Constructive ways to answer “What was your most challenging project? and why?”

Question

I am asked this question many times in the interviews.

What was your most challenging project -- and why?

I get confused about which project to tell them and why some project would look challenging or non-challenging. What are they looking for in the answer? Any software is a challenge before it gets started and it becomes a normal software engineering task after it has finished. All softwares I made were challenging until they got finished. Do I misunderstood the word "challenge"? What's wrong in my thinking?

What's an appropriate and constructive way to approach this question?

Answer 1

When I ask this question it's normally because I want to see their thought process on how they tackle a problem. Things like breaking a difficult project up into manageable tasks, referring to experts, how do they try to maximize their chance of success, etc. Lots of questions like this are just discussion points as well. Seeing how a person communicates is a large part of the hiring process.

Answer 2

Yes, all projects are challenging, but you likely remember one or two projects that was like ten times more challenging than usual:

• non-functional requirements were not set initially had to be identified by tedious trial and error and also
• designing seemed mission impossible and also
• thorough testing requied significant effort and also
• deployment package preparation seemed mission impossible

... so that it looked like everything was against you yet you shipped a good solution in reasonable time. Then you should surely name that project - your description of the major problems and their solutions will show how tough you are.

Answer 3

A new trend/fad/fashion in interviewing is called a "competency based interview". In this fashion, the interviewer is supposed to come up with a list of key job skills and then base some open-ended questions around those skills. Sample questions based on key skills.

It is my belief that more and more people trying to hire developers will turn to these sorts of questions and get away from the stupid trivia questions we've seen in the past (such as "what is the third parameter of the print function"). While those trivia questions are reasonable at determining if you have had some exposure to a language/framework, they aren't good at determining if you "fit" in with a team, or if you are a "good" (for any sort of value of "good") developer.

"What was your most challenging project? and why?"

This question is trying to determine your problem solving skills, with a side of determining what you consider to be challenging. In a high pressure environment, what you consider "challenging" might be something that they do every day.

Answer 4

This question could be an attempt to see how will you identify weaknesses that you had and what did you do to overcome them. While figuring something out is how I see a challenge, this question is aimed a bit at seeing where did I grow the most from being pushed to my limit. Here would be the main points of how I'd answer the question:

• Background of where I was at the start of this project.
• General nature of the project.
• Results from the project, so that this is concluding the basics of the story.
• Explain where I had problems and difficulties in getting this done, what did I do to conquer them and what other changes I'd make if I was in a similar situation now.

This question has lots of possible ways to sabotage oneself in answering as it can be rather easy to bad mouth a former employer or complain on something that if you get into too much of a rant, then you fell into the trap. The other point is being able to summarize something so that you aren't long-winded but yet give enough detail so that the interviewer can follow the story and understand what you did, how you did some of it and why it was so hard. Thus the question is asking you to walk a fine line and see how well you walk on that tight rope.

Answer 5

The best way to answer is truthfully. There are many factors that make projects challenging

• Technical Difficulty
• Personality conflicts
• Insane deadlines
• Boring, outdated platform/framework
• Cutting edge, untested, unstable platform/framework
• Personal issues at home

Pick something that was a challenge to you, and discuss how you overcame those challenges or even how you succumbed to the pressures but learned and grew from the experience. There's a difference between not succeeding and failing. You only fail when you don't learn a lesson from non-success.

Answer 6

There is no deeper sense in this question. It is a question phrased in a way such that you can freely, creatively talk about something that you deem

1. Interesting
2. Challenging
3. Worth telling... and...
4. Makes you proud a little bit

Imagine them asking about your most boring repetitive task? Who'd care? No one. But a story about the most challenging project in your career really tells a lot about you as a person and how you deal with things. So you can even tell them about taking your grandma to hospital or marrying your wife or constructing that remote-controlled airplane or whatever, as long as you think you can meet points 1-4.