How to Write Constructive Contractor Feedback

Author: Eugenija Steponkute
Published: 25/07/2021
constructive contractor feedback

With this article, we are reaching out to managing directors and consultancy owners who rely on outsourcing workforce. When it comes to contractors,  we tend to focus heavily on project management, invoicing and client billing. However, one crucial element often gets left out: providing contractor feedback.

Your regular employees get performance reviews. And you should not deprive your contractors of feedback either. Now why does it matter? The answer is rather easy: it will help them secure their future work opportunities. According to Fundera, 46% of full-time freelancers find work thanks to word-of-mouth. Your feedback might be what decides whether they secure their next gig or not. 

But what is in it for you? Providing honest and detailed feedback during and after the collaboration can mean getting your requirements met quicker. And it can help build an effective, long-term partnership with the contractor. So, how do you structure and communicate your feedback to the outsourced staff?

What is Constructive Feedback? 

Constructive feedback is the golden middle between praise and criticism. It is an objective evaluation that weighs both, the strengths and weaknesses and then uses the conclusion to help the receiver of the feedback improve. 

That is the ultimate goal you should have in mind when providing feedback to your contractors: to highlight what they’ve done great, to accentuate what didn’t go well, and to offer potential routes for improvement. 

Giving Feedback to Contractors 

You may have less direct responsibility for contractors. But that doesn’t mean that you can’t help make them feel secure and respected. For example, contractors can feel anxious over whether they are up to scratch. They know they can be removed from a job at any time, and this is stressful. Giving feedback will help contractors gauge how they are doing and provide valuable reassurance.

Build a Relationship

Feedback is part of a strategy to develop a warmer, trust-driven relationship with contractors. A strong relationship makes it easier to communicate and work together. It will also increase the likelihood that the contractor will return to work for you in the future. Such will result in enhanced performance, better alignment and lower recruitment costs.

As a manager, you set the tone for how a contractor is integrated into your team. Be sure to introduce the contractor warmly and make it clear that you expect team members to treat the contractor like their other colleagues.

Remember to include the contractor in social events, important meetings, email threads and discussions. Freelancing can be a lonely way of life. Contractors may appreciate someone making the effort to treat them as more than a work robot.

Treat the Contractor with Empathy

Why does the contractor want this job? What are their career goals or motivations? They might be pursuing new skills or taking their career in a new direction. Or maybe they simply need the money.

Either way, by understanding their motivation and needs, you will be able to tailor your approach and communication. Through empathy, you’ll know what a contractor wants from an assignment. It will also hint at how can you support them and make the work more rewarding. This makes it more likely that they will return for future contracts, and that they’ll put the effort into your current project. 

Adopt Radical Candor

If you’re not familiar with Kim Scott’s best-seller Radical Candor - get yourself a copy. Without making this article sound like a sponsored piece (it’s not!), we’ll try to summarise the main idea regarding feedback.

For feedback to be truly constructive and radically candid, you need to do two things: care personally and challenge directly. Giving either one too much or too little attention will have negative consequences. Scott titles them as ‘Ruinous Empathy’, ‘Manipulative Insincerity’ and ‘Obnoxious Aggression. To learn more about each and how to avoid them, we strongly recommend reading the book.

Regular Chats About Performance 

You do not need a formal review process for your contractor, but that doesn’t mean you can’t touch on performance. Put a little time aside for a 1-on-1 catch-up and discussion. It will let you explain where you think the contractor is succeeding and where they could improve. You could try referring back to the contractual documents at these moments to help inform your discussion. 

Many contractors will welcome you taking the time to do this. They may even give you helpful insights into your team and operations. Trust them - they have likely seen how many different teams work and can give an informed opinion on yours.

Be Frank About Underperformance

Remember: care personally and challenge directly. During your catch-up sessions, praise them on what you’re genuinely pleased with. But also clearly communicate the areas you’d like them to improve on.

If a contractor is not meeting your expectations, you might be tempted to either end the contract or not work with them moving forward. This is understandable. But sometimes with a little well-timed and radically candid feedback, you can turn things around. The problem might be something you can sort out. For example, a difficult dynamic with another member of the team. 

Stop Postponing It

Feedback should always be timely. If you give feedback promptly, it can be absorbed by the contractor and used to inform their next actions on a project. Let it wait and the chances are that both you and the contractor will be less focused and it will not feel relevant.

Easier Feedback Delivery

More often than not, contractors are remote workers and therefore an in-person feedback delivery is impossible. If you’re a bigger agency, you may find it difficult to navigate through big volumes of contractors and lose track of who is yet to receive feedback.

For this reason, at Timesheet Portal we’ve integrated a mailing tool within our Recruitment software. It gives you an inbox of clients and contractors being separated. Then, you can narrow down the contractor contact list by their placement status.


To achieve the best results, you need to give contractors regular, constructive feedback. Not only does this lead to better performance and satisfaction, but also contributes to strong, long-term bonds.

Having a trust-driven relationship with the contractor is beneficial for both parties. You offer them an opportunity to improve by being honest and empathetic. In return, they try to return the favour by exceeding expectations. Working alongside one another for an extended period of time creates better rapport and leads to better alignment.

Would you like to learn more about how you can improve your contract management processes? Book a demo and we’ll introduce you to many options you didn’t know you had.

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