Digging Up Your Past, and Looking at the Present

Your past is important, especially when your background is extremely relevant to the new position to which you’re applying. Also, it’s always beneficial to have a job while you’re job hunting, but sometimes circumstances don’t always allow for this. Lay-offs, dismissals, resignations, can all lead to a currently-unemployed status which is important to discuss as part of your current situation.

Alternative Questions

It’s common to be asked a lot about your past experience. They’ll want to hear how you relate your experience to their current role and mission. They may also want to hear about things they just find interesting. Some of these kinds of questions will come across more “psychological” than “practical”, but here are some of the more common variants:

  1. Tell me your top strengths and weaknesses.
  2. What is your greatest accomplishment?
  3. Give me a specific example of a time you failed, and how you handled the situation.

Don’t be a Cliche

We’ve all heard the advice of “turn a negative into a positive” but it can feel very “cliche”. You have to be careful not to sound like you’re saying the same phrase as every other candidate.

Strengths and Weaknesses

Companies want to hear where you feel particularly strong. They also want to see if you’re self-aware enough to know that you also have weaknesses. The distinction here is how you talk about them.

For strengths, talk about how you’ll apply these skills at the job, how you’ll help others to make progress on these same skills.

“I feel I’m particularly good at identifying portions of system architecture and how they communicate from a big-picture point of view. I like to know how the pieces fit together. I’m happy to dig in and learn as much depth on this as possible, because I feel it makes me a better programmer. When I work on a particular piece of code, I have a better idea how that will impact another system, and so on. I also like to teach and train people, and I think I’d like to work out a regular schedule of lunch-and-learns or other dedicated training time to review things like high-level system architecture etc so everyone on the team feels more confident.”

When it comes to weaknesses, it’s important to be genuine, but to also follow it up with how you became aware of this weakness and what you’re doing about it.

“Sometimes my time management can be a problem area. Having worked at so many startups in my career, I tend to notice gaps on the team and feel a need to fill that gap. It could be a gap in knowledge, or something not getting done, or an inefficiency, and next thing I know I’m down a ‘rabbit hole’ and not always spending my time on task. I was made aware of this at one job, and I tried to excuse it as being necessary for my role as a Sr Architect, but in reflection I can see how it hurt the team’s overall progress because I wasn’t focusing well on the task that was required of me. Because I’m aware of it now, I find it much easier to ’timebox’ my time, to allow myself a tiny portion of time, maybe a half hour or an hour, to explore a topic to see whether there actually IS value in that topic, make a note of it to ask higher-ups later, and then get back to the task I am responsible for.”

Explaining Previous Jobs

When I ask candidates about previous jobs, I’m listening for several indicators:

  1. Growth: Did you take that job to learn a new skill, or to keep using a skill you already had? How did your skills grow at that job, and by how much?
  2. Responsibility: Did you gain responsibility while at that role? Why or why not?
  3. Teamwork: What can you teach me about how your team worked there? (without giving away secrets you need to honor)
  4. Respect: How do you talk about your previous employers? Do you speak kindly about them, or does your language get more and more negative and resentful?

Explaining Your Current Job

You’ll probably be asked about your current job responsibilities. After talking through this, you’ll almost always be asked “Why do you want to leave?”

Like the previous note on explaining previous jobs, it’s important that you speak positively about your current role, even if it’s a horrible place to work.

Try to share ideas of things that you have learned at the job, and end the explanation with an idea of what you want next.

“I learned some interesting design idea there around X, Y, and Z, which I feel will be helpful in the future, or even just for perspective on different ways to accomplish a goal. I’m looking for a new opportunity where I can continue to grow in A, B, or C areas because I’d like my career to go in a slightly different direction.”

Explaining Why You’re Currently Unemployed

I’ve screened a lot of resumes and talked to people on the phone who were unemployed at the time.

In my experience, hiring managers and recruiters will be a lot more favorable toward you if the amount of time you’ve been unemployed is short. The longer you remain unemployed, the more they’ll be worried that you are “unemployable”. They’ll be thinking “Surely if this person knows what they claim to know, they would have found a job by now.”

This can also be a heavy bias. There may be fewer jobs in your region, and perhaps you lack the resources to relocate to an area where you’d find a job more easily. Not everyone can just pick up and move in a quick amount of time.

It’s important to keep working on things while unemployed. Find side projects, find some open source where you can contribute time and skill, attend meetups and give talks on topics where you have some knowledge. It’s important to keep “doing the thing” as if you were employed.