timing sometimes.


Be A Good Client

Once you’ve found your dream freelance team, there are a few things you can do to be a good client that freelancers and agencies love working with — 

  1. Know the rules — Legally, a business is not allowed to tell a contractor how and when to complete a project that is given to them because that would make them an employee in the IRS’ eyes. Providing future deadlines is fine, but stay away from micromanaging your contractor and do not expect same-day turnarounds unless it’s a one-off ask that the contractor agrees to.

  2. Don’t run from retainers — If you want someone to work for you on a monthly basis, respect their time and respect their request for a retainer. Without a retainer, the contractor will have to spend their time doing business development in order to find new work since you’re not guaranteeing work for them. Agreeing to a retainer ensures that your contractor will be available to complete work when you request it since they’ve already carved out time for you.

  3. If you can’t pay on time, communicate — Do not ghost someone that you plan on having a good working relationship with. If you’ll be late on payment for more than a week, communicate why and what your timeline is like. Just like you, your contractor has bills and people to pay and deserve an update so that they can communicate their timelines to their team.

  4. Don’t rely on mind-reading— When you begin working with someone new, communicate every single preference and expectation you have in mind. All of us have our own style of working and expectations and we shouldn’t assume others to have the same style and expectations. Communicate these things up front and it’ll help reduce a lot of transitional pains.

  5. Be a good client — Abide by an overarching principle to be a good client to your remote team. Regardless of the situation, view your relationship as a two-way street and always dictate your actions accordingly — be kind, thoughtful, listen, and respect the people you work with.


If you found this helpful, I send weekly action plans every Friday to help startups like yours grow their business. Sign up here if that’s your jam. 

Sophia Sunwoo