Probing Questions for Your Interview

I've worked for many organizations of different types during my long, perhaps not-so-illustrious professional career: software and business shops; Fortune 500 and VC-funded startups; in retail, financial, healthcare, hardware; bleeding-edge and technology laggards; as employee and contractor.

And despite the experience, despite the many interviews, the job reality is often different than the interview reality and what I thought I learned. Probably you'll never completely know without contact with recent experience working for the employer. Job boards are often a mix of mad ex-employees and frustrated current employees, while HR attempts to tell a more rosy story.

Lacking a try-before-you-buy employment option, all we can trust is the standard interviewing process. However, remember, you are interviewing them as much as they are interviewing you, and being prepared with your questions may lead you to the information needed to understand the organization better.

Any number of sites provide their important questions, and these are the questions I intend to ask. I've also attempted to explain the rationale of the question and what I hope to learn from the answers provided. This doesn't eliminate the more standard questions with their stock answers but is intended to make the interviewer think and answer more off-the-cuff, hopefully requiring more honesty than you might get otherwise. And yes, it's all a game!

Questions for Hiring Manager

What Are Your Team’s Objectives This Year?

I totally understand that as business conditions change, so do the business goals and roadmaps, but at a point in time — your interview — the hiring manager should be able to explain how her team's work contributes to the overall organizational success. The underlying goal, however, is to understand how connected or involved the manager is with the business and other leaders and whether she understands the work necessary to succeed.

I have had multiple managers who were less connected than me and had little understanding of business objectives or direction than I, even though they attended leadership and planning meetings that I wasn't part of. In one extreme situation, a manager actually asked me to write year-end performance reviews for his team because he didn't really understand what anyone did. That is not a good sign.

I once interviewed with a startup recently acquired by a Fortune 50 company. At the end of our time, I asked the hiring manager about her team's upcoming objectives. Her response: Honestly, a lot of work remains integrating us with the mothership, which likely consuming most of our time for the next 9-12 months. No business goals were identified, no deliverables were listed, no reason for hiring the role in the first place. Danger, Will Robinson!

What Are Your Objectives for This Role in the First Six to Nine Months?

Unquestionably an open-ended question, but one for the hiring manager to expound on her understanding of the role and what defines a successful hire.

First, remember that hiring managers rarely write the published job description — usually, it's Human Resources — so clarify what she is hiring for front-end engineer or UX designer, database administrator or data analyst, enterprise architect, or scrum master. DevOps engineer or Cloud Architect. Consider yourself fortunate when your and her interpretations align; conversely, I've ended interviews early when the gap between interpretations is too large or if the hiring manager is unsure what she's hiring for.

Second, I expect the hiring manager to be able to explain their need: backfill vs. new addition; specific work or projects; future new offerings; international market expansion; non-functional requirements, or compliance. Ask clarifying questions based on what the hiring manager is saying to understand better whether or not you can be successful in the role.

This question came about after an epic disconnect at a previous employer. I met with my CTO a month after starting, and when asked about her objectives for the role, she admitted to not really understanding the role but that leaders felt the role was needed as they grew. After I explained my definition of the role's responsibilities and goals, the engagement model within engineering, and the long-term benefits to an organization, she responded with Hmm, I'm not sure that's what we were expecting. Oops. The warning flag should have been when I received the offer before a completed job description (another story for another time).

How Are New Team Members Onboarded?

An attempt to understand if the organization and hiring manager are prepared can be productive as quickly as possible: nothing deflates the excitement of starting a new job than being told to hold tight and read outdated documentation. Your first week's crowing achievements should not be paperwork, training, and a team lunch.

From creating the requisition to making the offer and then starting, the end-to-end hiring process is expensive and does not provide value until you can contribute. Most organizations know this, and yet, more often than not, onboarding continues to be ad-hoc. More senior engineers have previous experiences to help mitigate, but straight-out-of-school and junior engineers require more explicit direction, instruction, and hand-holding: listening over cube walls is no longer an option with fully- or hybrid-remote work. I expected COVID to help change this, but overall progress has been minimal.

How Do You Measure Your Team’s Productivity?

Once team objectives are identified (above), how does the higher manager evaluate progress — or lack thereof — on those objectives?

Many quantifiable metrics exist, but are they appropriate? Is she looking at outages or the number of builds per day? Completed stories or hours entered? Test code coverage or lines of code?  It's no longer possible for managers to observe key clicks and butts-in-seats, but many have identified the replacement.

Managers often throw out pseudo-mission statements without context, justification, or explanations. A recent one was We must reduce cloud costs. However, the manager didn't know the current burn rate or year-over-year delta, current API call volume or year-over-year delta, breakdown of costs across the cloud resources used, etc. No question cloud costs can be reduced, but should we do the work? Should we spend $50K on engineering to recoup $10K/year? Is that an acceptable return on investment? Are we delaying other initiatives or incorporating this with existing work? The manager couldn't answer the questions and, in fact, totally misunderstood the ask from Cloud Ops.

Questions for Team Members

What Is the Most Enjoyable Part of Your Job?

Hopefully, this question gets the interviewers to talk freely about what they do and how they enjoy it. If you have a kick-butt CI/CD pipeline, if engineering is respected and empowered to make technical decisions, if team members are allowed to work on side projects, I want to hear about it!

Careful listening may also identify concerns: an uncomfortable pause; non-work aspects such as free drinks or onsite health facilities discussed; benefits, in particular, PTO; expectations of the manager not onerous. When non-work is front-and-center, experience says the actual work is going to be disappointing: one interview focused on amenities — we'll fix your bike for you! — and ultimately found out that working there was miserable. 

During a Normal Day, What Uninterrupted Time Is Available to Focus On Your Assigned Work?

The key part of this question is uninterrupted time: do team members have sufficient time set aside to focus on problem-solving?  Remember those academic discussions on memory fragmentation? Now replace memory with the schedule. Ahh, now you get it!

My mantra is Quality work requires quality time, and quality is reduced when the time available to focus is reduced. You ask this question to understand better how time is managed — for themselves, by their manager(s), by other teams — and how empowered they are to (re-)arrange their time: blocking time on calendars, ignoring emails, declining meeting invites, muting online communications, etc.

I previously worked with a Scrum Master who regularly rescheduled meetings minutes before their start and refused (or was unable) to understand what was convenient for her was disruptive to the team.  Frustrations grew, productivity declined, and — when a senior leader intervened — she finally started to respect others' time.  

On a Recent Vacation, Were You Contacted Directly by Team Members, or Did You Check Your Email, Slack, Teams, or Other Communications?

Almost all companies claim to provide work-life balance; let's test their claim.

By asking this question, you learn whether the employer respects your personal time. Can you go on vacation without constantly being badgered with questions about current feature development?   Do you feel guilty if you don't check your emails every few hours? Is your time off used to catch up on tasks that otherwise are unaddressed? And kudos if you can totally disconnect and perhaps even forget — temporarily — that a job awaits your return. It's a challenge for most of us.

Let's be honest: US employment law is not going to adopt laws similar to German law against after-hour emails. Even industries where absolute commitment is expected are seeing pushback for more reasonable working conditions, though it still remains a challenging environment. The goal is to discover their expectations and decide whether it fits your personal situation.

Questions for Human Resources

Where Is This Role Within the Organization? 

While more important for senior and leadership positions, even individual contributors should understand how their role is slotted within a team, a product, a division, etc.

Technical and non-technical leadership roles should be positioned so you can make an impact, provide value, and be successful. A software shop I'm familiar with had the enterprise architects reporting to a manager multiple levels removed from the CTO, making it difficult (impossible?) to effect change as other managers and directors, based on the reporting structure, viewed the role as unimportant.

For other reasons, individual contributors should understand the org structure. It should be a red flag when an engineering role is outside the core engineering unit or when the role appears segregated from the more mainstream engineering teams and, therefore, more difficult to be recognized for your work.

I admit that I've accepted positions without really understanding an organization's structure, leaving me frustrated and disappointed when it impedes my work. More recently, I've asked this question to understand better the structure and its impact on my (potential) success.

What Is Your Employee Retention Rate for the Past Year?

Generally, retention rate reflects the stability of a company: higher retention rates typically indicate a well-led organization, attracting and keeping key contributors, challenging people to grow personally and professionally, and compensating (including benefits) appropriately. Reasons for lower retention rates are more difficult to identify — usually, multiple issues to address within the organization — and in the meantime, current employees may be considering a change or at least attempting to read the tea leaves.

Unfortunately, the retention rate is just a calculation that can be skewed by changes within the business, such as a fast-growing company on a hiring spree or a downturn in business leading to layoffs and early retirement. You may need to ask clarifying questions to understand the true stability better:

• What percent of the employees employed by the organization last year are still here?
• How many employees voluntarily left the organization in the last year?
• What is the bell curve for the tenure of current employees?

Most people are searching for stable organizations, but less stable organizations may offer you opportunities otherwise not available to you — role, responsibilities, salary, career growth, influence, etc. — but the opportunity needs to align with your personal career roadmap.  Understanding the current stability of an organization needs to be considered in any role you may desire.

What Were the Bonus Payouts for the Previous Five Years?

Potential employers hope you view bonuses as additional base salary, though a single payment rather than paid out throughout the year. Remember that, other than Singapore civil servants and employees in some countries, bonuses are not guaranteed. It sounds nice but risky if your financial situation requires it.

Typically I do not consider bonus potential when evaluating the proposed salary, however tempting. Asking detailed questions about the bonus plan's structure and payout history provides additional information that may sway you to accept a salary lower than your target; that said, past performance is not a guarantee of future results, and unexpected events may quickly change the international finances.

Conclusion

It's basically impossible to know absolutely everything about an organization before joining, but with the right questions, you can at least go in with your eyes open.  It's all about being in control of your professional life, and having better information makes it possible.