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This article was published on December 3, 2021

Want that dev job? Make sure you can answer these 7 questions

How to frame insightful conversations with potential employers

Want that dev job? Make sure you can answer these 7 questions Image by: Unsplash

Note: please know that the views and opinions shared in this story are my own and do not reflect or represent my employer.

When you run a search for the “best developer interview questions to ask an employer”, the results come back with countless resources that all have fairly similar suggestions:

  • What does a successful new hire look like in the first six months?
  • What’s the company culture like?
  • What do you like about working for this company?

The list goes on.

You’ve probably come across these resources before — they’re everywhere. They all provide questions that work for many situations. At the same time, they’re also very typical interview questions and oftentimes lead to responses that only scratch the surface of all there is to know about your role and the organisation. With low-effort research on various hiring and social media platforms, you can probably find answers to most of these.

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For many candidates in search of a new gig, those types of interview questions serve their purpose. In other cases, perhaps for those who are already established, or for applicants who have a more specific idea of what they want for their developer career, there’s a nuanced approach to finding out the details about a company during a software engineering interview.

Quick aside: if you’re like me, you come from a background where you’re taught that asking difficult questions in a software developer interview is risky and could jeopardise your opportunity. That traditional mental model insists that you are applying to their company, so just show up, answer to the best of your ability, and hope to get an offer. It took me years to unlearn and transform that traditional way of thinking into what I currently practice. Nowadays, I believe that you should feel free to have a deeper dialogue with hiring managers and human resources, especially because this helps you make more informed career decisions.

Strive for the conversation

When it comes to interviewing advice, I encourage people to strive to have conversations as they sit down and meet with people in the organisation. Your meetings with the hiring team should not just be in Q&A format; those sorts of engagements lack depth and feel somewhat robotic. As someone who’s participated in hundreds of web developer interviews throughout my career (on both sides of the table), the most memorable experiences were the ones that included active and engaging conversations.

It’s a beautiful thing when a candidate and interviewer can get to that place where they’re able to organically weave conversational elements together, and through this discourse, they can mutually determine whether there’s an appropriate fit for all parties involved. Work history, qualifications, compensation, culture, and everything else that matters are all addressed in these exchanges. These encounters involve laughter, chemistry, and thoughtful discussions about the candidate, the organisation, and the opportunity.

But how do we frame these conversations and what are some appropriate topics to raise? I’m glad you asked.

Meaningful questions

In recent years, I’ve collected a list of prompts and talking points that help shape more substantial career discussions in developer interview settings. I’ve shared these ideas with colleagues who’ve used them in their experiences, and I’ve successfully used these in my job searches as well. These topics are designed to surface deeper insights about the role you’re applying for. In other words, these questions require that the interviewers offer more than just the typical responses to the common questions from above.

To be clear, the goal here is not to impress your interviewer with unique questions — we’re not here to play psychological games. The objective is to walk out with as much information as possible so that you have a full understanding of the opportunity you’re committing to.

Caveat: some of the following themes can be a little intimidating at first, but remember, you’re simply learning and gathering information. It’s okay to (respectfully) ask difficult questions. Let’s take a look at what these topics are, along with a few reasons that justify their importance.

1. The People Roadmap

The significance of this talking point is to get an understanding of how the organisation views your position over time, and not just the role you’re applying for or the business needs they have today. In the same way that companies roadmap their products or form strategies on driving client success, they should also be able to articulate their vision for your short, mid, and long term career path.


  • How does this position evolve, and what does that roadmap look like after 1-year, 3-years, and 5-years or more?
  • How does the expected roadmap for this position impact my title, expectations, and compensation?

2. A Fail-Safe Culture

Let’s face it — stocked fridges, free food, and ping pong tables are cool and all, but what’s really important for your career is having an environment where you can be yourself and thrive. With this matter, you’ll want to find evidence that the company fosters a safe place for employees to learn from their mistakes.


  • Tell me about how this company cultivates an environment that supports psychological safety.
  • How do you enable team members to leverage failure as a precursor to learning?
  • How does the company promote a blameless culture and how are learning reviews conducted so that everyone can benefit from mistakes?

3. A Recent Promotion

Once you’re in an organisation, the journey towards promotion can be ambiguous, but this is your chance to get some clarity. The key here: ask to speak with someone who was recently promoted from the role you’re applying for, to the next level; then, you can pick their brain on everything that’s involved, from documenting work to the promotion cycles and timelines.


  • How were you recognised for your contributions that led to your promotion?
  • What is it about your work ethic that sets you apart from others?
  • What systems are in place that allow you and your team members to track your accomplishments?

4. Leadership Accountability

The greatest leaders that you’ll encounter in your career, are the ones who know how to honour their mistakes, which requires self-awareness, demonstrates humility, and also shows respect for employees. The goal here is to gauge how transparent and honest leadership is with owning their miscalculations and errors.


  • Give me an example of the last time someone in a leadership role admitted to a mistake or failure.
  • How was information shared, how did the team respond, and what was learned?
  • What mechanisms are there which allow all employees to safely provide feedback to leadership?

5. Mental Health

This is an issue that has an impact on many people and their organisations. By bringing this up, you want to ensure your future employer is not only an advocate for mental health but that they also have a structure in place to support the holistic well-being of its employees. Remember, your overall happiness should be valued by your company, not just your happiness as it relates to productivity.


  • How does the organisation promote work-life balance?
  • How does the team help to mitigate burnout and stress, and what resources exist to support people who are going through difficulties?
  • What are the opportunities around work-from-home, personal days, and mental health days?

6. Mentorship

Anyone who’s been in an effective mentoring relationship can attest to the positive impact it can have on one’s career. In true mentorships, you learn from one another and both people can benefit. Receiving mentorship is vital to your professional growth, so having this conversation early on is essential.


  • What is the company’s internal mentorship model?
  • What evidence exists to show that your mentorship program is successful?
  • How do you help shape pairing opportunities for your team members?

7. Continuous learning culture

To stay relevant in the job market, we need to constantly learn and adapt to our respective industries — the company you’re speaking with should understand this. Raise this topic to discover how the hiring team will help you form goals and learn new skills over time.


  • What framework do you have around setting and tracking my professional goals, and how will you support me in growing my skillset?
  • How does the team support opportunities for establishing thought leadership in our industry?
  • What are the attitudes around advocating career goals that could be considered outside the realm of my job description?

To Hiring Managers and Human Resources

As we kick off the first quarter of the year and your hiring cycles pick up, be prepared to start addressing these sorts of topics. This is especially relevant as we progress into the next decade because the market continues to become more competitive in terms of finding the best applicants.

The strongest candidates nowadays are experienced, educated, and informed. You’ll put your company at an advantage going forward if your hiring teams are prepared for these conversations. I have faith that many of you will consider these ideas if you have not done so already.

To Applicants

As you may already know, we spend at least one-third of our day at work, committing our hearts and energy to our careers. Your job satisfaction is a significant component of your overall well-being, which justifies doing the proper vetting as you consider your next role.

I encourage you to talk about the things that matter to you, especially if the alignment of your values allow you to perform better in your role. If bringing up these topics make you uncomfortable, adjust them or even email the team after your software developer interview. The ideas presented here are just some of the themes that I believe are worthwhile; your list could be different or more comprehensive, and I’d love to hear what your developer interview conversations are like.

Remember, you deserve to be happy in your career, you deserve to be proud of the organisation you’re a part of, and you owe it to yourself to find a place where you’ll flourish, with all that you have to offer.

I wish you confidence, success, and most of all, happiness in your career.

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