Building A High-Performing Team With Independent Contractors

Building a high-performing team with independent contractors doesn't happen overnight. It takes diligence, the right tools, and, most importantly, the right frame of mind to bring everyone together. 

Contractors aren't employees. They're freelancers building their businesses. By learning how to work with them to satisfy their and your needs, you can make a team that thrives and enjoys working together. 

That's what this article will help you with today. Whether managing an in-person, remote, or hybrid team, you'll learn how to create an engaging, high-performing company culture with independent contractors. 

Ready to learn more?

Let's get started.

1. Use work scheduling software 

If you're managing employees and contractors or freelancers around the globe, you need a way to visualize everyone's availability. 

This is where work scheduling software comes in.

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While independent contractors often set their hours, you can still use software to plug in their availability for projects, the deadlines they can meet, and any blackout dates. You can also visualize backup plans if a contractor gets sick or doesn't meet a deadline. 

Work scheduling software also helps team leaders divvy out projects according to each contractor's capacity levels and preferred schedules. With this overview, team leads can do their due diligence to ensure nothing falls through the cracks.

Check out options such as Connecteam, Homebase, or TimeClock Plus. In place of work scheduling software, you can use project management tools, like monday.com, ClickUp, or Asana, to visualize team capacity.

Or, since independent contractors often operate across various platforms, you can centralize and process this data more efficiently by applying technologies like composable CDP. 

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This platform streamlines data integration from various contractor touchpoints and provides actionable insights. 

That way, you can leverage these insights to drive decision-making and data storytelling, ensuring that the joint efforts and data from all team members, contractors included, propel your business toward its overarching goals.

2. Provide access to team collaboration tools

Strong teams precisely understand their expectations, the projects they must handle, and the timelines they must adhere to. That is… if you provide access to team collaboration tools. 

While contractors work independently, they'll still need tools to help them complete their projects, check their work, and submit deliverables. 

This may mean access to Kanban tools to slide work from "doing" to "done," productivity tools to track daily assignments, or time trackers to record time spent on projects.

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Outline your operations and include where contractors fit in to uncover the best tools. Then, look for tools you can use to optimize the entire process with efficient workflows. 

For instance, if you're a product innovation brand, you might use a tool like ClickUp to build team assignment overview boards, individual agendas, and automated workflows to streamline approvals and deliverable submissions.

It would help if you also looked into multi-factor authentication for whatever tools you use to add a much-needed layer of security by keeping the ease of access.

3. Set team OKRs and integrate them into your company culture

Objectives and Key Results, or OKRs, help successful teams like Microsoft, Google, Amazon, and Adobe achieve ambitious business goals. Bill Gates has also raved about the benefits of OKRs, including how they've upleveled his management style and improved operational efficiency. 

Integrating OKRs into your company culture can motivate your team to stay focused and work toward the same team goals. 

Setting OKRs:

• Creates alignment in the organization between stakeholders, clients, management, internal employees, and external contractors
• Promotes open communication across the organization 
• Fosters collaboration and highlights opportunities for joint projects
• Provides a road map to help freelancers and team members achieve aspirational goals

If you've never used OKRs, here's a quick rundown on how to create them:

1. Set your objectives — ensure they're specific, relevant, and achievable.
2. Define key results to measure if you're hitting your goals (make sure these are time-bound). 
3. List initiatives that contractors and the rest of the team will need to take to help you reach your objectives. These include any tasks, projects, or specific action steps.
4. Choose tools and methods to track progress, such as automated data reports. 

TL;DR: Use OKRs to ensure everyone stays on the same page about company end goals.

4. Get aligned on workflows

Make sure contractors understand their role in maintaining crucial assignment workflows. While you'll be using a tool like Trello or Asana to set up the tech side, contractors still need to know what they're specifically responsible for. 

That might mean completing a digital checklist after a project so the automation can bump the task to the next team member. Or that might mean reviewing your company's processes to get work done — from start to finish. 

You might even consider uploading simple training videos using a platform like Trainual or sending screen-cast videos with Awesome Screenshot or Loom. This helps contractors visualize how to manage workflows and prevents unnecessary communication that can drain company time.

5. Host engaging and productive meetings

High-performing teams thrive on excellent communication. That's why having a plan that can help you host successful meetings is crucial. 

Enter Robert's Rules of Order, a set of practical rules that's been helping teams govern meaningful discussions and goal-oriented meetings since 1876! Here's how Robert's Rules of Order recommend organizing meeting stages:

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Other helpful tips include:

• Develop a meeting agenda to structure the discussion according to your business goals
• Take breaks during long or monotonous meetings 
• Keep a meeting schedule to make room for every core topic 
• Avoid discussing topics that have been voted on to prevent repetitive meetings 
• Ask freelancers if they have anything they'd like to discuss, such as challenges, ideas, or solutions 

Pro-Tip: Send minutes from the last meeting in advance to avoid reading them during the next meeting. This frees up time so you can focus on your key objectives and give everyone a chance to participate.

6. Create an assignment tracker

You have scheduling software, team collaboration tools, and operational workflows. But what about a hub you can reference to keep track of all assignments, deadlines, and payments? While the recommended tools can help you organize the nuts and bolts, you also need a way to see the big picture. 

That's where an assignment tracker comes in. 

To create one, you can set up a spreadsheet in Google Sheets with a column for projects, another column for deadlines, another for costs, and a final column that tracks which assignments you've paid for. 

Or you can create a custom board with a high-level overview using project management software, like monday.com.  The first option is relatively easy and quick to set up but requires manual tracking.

If you don't manage a lot of freelancers or prefer to manage the overview yourself, a spreadsheet is a great choice. 

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The latter can take an excellent time investment to set up, but it automates real-time tracking. If you manage a large pool of freelancers or prefer to be hands-off, a custom board may work better for you. 

7. Establish fair contracts 

If you want freelancers to do their best work, feel valued, and take your company seriously, they need fair contracts that protect their time. While it may feel tempting to add a clause that says you can terminate a contract anytime, doing so can lead to mistrust and unreliable contractors.

Instead, focus on including language that gives you and the freelancer-freelancer a chance to develop a new plan if you want to dissolve the contract. 

For instance, add a clause like: 

"Both Freelancer and Client agree to provide 30-days written notice to terminate this contract. Assignments will continue to be given and submitted at the same frequency until the 30-day period has ended. Freelancer also agrees to give Client all pending and partially completed work at the end of the period. If freelancerfreelancer fails to perform their duties without notice or an agreed resolution, the contract will terminate immediately."

Here are some other essential details to include in your contracts:

• A start date and end date with the option to renew 
• The exact deliverables the contractor will be responsible for 
• The deadlines the freelancer-freelancer will be accountable for 
• Payment details, including how much a project costs and how the contractor will receive payment 

*Important Note: This isn't legal advice. Please contact an attorney with any specific questions about contracts.

8. Build lasting relationships 

Effective teams need contractors that stick around and provide consistent quality work. But for that to happen, getting on the same page is crucial. That's why clarifying capacity levels and expectations is pivotal before assigning projects and deadlines.

Ask contractors questions like:

• "What do your bandwidth and capacity comfort levels look like?"
• "Are you available for short-term, mid-term, or long-term projects?" 
• "If we enjoy working together, could you see yourself maintaining a long-term relationship with our company?" 

Then, work on building a real relationship with each contractor. Know them by name. Know their specialties. And maybe even know a few personal tidbits, like where they live and what they enjoy doing. 

Remember, contractors are humans first, workers second. By fostering lasting relationships with them, you can continue leveling up the work you're doing together — and, best of all, enjoy the process.

9. Maintain positive and constructive communication

It's easy to get snippy with people not officially on your team, but promoting good spirits isn't just for internal employees. It's a way to build a positive company culture all the way through. This is especially important when delivering continuous feedback on projects and assignments.

The key? Focus on providing value when delivering feedback. Specific: What exactly does the contractor need to change to improve the assignment? Please give them a short and clear answer, and use positive language.

For instance …

Instead of saying: "Hey Marsha, this design could be better." 

Try: "Marsha I love this color palette! Can we go back to the original font and graphic, please?"

Instead of saying: "Got the updated report". 

Try: "Thanks for the report updates, Tom. Everything looks great on my end. I'll forward this to Melissa and get back to you shortly!"

These minor communication differences foster healthy relationships and encourage contractors to continue putting their best foot forward. 

10. Give access to meaningful work 

Contractors may not be your employees, but that doesn't mean you can't brainstorm ways to give them work they love. By providing access to meaningful work, you encourage freelancers to stick around and motivate them to build their expertise. 

The more expertise they infuse into their work, the better their deliverables will be!

Here are some ways to provide access to meaningful work:

• Give freelancers the option to complete more significant and better projects
• Ask them what kind of work they love doing — and do your best to give it to them 
• Dig deeper to uncover what "meaningful" means to them, i.e., does that mean pioneering a new creative project? Working in client-facing initiatives? Brainstorming product innovations?
• Check-in monthly or quarterly to see what they think about their new focus and if they'd like to make any adjustments 

Wrap up 

And that's it!

Are you ready to build a successful team with independent contractors? 

Remember to:

• 1. Use work scheduling software
• 2. Provide access to team collaboration tools
• 3. Set team OKRs and integrate them into your company culture
• 4. Get aligned on workflows
• 5. Host engaging and productive meetings
• 6. Create an assignment tracker
• 7. Establish fair contracts
• 8. Build lasting relationships
• 9. Maintain positive and constructive communication
• 10. Give access to meaningful work

Now it's your turn to put these insights into action! Meet with relevant decision-makers and decide which strategies you plan to adopt. 

Then, put them into practice. Be sure to course-correct your approach as needed, stay goal-oriented, and focus on building genuine relationships with your contractors. 

That's it for now.

Here's to your success!