A Developer‘s Guide to Interviewing: How to Probe Beyond the Surface

As developers, we‘re trained to rigorously test our code before shipping it to production. We write unit tests, conduct code reviews, and go through QA to ensure everything works as expected.

But when it comes to testing our careers, many of us take a much more laid-back approach. We show up to interviews, answer the questions asked of us, and hope for the best. We treat the process as a one-way evaluation rather than an opportunity to deeply assess the company, role, and team we‘re considering joining.

This is a mistake. Accepting a job offer is a major life decision, one that will impact your day-to-day happiness, career growth, and future opportunities. It‘s not something to take lightly.

Consider these sobering statistics:

• 1 in 3 developers leave their jobs within the first year, often citing poor fit with the role or company culture. ¹
• The average cost to a company of a bad hire is nearly $15,000, not to mention the toll on team morale and productivity. ²
• The top reasons developers leave jobs are lack of career growth, work-life balance issues, and poor management…all factors that can be sussed out in the interview process. ³

As a full-stack developer with 15+ years of experience across startups and large enterprises, I‘ve seen firsthand how important it is to treat interviews as a two-way street. The companies that probe thoughtfully into my background and ask for my input throughout the process are invariably the ones with the strongest engineering cultures. They understand that hiring is a mutual decision and that both parties need to do their due diligence.

Over the course of interviewing at dozens of companies, I‘ve honed a set of probing questions to help me look under the hood of engineering organizations. My goal is not to grill my interviewers but to surface insights that will help me make an eyes-wide-open decision.

In this post, I‘ll share my battle-tested questions for the three key personas you‘ll encounter in the interview process – software engineers, engineering managers, and company leadership. I‘ll also share tips for weaving these organically into your interview conversations and making the most of the valuable face-time you get with your potential future colleagues.

Probing the Day-to-Day: Questions for Software Engineers

The software engineers you interview with are your window into the day-to-day realities of the job. They can give you an unfiltered look at the development process, tech stack, and team dynamics. Here are some of my favorite questions to ask:

How does work get prioritized and assigned?

I‘m looking for a clear, systematic process for deciding what to build and who works on what. Ideally, there‘s a healthy balance between top-down strategic direction and bottom-up input from the engineers closest to the code.

Red flags include constantly shifting priorities, lack of clarity on assignments, or engineers feeling like they have no say in what they work on.

I also like to dig into the team‘s agile practices. How long are sprints? What happens in sprint planning? How often do they ship to production? What are retrospectives like? The more concrete details they can share, the better.

What‘s your testing strategy?

Automated testing is table stakes for any high-performing engineering team. I want to understand their approach to unit, integration, and end-to-end testing. Do they practice test-driven development? What testing frameworks do they use?

I‘m also curious about their stance on manual QA. Some teams rely heavily on manual testing while others aim to automate as much as possible. There‘s no one right answer, but it‘s important to understand their philosophy.

Beyond the mechanics of testing, I try to gauge how seriously the team takes quality. Is there a culture of writing tests? Are engineers empowered to invest time in testing infrastructure? The best teams view testing as a core part of the development process rather than an afterthought.

How is code reviewed and deployed?

Code reviews are an invaluable tool for maintaining code quality, sharing knowledge, and catching bugs early. I want to know the team‘s code review practices. Do all changes get reviewed? Who does the reviews? What kind of feedback is common?

Equally important is understanding the deployment process. How often does the team ship to production? What‘s the process for rolling out new features? How do they handle rollbacks?

Continuous integration and delivery (CI/CD) has become increasingly popular in recent years, with teams aiming to ship code multiple times per day. While this isn‘t feasible or necessary for every company, I do look for some level of automation in the build and deploy process.

What opportunities are there to work on open-source or write blog posts?

Contributing to open-source projects and writing technical blog posts are great ways to learn, give back to the community, and build your personal brand. The best companies encourage and even sponsor these activities.

I like to ask if any team members have contributed to open-source projects and if so, which ones. I‘m also curious if the company has an engineering blog and whether engineers are encouraged to write for it.

Even if the company doesn‘t have formal programs in place, I listen for a general openness to these pursuits. Do managers see them as valuable professional development or as distractions from "real" work? The latter is a red flag for me.

Evaluating Engineering Leadership: Questions for Managers

Your potential manager will have an outsized impact on your experience at the company. They set the tone for the team, advocate for resources, and play a key role in your career growth. Here are some questions to help evaluate their leadership style and approach:

What‘s your management philosophy?

I‘m looking for managers who see their role as enabling and empowering their team. The best managers view themselves as servant leaders, removing blockers and setting their reports up for success.

I also listen for how they balance the needs of their reports with the needs of the business. Strong managers are able to advocate for their team while also driving alignment with company goals.

Weak answers focus on command-and-control tactics or emphasize hitting arbitrary deadlines at all costs. The best managers recognize that their team‘s success and well-being are ultimately what drive business results.

How often do you have 1:1s and what do you discuss?

Regular 1:1s are a must-have for any high-performing team. They‘re an opportunity to build rapport, give and receive feedback, and discuss career goals. I want to know how often they happen (ideally weekly or biweekly) and what topics are typically covered.

The best managers use 1:1s as a two-way street, not just a status update. They ask for feedback on their own management style and look for ways to support their reports‘ growth.

I also listen for whether 1:1s are treated as sacrosanct or easily cancelled. Do managers prioritize them even in busy times? The answer speaks volumes about their commitment to their team.

Can you tell me about a time you had to have a difficult conversation with a direct report?

Managing underperformance is one of the hardest parts of being a manager. I want to know how they approach these situations. Do they address issues head-on or avoid difficult conversations?

The best managers are empathetic but direct. They seek to understand the root cause of underperformance and work with the employee on a clear improvement plan. They also recognize when someone is not a good fit for the role and are willing to make tough decisions.

Weak answers place all the blame on the employee or fail to articulate clear steps for improvement. The best managers take ownership for their part in the situation and see it as an opportunity for growth – both for the employee and themselves.

How have you supported your reports‘ professional development?

Great managers take an active interest in their reports‘ career aspirations and look for opportunities to help them grow. I want to hear specific examples of how they‘ve supported professional development.

Some concrete ways managers can support growth:

• Providing stretch assignments and opportunities to lead projects
• Encouraging conference attendance and training
• Connecting reports with mentors and sponsors
• Advocating for promotions and increased responsibility

The best managers view their reports‘ growth as a key part of their own job responsibilities. They‘re proactive in seeking out development opportunities and celebrating their team‘s successes.

Understanding the Big Picture: Questions for Company Leadership

Interviews with senior leaders are a chance to understand the company‘s overall direction and how engineering fits into the bigger picture. Here are some questions to help assess the company‘s trajectory and commitment to engineering:

What are the biggest lessons learned from past engineering challenges?

Every company faces technical and organizational challenges as it scales. I want to know how the leadership team has navigated past hurdles and what they‘ve learned from the experience.

Strong answers demonstrate a growth mindset and willingness to learn from failures. Leaders should be able to articulate not just what went wrong but what changes they made as a result.

Weak answers place blame on individuals or external factors. The best leaders take accountability for their part in challenges and share how they‘ve adapted their approach.

I also listen for a healthy balance of ambition and realism. The best leaders have bold visions but are also pragmatic about the work required to achieve them.

How do you see the engineering organization evolving over the next 3-5 years?

I want to understand the company‘s long-term vision for engineering and how it aligns with the overall business strategy. What investments are they making in the team? What new technologies or approaches are they exploring?

The best leaders have a clear roadmap for the engineering organization and can articulate how it supports the company‘s goals. They‘re also open to input and feedback from the team on how to improve.

Weak answers are vague or overly focused on short-term tactics. The best leaders balance the needs of the business with the long-term health and sustainability of the engineering team.

What are you doing to foster diversity and inclusion within engineering?

Building diverse and inclusive teams is not only the right thing to do – it‘s also been shown to drive better business outcomes. I want to know what concrete steps the company is taking to improve D&I.

Some examples of strong D&I initiatives:

• Partnerships with organizations that support underrepresented groups in tech
• Inclusive hiring practices like diverse interview panels and standardized rubrics
• Employee resource groups and mentorship programs
• Regular D&I training for managers and individual contributors

The best leaders view D&I as a core part of their job and a key enabler of innovation. They‘re vocal advocates for underrepresented groups and hold themselves and their teams accountable for progress.

Weak answers pay lip service to D&I without any concrete actions or metrics. The best leaders recognize that D&I is an ongoing journey and are transparent about their challenges and learnings.

Putting It All Together: Tips for Effective Interviewing

Asking probing questions is only half the battle. To truly make the most of your interviews, you need to be strategic about when and how you ask them. Here are a few tips:

Follow the conversation‘s natural flow

Avoid robotically running through your list of questions. Instead, listen actively to your interviewers and ask follow-ups based on what they share. The best interviews feel like genuine conversations, not interrogations.

Adapt your questions to what you‘ve already learned

If an interviewer has already covered a topic on your list, don‘t ask about it again. Use the opportunity to go deeper or move on to a different area. This shows that you‘re paying attention and value their time.

Don‘t be afraid to ask for specific examples

If an interviewer makes a general statement, ask for a specific example to back it up. This will give you a more concrete understanding of their experience and help you evaluate the credibility of their answers.

Share your own priorities and concerns

Interviews are a two-way street. Be upfront about what you‘re looking for in a role and company, and ask questions that will help you assess alignment. This not only helps you gather the information you need, but also demonstrates your thoughtfulness and self-awareness to your interviewers.

The Bottom Line

Interviewing is a skill, and like any skill, it takes practice to master. By asking probing questions and approaching interviews as a two-way evaluation, you‘ll not only gather the information you need to make an informed decision, but also demonstrate your own value as a candidate.

Remember, the goal is not to grill your interviewers or catch them off guard. It‘s to have an honest, mutually beneficial conversation about whether the opportunity is a good fit for both parties.

As a seasoned software engineer, I can attest firsthand to the power of this approach. The companies where I‘ve had the most positive interview experiences – and ultimately, the most rewarding tenures – are those that encouraged me to ask tough questions and dig beneath the surface.

So the next time you‘re preparing for an interview, don‘t just focus on crafting the perfect code sample or polishing your resume. Spend time thinking about what you really want to know about the company and role, and come up with questions that will help you get to the heart of those issues.

Your future self – and your future colleagues – will thank you.