Interviews are meant for companies and possible future employees to get to know each other and assess if they are a fit. Usually employers will lead interviews and try to get a sense of how proficient a candidate is. I have favorite programming interview questions that I use to achieve that goal.

I also have a set of questions that I do whenever I’m on the interviewee side. I’ll want to understand how I can add value to the company and how the company will add value to me, as a professional. If we’re to form an alliance we need to be mindfull of what’s ahead.

It’s very important to be aligned on values. So my questions try to cover values and practices, but also processes and habits. I try not to ask direct questions like: “What are your values?” - instead I try to ask open questions and infer the information from the responses.

Culture questions

Will this be a place that I’ll enjoy working at? I try to have a set of open questions that allow me to get a sense of that.

What’s not cool about working here?

This is my all time favorite question. This simple question may tell me a lot about the company. Usually people look far away and try to articulate what are the cons of working there. This will be a personal answer and we can tell a lot by how it’s delivered. Does the interviewer show honesty and easiness to talk about improvement points? Even with problems being stated, do I feel that the company provides a safe environment?

Sometimes interviewers look down. Or they may say that this is the best company and that there aren’t any improvement points. These are red flags for me. I know that all workplaces have improvement points. That’s part of the job and I’m ready to help overcome those issues. But I’ll feel tricked if I’m sold a heavenly place and then I find projects that no one wants to work at, for example.

What makes you stay?

This is the other side of the previous question. This will also be very personal and I need to understand that what I value may be different from what the interviewer values. But I’m just scavenging for information and this question tells a lot about a company. Specially when we ask it to several people. Do they focus on camaraderie, on the hability to make an impact, on perks, on how they have hard challenges to solve, on working smart or working hard, etc.

But do you know what I’m really after in this question? Unfortunately it’s not that common but what I’d really like to hear is: the leadership. Saying: I stay because I’m inspired by the company’s leadership and my managers will totally catch my attention.

What does it take to be successful at this company?

This may also be a question where people have their own view on the subject. Ideally all answers would be aligned. Do we have people saying ship fast and others saying ship perfectly? Does the company have a clear carrer path and properly sets expectations?

This is a complex question because we may have a hunch of what’s needed to be successful. We may see the senior people on the company and infer that we’d need to be like them somehow.

But measuring success is hard. If the company has a clear way to describe what it takes to be successful, that’s great.

How do you foster a safe environment?

Note that the question is not: Do you have a safe environment? That would probably generate a straight yes. By asking how I’ll have a sense of how conscious is the company on fostering a safe environment.

This could be natural. Maybe the leadership is great and trust occurs naturally. If this is the case it will be hard to answer this question. Again I’d expect people to look far ahead and try to come up with some justifications on why there’s a safe environment.

On the other hand we could have a fast and straightforward response. This will mean that the leadership consciously makes an effort to build a safe environment and that they foster a set of habits that aim to accomplish that goal.

Red flag if the interviewer doesn’t have a clue of how to answer and is not able to actually show that there’s a safe environment.

Business questions

Being aligned on the culture is very important. But I also want to know the business viability of the company. This, of course, can be very hard to understand. But making these questions to several people (from developers to leadership) will make me realise if there’s a strong, shared vision on where the company is heading.

Where do you see the company in one year?

Forecasting is very important. If we don’t know where we’re aiming at, it will be harder to take the best road to it. This question will allow me to get a sense of the vision of the company and If that’s something that inspires me.

By asking this question to developers I can also see if they take part in defining the future, or if for example they just follow a backlog.

Followup question: how about in three years?

What’s your major obstacle to success?

Is it technology? Will we need to scale? Is it generating demand and awareness? If we’re not aware of our major obstacles it will be hard to overcome them. Again each area should have a specific set of obstacles, and sometimes they conflict with each other. Sales may say that we need to build more and be faster, and customer success will say that we need more stability and less bugs. Developers may mention tech debt and quality practices.

So how to prioritize then? Does the company provide a set of goals that allow each team to work independently but aligned? Or do we have each squad rowing in a different direction?

How do you motivate people that need to do the same for long periods of time?

This is more of a typical pitfall I usually see. There are some tasks that companies need to take care of that may not be challenging on the long run. For example, people that do support, or that are in a “feature factory”. Doing this for years may take the edge out of us. Or maybe not, it may actually depend on how much we like to innovate and leave our comfort zone.

Having a strategy to handle these scenarios will make a difference.

How to handle a market crash?

Maybe this one is better suited for the company’s leadership. Does the company depend a lot on a specific customer? If the main sources of income go away, how can the company adapt and maybe pursuit other areas? How hard would it be for the business and development to adapt and change direction?

This will show the maturity and resourcefulness of the whole company.

What does the next iteration of awesome looks like?

If all companies paid really well and had an awesome culture… What’s next? How would a company make a difference?

This one is tricky and very hard to answer. But finding a company that has a great answer to this would be a great find indeed.


These are a lot of questions and naturally we may need to pick the better suited ones, specially because sometimes we don’t have much more time to do them. Asking them to several people from several roles yields great results and allows to have a sense of how the overall company works and what they stand for.

This will allow us to gather data to make a better informed decision on if we should join the company or not.