6 Delegation Tips for Startup Founders Working With Freelancers

Before we get into the nitty-gritty, it should be noted that this blog is inspired by a thought-provoking LinkedIn post from Quickly Hire’s founder, Brad Morrison. In his post, Brad touches on a concern we often hear from startup founders: 

“Contractors have burned us in the past.” 

Many business owners are familiar with ghosting, a lack of skills, and missed deadlines. Yet, sometimes, the culprit for a freelancer not working out may lie closer to home.

So, a big question: How good are your delegation skills? 

While there are indeed freelancers who might be out of their depth or a few who may not deliver as promised, the majority are earnestly striving to do their best. Yet, they often struggle due to either too little or too much direction from founders. Some are overly hands-off, while others might assign tasks but remain perpetually dissatisfied with the outcome. 

Leveraging the skills and time of freelancers can be the perfect fuel that sends your growth trajectory skyward. As a founder, you’re aware that the success of your startup hinges not just on your vision but also on your ability to work efficiently with a diverse team. 

You face a unique set of challenges. Time is scarce, resources are limited, and there’s constant pressure to move quickly and adapt. That’s why mastering the art of delegation is crucial to sustain momentum and scale your operations.

When you start delegating tasks to freelancers, it’s essential to communicate effectively and set clear expectations. 

Balancing control with trust can be tricky, especially when your startup is like a second home – intricately tied to your personal ambitions and hard work. Missteps in management can lead to bottlenecks, reducing the efficiency you seek to gain. Your role involves making strategic decisions, including knowing what to delegate, to whom, and when.

Understanding the core principles of delegating to freelancers can mitigate risks and enhance your working relationships, contributing positively to your startup’s growth. Effective delegation helps ensure that every task is in capable hands, freeing you to focus on high-level strategy and decision-making. 

This approach optimizes your time and empowers freelancers to contribute their best work, driving progress and innovation within your company.

1. Make sure your resources and tools are ready to use

Open laptop with program on the screen

Before you assign tasks to freelancers, providing them with a smooth runway is essential. This means having all the necessary resources and tools in place for optimal productivity.

A few project management tools we use at Quickly Hire

As a startup founder, your selection of project management tools should facilitate clear communication and efficient task tracking. A well-chosen tool can be a central hub for your projects and a pivotal resource for team collaboration

Here are some you might consider:

  • ClickUp: A toolA versatile tool that combines task management, document sharing, and timeline tracking in a user-friendly interface.
  • Monday: Provides a highly customizable platform to manage every aspect of your team’s work, from simple tasks to complex projects.
  • Slack: Enables quick communication and integration with other project management tools for real-time updates.


Standard Operating Procedures (SOPs) are your blueprint for consistency and quality assurance. They function as a comprehensive guide, showing freelancers how to execute tasks, thus mitigating errors and confusion.

  • Step-by-Step Guides: Clearly document your company-specific protocols with steps that are easy to follow.
  • Checklists: Include these in your documentation to ensure all steps are completed.

Proper SOPs leverage your expertise, making it easier to entrust tasks to freelancers without fear of miscommunication or mismatches in expectations.

2. Set the goal, then step back

Freelancer working on a project with laptop and coffee

When you set a clear goal for your freelancers, you empower them to deliver results. It’s critical to communicate your vision for the project clearly and then give them the autonomy to execute.

Avoid micromanaging

  • Clarify objectives: Make sure your freelancers understand the project’s end goal. Share your success metrics and any relevant deadlines.
  • Trust: Once the goal is set, trust in their expertise. Remember, you hired them for their skills and ability to contribute to your success.
  • Communication: Establish regular check-ins to stay informed without controlling every detail. This balances the need for updates with respect for autonomy.
  • Feedback: Provide constructive feedback to guide them, but allow space for freelancers to use their initiative and creativity.

By stepping back, you’re not just freeing up your time; you’re also cultivating a team that is proactive and invested in the success of your startup. Trust is a two-way street essential for a balanced founder-freelancer relationship.

3. Match tasks to those with the right skills

Founder looking at data on a piece of paper

In startup settings, delegating tasks effectively hinges on aligning each assignment with team members with the requisite skills and expertise. This strategic matching is foundational to ensuring that your venture maintains productivity and achieves its goals efficiently.

How to uncover hidden talents

Begin by cataloging the specific abilities and past work experiences of your freelancers. This can be achieved through reviewing resumes, portfolios, and professional social profiles before hiring.

To optimize the process, you could conduct a skills assessment test and engage in one-on-one discussions to garner insights into their skills that may not be immediately evident from their profiles. It is tempting to rush this process, but without understanding their prior project experiences and any unique skills that may be underrepresented, you are under-utilizing your human resources.

Once you have selected freelancers, observe their performance closely. At the same time, try not to be intrusive when monitoring how freelancers handle current tasks. If you are paying close enough attention, their performance on the job often reveals:

  • Depth of competence in specific areas
  • Problem-solving capabilities that can be applied to new tasks

4. Stay in the loop, but don’t hover

Boss making worker upset

A good analogy for this is being the captain of a ship—you need to know where your crew is heading, but you don’t need to steer every minor course correction. Staying in the loop after delegating a task is essential because it ensures that your vision is being translated into action correctly. 

However, remember that too much contact can be just as counterproductive as no contact at all. It’s all about balance. Trusting your freelancers and giving them enough space to bring their expertise to the table is vital. They need to feel your support and know you’ve got their back without feeling micromanaged.

This approach fosters a sense of responsibility and ownership in them, and let’s be honest, it also keeps you from getting overwhelmed with details. 

5. Schedule regular check-ins and give feedback

Startup founder looking at important documents

Establish a routine for regular check-ins to ensure your freelancers are aligned with your startup’s pace and expectations. Timing can be weekly or bi-weekly, depending on the project’s intensity and deadlines.

Remember, you are paying them for their time—if there is no reason for the meeting, don’t schedule one!

  • Use video calls: Opt for in-person communication tools like Zoom or Google Meet to effectively add a personal touch and clarify points.
  • Give specific feedback: Provide detailed, constructive feedback that pinpoints what’s working and areas for improvement.
  • Acknowledge achievements: Recognize efforts and accomplishments to maintain motivation and personal productivity.

By adhering to these practices, you build a foundation for clear communication and foster an environment where freelancers can thrive and contribute effectively to your startup’s growth.

6. Celebrate wins and give credit where It’s due

Friends having a drink after work

As a startup founder, acknowledging success reinforces your team members’ value and encourages continued high performance. Tangible recognition can significantly enhance morale and improve retention within your freelance workforce.

Giving testimonials

Providing testimonials is a powerful way to celebrate accomplishments. When freelancers exceed expectations, you can write a testimonial for their portfolio, acknowledging their contribution in a public, professional context. This serves as positive feedback for the freelancer and strengthens your relationship with them for future projects. 

Testimonials are a mutual benefit — they help freelancers attract new clients while showcasing your startup as a collaborative and appreciative workplace.

Try fractional or direct hire freelancers with Quickly Hire

Freelancer at his desk, celebrating

When managing a startup, leveraging the flexible workforce of freelancers can be an intelligent way to control costs while scaling operations. As you explore hiring options, consider fractional or direct hire freelancers through Quickly Hire to align with your startup’s dynamic needs. 

Outsourcing essential tasks to skilled freelancers is a strategic move for smart resource allocation. Whether opting for fractional or direct hires, selecting the right freelancers is pivotal. Look for commitment, a strong track record, and a transparent pricing model to grow your startup collaboratively.

Hiring, vetting, and onboarding freelancers can be laborious, but you can circumvent these challenges with a talent acquisition partner like Quickly Hire. Instead of wasting countless hours trying to find the perfect hire, let us handle it. 

Remember, the primary reason for opting for a freelancer was to free up your time, so let’s optimize the hiring process together!


  • Alex McInnes

    Alex is a Quickly Hire Pro Copywriter. He's a New Zealand-born, Thailand-residing copywriter extraordinaire. Dad to two beautiful girls, Alex loves playing rugby, reading, and running with his soi dog, Effie.