Managing Freelancers? How to Help Freelancers Meet Your Project’s Goals And Make Deadlines

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Managing Freelancers? How to Help Freelancers Meet Your Project’s Goals And Make Deadlines

There is a lot of focus on the best way to manage Millennials, the new generation of workers. Yet the exodus of Baby Boomers isn’t the only shift managers need to prepare for. There is also a spike in freelance workers, which presents new challenges for managers to consider.

I’ve identified four common challenges that occur when managing freelance employees. Previously I’ve covered inefficient communication, and difficult collaborations between freelance and full-time employees.

4 common challenges

This week, let’s look at projects not being completed correctly or on time by your freelance employees. First, let’s be honest – it’s inevitable that you and your freelance employee will be somewhat disconnected. You don’t see them, you don’t know what else they have on their plate, and you don’t even know if they are working from their desk or a remote island cabana.

The good news is, location doesn’t matter. Results do. So let’s take a look at a common scenario, discuss a solution, and go over some tips that will help solve this common freelance problem.

PROBLEM: Projects are not being completed by the stated timeline, and/or don’t meet the goal of the project.

Freelancer’s Perspective: I need to write copy for three PowerPoint decks that the Account Director will use for a kickoff meeting while she’s in Toronto next month. I’m so confused… is her goal to sell a product or to update her clients? When is the presentation? How many phases of review will the decks need to go through before being completed? Since it’s not clear, maybe they don’t care that much about this project. I’ll just put something basic together by the first of the month.

Manager’s Perspective: I asked Jonathan to write the copy for our client kickoff meeting in Toronto. The goal of the kickoff was to let the clients know what milestones lie ahead in our working relationship, and make them feel welcome by our team. He finished the assignment only two days before the actual presentation – what a difficult employee! My in-house team stayed late to finish his work and are now feeling stressed out. Plus, the copy doesn’t sound like a kickoff at all—it sounds like a sales pitch. We practically had to redo the entire project in 48 hours. Why did I hire him?

SOLUTION: Set your freelancer up for success by providing a clear plan of action for the project at hand. This plan should include the project goal, time lines, and what phases are needed to complete the project. It’s up to you as the manager to lay this information out clearly for any of your employees, especially for your freelancers since you don’t see them regularly. It’s amazing how doing this can turn around potentially difficult employees!

In the example above, both the freelancer and the manager would have had a much more positive working experience if the manager had stated that the goal of the PowerPoint decks is to let the client know what milestones lie ahead in their working relationship and make them feel welcome by the team, that the presentation will be on October 1st, and that three departments will need to review the drafts before the content can be finalized. Then, the manager should set clear dates for each deliverable.

Tips for Preventing Freelance Workers from Missing Deadlines and Not Meeting Project Goals

The following three tips will make a tremendous difference in your ability to set your freelancer up for success in assigned projects. You want to be as clear as possible about the goal of the project, how long it will take, what milestones will happen along the way, and the specific deadlines that need to be met. Here’s how to up your chances of success.

1. Ask Two Simple Questions at the Beginning and End of Each Project Discussion with Freelance Workers

At the beginning of a call or meeting, state: “My intention for this meeting/call is X.” That way, the freelance team or team member can frame the meeting content within the stated intentions.

At the end of the meeting or call, ask for feedback by saying “My intention for this meeting/call was X. How did I do?” This reiterates your intention to the freelance team member or members, and creates a welcoming environment for clarifying questions.

Listen carefully to the reply to see if your freelance employee understands the goal of the project and when it should be completed.

2. Take a Training Approach

There is a very simple training model you can use in order to limit misinterpreted goals and deadlines.

When speaking about the project:

A. Tell them what you are going to talk about.
B. Talk about it.
C. Tell them what you just talked about.
D. Ask for questions.

An example using the above scenario would be:

A) Today I want to discuss creating the copy for the deck our account director will use in a kickoff meeting in Toronto on October 1st. I will let you know the goal of the project, what steps will happen along the way, and review the deadlines.
B) We want this deck to be authoritative and fun. The goal is to inform the client about what milestones lie ahead in our working relationship, and make them feel welcome by our team. You will get all of the details from the project manager this Friday. We need the first draft on September 10th, which will be reviewed and returned to you September 12th. We need the final deck complete by September 20th.
C) I’ve reviewed the goal of the project, the process by which it will be completed and given you the deadlines for each phase.
D) What questions do you have?

3. Approach Misunderstandings With Compassion

It’s easy to think an employee who did not do a project correctly was wrong. You may think, “What’s wrong with Jonathan? Why can’t he understand what I’m saying?” Remember that each employee is a human being with his or her own lives and challenges that extend outside of work. So approach misunderstandings with openness and compassion and take responsibility for your role as a manager to make sure all projects and expectations are communicated effectively.

These three tips are easy ways to make a positive impact with your management skills. With freelance employees in particular, there is less room to skimp on the basics, so make sure you are doing your part to set them up for success.

Have you ever struggled with a freelancer who has missed deadlines or not met project goals? How did you handle the situation? Any freelancers out there who want to add to this advice? I’d really love to hear about your experiences. Leave a comment below, send me an email, or find me on Twitter.


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