How to hire a freelancer for the first time

As businesses increasingly embrace remote work and flexible options for staffing, the freelance economy is booming.

With lots of platforms showcasing diverse skillsets – from graphic design to web development – it's easy to get lost in the sea of profiles, reviews and rates.

Hiring successfully means approaching the process with a clear understanding of your needs and what to look for in a freelancer.

A strategic approach like this will save you time and money while making sure your chosen freelancer is the perfect fit for your project.

In this blog, we set out some essential tips and best practices to guide you through hiring a freelancer for the first time, helping you avoid common mistakes and make informed decisions every step of the way.

1. Why hire a freelancer?

For small businesses, there are so many benefits to hiring a freelancer – particularly if you're looking for a flexible, cost-effective solution to your problem.

Here are some key reasons why outsourcing work to a freelancer might be the best business decision you could make.

The benefits of hiring a freelancer

Rita Peacock, Enterprise Nation adviser and business consultant, says it's common to find working with freelancers daunting.

"Generally, the world of outsourcing can be challenging to navigate due to the level of work involved.

"Hence many entrepreneurs and small businesses tend to wear a lot of hats, particularly at the start of their business.

"But when done right, working with freelancers can be great. Not only does it save you time, but it gives you access to specialised professionals with expertise and experience who can perform the tasks you aren't familiar with."

Here are a few of the main benefits:

It's economical

One of the biggest advantages of hiring a freelancer is the money you can save. Unlike with full-time employees, you'd typically pay a freelancer per project, per hour or on a retainer basis.

This means you don't have to worry about expenses like:

• monthly salaries

• employee benefits (pension contributions, sick leave and so on)

• costs associated with providing office space and equipment

If, like many small businesses, you're operating on a limited budget, hiring a freelancer can be a smart way to get high-quality work without the long-term financial commitment.

It allows you flexibility

Freelancers offer on-demand services, meaning you can hire them as needed.

Whether you require short-term support for a marketing campaign or long-term help with bookkeeping, freelancers provide flexible solutions that can scale with your business's needs.

It gives you access to specialised skills

Many small business owners try to do too much themselves, often spending time on tasks outside their expertise.

Instead of struggling with website development or graphic design, you can hire a freelancer with the exact skills you need. This lets you focus on running your business while an expert handles the technical work.

It's often quicker

Freelancers tend to work independently and are used to handling a number of projects at the same time – and efficiently.

Without the bureaucracy of traditional employment, they can often deliver work much faster than an in-house team.

It means less admin

Employing a full-time staff member comes with legal responsibilities and financial admin, like managing payroll and making sure your tax payments are correct.

With freelancers, you only need to agree on terms and pay them for their completed work to avoid many HR-related hassles.

Common use cases for small businesses

Hiring a freelancer can be particularly useful if you need specific expertise or skills. Some common freelance roles include the following:

• Marketing and social media management: Content creation, social media strategy, email marketing.

• Website development and graphic design: Web development, branding and logo design.

• Accounting and bookkeeping: Freelance accountants can help manage your finances without the cost of hiring a full-time finance officer.

• Virtual assistance and admin support: Handling emails, scheduling and customer service tasks.

Case study: Sarah's sustainable skincare business

Sarah owns an organic skincare brand in Glasgow. She struggles with managing her social media accounts while handling production and customer service at the same time.

She hires a freelance social media manager, who she tasks with creating her content and boosting engagement.

Not only does this increase her online sales by 40% within six months, but she's able to use the time to develop new products and expand her business.

VIDEO: How to gain time back by outsourcing

Caroline Marshall, founder of virtual assistant agency Upsource, explains how outsourcing can set you free, what the best delegators have in common, and where to start with outsourcing yourself:

2. Understanding your business needs before hiring

Before you start looking for a freelancer, you must be clear on what you actually need them to do for you.

Knowing this will help you find the right person for the job and make sure your collaboration with them goes smoothly.

Melissa Gauge, Enterprise Nation member and founder of SpareMyTime, recommends keeping your desired skillset tightly focused.

"It's very tempting to opt for someone who has a broad range of skills. But you're likely to get frustrated and disappointed if the freelancer you choose turns out not to have the appropriate skillset or experience."

Identifying tasks to outsource

Not every business task needs to be outsourced, and not every freelancer will be a good fit for your business.

Start by listing the tasks you struggle with or those that take too much of your time.

Here are some tasks you might want a freelancer to handle for you:

• Marketing and social media: If creating content, managing your social media accounts or setting up paid advertising is outside your expertise, hiring a specialist can increase online engagement and get more visitors converting into customers.

• Graphic and web design: A strong brand presence is crucial for attracting customers. A freelancer can help design a logo, build and maintain your website or online store, and produce high-quality marketing materials.

• Customer service and admin support: If you find responding to customer emails, managing bookings or handling enquiries overwhelming, a virtual assistant can take over and make the whole process much simpler and more efficient.

• Accounting and bookkeeping: Financial management is a crucial and unavoidable part of running a business. If you don't feel confident doing it all yourself, a freelance accountant can keep your accounts in order and make sure you're complying with the relevant tax laws.

Setting a budget

What a freelancer charges for their work will depend on their expertise and experience and how the complexity of the job.

When setting a budget:

• research industry-standard rates for the service you need

• consider your business's financial situation and how much you can afford to spend

• factor in long-term vs. short-term hiring – sometimes paying more for an experienced freelancer saves money in the long run

Determining what level of experience and skills you need

Not all freelancers have the same knowledge and skills – some are just starting out while others are established and highly experienced.

As such, you should ask yourself the following:

• Do I need someone with years of experience, or will a junior freelancer be OK?

• Does my project require specific software or technical skills?

• Should I prioritise qualifications, portfolio work or reviews from past clients?

Creating a job brief

Having a clear and concise job brief helps you find the right freelancer. Your brief should include:

• a description of your business and industry

• the specific tasks you need help with

• what you expect the freelancer to deliver for you (often called "deliverables") and the deadlines for doing so

• any tools or software the freelancer should be familiar with

• your budget range and payment terms

Example: "We're a London-based online fashion business looking for a freelance social media manager to increase engagement on Instagram and Facebook.

"Tasks include creating content, devising a hashtag strategy and managing our online community. Experience in fashion and retail marketing preferred. Budget: £500 per month."

Case study: David's café in Manchester

Café owner David wants to give his business more of an online presence, but has no digital marketing experience himself.

After establishing exactly what he needs, he researches freelance social media experts and hires the one he thinks most suitable to handle his Instagram account and updates to his Google Business Profile. Within three months, his online orders increase by 25%.

VIDEO: When to outsource support for your business

In this Lunch and Learn, recruitment expert Karen Watkins shares your options for outsourcing and how to find the right options for your business:

3. Where to find the right freelancer

As soon as you've determined the tasks you want to outsource, you can start looking for your freelancer.

There are several platforms and ways to connect with talented freelancers, each with its own advantages. Here's where to go:

Freelance marketplaces

Freelance marketplaces are some of the most popular and convenient places to find skilled professionals.

These platforms allow you to post job listings, browse freelancers' profiles, review ratings and manage payments securely.

Some of the most widely used platforms include the following:

• Upwork: A leading marketplace with freelancers across various industries, from marketing to software development. You can review freelancer ratings and hire on an hourly or project basis.

• Fiverr: Best for small, specific tasks and short-term projects. Freelancers offer predefined services at set prices, making it easy to compare options.

• PeoplePerHour: A UK-based platform that connects small businesses with freelancers. Particularly useful for digital marketing, content creation and web development.

• Freelancer.com: Offers a vast pool of freelancers across the world, with the option to post projects and hold competitions to find the best candidate.

Best for: Businesses that want flexibility and a wide range of freelancers to choose from.

Local and industry-specific networks

If you prefer to get more specific, consider looking for people among the networks in your local area or industry.

These communities can connect you with freelancers who have experience in your field and understand regional market trends.

Here are some options:

• LinkedIn: A powerful professional network where you can search for freelancers, join relevant groups and post job opportunities.

• Enterprise Nation: We're a network that supports small businesses in the UK and Ireland and helps connect them with service providers, including freelancers.

• Small business forums and industry associations: Many trade associations and online communities have directories or discussion boards where freelancers showcase their services.

Best for: Finding freelancers with local knowledge or industry-specific expertise.

Referrals and recommendations

A reliable way to find a freelancer is through word of mouth. Ask fellow business owners, colleagues or industry contacts if they've worked with a freelancer they'd recommend.

Personal recommendations can give you valuable insight into a freelancer's reliability, communication style and quality of work.

Some ways to gather referrals include:

• posting in local business Facebook groups or WhatsApp networks

• attending small business networking events

• asking professional contacts in your industry for recommendations

Best for: Ensuring trust and quality through proven recommendations.

4. How to write a job listing that attracts the right freelancer

Knowing who and what you need, and where to find them, is one thing. But how do you connect with them? Your best bet is to write a really strong job listing.

If your post is vague or lacks key details, you may find you're getting applications from candidates who don't have the qualifications or are simply unsuitable.

Make sure your job post stands out and draws in the best talent by following the key steps below.

Key elements of a strong job description

Your job posting should clearly outline what you need, who you're looking for and how you plan to work with them. Here's what to include:

What the project entails ("scope") and what you want to achieve ("objectives")

Freelancers need to understand exactly what you expect from them. Be specific about:

• the purpose of the project

• the tasks and deliverables involved

• any tools, software or platforms they will need to use

Example: Instead of saying "I need help with social media", say "I need a freelancer to create and schedule 12 Instagram posts each month, write engaging captions and respond to comments".

Skills and experience needed

Make it clear what qualifications or experience the ideal candidate should have. This helps you filter out applicants who aren't a good fit.

Specify:

• technical skills (such as graphic design, coding or copywriting)

• industry experience (like familiarity with e-commerce, finance or hospitality)

• examples of past work (for example, links to a portfolio or case studies)

Example: If you're hiring a web designer, say you need someone proficient in WordPress, Shopify or custom coding.

Timeline and expected deliverables

Most freelancers work with several clients at a time, so setting clear deadlines is essential. Include:

• a start date and how long you estimate the project will run for

• any milestones (if this applies)

• any time-sensitive deadlines

Example: "You should submit the first draft of the website homepage within two weeks, and complete final revisions within four weeks."

Payment terms and budget

Freelancers appreciate transparency when it comes to payment. If possible, provide the following information in the brief:

• Your budget range (i.e. is it an hourly rate or a fixed fee for the whole project?)

• The schedule for making payment (for example, an upfront deposit, milestone-based payments, or full payment on completion)

• Your preferred payment method (for example, PayPal, bank transfer, platform escrow).

Example: Instead of saying "Rate to be discussed", say "Budget is £500 to £700 for the full project, with a 30% deposit upfront and the rest on completion".

Mistakes to avoid

Even a well-intentioned job posting can go unnoticed if it has any of these common pitfalls:

• Vague descriptions: A lack of detail makes it hard for freelancers to assess whether they're a good fit.

• Unrealistic budgets: Underpaying for skilled work may attract low-quality freelancers or deter experienced professionals.

• Overly complicated wording: A long-winded post can be overwhelming, so keep it clear and structured.

• Lack of professionalism: Poor grammar, spelling errors or unclear instructions can make your posting look untrustworthy.

5. Evaluating and shortlisting freelancers

Once your job posting is live and you begin receiving applications, you'll need to assess and shortlist suitable candidates.

Choosing the right freelancer can make or break your project, so you must evaluate applicants carefully before making your decision. Here's how to do it.

Reviewing portfolios and past work

A freelancer's portfolio is often the best indicator of their skills and experience. When reviewing portfolios:

• look for work that fits what your project needs

• assess the quality, style and consistency of their past work

• check if they have experience in your industry

Example: If you're hiring a graphic designer for a rebranding project, look for case studies of businesses they've worked with, or examples of past work building a brand identity for another small business, rather than just general design samples.

Checking testimonials and ratings

Many freelance platforms allow clients to leave reviews and ratings, which can give you insight into a freelancer's reliability, professionalism and communication skills.

When checking these testimonials:

• look for feedback on communication, timeliness and quality of work

• pay attention when reviews mention certain strengths or weaknesses repeatedly

• be cautious if a freelancer has no reviews or a history of missing deadlines

If you're hiring outside a freelance marketplace, ask candidates directly for references or client testimonials.

Conducting initial interviews (questions to ask)

A short interview – via email, chat or video call – can help you assess whether a freelancer is the right fit for your business. SpareMyTime's Melissa Gauge has some advice:

"Request a discovery call with the freelancer. Be specific with your questions and ask about relevant experience.

"Don't forget to consider softer skills too: do their values align with yours, are they emotionally intelligent and do they have a positive attitude?"

Here are some useful questions to ask:

• Experience and expertise: "Have you worked on similar projects before? Can you share examples?"

• Work process: "How do you typically approach a project like this?"

• Availability: "What's your current workload and when can you start?"

• Communication: "How do you prefer to stay in touch (email, Slack, Trello, Zoom etc.)?"

• Problem-solving: "What do you do if you encounter an unexpected challenge during a project?"

A good freelancer should communicate clearly, show confidence in their skills and be proactive about solving your problems.

Running a test project

If you're not fully sure about a freelancer, a small paid test project can be a great way to assess their skills and working style before making a long-term commitment.

A test project should be:

• relevant to the actual work (for example, a small design task, a short blog post or a sample data entry job)

• paid (even if it's a small amount), as it's important to respect the freelancer's time

• clear in its scope and deadline

Example: Instead of hiring a social media manager for three months upfront, start with a one-week trial where they create and schedule a few posts.

6. Setting clear expectations and agreements

With your freelancer chosen, you can now begin to set expectations and lay out a formal agreement.

This makes sure that both you and the freelancer understand the project's scope, deadlines and payment terms, so there are no misunderstandings or disputes later on.

Melissa Gauge recommends being as specific about your requirements as possible. The more specific you are, the higher the chances that the freelancer will deliver what you want, how you want it.

"Don't make assumptions. Even if your freelancer is highly experienced, don't assume they'll know exactly how you like things done. Time taken explaining is time well spent."

Drafting a freelancer contract

You should always put together a written agreement, even if you're only hiring a freelancer for a short time.

A contract sets out clear terms, protects both parties and is your reference point if disputes arise.

Your freelancer contract should include the following:

• Scope of work: A detailed breakdown of the tasks, deliverables and expectations.

• Deadlines and milestones: Specific due dates and key "checkpoints" for progress.

• Payment terms: Rates you've agreed on, the schedule for payment and your preferred payment method.

• Revisions and edits: How many revisions are included in the contract before the freelancer can make extra charges.

• Confidentiality and ownership: Who owns the final work and whether the freelancer can showcase it in their portfolio.

• Termination clause: Conditions under which either party can end the contract.

If you're hiring through a freelance marketplace like Upwork or Fiverr, these platforms often have built-in contracts and payment protections.

If you're hiring independently, you may want to consult a simple freelance contract template (search for these online) or use online legal services.

Agreeing on a communication plan

Any successful freelancer relationship depends on effective communication. Setting clear expectations on how and when you'll communicate helps keep projects on track.

Melissa advises:

"It's so important to communicate. Schedule regular check-in sessions to understand your freelancer's progress, to refine deadlines and tasks and to provide feedback.

"Make sure your meetings are short and to the point. By communicating often and well, you'll be able to improve productivity."

Consider discussing the following:

• Preferred communication tools: Email, Slack, Trello, Asana or Zoom calls.

• How often you'll check in: Weekly updates? Daily stand-ups? End-of-project reports?

• Expected response times: How quickly should you expect a response (for example, within 24 hours)?

Example: For a freelance social media manager, you might agree to use Trello for content planning, Slack for quick questions and a weekly Zoom call for updates.

Understanding financial and legal considerations

If you're hiring a freelancer in the UK or Ireland, there are specific laws and regulations you must follow.

• Freelancers as independent contractors: Unlike employees, freelancers handle their own taxes and National Insurance contributions. You don't need to provide benefits or deduct PAYE tax, but you should confirm they're registered as self-employed.

• IR35 considerations (UK): If you're hiring a freelancer for long-term work, make sure their status falls outside IR35 regulations so they're not misclassified as an employee.

• VAT and invoices: Some freelancers charge VAT, so check whether this applies before agreeing on rates. Always request proper invoices for accounting purposes.

• Data protection and GDPR: If your freelancer handles customer data (for marketing or web development, for example), make sure they abide by GDPR rules for data protection.

If you're not sure about your legal responsibilities, consult an accountant or solicitor.

7. Managing a freelancer effectively

Hiring a freelancer is just the first step – managing them effectively makes sure that projects are completed on time, to a high standard and with as little friction as possible.

Unlike employees, freelancers work independently, often juggling a number of different clients. Establishing clear processes and plans for communication will help you get the best results.

How to provide clear instructions and feedback

One of the biggest mistakes small business owners make is assuming freelancers will "just know" what to do. Since they're not part of your daily operations, they need structured guidance.

Here are some tips:

• Be specific: Outline the goals for the project, your preferred working styles, and any considerations around branding, tone of voice and so on.

• Use examples: Share reference materials, templates or previous work to illustrate your expectations.

• Define priorities: If a project has several tasks, clarify what the freelancer should tackle first.

• Give feedback that can be put into action: Instead of making vague comments like "I don't like this", say "Could you adjust the colour palette to match our brand blue?"

Example: If you're hiring someone to write content for you, provide clear guidelines on tone, target audience, word count and formatting preferences.

Tracking progress without micromanaging

Freelancers value autonomy, so finding the right balance between oversight and trust is key.

• Set clear milestones: Break down large projects into smaller, trackable stages with review points.

• Schedule regular check-ins: A weekly email or short call can keep projects on track without constant monitoring.

• Use project management tools: Platforms like Trello, Asana or ClickUp help track progress without back-and-forth emails.

Example: For a web development project, set milestones like "Homepage design draft due by 10 March," rather than just giving a final date for delivery.

Building long-term relationships with reliable freelancers

When you find a freelancer who delivers high-quality work and communicates well, investing in a long-term partnership can benefit your business.

You can do this by:

• offering ongoing work – instead of hiring them for one-off tasks, consider a retainer agreement for continuous support

• recognising good work – positive feedback, testimonials and referrals encourage loyalty

• respecting their time – avoid making last-minute requests or setting unrealistic deadlines

A trusted freelancer who understands your brand can become a valuable extension of your team, saving you the hassle of retraining new staff.

8. Handling challenges when hiring a freelancer

Even with careful hiring and clear agreements in place, it's still possible that challenges arise when you're working with freelancers.

Whether it's a missed deadline, a communication issue or a mismatch in expectations, handling these situations professionally is crucial to maintaining a productive work relationship.

Here's how to navigate some of the most common challenges.

What to do if a freelancer isn't meeting expectations

If the work your freelancer delivers doesn't meet the standards you agreed on, start by assessing the situation:

• Revisit the original agreement: Check the job description, contract and any prior communication to make sure your expectations were clear.

• Communicate concerns early: Provide specific feedback and give the freelancer an opportunity to improve.

• Identify possible roadblocks: Are they struggling due to unclear instructions, a lack of resources or unrealistic deadlines?

Example: Instead of saying "This isn't what I wanted", say "The design needs to be more modern and in line with our brand. Can you adjust the colour scheme to match our website?"

If you're still encountering issues after providing several rounds of feedback, consider discussing an exit strategy or reducing the scope of the project.

Navigating missed deadlines or communication breakdowns

Delays and communication issues can be frustrating, but they're not always deal-breakers. Here's how to address them:

• Check in politely: A simple message like "Just checking in on the status of the project. Let me know if you need anything from my side." can help.

• Ask about challenges: If you're not getting much of a response from the freelancer, they may be overwhelmed. Offer them some flexibility (if appropriate) but set a clear deadline.

• Set new expectations: If delays are unavoidable, agree on a new timeline and record it in your agreement.

If a freelancer repeatedly misses deadlines or disappears without explanation, it may be best to end the contract and find an alternative.

How to end a freelancer contract professionally

If the project isn't working out, ending a contract professionally ensures there are no hard feelings and keeps your reputation intact.

• Refer to your contract: If the freelancer isn't meeting deadlines or your expectations for the quality of work, make sure you follow the termination clause (see step 6).

• Provide constructive feedback: Keep it professional: "Unfortunately, this project isn't progressing as we'd hoped. We appreciate your effort, but we've decided to go in another direction."

• Make any outstanding payments: Pay for agreed-upon work that the freelancer has completed, even if the overall project didn't work out.

• Leave honest but fair reviews: If you recruited the freelancer through a freelance marketplace, your review can help other businesses while also acknowledging the freelancer's strengths.

If you've had a generally positive experience but need to end the project, consider keeping the door open for future work on different terms.

Final thoughts

Hiring a freelancer can benefit your small business in so many ways.

By understanding your needs, crafting a strong job posting and carefully evaluating candidates, you increase the chances of finding the right freelancer.

Next steps

If you're still unsure, start with a small, low-risk project to test the process. For example, you could:

• hire a freelancer to design one social media post before committing to a long-term content plan

• work with a virtual assistant for five hours per week before increasing their workload

• engage a writer for a single blog post before commissioning ongoing content

This allows you to gain experience in working with freelancers without making a large investment upfront.

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