Questions Every Freelancer Must Ask A Potential Collaborator

We adhere to strict standards of editorial integrity. Please be aware that some (or all) products and services linked in this article are from our sponsors. Disclaimer

The best way to work with someone is when you know what motivates them. Too often, companies and HR departments assume that is money. While many studies have debunked that, citing things like time off and flexible work conditions as more important than a salary bump, those features refer to employee engagement and retention. These are fundamentally surface-level things that will keep someone working hard and keep them around long enough to get value from your salary investment.

I prefer to go a bit deeper than surface level motivation. To get there requires a comfort with asking blunt questions on your side and some self-awareness on the candidate’s side. The result, though, can be magical: an intrinsically motivated team that needs guidance, not a carrot, to do their work and do it well.

In my experience interviewing a couple hundred candidates myself and dozens of HR professionals who have decades of experience interviewing thousands of candidates between them, I’ve discovered the three questions that, when asked in the right order and with the right words, help bring to light:

  1. A candidate’s self-awareness
  2. What intrinsically motivates them
  3. Win-win external motivation levers

Question 1: Where does this job fit in your career path?

Question 1: Where does this job fit in your career path?

Asking this question makes a few things really clear. For one, you show awareness that you don’t expect the candidate to stay at your company for the rest of their career. The second thing is that you give the candidate the opportunity to be up-front, honest, and genuine. It’s a great opportunity to learn more about them as a person.

How to ask

This one doesn’t need much sugar coating or changing. The only advice is to say it in the way you say it, “um’s” and “ah’s” included. Speak naturally when you ask this one – otherwise it may seem scripted and the candidate will be less likely to be honest.

When to ask

This can be added at almost any point during the interview, except perhaps not as the first question. It can be fairly raw and personal, depending on the person’s story and journey, so coming out of the gate with this question may put people off (and you won’t get the insight you’re looking for).

Question 2: What are you good at?

Question 2: What are you good at?

It’s a fairly blunt question, especially in the context of a job interview where you’re literally assessing if they would be good for your role and company.

But here’s the difference: this question is about them and about how they see themselves. It’s also very direct and thus difficult to misunderstand.

How to ask question 2

If you’re uncomfortable asking the question so directly or feel you may alienate the candidate, explain the context a bit more. For example:

“Either in the context of this job or more high level in your life and experience, what are you good at? I don’t ask to make you defend yourself, I genuinely want to know something you know you are good at.”

However, the question must remain blunt as that will show you someone’s self-awareness and, to some extent, their self confidence. Asking the question this way all but requires the candidate to stand up for themself. You’ll quickly uncover if they are someone who gets defensive when they perceive they are being questioned. You may also learn something about them that you didn’t know before.

When to ask

Ask this question about half way through the interview or conversation. It’s usually brought up when there’s a conversation about the company as a whole or the more holistic view of the job. That way, you don’t ask it with the implication that they have to respond with job-specific skills.

Question 3: What do you want? (Because that’s not always the same thing as what you are good at)

Question 3: What do you want? (Because that’s not always the same thing as what you are good at)

We’re all good at things we hate doing. In a job interview, people are more likely to highlight what they are good at – i.e. their marketable and valuable skills – to get hired, often regardless of if they actually like the task.

This question differentiates between a skill they possess and a skill they want to develop or use.

Of course, you’re going to need some overlap here for the fit to work. For example, if you are hiring a coder that is great at coding but hates it, you’ll likely have an engagement and retention problem on your hands. But this question also opens the door for the candidate to talk a bit more about their hopes, dreams, and aspirations.

That candidate may love coding now but see themselves moving into marketing later on – something that can help with motivation, additional projects, and performance management if they join your organization.

Ideally, this question uncovers if they actually enjoy doing the thing you would be hiring them for or if there’s something else they may be more suited to. It also shows that you care about their wants and needs, not just their ability to be a resource for the company.

How to ask question 3

Kindly and with curiosity. This is about what this person wants out of life, after all. Treat it with the care and thoughtfulness you want them to show you in their answer.

When to ask

I typically ask this as a direct follow up to “what are you good at?”. I also often add some version of “sometimes those aren’t the same thing, so I wanted to ask the two questions.”

In many cases the person will reiterate what they are good at as the thing they want. There’s no harm in wanting something you are good at. But it opens the door for a more in-depth conversation.

Question 4: What’s your selfish reason for being here? (or applying to this job, or wanting to join this company, etc.)

Question 4: What’s your selfish reason for being here? (or applying to this job, or wanting to join this company, etc.)

We all have motivations in our lives that are outside or not part of our direct job description. Not only is this ok, it’s simply a fact of life.

When I used to ask this question, I’d use an indirect path, asking about their life goals or other lofty, more positive sounding words – the word ‘selfish’ has a bad reputation. But it shouldn’t, and this question calls that out immediately.

I once had a candidate respond to this question incredibly bluntly. They said they were applying to my organization because we had a good brand and they wanted to pad their resume as a jumping-off point for their career. They saw themselves working for 1-2 years and then moving on, either up in the organization or out to another.

That person ended up doing a wonderful job with the organization for 2 years. They had the skills necessary and the role they applied for typically had a 1-2 year tenure, so their ‘selfish reason’ actually aligned perfectly; I knew this person would be motivated to hit targets and get success because that would raise their personal brand. Further, they weren’t planning on sticking around, so I knew there was motivation to get impact quickly for their ‘selfish’ goals.

By acknowledging that it’s ok to have a ‘selfish’ reason for wanting something, you get a much closer relationship with the person who shares that with you. Not only do you know a bit more about their motivations, you can use that to learn more about their background. It also helps assess suitability for the role and company, since if they want something you have no means of providing, they may not stick around long.

How to ask question 4

I often follow this question up with some form of “this question isn’t about making a decision to hire you, but instead knowing where you’re aiming to go so we can best empower you or provide what we can.”

When to ask

This, for, me, comes near the end of the interview. Potentially even after you’ve given them the offer, if you’re worried that asking during the interview will taint the process and leave the candidate with the impression you’re judging them.

Asking it up front may put the person on the defensive or think that I am judging their candidacy based on external factors. On the contrary, this is for me to decide how I can help them if we end up working together.

Turning the questions inward

If you don’t have a team or aren’t planning to hire for your business, try asking these questions honestly of yourself (or ask someone to “interview” you for the role you already have – CEO). You may learn a lot more about why you love or hate certain tasks, since you can look at them through the lens of what you’re good at, what you want, and what your selfish reasons for working are.

Regardless of the person answering these questions – whether a candidate or yourself – be genuine in asking them so you have the best chance of getting genuine answers.

More great stories from PulseBlueprint

  • The three things this founder looks for in top talent


* indicates required


Photo courtesy Sarah Pflug from Burst