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.
đ˛ Happy Lunar New Year, everyone đ˛.
Iâm feeling physically much better these days â 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 Iâm able to enjoy the moments when I feel more energetic and motivated to do things, and more accepting of the times Iâm not.
Iâve just been responding to some email replies from my last post, where I invited you all to share thoughts about interviewing and also how youâre thinking about how work fits into your life.
There are so many common things top of mind for people right now, and yet, there isnât 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.).
Iâm 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 youâd like to participate, please reply or email me at jean@jeanhsu.com with the subject line Reader Mailbag so I know youâre 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. Iâve 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.
Iâve 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 someoneâs 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.
âCulture fitâ interviews can be useful, but often the questions asked are ones that the candidate has a rehearsed answer for: âWhat are your strengths?â âWhat is an area for improvement?â âDescribe a recent challenge and how you worked through it.â Youâll often get a polished response that doesnât 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. Itâs 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?
The Basics
Start with sharing that the interview is a structured walkthrough of the last few years of career history.
âFor each job/team/role, Iâll ask you a set of questions. We have limited time, so I may sometimes have to cut you off to move on.â
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 âHow 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?Â
Rinse and repeat for each grouping, in chronological order, so you end on the most recent role. Time management is critical.
Preparation
Print out the candidateâs 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 âjobâ - consulting. If they spend 5 years at one company, moving from IC to management in the middle, those can be two separate âjobs.â
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, Iâll usually choose the 3-4 most recent roles, and let them know that thatâs where weâll start for the sake of time management.
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. Youâll 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 candidateâs 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 youâre 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 youâre 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 thatâs being filled. For individual contributor roles, I mostly look for red flags around productivity, self-awareness, communication, and initiative-taking. For leadership roles, Iâm 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, youâre 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:
Poor communication
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 youâre only â or ½ way through asking a question.
This needs to be calibrated to what a candidate needs to be effective for the role âwhat 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.
âThe world is chaoticâ mindset
Candidate describes changes to their role or jobs as always blamed on external factors â the economy, re-orgs, etc. As one-offs, itâs 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 âWhat would your manager have said were areas for improvement?â 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, thatâs a red flag. If you notice this in the interview, you can address it directly: âI remember that you had received this sort of feedback before. What did you do about it?â
Lack of awareness
Asking candidates to think about how others view them can reveal how candidates empathize with others. Do they just say âShe probably would have said I was a fast coder?â Or do they reflect on their managerâs 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 âWell how could I possibly know, youâd have to ask them!â which also reflects a lack of empathy.
Negativity
Does the candidate consistently speak poorly of ex-coworkers and previous places of employment? Ideally youâd want candidates who have taken actions to try to improve situations (though as specific instances, itâs 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 âReasons for leavingâ question. Itâs possible they were all legit reasons, but could also be something else.
Common Green Flags
Green flags depend a bit on what youâre looking for in your open role, but here are some that Iâve seen over the years (keep in mind, my last 13 years have been at early-stage startups, so this also reflects what Iâve been screening for).
Ability to dive into new areas and learn
Adaptability is important for early-stage startups, so someone who has time and time again immersed themselves hungrily in an area they know nothing about, gotten up to speed quickly, and are able to contribute on a short time frame is invaluable.
This adaptability and confidence that they can learn what you donât know is hard to test for in purely technical (or whatever the equivalent is for your role) interviews. You may want to probe into timelines â if someone shares about a project they completed, ask about the timeline from start to completion. Often people who do this naturally arenât super aware that this is a superpower, so it may require some probing on your part to expose this strength.
Awareness of different perspectives
If you unearth a challenging relationship they had with someone, itâs a good sign if they have done some reflection and are able to put themself in that personâs shoes. This might look like, âI had a lot of challenges working with the product manager, but they were also put in an impossible situation, with lots of pressure from above.â Or even better, reflections on how they could have handled themselves differently.
Previous teammates want to work with them again
This one will show up in the transitions. People repeatedly being recruited into next roles by people they already worked with is a strong green flag.
What theyâre proud of
Pay attention to what people will say they were most proud of â itâs an interesting question, because itâs not really asking about their strengths, but what they really care about.
For many candidates, they will go immediately into their most successful âwork accomplishmentâ â a large project executed well, increasing conversion by 50%, etc.
Itâs not a red flag if those are what a candidate is proud of, but I always appreciate when what theyâre proud of is overcoming an interpersonal challenge, something related to their own growth, or how they showed up in a difficult situation.
Vulnerability in sharing lowlights
Similarly, lowlights can often be more surface-level: âIt was challenging to get ahold of my teammate.â
I consider it a green flag when candidates share something a bit more below the surface. A challenging company culture that they had to figure out how to navigate. A work relationship that hit rock bottom. Navigating their own uncertainties about their role or future at a company.
I especially look for this in candidates for leadership roles â vulnerability is so important in building cross-functional relationships, and for leading effectively.
There is no checklist for how many green flags and red flags you want to see in a career history interview. A lot are also influenced by how much privilege someone has and other systemic factors. Treat them as signals to understand what a person is like and if they can be effective in your open role.
Sharing feedback with the team
Youâll likely take a ton of notes â sharing these raw notes can be overwhelming.
Summarize key positives, negatives, and concerns. Highlight any key stories and anecdotes that may be helpful in the hiring decision. Also include a short list of names for front-door references.
Be mindful about privacy â people often share quite personal stories that they may not want available to an entire company of people.
How it fits into a full panel
The career history interview fits into a fuller panel that assesses a candidate more fully â it is not meant to be taken in isolation as a hiring decision, but as a helpful signal to determine whether the candidate is a good fit for your team. It can touch on but doesnât explicitly assess a candidateâs skillset or experience in a domain. Iâve certainly left interviews with questions that were mitigated by others via interviews or reference checks.
It intentionally surfaces data around communication, trajectory, and mindsets that other types of interviews typically do not get at.
References
The cherry on top of the career history interview is that you can follow up with the candidate via email and say, âHey Iâd love to speak to the manager you mentioned â <name>. Would you mind introducing me by email?âÂ
Most reference checks are overwhelmingly positive. Unless the person providing a reference is a trusted friend of yours, people generally stay away from saying anything negative. The career history interview gives you talking points to get a more useful reference check that doesnât just check a box.
You can use the notes from the interview to say something like âSarah said that you would have said learning quickly was one of her strengths, can you tell me more about that?â and then âSarah also said that you might say that she could improved in communicating with the rest of the team, can you tell me more about that?â and it opens the door to talk about those things openly.
A little about why this interview works
The structured nature of this interview is important. The positives always come first â people love to talk about their accomplishments, and this makes them more open to talking about low points later. The same goes for talking about strengths and areas for improvements. By having them share what a coworker might have said positively about them, they will be more willing to offer some areas of improvement as well.Â
After other more common types of interviews, I am often unsure of if I got an accurate read on a candidateâs abilities, or just that they are very skilled at being interviewed. While people generally are prepared for âculture fitâ interviews, most people have not rehearsed for something like this, so it allows you to get more real answers.
Even if they have, you can ask followup questions and improvise to get to less rehearsed territory. Sometimes people are very guarded and their responses are extremely guarded and superficial. I would consider that a red flag or at least something to follow-up on for management roles, as those generally require people to make themselves vulnerable to build trust with others.
As an additional bonus, people are so unused to an interviewer really trying to understand their journey and underlying motivations, that they usually leave the interview feeling really seen and understood. If you decide to make an offer to the candidate, you can really customize the conversation based on what youâve learned about what motivates them, what theyâre looking for next in their career, and how it might be the perfect fit for them.
Leave a comment or email me if you have any questions about career history interviews, and please let me know if you try it out and what you learn. Remember, time management is key! The first few may feel a little uncomfortable â if youâd like, you can practice on an existing coworker or friend.