Career interview questions

Tech job descriptions are the professional version of a tween “dream boyfriend” checklist. 🙊

It’s normally a lot of bullet points, some of them likely much more meaningful than others. Learning what really matters in a partner new hire is hard. Articulating it is even harder.

The problem is all candidates have to go on for quite a while is the job description. There’s room for negotiation somewhere.1 As a candidate, I always have questions to ask - there’s a lot to find out. After a conversation at a local meetup2 with some university students looking for internships and first jobs, I promised to share my list of questions to determine if I really want that job. The goal of these questions is figuring out what’s not in the job description, what should be there, and how much you’ll like this new place.


My favorite questions

We usually don’t have a ton of time for this chat, so these are what I’ve found to be the most impactful questions.

What are you looking for in the perfect person to fill this role that isn’t in the req?

Going back to that whole idea of lists that have many “must haves” that probably aren’t “must haves”, there’s probably a lot they still left off. This question gets at what’s really important. Some of the more enlightening answers I’ve received:

  • “Can do” attitude - This ended up being extremely true. My move from engineering into a sales engineer role was full of things that I used to say “not my job” to. There’s a lot less of that in roles where getting things done (if not perfectly) is pressing.
  • Cross-functional team experience - I’ve received this one a few times, all for senior and above roles.3 It’s been important in every job I’ve had since leaving college, though. Learning to influence without authority, communicate with other teams to move a project forward, and manage expectations are valuable. It’s handy to have a good story to tell on any of these skills.
  • A tech that’s immediately pressing - This will yield follow up questions to understand what’s important to the team and more importantly, why? If the role is for a front-end developer, but they REALLY need in-depth SQL database operations expertise from this person, there’s a lot to discover in a short amount of time as to why this role at this time.

What’s the last cool thing you built at work?

If recruiting gives any names, definitely look them all up! As a candidate, I’ve at least browsed your blog, LinkedIn, GitHub, etc. to ask you things based on what I’ve found. Sometimes, a good story that comes from this question and if not, it’s something to pull on a bit to discover more about the company and/or role. Good follow ups to this include:

  • What was the impact of the thing you built?
  • Why’d you make some of the choices you did?
  • Why aren’t you building things?
  • Who’d you work with on it?

The thing built doesn’t have to be technical. It could be building a team, a strategy, a policy or process, or a product roadmap. I’m trying to figure out how the place works, not critique your code.

Do you have any concerns or hesitations about my fit for this role?

Indirectly asking for direct constructive feedback works well. Try to work this into the conversation as best as possible. The folks in the interview loop have likely been trained to not give this information when asked directly for feedback. Some fantastic answers from loops that ended with an offer:

  • “The skills that made you successful at old job will not be the skills that make you successful here.” This is true in every new job. Use this to explore more by asking “what do you mean here?”.
  • “Great DIB4 and federal experience, but no SLED5 experience.” This is a fabulous example of specific concerns on prior experience and how that maps to the role - exactly what we’re wanting here.
  • “We don’t see you being successful at this company at this time/role.” Great feedback, use it to ask if it’s expectations, levels, needs of the company or move on.
  • “I see what you did there and I appreciate the social engineering.” It’s okay to be called out on doing this! An ability to chat with people and get information from them in conversation is valubale in consulting, sales, tech support, and so much more. 🕵🏻‍♀️

Do not ask this if you can’t take the feedback and quietly tuck it away for analysis later no matter what it is. Don’t argue or get defensive, as this can backfire. Write it down, say “thank you”, and keep the conversation moving.

Have I answered all of your questions?

Be considerate and give the floor back to your interviewer. I’ve never received anything other than a “yes” here, but it’s the thought that counts. 💝

What are the next steps or timeline here?

Keep in mind that you’re still selling yourself as an investment. For engineers, that’s a minimum of several hundred thousand USD for total compensation multiplied by years of expected tenure. It’s not rude to ask about the process and next steps - it’s expected!

Other questions

Pick and choose a few as you see fit, based on what you want to know and who you’re talking to.

About the role

  • My read on this role is <INSERT A FEW WORDS>. From your perspective, is that about right? (How would you describe the role and are we on the same page here)
  • How do you measure success for this role?
  • How are you distinguishing this role at staff/principal from a career/senior level? (or career/senior and developing/mid and entry/junior, as fits what you’re looking for)
  • Let’s say we come to an agreement and I join your team - what can I do to surprise or delight you prior to day 1?
  • Is this role backfill, new to accommodate growth, etc? (Why is this open now and why did this team get a req? - I want to be on a growing team tackling hard problems that the business prioritizes.)
  • Pick a tech or two on the job description and ask about it - why language or what’s the expected depth of knowledge for years of technology?

About you and the team

  • How would your coworkers best describe your work style? How about your other / past direct reports?
  • How’d you get into tech?
  • Why leadership? It’s my understanding there senior IC roles available here.
  • Why company? You’ve been there a few years now.
  • What’s your favorite and/or least favorite part of the job?
  • What are you most excited about for the future here?
  • What are some of the challenges your team faces? (technical, political, anything else)
  • If I’m not meeting expectations, how will I know?
  • Where do you see the team in a year? 5?

On systems integrators and defense contractors

There’s a few more things to know about roles in this space. The impact and work-life balance at these companies tends to be fantastic, but the pay typically isn’t stellar. Some questions to consider asking here:

  • Is this client facing? Internal roles don’t bring in money and instead are treated as cost centers. While it may not affect much of the day-to-day responsibilities, being on the side of the business that brings money in is generally a better career move.
  • Is it sold and funded work? This means that the position is already aligned to a contract that the company holds and the customer has funded the work - yes means there’s actually a job here. “Contingent upon award” listings mean that it’s an open position that’s holding interviews, but will only hire if the contract is awarded to that company.
  • What’s your billable target? For customer facing work not having one is a red flag, not sharing it or saying it’s 100% is a yellow flag. A reasonable number is somewhere around 90-ish percent or below. Folks need to answer emails, maintain their licensures or certifications, etc. and that balance is around how much time is spent doing customer stuff versus internal business tasks.

One of the benefits of this space is that when bored, there’s always a new project at any reasonably large company. It’s also common to have a job manager responsible for day-to-day task management and a career manager who will gather review feedback and provide guidance across the larger company. This provides a built-in resource to grow even if it means leaving the contract you’re assigned to. The space can have a big downside too - “the bench” or lack of work. There’s only a certain amount of time anyone can spend unassigned to a contract before being let go.

A few more thoughts

🚩 Vague answers to specific questions are a red flag. It depends on who you’re talking with, of course, but contradictions or hand-waving around on-site/hybrid/remote schedule, compensation, role, or the process we’re going through isn’t a good sign.

🚩 Technical screen questions/take-homes that seem way too easy, way too difficult, or otherwise poorly calibrated are concerning. Make sure everyone’s on the same page as to what the job is and does day-to-day.

🦘 The answer to “should I get a new job” is usually “yes” (assuming basic responsibility). I think folks in tech spend way too much time worrying about improving awful job situations versus moving until something is great. Once you start deliberating on moving to a new job, you’re already unhappy somewhere. Don’t forget the world is full of great places to work looking for smart people who get things done.

💘 Having been on the other side too, your new team is trying to figure out the same with just a résumé and a little bit of conversation.

📝 Yes, you can take notes in an interview. Take notes, come prepared with questions, and ask all the questions you need. It’s not weird.

🌟 Your résumé, public presence on social media, blogs, open source projects, etc. are also sales collateral to help you shine. It doesn’t have to be no jokes, no hobbies, no life or existence online.

🎉 Got an offer? Congrats! Salary Negotiation: Make More Money, Be More Valued is probably the definitive link on salary negotiation as a software engineer. The Business 2023 walks through negotiating the whole offer. Both have helped me tremendously in that next stage. 🍀


  1. So … there isn’t always room for negotiation. Sometimes the role is written for an internal transfer or other unsaid shenanigans. 🦄 Unicorn hunting 🦄 is where there’s an unlikely combination of skills that would consider this company/role/compensation with a willingness to wait indefinitely. It sucks, but nothing I can say will help here. 

  2. I can’t recommend using the “in-person” network enough for job hunting, learning what’s actually in use or up-and-coming for technologies to learn, and commiseration camaraderie. 🍻 

  3. The most common leveling framework seems to be from Radford. A writeup of expected scope and impact by level is at Sourcegraph. Companies may have their own, though, so if it matters to you, make sure to ask! 

  4. Defense Industrial Base, or the defense contracting, manufacturing, and federal consulting firms. More about the bounds of this from CISA

  5. State, Local, and Education markets. 

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