10 questions to ask a contractor before hiring them

As far as skills assessment is concerned, one of the most crucial stages in the hiring cycle is the interview.

For end-clients, interviews provide the opportunity to learn more about a contractor's experience and capabilities, beyond their CV and LinkedIn profile. But interviews also let the interviewer dig deeper into the contractor’s personality. Yikes! 

Top 10 interview questions for contractor candidates

So here, exclusively for ContractorUK, we present 10 questions clients should ask a contractor before hiring them, writes Adrian Smith, senior director of operations at Randstad.

And as an engager, your eleventh question -- should you choose to add one of your own, must be like these featured 10. That is; designed to help evaluate if the contractor is going to be a good fit, for the assignment/project, for the line-manager/decision-maker, and for the department/organisation at large.


Here, engagers check the candidate has the right skill and experience level to carry out the role -- but also probe whether the contractor has a genuine interest to perform the contract’s requirements.

1. Which aspects of this assignment do you think you would find most interesting/ enjoyable?  

This is sort of the contractor version of the age-old permie-focussed probe ‘Why do you want to work here?’

It’s a good way for engagers to check that the contractor fully understands the contract’s requirements/milestones. Despite being different to the more in-depth probe permie applicants face at this initial stage, it is natural for engagers to see if the contractor has taken time to look into the organisation/project. 

2. After your last big assignment, what did your manager say was your biggest strength?  

Freelance and temporary professionals should know their strengths, but this question should help decision-makers find out more about how competent a candidate is -- and whether they have other ‘soft skills.’

If Joe Contractor goes in all guns blazing with strengths that aren’t related to the specifications of the assignment, we recommend engagers pause. Oh, and watch out for cliched, vacuous answers!

3. What do you think your key areas to achieve better execution/delivery were?  

This is a slightly different spin on the age-old permie question, ‘What are your greatest weaknesses?’

So despite being on the independent market, contractors should still be prepared for this sort of enquiry into their past performance. Perhaps even assume it’s coming and will be asked of you! Engagers, you will want to see if an honest-sounding answer is forthcoming.

Is the candidate self-aware? Is the weakness disclosed solvable? 

As interviewers, we look for indications that the interviewee is aware of their shortcomings, but is eager to develop and expand their skill-set.

Someone who is conscientious could make a better hire than someone who is technically competent but lacks motivation, or regards themselves as the finished article. You could also ask, as an interviewer before hiring a contractor, ‘Which parts of the contract / project do you think will challenge you most, and why?’


Relationships between client/line managers and contractors are a critical part of the overall health, efficiency and productivity of the client’s organisation. 

While managers and leaders need to be adaptable and capable of working with a diverse workforce, ultimately managers and their contractors need to be compatible -- certainly in terms of values and expectations. Contrary to what you might think, the best contractors do fit in – it’s less and less a case of having the advertised skills for the three months of your assignment and then just leaving!

4. Who was the best manager you ever had on an assignment and why did you enjoy working with them?

5. Can you tell me about a time when you found it difficult working with a particular line-manager/supervisor? What, specifically, did you dislike about their approach and how did you handle this situation?

By asking questions (4) and (5) engagers can analyse the contractor's responses in the context of common management styles used in organisations. 

This is particularly important if the person with whom this contractor could be working - whether that's you as interviewer or someone else -- has a very particular approach to management, or a unique way of communicating and motivating their team.


The final questions below will help you (the end-client) judge the contractor’s suitability for your work environment, existing perm staff, and organisation’s values. 

Are they motivated by the working environment offered by your organisation? 

Do they demonstrate the ability to work well with the others?

6. Which of your past projects did you most enjoy working for and why?

7. Can you tell me about a time when you were part of a highly successful team?  

8. What was the key to that team's success?

9. What do you know about our company/organisation?

Key indicators to look out for in the answers to the above include common uses of 'we', 'us' and 'our', rather than 'I', 'me' and 'mine', which you could take as a sign that this person is a natural team player. 

It's also worth remembering that workplace conflicts and disagreements are inevitable, and the most important thing to focus on is the contractor’s ability to manage these situations when they occur.


10. Do you have any questions?  

This isn’t admin. Are they interested in unprofessional stuff? Do they care enough to turn up, or get the code in on time? 

No questions at all from Joe Contractor?! Okay, are you really sure that this contractor is in the least bit excited about the project?! Next…

Monday 1st Aug 2022
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Written by Adrian Smith

Adrian Smith is the senior director of operations for recruiter Randstad UK. He has worked for Randstad since 2002 when he joined as a consultant. Educated at Loughborough and the Sorbonne, he enjoys rugby, sailing, and winter sports.


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