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7 Challenges Businesses Face Working with Freelancers (And How To Address Them)

Workspace of a freelance designer with dual monitors, a graphics tablet, sketchbooks, and a desk organized with design tools and materials. The designer is using a project management tool on the computer screen to manage tasks and projects
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As someone working in a marketing team, you understand the constant need for fresh perspectives and specialized skills to stay ahead of the competition. Tight deadlines and limited resources can often leave your team in need of additional support. This is where the freelancers come in, offering a seemingly simple solution that can extend your team’s capabilities.

Hiring freelancers has become increasingly popular in recent years. 1.57 billion people in the world are freelancers, which is almost 47% of the global workforce. (Source: World Bank).

While there are numerous benefits of outsourcing your projects, finding good and reliable freelancers whose skill sets align with your project goals can be a daunting task. One wrong step can hamper the project’s progress and you are back to square one!

We delved into the experiences of teams working with freelancers and it became evident that teams face many challenges.

In this post, we’ll discuss those challenges, the reasons they arise, along with tactical advice on how to mitigate them in order to achieve seamless collaboration with your freelancers and outstanding project outcomes.

1. Finding Good Talent

Sifting through a vast pool of portfolios, profiles, and proposals to find the right freelancer can be time-consuming. The pressure is even higher when deadlines are looming overhead thus making it overwhelming to narrow down the right candidates.

Potential reasons for this challenge

  • Vast talent pool
  • Time and budget constraints
  • Skills and expertise mismatch
  • Lack of understanding of project requirements
  • No prior experience in hiring or evaluating the freelancers

How do you mitigate this challenge

Plan ahead

Beginning your talent search well in advance of the project start date gives you ample time for the hiring process. From interviewing, comparing candidates against the project requirements, and onboarding the freelancers, you’ll be in a better position to negotiate the terms, deliverables, budget, and other details of the project. Rushing the process may lead to negative outcomes affecting the success of the project.

Clearly define project requirements

You are in a better position to evaluate freelancers when you have clearly defined project requirements. This will save you time assessing portfolios, work samples, and proposals against your project criteria – thus making the process more efficient and focused. It also enables you to find talent with the right combination of skills and expertise who have worked on similar projects in the past. 

Utilize referrals and recommendations

When hiring freelancers, get referrals and recommendations from your trusted sources, colleagues, and professional network. Tap into their knowledge and connections to find freelancers who are reliable, professional, and deliver quality work. This can save you a lot of time in the initial screening phase.

2. Reliability and Availability Issues

While many freelancers are reliable and professional, others may not exhibit the same level of reliability and commitment. Freelancers typically have multiple ongoing projects and their availability might not perfectly align with your project timelines. Less reliable freelancers lead to project delays, reduced quality, employee frustration, or sudden discontinuation in the middle of the project, eventually wasting the time and resources of the business. While there could be unforeseen circumstances, some essential measures can help you mitigate these challenges.

Potential reasons for this challenge

  • Rushed hiring
  • Scheduling conflicts / Different time zones
  • Unrealistic expectations
  • Poor communication
  • Unforeseen circumstances

How do you mitigate this challenge

Thorough vetting

It is crucial to assess a freelancer’s reliability and availability before engaging them. Look for indications of their past performance, promptness in responding to inquiries, and reviews/testimonials from previous clients. Setting regular check-in and update calls to track the progress of the project can help you detect communication breakdowns early on.

Setup effective communication channels

Over-communication is the key here. Hiring managers need to ensure that freelancers understand project timelines, deliverables, and milestones. Coordinating multiple freelancers, tracking progress, and addressing any potential delays or roadblocks require meticulous planning and efficient communication. You can use tools like Asana, Trello, and Slack to streamline tasks, track progress, and communicate proactively to ensure everyone stays informed and organized.

Set realistic expectations

Unrealistic project timelines, excessive workloads, or expecting immediate availability discourage reliable freelancers and attract those who may overpromise but underdeliver.

3. Limited Brand Understanding

Unlike employee hiring, rushed hiring and impromptu onboarding of freelancers sometimes don’t allow them time to fully understand the brand’s unique voice, tone, and visual identity. This can lead to subpar results and campaigns that fail to resonate with the target audience. 

Potential reasons for this challenge

  • Rushed hiring
  • Impromptu onboarding
  • Vague project brief
  • Limited branding guidelines
  • Limited communication

How do you mitigate this challenge

Thorough screening and evaluation 

Thoroughly review work samples, portfolios, and testimonials to assess skills. During the interview stage, gauge their understanding of branding concepts and their ability to align with your brand’s identity. Freelancers who have prior experience working in a similar industry should be preferred over others.

Comprehensive brand guidelines and project brief 

Share a detailed project brief with all the relevant information including values, target audience, positioning, and branding guidelines. These guidelines will serve as the reference ensuring consistency and helping them align their work according to the brand’s objectives.

Have a collaborative approach

Encourage more collaboration between freelancers and your in-house team. Inviting them to your discussions, brainstorming sessions and planning meetings will significantly improve their understanding of your business. Doing regular check-ins, giving constructive feedback, and addressing any of their concerns will help the freelancer deeply understand your needs and align perfectly with your mission. 

4. Ensuring Data Security

Confidential information and data security is a critical concern when engaging freelancers. Hiring managers must take appropriate measures to mitigate the risk of data breaches, unauthorized access, and potential leakages. The absence of robust security measures can lead to financial loss, reputational damage, legal headaches and loss of trust from clients and customers.

Potential reasons for this challenge

  • Inadequate contractual agreements
  • Lack of awareness and control
  • Communication gaps
  • Varying security standards
  • Compromised third-party tools

How to mitigate this challenge

Sign non-disclosure agreements

Once you have hired a freelancer, have them sign a legally binding non-disclosure before sharing any sensitive information. An NDA will establish confidentiality obligations and add the threat of legal consequences for unauthorized disclosure of sensitive data.

Limit access and set strong password policies

Implement user permissions and access control policies to ensure freelancers can only access the bare minimum information they need to do their jobs. Encourage a strong password policy along with two-factor authentication to enhance account security.

Secure file sharing and data encryption

Using secure file-sharing platforms and encrypted communication channels can mitigate the risk of data breaches. Use 2 factor-protected platforms like Dropbox, Google Drive, and encrypted cloud storage services to safeguard data during transit and for regular access.

5. Short-term Focus and Cultural Misalignment

Unlike full-time employees of the company, freelancers are not fully immersed into the company’s internal culture. They work on a per-project basis, with a short-term mindset focused solely on completing the assigned task. Sometimes this can lead to cultural misalignment where freelancers do not fully understand the work dynamics and communication style in the organization. This hampers their ability to align their work with the company’s long-term vision and mission. 

Potential reasons for this challenge

  • Short-term project based focus
  • Time constraints preventing complete cultural immersion
  • Limited access to information or communication gap
  • Lack of understanding of long-term vision
  • Not a cultural fit 

How to mitigate this challenge

Provide contextual information

Providing detailed and comprehensive project brief, project context, and relevant information about the project’s objectives, scope, and timelines. This can help the freelancer adapt and align their approach according to the company’s dynamics and understand the bigger picture and long-term goals.

Provide feedback and recognition

Regular constructive feedback and recognition help them to understand the impact of their work and align their efforts with the broader goals of the project and company.

Long-term engagement

You have hit a jackpot if you have found freelancers who consistently deliver quality work and show an understanding of what the company’s goal means. Consider developing a long-term work relationship with them by engaging them repeatedly. They will develop a better understanding of the vision over time and their contributions will be more aligned and impactful. What’s better than the benefits of freelancers with the reliability and convenience of a dedicated team?

6. Project Management with Multiple Freelancers

Freelancers often have specialized skills - which is an advantage and a challenge at the same time. While some excel in the ideation and conceptualization stage, others are better suited for fine-tuning and iterating on existing designs. Assembling a team of freelancers with complimentary skill sets can be a strength for your project but even with a well-rounded team, there’s a certain administrative overhead to ensure a successful outcome.

In particular, managing the entire lifecycle of a project from conception to delivery requires careful planning, meticulous organization and constant communication.

Potential reasons for this challenge

  • Different work styles and processes
  • Varied creative approaches
  • Lack of clearly defined goals or expectations
  • Poor planning and organization

How to mitigate these challenges

Centralized project management

Use project management tools to centralize project information, tasks, and deadlines. This will enable you to track the progress and monitor the timelines easily. Having a centralized platform ensures that multiple freelancers have access to all the necessary details and can collaborate effectively. Project management along with regular check-ins will ensure that everyone is well informed and any setbacks, issues or problems can be dealt with in a timely manner. Asana, Trello, Monday, and ClickUp are some commonly used software for project management.

Standardized processes

Standardized workflows, templates, and guidelines will streamline work processes for all stakeholders. Provide and document clear instructions on file naming, formatting, and submission protocols to ensure consistency. This will minimize team confusion and enhance overall productivity across different touchpoints. You can use knowledge management tools like Scribe or Notion Wiki template to help with this. 

 Time Management and Deadlines

Managing multiple freelancers means juggling multiple schedules and deadlines. To mitigate this challenge, establish realistic deadlines and communicate project priorities. Make sure you keep buffer time while setting these deadlines to manage any last-minute emergencies on the project. Regularly monitor progress to detect any potential delays early on and provide support and resources as needed. You can use this Notion template to manage the progress of the project and manage timelines. Other tools that you can use are Monday and Wrike

7.  Varying Rates

Freelancers' rates can vary significantly based on factors such as experience, expertise, location, and demand. It can be challenging to navigate these varying rates and find a freelancer who fits within your budget while still meeting your quality and skill requirements. Balancing cost-effectiveness with the desired level of expertise is a delicate task.

Potential reasons for this challenge

  • Skills and expertise variance
  • Project complexity and scope
  • Geographic location
  • Subjective value perception

How to mitigate this challenge

Request detailed quotes

Detailed quotes and proposals will give you an outline of the scope of work along with deliverables and timelines. This will help you compare the value offered by different freelancers, thus helping you make informed decisions about the payment model, timelines, and engagement terms.

Evaluate value proposition

While some freelancers may suggest you lower rates you need to look beyond the rates and assess the overall value proposition of freelancers. Look at their portfolios, expertise, experience, and the value they bring to the project. Then evaluate if their rates are justified. Make sure short-term cost-cutting doesn’t lead to long-term consequences and higher expenses down the line.

Negotiation and flexibility

Engage in open and transparent communication with freelancers regarding their rates. Discuss your project requirements and budget constraints to see if there is room for negotiation. Flexibility on terms and deliverables can help reach a mutually beneficial agreement.

Conclusion

In conclusion, the challenges of hiring freelancers can be overcome by implementing a few key strategies. Organizations can mitigate the risks associated with hiring freelancers by thorough vetting and defining clear project requirements (because nobody wants a surprise ending like a plot twist in a bad movie!). Additionally, setting realistic expectations, providing clear feedback, and establishing a strong working relationship can contribute fruitful collaborations with freelancers and thereby, successful project outcomes.

Or another way to save all this hassle is to use a Creative-as-a-Service such as Frontmatter to get a modern, software-like experience for getting your creative projects done consistently day after day. Do check us out!

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