Questions to ask on a new job search

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During my search for a new role, I kept a list of questions to use during the process. In case they're useful to me in the future (or anyone else for that matter!), I wanted to write a post with the key ones.

The questions that I ask tend to be split into a few key areas: about the role and what people expect, about the company more broadly, the culture, and then practical specifics.

I tend to ask most of these on an initial call to see whether it’s worth us both taking this any further, but I also like asking people at different stages of the process the same (more opinion-based) questions to hear answers from different levels of seniority, tenure, and role focus.

👩🏻‍💻 The role and expectations

What does this job entail?

I don’t tend to get on a call unless I’ve seen a job spec and think we have something to talk about, but in the case that you haven’t for whatever reason (maybe they’re creating a job for you), it’s vital to talk this through! An interesting way to do this is ask someone who does the job what their day/week/month looks like.

What’s driving the hire?

If there was someone else in the role previously, why didn’t it work out?

What are the biggest challenges?

It’s good to get a sense of both challenges the business is facing, and challenges that you’re likely to face should you come in. I find this a really important part of the conversation, as it helps me to understand what I can bring.

I specifically tend to follow up with “and what are the biggest engineering | people | process challenges you’re facing” to understand key areas that haven’t been mentioned.

What scope is there to do x, y, z?

If there are particular things that you want to do to further your career, is this a match? Some examples may be working with a particular technology, being mentored by someone you admire, managing managers, etc.

How/when/why would you consider hiring me to be successful?

Specifics around this will likely be set once you start, but it can again help to know what they think is most pressing around the hire, and what good looks like.

What does progression from here look like?

Getting a view of where you could go next, and the associated timescales can help you see not only whether this job fits you for right now, but also whether it’ll work for you in the future.

What’s the biggest mistake I could make?

I love asking this to people at varying stages of the process. It usually gives the interviewer pause for thought, and I’ve had some really interesting insight as a result of this!

💼 The wider business

Can you tell me a bit about the company?

Again, it’s likely that you know enough to be speaking to someone, but if not it’s good to hear about the work that they do, the size, locations, and what their plans are for the future.

What about the culture?

Everyone will answer this by telling you how amazing it is to work there! Try to get a feel for the vision, mission, and values.

How does diversity, equity, and inclusion play into this?

Again, everyone will say that it’s important to them. Ask for specific examples - do they have a report they can share? Is the leadership team diverse? Can they give an example of changes made to make the workplace more inclusive? What would be the makeup of the team that you’re working in?

What’s the most exciting thing on the company horizon?

You may not get a fully honest answer here (new un-announced products, etc), but it’s a chance to see how excitedly people speak, and get a sense of what you may be working towards.

What’s been the impact of COVID-19 on company finances/strategy?

Hopefully not one to ask forever, but if you’re coming into a new role right now it’s important to know exactly what you’re getting yourself into. Have there been redundancies? Are any considered? Is the company on track to meet targets? At a very early stage you’re extremely unlikely to get the full picture, but try to get a feel for how comfortable the people are talking about this.

What are the best and worst things about working here?

An oldie, but a goodie. Make sure they answer both sides!

📅 Day to day

What’s the size/structure of the team I’d be around/have reporting to me?

Pretty straightforward. You want to get a quick feel for the size and shape of teams, how everything is set up, and where you fit into it.

Which other people would I work most closely with?

Similar to the above, but maybe thinking about other disciplines - e.g. how engineering works with product, design, or user research, or how you’d interact with senior management or the board.

What technologies/tools would I work with?

You can either go broad here to understand the full company tech stack, or narrow to hear about what specifically this role would work with, down to the nitty-gritty if you so desire. However, try to keep and open mind - interviewers are never keen if you jump in and judge their approaches without knowing the full story!

What could I do that would make your life easier?

This is one that will vary depending on who you’re speaking to. It’s often useful to hear what’s at the forefront of their mind, and to get a stronger picture of specific working dynamics. Outside of what the company wants from this hire, you may find some nice extra personal insights by asking this.

💸 The practical bits

What salary are you offering for this role?

Ok, so here’s the question it’s all been boiling down to. Very often on an initial call the interviewer will want to check that you’re not wildly out of their range, and vice versa. However, for many people, talking about money is hard. Here’s how I tend to approach this topic:

If you’re asked what your current salary is, never disclose it. There are tons of reason for this, not least that the situation at your old company is not the same as the new one, and you could be hugely underpaid.

A better question to be asked is “what are your salary expectations for this role?”, however this too is liable to ‘anchor’ you unnecessarily.

If you’re asked either of these questions, how you answer will depend on the relationship to the interviewer, and the situation. For example, I recently interviewed with someone who was extremely familiar with my previous work pay structure and situation, and so I was able to talk about specifics. In other situations you may choose to disclose absolutely nothing. Here’s how I tend to approach it:

👩🏽: “To make sure we’re not a million miles away, what are your salary expectations?"

👱🏽‍♀️: “If it’s ok, I’d instead prefer for you to tell me a bit about your pay structure and levels, and where you see this role fitting into that? I’d be happy to confirm whether that sounds about right."

Hopefully this business works with a transparent structure which is intended to support pay equality. They may be able to talk you through a progression framework or similar. It’s likely that there will be a range (e.g. someone hiring for an engineer is likely to have higher salaries for a more senior engineer), but if nothing else they should at least have a budget in mind.

However! Some businesses won’t answer this. Maybe they’re a small start-up and haven’t got any structure. Maybe they’re like one large corp I spoke to, where it’s all a matter of what you negotiate (😒). If they refuse to answer and press you, you can answer, or if you still feel that it’s detrimental to answer you can push back. Personally, in some situations I’ve shared similar to this:

👱🏽‍♀️: “I’m really not trying to be a pain, but I’d rather not give you a specific figure at this point. I’d love to understand how else I may be able to give you the information you need? For example, if you’re able to give me some hypothetical salaries that you could offer and what that would entail, I’ll be able to let you know whether I’m likely to accept an offer at that level. As we don’t yet know much about each other I’d hate to anchor myself to an arbitrary number before we’ve really explored everything I can bring to this role, and everything that you’re hoping for. This is something that’s really important to me - it’s pretty well known that this question can put people (especially from more marginalised groups) at risk of undervaluing themselves, so I try to see if we can tackle it in another way. I hope you can understand."

Your mileage may vary with the last part, but personally I like to explain why I’m sticking to my guns. Stay polite, try to explain that you’re not trying to be awkward for the sake of it, and appeal to their human side. How a company deals with this interaction can also tell you a lot about their culture and values.

Finally, if this is an initial call, this is not the time to quibble over specifics! If they quote you £30k but you’re really after £35k, leave that til the offer stage. If they quote £30k when you’re after £130k… this probably is the time to bow out gracefully.

Additional package/benefits

The salary that you’ve just spoken about could be a base salary, or it could be topped up with a bonus. Make sure to understand exactly how this works. Some companies may also offer equity, commission, or other structures around your core pay.

Ideally ask the person about all of the other benefits that they offer, and get them to run through everything rather than picking out individual topics. Perhaps you have a medical condition and are wanting to hear about insurance. Maybe you’re planning on having a child, and wanting to know about parental leave. As illegal as it is, at best case bias could come into play if you disclose something they don’t want to hear, and at worst they may flat out discriminate against you regardless of the law.

How do you approach distributed working, and is there scope for this?

Speaking of which, I recently spoke to someone who asked me about how to approach asking to work from home because it’s better for their disability. My answer: only disclose as much as you feel is relevant for them to know for the role.

I don’t live near… anywhere, and so it’s extremely important for me to know up front whether roles are expected to be based fully in an office, or whether I’m able to work from home at least some of the time. The way that I’ve approached this before is to say:

“I’m very happy to come into London at points, but ideally this would be around X day(s) a week or similar. I’ve primarily been looking at roles that are mostly remote, because I find that it makes a big difference to my productivity, health and happiness."

This applies to people who just hate being stuck on trains as much as it does for someone who struggles to walk for long distances, or be around a noisy office. Again, it’s giving some context, whilst not being difficult or demanding.

The other half of this point is to hear how well set up the company is, even if they’re happy for you to work remotely. Maybe the entire company is globally distributed, and this is baked into everything. Or maybe you’d be the only person not in the office, with absolutely no existing thought to making this work well.

What timescales are you hoping for?

Knowing how flexible the timings can be can help you know how to play your next move. Think about how this answer compares to your notice period, saved cash buffer, or time off you need to recharge between roles. Most people will again say “as soon as possible!", so instead you may want to ask something like “when does this role become a problem if you haven’t got someone in?".


Pretty straightforward, but asking about things like paid holiday, scope for unpaid holiday, and whether it’s mandatory to take UK bank holidays (some companies allow people to move these to more meaningful individual dates if they don’t celebrate the bank holiday events) are all good to ask about.

Job title

Probably not one for an early-stage conversation, but if job titles matter to you (and I personally believe they do), it may be worth asking whether there’s scope to change it if something doesn’t feel right. Maybe you can bring more seniority, or are concerned about how it would look on your CV. It’s worth being up-front and asking if there’s any flex if this is something that’s holding you back.

Give yourself an extra shot

Is there anything I’ve said today that makes you hesitate?

This is a really tough question to ask as it can leave you very vulnerable, and also puts the interviewer(s) on the spot. You may not get a fully truthful answer at this point, which is fine. However, just in case, it does give the interviewer a chance to get extra signal on anything that’s making them more concerned, and it gives you the chance to address it immediately if you’ve made any unintentional mis-steps!

Follow up with what’s next

Make sure that you wrap up by understanding what the process looks like, establishing whether there are any specific expectations on both sides, and setting out what will happen next.

If you’re going through a job search at the moment I hope these questions help a little bit. Good luck, and let me know if they help you get to where you want to be!

Thanks to Jess Bailey on Unsplash for the header photo