Articles · · 3 min read

A quick, 3-step process to ask better questions during job interviews

Fundamentally, I want to know if the job I’m interviewing for will be a good fit for me. Here’s a quick, 3-step process to find the signals that tell you this is the job for you.

Over my career, I’ve had great roles, and I’ve had not-so-great roles. Unfortunately, I've been burned too many times by not asking enough probing questions about a role that I later wished I had asked.

Fundamentally, I want to know who will be responsible and accountable for defining the things in a job description, how mature the company is in that journey, and if I will be the person who has decision rights around hiring and prioritizing to meet those things.

Here’s a quick, 3-step process to determine the questions I want to ask a potential employer about a role.

Step 1: Work backwards from the job description

Rather than look at all the bullet list stuff, copy the summary of the description and paste it into a document.

Step 2: Highlight the "perceived value" words

Once I have the description in my new document, I highlight all the "perceived value" words and phrases. These are the words that seem super vital but are concepts that need a lot of clarification to understand or are difficult to calculate.

Example "perceived value" phrases are:

Step 3: Ask curious questions

My last step is to look at those highlighted phrases and jot down some curious questions with my historian hat on.

I want to try and find out how this stuff is going right now, to understand how I'll be expected to help. These “perceived value” areas are the spaces I want to investigate further and look for any hints of innovation theatre, politics, toxic culture, or other factors that may be unhealthy to my mental state.

The benefits I get from using this technique

Generally speaking, I'm tired of fighting to do the job I've been hired to do. By highlighting the “perceived value” words, I can focus in on the questions I want to ask and frame them in a way that isn’t confrontational but curious. It helps me gauge whether or not the role is a good fit for me.

Here are some of the questions I’ve used in the past:

When really fuzzy phrases like "best-in-class" show up, these are like bat signals for me. I really want to know if that's already defined.

I also want to know more about the skills and capabilities across the team and partners.

Perhaps most importantly, I want to know about people, teams, and culture already in place and whether or not motivation and morale are issues. Multiple times, I’ve taken a role only to find out that members of the team have been on multiple performance improvement plans, have been demoted, have lost responsibilities, or have lost the trust of team members. That’s a really difficult way to start a role if you don’t know this stuff ahead of time.

Teams and people are the most important piece of the puzzle for me. I need to understand where teams and people are currently aligned and where they're not.

A healthy team is in a great position to learn and develop. An unhealthy team can’t get to that place until they become healthy first.

A word of caution

Not all companies or interviewers like it when I ask these questions. They may be worried I'll ask these questions if I take the job. I'm ok with that, though, because if they're afraid of me asking questions, that's probably not a gig I'll enjoy.

I also understand the enormous privilege I have to be in a position to ask these questions.

That’s it. That's my three-step approach to finding questions to ask during job interviews.

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