Co-Founder and Advisor at FlexTeam and CXO at Liquid, an operating system for agile businesses starting with contracts and global payments.
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Communication is key to building strong working relationships, whether with employees or with freelancers. While most organizations have built-in methods and procedures for giving feedback to employees, such as regular 1:1 meetings, I’ve found that many companies lack processes for giving feedback to freelancers, contractors or other members of their virtual talent bench. Given that working with freelancers tends to be temporary, it’s too easy to skip over providing feedback to your liquid workforce.
Understand When To Give Feedback
During each project, review the scope of work frequently to make sure milestones are met. If your freelancers or consultants are falling flat, say so. Most freelancers crave feedback, as they know feedback helps them improve their work product and increases the likelihood of a successful outcome for both parties. If they’re providing valuable contributions, be sure to thank them.
At the end of each project, spend some time going over what went well during the engagement and also what could have been improved. These retrospective meetings help ensure future engagements run smoothly.
Whenever possible, critique in private and praise in public. No one likes to be publicly called out for failures or mistakes. Critique publicly, and you’re likely to be met with defensiveness. This should go without saying, but if you’re in a bad mood, give yourself some time to clear your head — when giving feedback while upset, your tone will likely make more of an impact than the actual content of the message.
Set Expectations
The first step in giving feedback to your freelancers, contractors, and other remote workers is setting expectations. Make sure you’ve got a clear scope of work with detailed milestones and timelines. The scope should be detailed enough so that all parties understand what is expected and when items are due.
Once you’re ready to give feedback, Daniel Coyle, author of several books on talent, suggests starting each feedback conversation with one magical 19-word phrase: "I’m giving you these comments because I have very high expectations, and I know that you can reach them."
This statement helps your freelancers, contractors and virtual talent bench — and even your employees — feel valued and connected to your business.
Skip The Compliment Sandwich
In my career advising startup founders and small business owners, I’ve known all too many managers whose preferred method of providing feedback was the compliment sandwich. This is when you sandwich a negative piece of feedback between two positive pieces. The idea is that you don’t want to get anyone down and that focusing on the positive helps blunt the negative.
I’ve found that the feedback sandwich both undermines the constructive (negative) feedback being conveyed while also making people suspicious of positive feedback. Instead, follow these steps to give clear, concise, specific and constructive feedback after asking for permission.
Ask For Permission
Before you start with Coyle’s magical 19 words, ask for permission to have a feedback conversation. This can, and should, be as simple as asking a question like: Do you have 20 minutes to talk about X? If the answer is yes, then you can move on to those magical 19 words. If the answer is no, then ask when a good time to talk about X is and schedule a time on the calendar. Asking for permission allows the person to prepare mentally for receiving feedback, making the conversation more likely to lead to actionable results.
Start With Statements, Then Ask Questions
Start by stating what you observed, what impact it did or could have, and then ask questions. Try to be objective and refrain from judging or inferring what happened, giving the freelancer, consultant or contractor time and space to explain. For example: I noticed X, and that could have impacted Y, and I was hoping you could give me your thoughts. This framing can help you uncover additional issues that you may have overlooked. In addition, asking questions can encourage self-reflection — allowing the freelancer, consultant or contractor to come up with creative solutions for addressing your concerns. Make sure you listen to what they have to say.
Be Specific And Clear
Be specific with your critique as well as your praise. The more specific your feedback, the more likely it is to be actionable and useful. Aim for concise clarity — using too many words to blunt the emotional impact of negative feedback will make your message fuzzy. Be intentional with your words and tone. Avoid overgeneralizing, being judgemental or making assumptions about intent. When providing negative feedback, make sure the conversation ends with clearly defined next steps for improvement — this is what separates criticism from constructive feedback.
Don’t shy away from giving negative feedback, but strive to give positive feedback more often. Increasing the ratio of positive to negative feedback creates a culture where feedback is valued, not feared. When giving positive feedback, do so with explicit information about what was done well — this helps to reinforce positive behavior. In contrast, vague positive feedback simply makes the receiver feel good.
Ask For Feedback
If you don’t ask for feedback, you’re unlikely to get it. Don’t forget to also ask for feedback from your freelancers, consultants and independent contractors. Being external to your organization gives them a valuable vantage point. Their outside perspective can help them notice things that employees might miss. In addition, working with many clients means that your liquid workforce may have gleaned insights from working with similar organizations. Prioritize asking for feedback, as this builds the relationships you have with your virtual talent bench. When they start to see you as a partner — and not just a client — they’ll be more likely to make time for your projects.
Create A Culture Of Feedback
Providing candid, thoughtful and positive feedback is essential to building strong relationships. Plus, having two-way feedback loops builds trust. Creating a culture of feedback generates a high-performing culture, boosting your team’s performance.
Start taking your relationships with freelancers, contractors and remote workers to the next level.
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