Uncomfortable Questions You Should Ask Before Accepting a Job Offer

Matt Boegner -

In job interviews, there are numerous information asymmetries. Job descriptions lack details about what the position really entails and are vague about what the company actually needs. Employers hide weaknesses in leadership, revenue growth, and employee morale. Hiring managers and HR departments aren't transparent about your fair market value.

Having conducted dozens of interviews as a tech lead at Upside, I know the vast majority of people aren't making effective use of the "Do you have any questions for us?" part of the interview process, especially in later stages where an offer seems imminent.

One reason is lack of preparation. It seems like common sense to devote time and effort to making a decision as significant as a new job, but we know human nature is not always perfectly rational.

Another reason is the (perceived) social pressure to avoid offending the interviewer, which is the inspiration for this post. Partly it's the age-old challenge that all introverts struggle with. But more universally, it's a desire to "fit in" with the company culture/identity: something that minorities, women, and other underrepresented groups have to battle more directly.

The questions below are uncomfortable to ask, yet critical for understanding the organization you may devote years of your life to. They are intentionally direct, so the company isn't able to evade using vapid, formulaic responses. Rehearse the questions 40 times if that's what it takes to feel comfortable. Schedule a post-offer call if you need to: if the company is willing to offer you a position, they will be willing to talk to you for 30 minutes more.

What are the worst case scenarios? Their answers unearth some serious issues with the team/company. Congrats, you just saved yourself months or years of stress. Or - the interviewer avoids the question and answers in generalities. It doesn't sound like the workplace is transparent or open to new ideas. Ditto to saving yourself time and stress.

Note: My tech & startup bias shows in the questions below, but each point can be amended for an equally useful question to ask at larger companies in other industries.

Culture

  • Is everyone on the team willing to interrupt his/her work to help another team member?

Of course this is not something that should happen all the time, but it's a sign of a healthy and collaborative environment where office politics or team agendas aren't an issue.

  • In the last week, have you received recognition or praise for doing good work?

Formalized performance reviews should not be your sole way of receiving feedback. Bi-weekly one-on-one's are useful, but once again are incomplete. You should seek out organizations where feedback flows freely and constructively.

  • How do you determine if someone is a poor fit for your company?

I asked this to a CTO of a company (whose offer I declined). The individual described some heuristics, presumably meant to encourage an energetic, diverse workplace. But in the context of hiring, the heuristics seemed to offer no new information as to whether a candidate would be good in the job and instead seemed to subjectively filter out wide swaths of the workforce: culture fit (euphemism for no Asians/Indians), hanging out after work/happy hours (no one with families), no tech bros (who knows how they defined it), etc.

  • If the infamous Google diversity memo occurred at your organization, what would be the reaction?

Admittedly this question's a bit more delicate, but I think useful (especially for underrepresented groups). If an interviewer hasn't heard of it, note that as a red flag. Conversely, if he/she rushes to appease any and all concerns (the diversity pep talk), I would have concerns that it's not a genuine response. A good answer on this might reiterate the organization's core values, commitment to transparency, and note areas where the company is trying to address disparities.

  • If you had not joined this company, where would you have gone to work? Why?
  • How much longer do you see yourself working here?

Many organizations hype their "mission-driven" ethos. You may find that employees value their paycheck far more, and don't think the work is intrinsically valuable.

  • On Glassdoor, I noticed negative reviews focusing on [A,B, and C]. Can you address those criticisms?

Ineffective employees being fired can be a sign of a healthy company. Layoffs or high turnover can be symptoms of major issues with finances, leadership, or product strategy. Badmouthing former employees is a red flag to look out for.

  • What's the one thing you wish you could improve or change about your everyday work life here?

If people claim "this is my dream job, I wouldn't change a thing!" - they're lying. It shows the organization may foster an environment where individuals don't speak openly about ways to improve, or it's a place treating themselves with VC money without a business model in sight.

  • Where do you believe the industry/profession will be in 5 or 10 years?

At startups, you want some basic assurances that people are committing for the long term - unfortunately, many hop on board as a get-rich-quick scheme and jump ship at the first sign of turbulence. Questions like this show how well the leadership/product team convey their visions for the future and whether the engineers feel like a part of the mission.

  • How many employees are working full-time on XYZ buzzwordy tech?

If the company tries to sell itself as innovative by virtue of ML, AI, blockchain, < insert buzzword here >, ask about it. Companies can fake marketing but it's a lot harder to fake salaries.

  • Do engineers have freedom to experiment with new tools? What are examples? Why or why not?

Once again, every company claims they are innovative. But do you have flexibility to choose the best tool for the job? Or are you stuck implementing the "resumé-driven development" of some senior architect (or worse, the fired person you are replacing)?

  • Use small talk to ask, "Have you gone on any fun vacations recently?"

This can be a discreet way of asking "How's the work-life balance?" without the BS answer, "Great!" If there’s “unlimited” vacation, how much vacation do people normally take?

Project Management

  • What's the balance between firefighting and project work in an average week?

  • Can you tell me about a recent product or feature that failed?

  • Can you tell me about the most recent time that a project missed deadlines and how your team handled it?

Intentionally probe on the relation between product and engineering: in a healthy organization, PM's set the priority while engineers gauge how long technical efforts will take. Be scared if the leadership team is enforcing deadlines without reducing scope - that's a recipe for technical debt and employee burnout.

Don't be satisfied with a "We worked hard and everything was great!" answer.

Product and Sales Strategy

  • What's the biggest problem you're facing right now? What could upend the company in the short-term?

  • What is the sales strategy? Does the product have traction? Are there paying customers or energetic supporters of what you are building? How does leadership assess threats in the industry?

  • How often do you interact with the CEO/CTO/< insert title >?

  • Do you have input into wider strategic decisions or is that handled by a smaller group?

Startups often fail despite talented engineering teams. Figure out how the other teams operate, outside of the areas you will be involved with. Executing at a high level while watching another department make poor choices can be incredibly frustrating and has a direct impact on your financial well-being.

Finances

  • How much runway is left?

  • What are the next fundraising milestones?

  • Equity and vesting schedule details, dilution, etc

There isn't anything unique about these questions, but they definitely are uncomfortable to ask.

Understanding the financial situation will help you understand when the company might run out of cash, how to value any equity component of your compensation, and the overall growth outlook. Refusing to answer or skirting these questions is a huge red flag.

  • Outside work policy, non-disclosure agreement, non-compete, non-solicitation, compensation, forced arbitration, etc

Many companies hide these until your first day. I received an offer for a remote opportunity only to find out that no work could be done while I traveled outside the United States. I balked at another one with an extremely broad non-compete. The latter was probably unenforceable in court, but it's not worth even putting myself into that position. The outside work policy is especially important if you desire to start or continue any side projects.

Parting Advice

A guiding principle on asking direct questions: avoid binary (yes/no) answers. Rather than asking, "Does the team have a good work/life balance?" [answer is always Yes!], ask "How often do you feel the need to work on the weekends?" Free-form responses give you better insight into the company than multiple-choice answers.

A criticism of this post may be that asking tough questions could be a red flag to your employer - that you aren't willing to work every weekend, take a pay cut, or suck it up and work for a bad manager. Good. The job market is strong, take the time to find teams where you can thrive. Life is too short to work for shitty managers.

These questions are meant to inspire debate. Post in the comments if there are other questions you find useful!