Things it's perfectly reasonable to ask a freelancer – from someone who's been on both sides of the table

Commissioning a freelancer can be a significant investment, particularly for a smaller charity. Nicola Upton, who has experience both commissioning freelance support and working as a freelancer herself, shares some practical advice on the questions it's reasonable to ask, and how to get the relationship off to a good start.

I've commissioned freelancers as a charity CEO and senior leader, and these days I am among the Blume freelancer community. I've experienced both sides of the relationship, including some of the uncertainties that can come with it.

For charities, bringing in a freelancer can mean trusting them with sensitive information, important relationships or a project that really matters, trustees or beneficiaries, plus a significant financial investment. If you don't commission freelance support regularly, it isn't always obvious what you should ask before committing.
I've learnt lessons on both sides of the table, including making a few manageable but avoidable mistakes. So here are some things I think it's perfectly reasonable to ask a freelancer before you commit.

Is a freelancer actually the right solution?

Before we start, consider this question! Sometimes an external specialist is exactly what's needed: expertise you don't have internally, additional capacity or an independent perspective.
Sometimes, though, you haven't yet worked out what you need. You might know there's a problem with a service, without knowing whether you need a review, a new delivery model or additional management capacity.
It's reasonable to discuss whether a freelancer's expertise is a good fit, but there's a difference between discussing a potential commission and expecting substantial consultancy for free.
One option is to commission a day or two of ‘discovery’ work to help you understand the problem, explore possible approaches and develop a clearer brief. I love helping people refine their thinking about what they need. Oftentimes this leads to a longer project, sometimes it doesn’t – and that’s fine too!
Have you done anything like this before?
It's reasonable to ask about relevant experience and examples of previous work, although some will understandably be confidential.
I wouldn’t look for someone who has delivered an identical project, as every project and charity is unique in some ways. What's important is whether they can demonstrate that they understand your challenge and have the skills and experience to help.
Can I speak to someone you've worked with?
Testimonials are useful, but they're selected to showcase positive feedback! A conversation with a previous client, ideally by phone, can tell you more about what someone's like to work with.
Were they reliable? Did they communicate well? How did they respond when something unexpected happened? Would the client work with them again?
Be considerate about when you ask for references. suggest doing this once you've made an offer, (subject to references, of course!).
How would you approach this work?
You don't necessarily need a lengthy written proposal, but you do need confidence that the freelancer understands what you're trying to achieve and has thought about how to get there.
Ask them to explain their proposed approach, the key stages and what they expect to deliver. Be open-minded – they may have ideas that could improve on your original brief. A good freelancer should be able to explain their approach and the thinking behind it in language you understand.
There's a difference between asking someone to outline how they'd approach a project and asking them to make initial recommendations or complete a task. The latter is a good way to put freelancers off working with you as it feels like what it is – asking them to work for free.
What do you need from us to make this work?
This is one of the most important questions, and one that's surprisingly easy to overlook.
A freelancer may need access to staff, trustees, beneficiaries, financial information or other data, alongside someone who can make decisions and provide timely feedback.
Ask the freelancer what they're assuming your organisation will contribute and be realistic about whether and in what timeframe you can deliver it.
What exactly are we paying for?
Make sure you understand what's included in the price, and what isn't. Being clear about costs for travel and expenses, number of rounds of edits, presentation of findings from the start.
Your freelancer should be able to explain their recommended approach to using the time you are buying, including what they’ll do if it becomes clear more (or less!) time is needed.
Agree payment terms at the outset, including when invoices will be submitted and paid. Please pay on time too, late payments cause a lot of avoidable hassle. Get all your finance stuff set up as soon as you appoint. 
What happens if things change?
Projects rarely unfold exactly as expected. New information emerges, priorities shift, people leave or a piece of work turns out to be more complicated than anyone anticipated.
Ask how the freelancer would handle changes to the brief, additional work or delays outside their control. Agree how you'll discuss these changes before expectations, timescales or costs start to drift.
What safeguards are in place?
Depending on the work, think about insurance, confidentiality, and intellectual property. Consider your own responsibilities too, particularly with data and safeguarding. A desk-based research project will have different requirements from someone working directly with vulnerable people.
Most freelancers have their own contract. Read it carefully and discuss anything you feel might be missing. My contract is stronger now thanks to questions from early clients.
Who will actually be doing the work?
If you're commissioning through an agency or group of associates, ask who will deliver the project, what their experience is, and ask to meet them. If you’re talking to a sole trader, ask them if they ever bring in associates and how that works.
There's nothing wrong with a team approach, but you should understand what you're buying.
 Freelancer contracts usually have a clause about providing a ‘substitute’ if they can’t do the work. These clauses can be relevant to employment status and IR35 considerations, although the contractual wording alone doesn't determine status. Ask if you're unsure what it means in practice (and check in with your own HR resource too).
And finally, remember it's a two-way relationship
As a client, you're entitled to ask searching questions. You're deciding whether to trust someone with your organisation's money, people, information and other precious and/or difficult stuff.
The freelancer is also deciding whether they can work effectively with you. They need confidence that expectations, budgets and timescales are realistic, and that they'll have the support they need.
I've experienced situations where apparently clear assumptions turned out to be quite different on each side. Better to discover that before starting than three weeks into a project.
There is, of course, a balance. Sensible due diligence is important. Asking someone to complete a lengthy application form, write a 3,000-word proposal, deliver a presentation and attend three interviews for a five-day project probably isn't proportionate.
Good commissioning isn't about the most demanding selection process. It's about asking the right questions, agreeing expectations and building a productive working relationship.
Commissioning a freelancer can be a significant investment, particularly for a smaller charity. Nicola Upton, who has experience both commissioning freelance support and working as a freelancer herself, shares some practical advice on the questions it's reasonable to ask, and how to get the relationship off to a good start.
I've commissioned freelancers as a charity CEO and senior leader, and these days I am among the Blume freelancer community. I've experienced both sides of the relationship, including some of the uncertainties that can come with it.
For charities, bringing in a freelancer can mean trusting them with sensitive information, important relationships or a project that really matters, trustees or beneficiaries, plus a significant financial investment. If you don't commission freelance support regularly, it isn't always obvious what you should ask before committing.
I've learnt lessons on both sides of the table, including making a few manageable but avoidable mistakes. So here are some things I think it's perfectly reasonable to ask a freelancer before you commit.
Is a freelancer actually the right solution?
Before we start, consider this question! Sometimes an external specialist is exactly what's needed: expertise you don't have internally, additional capacity or an independent perspective.
Sometimes, though, you haven't yet worked out what you need. You might know there's a problem with a service, without knowing whether you need a review, a new delivery model or additional management capacity.
It's reasonable to discuss whether a freelancer's expertise is a good fit, but there's a difference between discussing a potential commission and expecting substantial consultancy for free.
One option is to commission a day or two of ‘discovery’ work to help you understand the problem, explore possible approaches and develop a clearer brief. I love helping people refine their thinking about what they need. Oftentimes this leads to a longer project, sometimes it doesn’t – and that’s fine too!
Have you done anything like this before?
It's reasonable to ask about relevant experience and examples of previous work, although some will understandably be confidential.
I wouldn’t look for someone who has delivered an identical project, as every project and charity is unique in some ways. What's important is whether they can demonstrate that they understand your challenge and have the skills and experience to help.
Can I speak to someone you've worked with?
Testimonials are useful, but they're selected to showcase positive feedback! A conversation with a previous client, ideally by phone, can tell you more about what someone's like to work with.
Were they reliable? Did they communicate well? How did they respond when something unexpected happened? Would the client work with them again?
Be considerate about when you ask for references. suggest doing this once you've made an offer, (subject to references, of course!).
How would you approach this work?
You don't necessarily need a lengthy written proposal, but you do need confidence that the freelancer understands what you're trying to achieve and has thought about how to get there.
Ask them to explain their proposed approach, the key stages and what they expect to deliver. Be open-minded – they may have ideas that could improve on your original brief. A good freelancer should be able to explain their approach and the thinking behind it in language you understand.
There's a difference between asking someone to outline how they'd approach a project and asking them to make initial recommendations or complete a task. The latter is a good way to put freelancers off working with you as it feels like what it is – asking them to work for free.
What do you need from us to make this work?
This is one of the most important questions, and one that's surprisingly easy to overlook.
A freelancer may need access to staff, trustees, beneficiaries, financial information or other data, alongside someone who can make decisions and provide timely feedback.
Ask the freelancer what they're assuming your organisation will contribute and be realistic about whether and in what timeframe you can deliver it.
What exactly are we paying for?
Make sure you understand what's included in the price, and what isn't. Being clear about costs for travel and expenses, number of rounds of edits, presentation of findings from the start.
Your freelancer should be able to explain their recommended approach to using the time you are buying, including what they’ll do if it becomes clear more (or less!) time is needed.
Agree payment terms at the outset, including when invoices will be submitted and paid. Please pay on time too, late payments cause a lot of avoidable hassle. Get all your finance stuff set up as soon as you appoint. 
What happens if things change?
Projects rarely unfold exactly as expected. New information emerges, priorities shift, people leave or a piece of work turns out to be more complicated than anyone anticipated.
Ask how the freelancer would handle changes to the brief, additional work or delays outside their control. Agree how you'll discuss these changes before expectations, timescales or costs start to drift.
What safeguards are in place?
Depending on the work, think about insurance, confidentiality, and intellectual property. Consider your own responsibilities too, particularly with data and safeguarding. A desk-based research project will have different requirements from someone working directly with vulnerable people.
Most freelancers have their own contract. Read it carefully and discuss anything you feel might be missing. My contract is stronger now thanks to questions from early clients.
Who will actually be doing the work?
If you're commissioning through an agency or group of associates, ask who will deliver the project, what their experience is, and ask to meet them. If you’re talking to a sole trader, ask them if they ever bring in associates and how that works.
There's nothing wrong with a team approach, but you should understand what you're buying.
 Freelancer contracts usually have a clause about providing a ‘substitute’ if they can’t do the work. These clauses can be relevant to employment status and IR35 considerations, although the contractual wording alone doesn't determine status. Ask if you're unsure what it means in practice (and check in with your own HR resource too).
And finally, remember it's a two-way relationship
As a client, you're entitled to ask searching questions. You're deciding whether to trust someone with your organisation's money, people, information and other precious and/or difficult stuff.
The freelancer is also deciding whether they can work effectively with you. They need confidence that expectations, budgets and timescales are realistic, and that they'll have the support they need.
I've experienced situations where apparently clear assumptions turned out to be quite different on each side. Better to discover that before starting than three weeks into a project.
There is, of course, a balance. Sensible due diligence is important. Asking someone to complete a lengthy application form, write a 3,000-word proposal, deliver a presentation and attend three interviews for a five-day project probably isn't proportionate.
Good commissioning isn't about the most demanding selection process. It's about asking the right questions, agreeing expectations and building a productive working relationship.