All About Career History Interviews
How to suss out what motivates a candidate, their potential beyond their current skillset, initiative-taking, behavioral challenges, and more.
🐲 Happy Lunar New Year, everyone 🐲.
I’m feeling physically much better these days — I also realized that while I objectively feel better in the second trimester than the first, the gap between how I expected to feel (basically normal with good energy) and how I actually feel (unpredictably up and down energy) is much much wider than in the first trimester (when I fully expected to feel horrible, and did). Funny how that extra layer of expectation and judgment and disappointment can be so powerful. In trying to let go of those expectations, I find I’m able to enjoy the moments when I feel more energetic and motivated to do things, and more accepting of the times I’m not.
I’ve just been responding to some email replies from my last post, where I invited you all to share thoughts about interviewing and also how you’re thinking about how work fits into your life.
There are so many common things top of mind for people right now, and yet, there isn’t a lot of public content around these topics (what do I really want to do, how does work fit into my life with my priorities shifting, what would it mean to take a step back or move into a different role, etc.).
I’m feeling excited to kick-off a series of Reader Mailbag posts where I share anonymized reader emails and my responses to create more visibility around these common issues you all are facing. If you’d like to participate, please reply or email me at firstname.lastname@example.org with the subject line Reader Mailbag so I know you’re ok with me responding in a future post. I will remove any names and identifying details.
For now, please enjoy this guide to Career History Interviews, loosely inspired by topgrading interviews. I’ve been running these for years now for all roles (not just engineering), and I find them to be a reliable way to get a read on how someone will behave in a work setting, what sort of mindsets they have about themselves, the level of self-awareness they have and empathy for others, and what potential for growth they may have beyond their core experiences and skillset.
I’ve shared a version of this guide on request as a Google doc with many engineering leaders over the past few years and am now pleased to share it here with you.
All About Career History Interviews
Why should you do a career history interview?
Most interviews tell you where someone’s abilities are at that moment, but not that much about their trajectory, capacity to learn, track record for success, and how they think through interpersonal or environmental challenges.
“Culture fit” interviews can be useful, but often the questions asked are ones that the candidate has a rehearsed answer for: “What are your strengths?” “What is an area for improvement?” “Describe a recent challenge and how you worked through it.” You’ll often get a polished response that doesn’t tell you much beyond whether or not the candidate is a skilled and prepared interviewee.
A career history interview is a structured way to get valuable information about how a candidate learns, adapts, and deals with challenges over time. It’s useful for spotting mindset patterns, evaluating empathy and self-awareness, and usually unearths different information than what comes up in technical or culture fit interviews.
How do you run a career history interview?
Start with sharing that the interview is a structured walkthrough of the last few years of career history.
“For each job/team/role, I’ll ask you a set of questions. We have limited time, so I may sometimes have to cut you off to move on.”
You want to frame it as structured, otherwise people often go into their typical rehearsed walkthrough of their career history.
For each job or project (each should be roughly 1-3 years, or a total of 3-4 distinct groupings), you ask a structured set of questions. These are the ones I usually ask:
How did you end up in this role? / What were you hired to do?
Get some context on team size and setup —How large was the team when you started, and how large was it by the end of your time there?
During your time there, what are you most proud of? Reflect back some of the positive things and accomplishments.
Who did you report to? At the time, what would that person would have said were your strengths? At the time, what would that person have said were some areas for improvement?
If there are peers/close collaborators/direct reports that seem relevant, ask the same set of questions regarding strengths and areas for improvement.
Highlight some of the positives and their accomplishments, and say something like every job/team has some low points, what would you say were some of the lowpoints?
How/why did you decide to leave?
Rinse and repeat for each grouping, in chronological order, so you end on the most recent role. Time management is critical.
Print out the candidate’s resume, and spend 10-15 minutes beforehand figuring out the teams/projects you will use. For example, if a candidate spent 6 months each at 4 companies doing consulting gigs, you can group that as one “job” - consulting. If they spend 5 years at one company, moving from IC to management in the middle, those can be two separate “jobs.”
Schedule at least an hour for this interview. Mark up the resume, putting asterisks next to the positions to cover. If someone has many roles, I’ll usually choose the 3-4 most recent roles, and let them know that that’s where we’ll start for the sake of time management.
Time management is tricky, and one of the most difficult things is cutting people off when they go on about things that they find interesting (technical details in implementation, backstory of team strategy, etc) but not relevant to the interview.
Keep an eye on the clock and have a sense for how much time you have for each position. You’ll quickly get a sense of how long-winded a candidate is and how much guidance you have to give them. Save at least 10 min at the end, to ask them about their ideal role, and answer some of their questions.
If you get some feedback from previous interviews to probe around specific issues (timeline of getting projects done, what specific contributions they did on a project, etc) use some of your time to dig into those and ask specific questions.
What to look for in communication style
How a candidate handles a career history interview is an important signal of a candidate’s ability to communicate effectively. From a purely communication management perspective, watch out for:
How hard they are to cut off
How well they take feedback and redirection
How much they listen or are respectful of your having to get the information you need to make a hiring recommendation
This is all useful feedback that should not be ignored. For me, a great interviewer experience that reflects well on the candidate is with someone who communicates clearly, can organize their thoughts, shares them at an appropriate level of granularity, and checks if I want more details before diving into long-winded explanations.
You may deviate from the structure and develop your own style, but I suggest starting with this basic structure and getting a few reps in. If you’re conducting the interview in person, you can keep a post-in in your interview notebook with the set of questions, to remind yourself to get through them for each position. If you’re conducting the interview remotely, copy the bulleted questions into a google doc (or similar) and take thorough notes.
Beyond basic communication skills, what to look for can depend on the role that’s being filled. For individual contributor roles, I mostly look for red flags around productivity, self-awareness, communication, and initiative-taking. For leadership roles, I’m looking also for a history of people wanting to work with them (often across multiple companies), enthusiasm and effectiveness in empowering those around them, strong history of collaboration with cross-functional peers, etc.
Common red flags
For the career history interview, you’re not necessarily looking for specific answers for each question, but rather looking for patterns across the entire interview. Here are some examples of red flags:
This can manifest as unfocused communication in the form of rambling, too much context unprompted, or difficulty answering a question despite saying many words. It might also look like the candidate constantly interrupting you and repeatedly starting to talk when you’re only ⅓ or ½ way through asking a question.
This needs to be calibrated to what a candidate needs to be effective for the role —what I would look for regarding clear communication in a product manager or executive candidate who needs to present and communicate clearly across the company is different than what I would look for in an IC or other roles.
“The world is chaotic” mindset
Candidate describes changes to their role or jobs as always blamed on external factors — the economy, re-orgs, etc. As one-offs, it’s not a red-flag, but a long pattern of hopelessness rather than taking initiative in times of change can be worrying. It can point to a victim mindset, rather than a more nuanced understanding of what is actually in their control and what they can take accountability for.
Recurring areas for improvement
When candidates respond to “What would your manager have said were areas for improvement?” you generally want to see improvements in those areas over time and over different jobs. If the same issues around, say, productivity or communication, persist across many managers and jobs, that’s a red flag. If you notice this in the interview, you can address it directly: “I remember that you had received this sort of feedback before. What did you do about it?”
Lack of awareness
Asking candidates to think about how others view them can reveal how candidates empathize with others. Do they just say “She probably would have said I was a fast coder?” Or do they reflect on their manager’s perspective on how they could have done things better, especially if they had a challenging relationship? Sometimes candidates are completely baffled by these questions, and say things like “Well how could I possibly know, you’d have to ask them!” which also reflects a lack of empathy.
Does the candidate consistently speak poorly of ex-coworkers and previous places of employment? Ideally you’d want candidates who have taken actions to try to improve situations (though as specific instances, it’s hard to know if a certain company/team was just too toxic). If a candidate has worked <1 year at 4-5 companies, make sure you probe the “Reasons for leaving” question. It’s possible they were all legit reasons, but could also be something else.
Common Green Flags
Green flags depend a bit on what you’re looking for in your open role, but here are some that I’ve seen over the years (keep in mind, my last 13 years have been at early-stage startups, so this also reflects what I’ve been screening for).