Freelancer Management: Tips for Building a Sustainable Freelance Team

There’s a lot of advice for freelancers about how to keep clients happy. But it’s seldom discussed how clients should behave and work on building a solid relationship with freelancers.

As a service provider, we’ve worked with thousands of freelancers, and when we asked them about their freelance experiences, the stories they shared were upsetting. Get a peek here.⬇️

Quotes from different freelancers when they were asked "what bothers them the most about clients"

This inspired us to dedicate this post to addressing freelancers’ concerns and educating other employers on creating good rapport and building a positive and sustainable relationship with their freelance team.

1. Be responsive

Ever heard of follow what you preach? That’s applicable when dealing with freelancers as well. If you expect them to be responsive and share timely updates, give them the same treatment. It’s understandable that you sometimes can’t prioritize responding to their messages immediately because of time limitations, but if you go silent for days or weeks, it not only concerns your freelancers but also hugely affect their morale to work with you.

2. Get clarity on what you want

3 out of 5 freelancers we spoke with shared that their clients didn’t instruct clearly but still expected them to deliver high-quality work. Freelancers could be great at what they do, but they don’t come with this superpower of reading minds – if that’s what you expect them to do too. At Klarecon, we emphasize minimizing confusion by maintaining project guidelines and keeping them up to date. Hence, we recommend it to other companies who delegate tasks to freelancers. It helps them understand any task’s major and minor requirements and saves trainers and managers tons of time when onboarding new freelancers.

3. Communicate good and bad news

Ok, we get that – communicating bad news may put you out of your comfort zone, but it’s way better than not communicating at all. When you love your freelancers’ work – let them know so they can double down on what works. When you don’t, let them know what’s missing and how to improve it. A situation when communication becomes more crucial is when there’s an unexpected delay in payments. Even we’re guilty of making this mistake. Since we work with a vast team of freelancers on a retainer basis and have a great history of paying on time, we assumed our freelance team would understand even if we didn’t inform them of slightly delayed payments. Yes, they will understand if you have to delay payments because of any urgencies, but it doesn’t free you from the responsibility to inform. For many freelancers, you might be the only customer at a given time, which means they depend on a single income source. So even if you assume it’s just a couple of days of delay, it may cause them stress due to pending bills or other needs dependent on this income. Prepare your payment arrangements in advance to avoid such situations.

4. Don’t give false hope

Imagine this – you’re a kid whose parents promised big ice cream for the weekend, and you counted each moment until then. And when the day arrived, you got an ice cream, but a smaller one.

Would you be disappointed? Of course.

A picture showing how a kid waits for a huge ice-cream and how they feel when they get a small ice-cream instead.

The same kind of disappointment your freelancers experience when you give them false hope. A well-known reason employers do this is to prevent freelancer turnover because finding good ones is not easy.

We have been in uncertain situations, too, so we understand. We hire dozens of freelancers to help our clients scale, and when the workload suddenly drops, it’s natural for freelancers to wonder when things will return to normal.

Instead of keeping them in the dark, we prefer to tell them the situation so they can make informed decisions instead of just waiting for work and losing other opportunities. We may lose some good ones that way, but we’ll at least retain their trust shall we have new opportunities to offer in the future.

5. Be mindful of the difference between assertiveness and aggressiveness

We work with freelancers from across the globe, and it has taught us a powerful lesson – good working relationships are a must-have for a business to flourish.

That said, “good working relationships” are often mistaken for being nice always. That’s not how you build them. Be nice, but be assertive when needed. Just be careful that assertiveness doesn’t turn into aggressiveness.

Look at this example:

An example showing the difference between assertiveness and aggressiveness when communicating with freelancers

An imaginary conversation between a client and his freelancer

6. Set reasonable time boundaries

Hiring freelancers is often associated with this misconception that they would (and should) agree to whatever you demand as a client. For example, asking to jump on a call at 11 pm (in their time zone) to discuss matters that can wait until the next working day. This type of expectation comes with an assumption that freelancers are available 25/7. No, they aren’t and shouldn’t be. Asking them to work beyond reasonable hours or expecting unrealistic turnaround times can be detrimental to their professional lives and your project outcomes. If having a cordial relationship with your freelance team matters to you, set boundaries that work for you and them. This includes setting turnaround times for first-time and revised submissions and ensuring a clear understanding of the project’s scope.

7. Encourage them to express opinions

If your freelancer(s) have a valuable opinion and know how to share it confidently, you’ve most likely found a thinker, not just a doer. The more a resource can think and share a healthy suggestion, the less they depend on you. At Klarecon, one of the first things we encourage our remote team members to share opinions and criticism without hesitation, no matter how senior their colleagues are. This helps us promote a growth-oriented environment and spot talents that can be promoted.

For this to work, we encourage our managers to listen to negative and positive feedback. It’s essential because encouraging one party to express without educating the other party to listen brings no value.

8. Know when “firing fast” is inappropriate

Before working with us, some of our clients had this incorrect notion that freelancers must deliver flawless work every time and yield instant results, or else they should be fired. Although it’s OK to expect results for the money you’re paying, you should know which situations actually call for firing decisions. Look at these examples:

  • You hired an assistant to manage your email inbox. You tested them for good English writing skills, and they passed very well. However, just a day after they start working for you, you notice that the emails they draft are full of basic English errors, and you instantly understand that it’s a fraud case. Should you fire on the spot: Yes. The hired freelancer committed fraud, and giving them another chance won’t be wise.

  • You hired a copywriter to write PPC ads. They show all signs of a good resource – from communication to regularity to understanding ad policies. But their ads don’t bring the results you need despite a week of testing. Should you fire on the spot: No. Several factors decide the ads’ performance, including the copy. Holding only the copywriter responsible for the ads’ success would be unfair in this case. Also, a week is insufficient for them to thoroughly understand what works and what doesn’t. Since they have already displayed the kind of sincerity you expect, it’s well-deserving of them to get good-enough time to start producing profitable results.

9. Keep your expectations realistic

The expectations of several companies when working with freelancers are often sky-high. They are assumed to do more than their current skill set without training. So how to differentiate between realistic and unrealistic?

Keep in mind a freelancer’s core skill set and abilities. Let’s say you hire a beginner-level developer, it’s realistic to expect beginner-level code writing from them. It would be unrealistic to expect them to write advanced code without additional training.

Similarly, if you hire a general virtual assistant, it’s realistic to expect that they know basic computer operations. Expecting them to write marketing emails for your business would be unrealistic.

Although you may find exceptional talents who are multi-skilled or could be easily upskilled through training, it’s not practical to make it a general expectation when hiring freelancers (or even in-house employees, for that matter).

10. Stop assuming freelancers don’t need management

Although freelancers are generally independent contractors, not all can self-manage, especially beginners. As a client, you need to know how your freelancer manages their time, especially when working with you on a retainer basis. Regular and pre-scheduled check-ins with them will help you stay updated on their routine and overall project progress. It will also make things more manageable if you set KPIs and monitor them periodically to see if your project is on course.

Managing a freelance team can be challenging, and finding reliable freelancers who continuously deliver high-quality work is even more difficult. So when you find such resources, it’s of enormous importance that you maintain a strong relationship with them.

By retaining them, you will experience much less hassle of replacement and a continuous hunt for good freelancers. You may even find people who could become FTEs and turn into invaluable assets for your business.

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