How to Spot Red Flags when Interviewing for an Engineering Manager Position

There comes the stage in every interview process about questions you, as a candidate, might have from the interviewers. It’s wise to use this opportunity to further prove your interest in the position by showing curiosity and engagement, but another important task is discovering red flags to rule out a potentially bad career move. The more advanced you are in your career, the higher the risk is in a job change. The current climate with fewer opportunities and tighter hiring processes makes this risk of ending up in a bad position even higher. Confidently spotting red flags is an important skill in an interview process and can help you make a good decision when receiving an offer.

Red flags are not entirely objective though, in fact, they can be highly personal, depending on family priorities, experience, financial status, and other preferences. For example, a fast-moving company culture can be an advantage for some, who are excited by new challenges; and a disadvantage for others, who prefer a steady pace of progress. So first be clear in your own preferences, and take the list below as a list of potential red flags.

I’m grouping the questions based on the risk area they are probing at. Focus on one or two max, depending on your preferences.

1. Limited Agency in the Role

This is usually the product of micromanaging leadership and a command and control management culture. It’s more difficult to spot when the company is aware that this is problematic and would like to move away from it, because interviewers might emphasize the intentions and not the current reality. Even if they are looking for a new joiner to help push the culture in the right direction, you must be aware of what you’re signing up for, and think about why they haven’t done enough yet. Questions that can help you uncover the level of agency you’ll have in your new role (best asked from the hiring manager):

• "Walk me through your planning process - who sets priorities and how?" - Is Engineering involved in the problem / opportunity definition phase, or Product brings a ready roadmap to implement? Does the team participate, or is it all between managers? How far are they planning ahead? How is technical work represented?
• "How was the last significant technical direction change handled?” - Pay special attention to what initiated the change (top-down or from the team) and how it was implemented (planned and executed, or more iteratively, with potential feedback loops and adjustment opportunities).
• "What's the most controversial decision your team made recently?" - Was it something that should be just in the scope of the team (eg: changing the time of the standup) or something with a much wider impact (eg: delaying a feature to address tech debt)? How were disagreements handled? Is there psychological safety in the organization to disagree and argue? Does management step in to resolve conflicts or is the culture encouraging people to be autonomous and mature enough to handle these themselves?
• "What's your day-to-day involvement with your teams' work?" - It’s kind of a trick question because any answer that focuses on the process and its day-to-day details might indicate micromanagement tendencies, difficulties in delegating, or low trust and discomfort with ambiguity. Answers that focus on the outcome over the process, allowing teams to own execution by only providing context and removing obstacles, are a great sign of high agency in the EM role.

2. Low Technical Maturity

Besides having to use a legacy stack, this can also mean a lack of processes, poor toolings, low developer experience, and an inefficient development environment. Questions that can help you probe without being too direct:

• "What's the biggest technical challenge your team is facing right now?" - Besides the content of the answer, look at how confident the person is in the team being able to resolve these problems. Also, how realistic does their plan sound like?
• "How long does it typically take a new engineer to make their first production change?" - Besides onboarding processes, this can uncover the health of CI/CD pipelines, deployment strategies, the team’s trust in their systems, and can hint at the level of empowerment and autonomy in engineering.
• "What's your deploy process like?" - A variation of the above, showing how high is the level of fear in deployments, and how autonomous are teams in deploying their code. Do they need to coordinate with others? Get permissions from different teams and departments? Regulated industries might make things more complex, but this can still be a big red flag to someone comfortable with frequent and autonomous deployments.
• "How do you handle incidents - can you walk me through your last major one?" - Do they have playbooks, on-call rotation, and blameless postmortems? Do incidents require the assistance of the person who wrote the code?

3. Unhealthy Work-Life Balance

This can be super tricky to discover because you have conflicting incentives: you want to seem eager to work, but at the same time, you need to know what to expect. Asking too many questions focusing on this area might portray you as not having the right priorities. A useful approach is focusing on the team aspect, asking operational questions about team effectiveness rather than personal preferences. You're not asking for special treatment - you're assessing if the organization has sustainable engineering practices. Still, don’t circle too much around this topic, and make sure these aren’t one of your first questions.

• "How does the team ensure sufficient coverage during vacation periods?" - Lack of any processes can be a red flag, even more so if they expect availability from engineers during their time off. Any answer that approaches the problem from the capacity planning angle instead of personal availability is a reassuring one.
• "What's your meeting culture like? How do you protect maker time?" - Any conscious, proactive approach to this can be a good sign - and the lack of it a red flag.

4. Lack of Career Development Opportunities

You can use more straightforward questions in this area because ambition to learn and grow are signs in a candidate that hiring companies are usually looking for. However, asking too many of these might send a message that you only consider the current position as a jumping board, and will get disengaged if a fast promotion is not happening. So, like similar red flag discovering areas, tread carefully.

• "Can you tell me about someone in your org who's grown significantly in the past year?" - Red flags could be any kind of dismissal or too generic answer. Another warning sign is opportunistic promotion, when the need to fill the role of someone who left the company drove the events.
• “Who’s the highest seniority engineer in the org, and what are her duties?” - Having a separate career path for ICs and managers is, fortunately, more common now than it was 5-10 years ago. Still, it’s a sign of immaturity if the organization is not using the contributions from Staff or Principal engineers maturely. They should be on the same level as senior or director EMs, supporting their work across multiple teams.
• “What’s the typical tenure at your organization, on different levels?” - Anything extreme can be a red flag to some, it depends on your personal preferences. Most managers being around for many years might mean stability to some — but lack of opportunities to grow for others. Similarly, a very new leadership team can indicate chaos and high turnover — or fast promotion to the eager ones. The reassuring answers tend to be transparent about challenges and show a healthy mix of tenures.
• "How do you develop technical leaders in the organization?" - Any answer that emphasizes people’s ambition and eagerness to take on new responsibilities sounds good on the surface, but can be a red flag because it might hide the lack of structured development programs. If this area is important for you, expect clear progression frameworks, some kind of mentorship program, or other initiatives that allow the gradual increase of responsibilities.
• “Tell me about your career at the company!” - A variation to the previous one that can be used if the interviewer is a long-tenured leader (check them on LinkedIn in advance!). If the only thing the organization did was not prevent the person to grow into who they are today, then it’s not showing a very strong supporting culture.

5. Poor Organizational Transparency

Problems in this area are usually easier to pick up if you have multiple chances to talk with different people in the company. Still, it often just comes up as a gut feeling, so some probing questions like the following ones can come in handy to confirm your suspicion.

• "How are difficult company messages communicated?" - Three things to watch out for: the frequency of messaging (ideally there are regular transparent updates covering challenges too, and fewer ad-hoc big announcement calls), the scope (pointing out that you’ll hear about changes that impact you from your manager is a red flag for people who prefer working in more transparent organizations), and the direction of the communication (are there Q&A or similar sessions to discuss, raise concerns and give feedback?). Dismissing the question and trying to paint a rosy picture can also be a red flag, hinting at toxic positivity.
• "How does engineering get updated about product strategy changes?" Red flags could be anything that isolates engineering from the product aspect or indicates unidirectional communication (”PMs let impacted EMs know about what to develop” or ”updates are announced during the quarterly product summit,” etc.).
• "What was the latest surprise you learned during a skip level one-on-one?" - Not being able to come up with anything, or outright admitting not doing skip levels can be a red flag, because it shows low information flow across organizational layers.

6. Business Risks

These might be easier to ask, especially for early-stage startups, because it’s normal that you want to know what you’re signing up for. However, because this topic is not closely related to engineering, it’s best to bring these up with either the recruiter or a high-ranking leader. Note that the answers to all of these questions (or the lack of) can also hint at the level of organizational transparency.

• “Are you profitable? What's your path to profitability?” - A seemingly simple question, but you can spot some red flags in seemingly positive answers too. One of them is moving the discussion from profitability to being cashflow positive, as this metric can hide the impact of annual subscriptions collected up-front, future obligations, deferred expenses, depreciation, etc.
• "What's your churn rate, and how has it changed?" - The percentage of customers or revenue lost during a year is an important health metric for startups, but without knowing the industry and the maturity of the business, it’s hard to give benchmarks (prepare in advance if you suspect problems in this area). Still, the second part of the question can open a discussion, that's helpful to pick up hints on financial sustainability.
• "What percentage of revenue comes from your top 3 customers?" - The lower the number, the more sustainable the business is. A very high number could also mean custom developments for VIP customers, which might be a red flag for some.

Conclusion

Even in more desperate personal situations, you should confirm at least the most important red flags you prefer avoiding. Spotting these during interviews is an important skill that can save you from a poor career move – and asked well, can even show your maturity in choosing where to work at. Remember to adapt the question to the company, the interviewer, and of course your personal preferences. Also, check out my earlier article on Interviewing for an EM position for a more holistic look at the topic.

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