Posted: 26 June 2025

Continuous Hiring: Career Deep Dive (Part 4)

In the previous article in this series we looked at how to use a hiring scorecard to conduct a series of skills based “competency” interviews.

In particular we looked at the importance of using “behavioural” interview questions to prompt candidates to share real examples from their current and previous work experiences, as opposed to asking what they might do in hypothetical situations.

We also covered the importance of regularly using “drill down” questions to test the veracity of a candidate’s answers.

In this article we will look at arguably the most important stage of our structured interview process, Stage 3 – the career deep dive stage.

1	Screening stage
2	Skills stage
3	Career deep dive stage
4	Simulated work exercise stage
5	References stage

Table 1: Minimum recommended interview stages

Purpose of the career deep dive stage

You may be wondering why, after a thorough assessment of a candidate’s skills and experience in Stage 2, is it necessary to delve deeper into their work history?

The answer lies in one of the key hiring principles we introduced in the first article in this series, specifically that…

“…the biggest predictor of success in a role is a candidate’s past and present behaviour”

Or to put it another way, even if you have concluded after Stage 2 that a candidate has the required skills and experience, people whose behaviour doesn’t fit the role, team or company, ultimately fail.

This is why the goal of the career deep dive stage is to determine a candidate’s behavioral fit by looking at patterns in their career history.

Two heads

Stage 3 comprises a single 90 minute interview, but requires two interviewers – one person conducting the interview, the other taking detailed notes (and interjecting with their own questions and follow ups if needed).

Assessing patterns of behaviour requires a great deal of focus and attention and if conducted correctly, a career deep dive interview also generates a large amount of candidate data that needs to be captured.

This is why involving a co-founder or other senior leader to do the data collection (observe and take notes) whilst you lead the interview is recommended.

Having two interviewers also minimises the chances of any important follow up questions being missed as well as providing you with a valuable additional perspective on the candidate.

Common set of questions

Similar to conducting an initial screening interview, using a common set of questions during the career deep dive interview makes it much easier to compare candidates.

Specifically, for each role on the candidate’s resume, ask the following –

What were you hired to do?
What accomplishments are you most proud of in that job?
What were some of the low points in that job?
What was your boss’s name and what will they say are your biggest strengths and areas of development when I speak with them?
Why did you leave that job?

These questions are designed to understand a candidate’s behaviours and “how” they like to do things. Table 2 provides a detailed breakdown of what to look out for in their answers.

As with every other interview stage, the effectiveness of these questions is greatly enhanced by “drilling down” into every answer with one or more of the following –

What – e.g. What is an example of that? What did you do? What happened next? What did you do next? What was your role? What did your boss say? What were the results? What do you mean by that?
How – e.g. How did you go about it? How did the team react? How did you deal with it? How did that feel? How so?
Tell me more? – this is a simple and highly effective open ended question designed to get the candidate to elaborate and share more detail about their initial answer

Reverse chronology

Assessing a candidate’s career history in reverse chronological order is an effective technique to see if their behaviours have evolved as their career has progressed, or if they have remained static.

Either is fine, so long as the behaviours you identify match what you are looking for in your role, team and company.

Ideally, you should begin the career deep dive interview at the very earliest role on their resume and work your way up to their current job, asking the common set of questions for each role.

If the candidate has a long career history, starting at their very first role may not be feasible from a time perspective, so starting several roles into their career may make more sense.

Regardless, as part of your preparation for the interview, it is important to mark-up each role on their resume with how much time you want to spend on it, with less time allocated for their earlier roles and the most time allotted to their current position.

Identifying additional referees

As part of their answers, candidates regularly reference other people they have worked for or with. These colleagues, peers, managers or executives can often provide greater insight into the candidate than the referees they have provided on their resume.

At the very least these people may be able to provide additional validation (or not) of the things you have learned from the candidate.

If a candidate speaks about a project or initiative, “drill down” further to identify other potential referees by asking things like –

“Who did you work with on that?”
“Who else was part of the team?
“What was the name of the project leader?”
“Who did you ask for advice about that situation?”

In the final article in this series we will cover how to conduct an effective reference interview but for now, during the career deep dive interview, it is important to make note of any people the candidate mentions that you feel would be valuable to speak with.

If the candidate makes it successfully through the rest of the structured interview process, you can then ask them if they are willing and able to set up some time for you with these additional referees.

Table 2 provides a template, questions and tips for conducting a career deep dive interview.

Career deep dive interview template

Who:	Founder + one other senior leader and/or co-founder to take notes
Format:	90 minutes (preferably in person)
Goal:	Drill down into the candidate’s behaviours by looking for patterns in their career history
Interview framing:	The following can be a useful way to frame the interview format with the candidate – “What I’d like to do in the next 90 minutes or so is to work through your career history, starting with your earliest job to your current position. You’ll notice there is some repetition to the questions, so don’t be surprised as we walk through your career history if you can anticipate what I’m going to ask next.”
Common set of questions:	Ask these questions for every role on their resume (starting with the earliest to the present, allocating more time to the more recent roles) “What were you hired to do?” “What accomplishments in that job are you most proud of?” “What were some of the low points in that job?” “What was your boss’s name? What will they say are your biggest strengths and areas for development when* I speak to them?”* “Why did you leave that job?”
Things to look out for:	*“What were you hired to do?”* Can they give a clear & concise articulation of each role and its targets? i.e. The mission of the role (why did it exist?) The outcomes of the role (what they needed to achieve?) What skills and behaviours mattered in this role? Do they match your role? Tip: try to build a mental image of what their role’s scorecard might have looked like and probe further on it *“What accomplishments in that job are you most proud of?”* Do they share stories based on their actual experience in the role? Do their accomplishments match the outcomes for that job? Do their accomplishments match the expectations for that job? Do their accomplishments match your hiring scorecard? Tip: high achievers talk about accomplishments and results linked to expectations. Average candidates talk about events, people, things they liked (not results) *“What were some of the low points in that job?”* Does the candidate demonstrate self-awareness? Do they display honesty? Do they speak negatively or blame others? Are their answers unprofessional? Do they claim to have no low points? Tip: candidates may be hesitant, so reframe the question e.g. What really went wrong? What part of that job did you really not like? What was your biggest mistake? What would you have done differently? *“What was your boss’s name? What will they say are your biggest strengths and areas for development when I speak to them?”* Do they hesitate or seem reluctant to name their previous bosses? Do they struggle to articulate any areas of development? Have they mentioned similar development areas in previous roles? Tip: ask them to spell their boss’s name (even if it is simple) Tip: make it subtly clear you will be validating everything with their boss by using “What will they say…” and “When I speak to them” *“Why did you leave that job?”* Did they leave to advance their career or for some other reason? Were they promoted in that role? If so, why did they leave? Are they evasive about why they left? Are their reasons plausible? Is there a pattern of getting bored easily in roles? Do they think the “grass is always greener”? Were they recruited for their next role? Tip: this question is vital as it often provides the most insight on their behaviour, so do not forget to ask it Tip: high achievers leave after being successful and their bosses are disappointed. Average candidates are often “nudged” / pushed out of the job and their bosses are indifferent Tip: Useful “drill down” questions are – “What did your boss say when you resigned?” “How did your team react?” “Tell me more about why you left?”

Table 2: Career deep dive interview template

Summary

In the next article in this series we will look at best practices for giving Account Executive candidates an exercise that simulates the work they will be doing, as well as how to conduct an effective reference interview.

In the meantime, if you are interested in learning more about conducting a career deep dive interview and using behavioural and drill down questions, you might like to read “Who” by Geoff Smart and Randy Street, or feel free to DM or email me at rav@crane.vc if you have any questions.