Nearshore Americas

Technical Interviews: Why Getting Questions Right Helps Build a Strong Team

In a world where employee attrition is rising and employees can work for companies from anywhere, successful interviewing techniques are a crucial part in keeping a company’s hiring pipeline healthy.

Interview questions often focus on getting the candidate to list skills and work experience, and simply elaborate on their employment history. While this information is needed, it isn’t often very telling. Instead, to really help understand more about the candidate, I request that they tell me their views and personal experiences.  My favorite questions start with phrases like “Tell me about a time when…”

To better understand how someone will work in a team, how they collaborate and communicate with peers and customers, it can be very insightful to get them to tell a story. This is referred to as behavioral interviewing.

An Unorthodox Opener

When I’m interviewing technical staff, my favorite behavioral interview question is:

“Can you tell me about a time when a project or task you worked on was late?”

Often this question elicits some stammering from the candidate. They don’t want to admit when things went poorly, or they made a mistake. They may ask me to clarify what I mean, while they try to think about which of the many times that they were late on a project, and how to discuss it in a way that makes them look good.

If they are slow to answer, I’ll follow up with: “When you realized your work was going to be late, how did you handle that?”

The answers I have received to this are very revealing about how a person works within a team, how they view their own work in relation to peers, and how they interact with their customers or the business.

Little White Lies

One of the worst answers to this question that I ever received came from a software developer who said: “I’ve never been late on a project.”

Really? That was a very big warning sign, and I was tempted to stop wasting my time and end the interview right away. Surely this person was joking, or is just flat out lying to me?

Software development is hard, and even the most talented developers can struggle to accurately estimate how much time a task will take. Successful teams account for this risk in software estimation, and don’t trust their own initial optimistic assumptions about a task. They also encourage open communication so that the team can solve difficult challenges together, and create a culture where team members are not afraid to discuss problems they are running into.

Curious, I pressed him further: “You’ve never been late on a software project? Your work has never been behind schedule?” 

“Well, I’ve never been late due to me. Sometimes the testing team takes too long to test my work and then it’s late because of them.”

Software development is hard, and even the most talented developers can struggle to accurately estimate how much time a task will take

I had to suppress a laugh, but my video was on and I have no doubt my face gave my thoughts away. There was no way I was going to hire this developer, it no longer mattered to me how much technical skill he may have.

Usually, the candidates who fail this question give a more oblique answer, but this guy just came right out and said it. He clearly believes his work products are perfect, and if they are ever late or of low quality, his first reaction will likely be to blame someone else, and these team members don’t often help bolster cooperation.

Communication is Vital, Especially for Technical Staff

As I said, rarely will an answer be as obviously wrong as this one. But what is the ideal answer? It’s all about communication.

An engineer may first answer my question by talking about the technical complexity of the project they were on, how they had to learn new skills, or how they worked all weekend to try and make up for being late. Those may be fine answers, but it’s not what I really want to hear.

I want to hear them talk about how, and when, they communicated this to their manager, to their team, and/or to their customer.

Technical people are often introverted by nature, and judge themselves by the quality of what they produce.

Technical people are often introverted by nature, and judge themselves by the quality of what they produce. Throw on top of that a deep sense of pride in their work and a desire to please, and they will likely avoid the hard conversations when they are late with a project.

Instead of communicating the problem, they may work longer hours, simply beat their heads against the keyboard, or desperately try alternative solutions to the task right up until the deadline. In an unhealthy company, they may have been inadvertently taught this behavior by poor management who criticized them personally when they made honest mistakes in the past.

When they show up to the product demo on the day of the deadline, feeling rejected, they have already lost a lot of goodwill with their management or the customer.

The Answer You’re Looking for

What I’m looking for from my interviewees, is an understanding and appreciation of personal responsibility and communication.

A great answer would be something like: “As soon as I knew I was going to be late, I talked to my manager (or the customer, or my team). I let them know that I would keep trying, and how I was hoping to fix the issue, or if I needed help. But I didn’t want them to be surprised that it was running late, I figured it was better for them to know sooner rather than later.”

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Delays are always bad news, but the damage of a delay can always be mitigated with open communication.

In companies with strong organization, managers will recognize and be grateful when issues are raised with them while they still have time to act. Decisions can then be made on how best to proceed.

These are the sorts of decisions that healthy teams make all the time, but for a team to have the opportunity to make those decisions, we must be careful in our hiring practices. The best teams don’t expect perfection, but they do expect strong communication and collaboration from their teammates to overcome the inevitable challenges they will encounter.

Arin Sime

Arin Sime is the CEO and Founder of AgilityFeat, a boutique software development agency founded in 2010. The company is based in the US and Panama, but works with remote talent throughout Latin America. Arin is also founder of, a development agency specializing in building live video applications for web and mobile.

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