The BOLD questions job candidates should be asking you
You want to be challenged as a leader, right? Today, I'm giving you a newsletter from a reverse perspective by sharing bold questions a candidate should ask you in the hiring process. Do you have the answers?
Thank you to Val Geisler, who you can follow on Twitter here, for inspiring me to write this as a follow-up to the newsletter I wrote on what questions to ask before hiring a full-time employee. The squeaky wheel gets the grease.
Let me preface that my questions are unrelated to practical HR issues. You can ask many questions when you're interviewing for a job regarding that, and I'll link to some resources at the bottom to help you ask the right questions about healthcare, 401k's, salary, etc.
I've intended for my questions to put the leadership on the hot seat to help the employee learn how the company thinks and also, as a reader of this newsletter, test you to see how you would answer them as a leader. Here they are:
What is an example of a project or opportunity that your company said "No" to in the last year?
Why this: Shiny objective syndrome is a top contributor to lousy company culture. If the boss across from you can't come up with one thing the company decided not to do, odds are they're trying to do it all.
What feedback have you gotten in an exit interview that you immediately resolved within the company?
Why this: Do they listen to employees? Do they even hold exit interviews for their employees? Do they do anything with the content from those interviews? In rare circumstances at a startup, they've never let anyone go (which might be a red flag), but if that's the case, ask them to share something they took on as feedback and corrected from a current employee.
Can you give me an example of a time you chose to care for a person over profit?
Why this: Drill home the need for an "example" here. A good leader remembers these moments because they should be memorable for them. You want to work for someone who sees you as a person, not an expense.
What is your company's strategy to win, and how have you structured teams to support that?
Why this: You want to work for a company playing to win, not playing to play. The essence of strategy is making bold choices to position yourself to win in a market. Everyone in the company should be able to articulate the business's choices to win, and you want to work for a company with a clearly communicated strategy.
After making these choices, the leadership should structure teams to be great in the areas of responsibility that support these choices. Thus, the structured teams part of the question. It also tells the employee how their role contributes to the overall strategy. This question may knock their 🧦 off.
Imagine you hire me for the role. After 90 days, you come by my desk or jump on a Zoom with me and tell me I've crushed it for the company. What have I achieved?
Why this: Sure, you want to know what success looks like so you can do well in your role, but you want to see if they know what success looks like for you. Do they mention measurable outcomes you feel confident you can achieve? Often companies bring someone on because fires are burning, and they need another set of hands, which is okay, but you should at least know what you're trying to grow in your garden if you're asked to get your hands dirty.
What is something your company believes to be true, that very few other companies would agree with you on?
Why this: In Peter Thiel's book Zero to One, he shares one of his favorite interview questions, "What important truth do few people agree with you on?" Here are his thoughts from his book on the question:
This question sounds easy because it’s straightforward. Actually, it’s very hard to answer. It’s intellectually difficult because the knowledge that everyone is taught in school is by definition agreed upon. And it’s psychologically difficult because anyone trying to answer must say something she knows to be unpopular. Brilliant thinking is rare, but courage is in even shorter supply than genius.
A good answer takes the following form: “Most people believe in x, but the truth is the opposite of x.” - Peter Thiel
Framing the question as I have above is flipping the script on the interviewer. I would expect them to have a vague answer, but seeing what they come up with could be cool. How safe will they play it?
Cards on the table. What are your concerns about my ability to do this job better than other candidates?
Why this: Don't leave the room without hearing and overcoming every objection. It's a sales process for you as much as it is for them. If they ghost you or go with another option, you want to understand why. It's an uncomfortable question that will catch them off guard, but you have to give yourself the best chance to win in the room and see how willing they are to tell the truth.
Bonus: Some others that didn't make my list.
What results in the company will my daily work have the most profound impact on?
Is there anyone at the company now who started in the role I'm in and has moved up to a more senior position?
If I was also interviewing for one of your competitors, why would you tell me to choose you?
What type of person would thrive within your culture?
What is the most unique benefit you provide for your employees?
Do you have a leader you admire?
I had to stop brainstorming this newsletter because there were SO many good questions I could have included. I hope this change of perspective was an intriguing one for you. If you're reading this as someone interviewing, these questions take courage, but most worthwhile things do.
If you use them, I would love to hear stories of how these questions went. Please email me at kc@solvinghollow.com, and I can add your real-life experience to this newsletter.
If you read this as a founder or CEO, and you thought about how uncomfortable you'd be in the room if a candidate asked you these questions, I've done my job.
But, here's a cartoon to lighten the mood.
Resources on the practical side of employment:
https://hbr.org/2014/04/15-rules-for-negotiating-a-job-offer
https://hbr.org/2022/05/38-smart-questions-to-ask-in-a-job-interview
