top of page

Questions to Hire By

I don’t like interviews. Not behavioral. Not situational. Not case. Not stress. Yes, stress interviews are a thing in certain circles. I’m familiar with a host of others, including Rorschach tests, but the question is… how useful are they? By this I mean, how well do they predict a person’s ability to excel in the job?

More often than not the interview process is plagued by inaccurate job descriptions, a whole bouquet of biases, and affected by mood, sleep patterns, state of hunger and past encounters.  As if this weren’t bad enough, the pace of change in organizations ensures that whatever “requirements” were put in place for the original, and often protracted, interview process, will surely be blown to bits by month 4 of employment.

Wait, but that’s not all. When hiring into leadership positions the game is different. You find yourself sitting across from self-assured, articulate (I hope) candidate, who won’t easily show her hand, and has much more experience managing people than you do. You’ve got your questions and your poker face, but these folks can, and often do, “manage” the interview and interviewer quite handily. Trust me, the guy sitting there in an over-pressed shirt, gold cufflinks and shiny shoes will not give you any indication that he’s gonna curl up into a ball or throw a raging tantrum every time the shit hits the fan.

So how do we produce an accurate read on the candidate, her fit for the job, his fit in the culture, and the likelihood of their long-term success? Well, it helps to know exactly what you’re looking for and have a way to cut through the smoke and mirrors.

For this, I  recommend two steps:

I. Get Clear on What’s Important &

II. Deepen the Questions

Here’s a “Deep Interview” Tool Kit for a leadership role where "keeping the ball moving in a volatile work environment" was a top priority.

The first step is clarity: What’s Important?

For that let's go to my Leadership Characteristics in a VUCA world.

2 Types of Leadership Characteristics: Technical (T1) and Temperament (T2)

Type 1 Characteristics - "Technical" measure depth of analytical, technical, complexity and judgement capabilities, and

Type 2 Characteristics - "Temperament" measure the depth of human and leadership capabilities, and behavioral and temperamental maturity of the candidate. However, all are inter-connected and influence one another.


1. Decision Making capability (T1).

How well does the candidate make decisions? You’re looking for the process and for any rigor in it. Does s/he rely on decision models? Gut instinct? Experience? Objectivity? Incorporation of others input? Ability and courage to navigate decision complexity and act? Finally, I   suggest you don't focus on outcomes of his/her decisions. You will almost never get a clean read on the outcomes.

2. Empathy (T2).

What kind of human instincts does the candidate have? How clued in is s/he to others? Empathy is vital to healthy leadership (impossible to have servant leadership without it). Empathy does not mean capitulation. It means being able to put yourself in someone else’s shoes; to be able to approach the whole person and work effectively with complex individuals. Empathy can be a huge strategic advantage because people instinctively recognize it and respond to it (same for authenticity); it builds good will and drives motivation, loyalty and resilience.

3. Learning Capacity (T1)

How nimble and resilient is the candidate? You’re looking for an openness to information, mental flexibility and experience in overcoming failure. You’re looking for a "healthy relationship" with mistakes and ability to enact quick strategies to minimize and mitigate fallout. You want to ensure that the candidate's confidence is not borne of an oversized ego. While this is important to humility (see below), too much ego can be an enormous impediment to learning and all but assures ossified and stagnant thinking, stilted leadership style and self centeredness that impedes motivation and innovation.

4. Insight (T1)

How deep is the candidates knowledge of the area s/he will be leading? This is a place to ask job/industry-specific questions and ascertain depth of knowledge, technical skills, etc.

5. Self Awareness (T2)

Here, you’re looking for the depth of awareness of the candidate’s own strengths and weaknesses without asking outright. You want to know just how objective the candidate is about him/herself. This aides in learning, quickly correcting mistakes and relating to other “flawed humans.” How "relatable" your candidate is is an indicator of how well and how quickly s/he will be able to engage and lead his/her team.

6. Humility (T2)

This is a measure of the ability to squelch one's status, position or ego temporarily for the larger good. You are not looking for Mother Theresa, only the willingness to act for the greater good so the benefits of can accrue to the teams s/he is leading (servant leadership). In a fast moving organization, this is preferable to someone who is concerned with his/her own status, empire-building, silo-reinforcing, etc. You want the leader's focus to be on the larger goals, which yields better, faster decisions and output.


II. Now that you have a roadmap, let's deepen the Interview Questions

The above six characteristics roll up into one unlikely, slightly ridiculous and certainly accidental acronym DELISH, which I put out there as entertainment while I search for something better. (However, my track record with acronyms is CRAP).

Before we move on the Deep Questions, I need to point out that the key to their value lies in interpreting the answers and knowing what to look for. To that end, I  provide some guidance in italics below each set of sample questions. But this only scratches the surface of the possibilities.

Decision Making (Type 1)

DQ - Describe situation which required you to make a complex decision? How did you go about it?

DQ - What decision models did you employ in this case? Which do you usually lean on?

DQ - What was particularly helpful to make the decision? Why?

DQ - How close were you to deciding differently? What changed your mind?

For all questions, allow the candidate to completely answer the first question before moving on to the next. Watch for: clarity of thinking and explanation of the decision and its complexity. What, if any, decision models did s/he use? This is an important measure of rigor of thought. Did all the information come from him/her? To what extent did the person use sources outside himself? How good were those sources?

Empathy (Type 2)

DQ - Describe an important disagreement you had with a colleague?

DQ - What was their point of view? (if you need to ask this question, it's a red flag)

DQ - Tell me how you have dealt with your team’s needs. (leave it open ended)

DQ - What takes a toll on you?

Again, wait for the full answer to the first question before moving on. Look for how does s/he define “colleague” - as a peer or a subordinate? Is it a person s/he trusts or not? Did s/he volunteer the other person’s point of view or did you have to ask?  Does s/he value or try to de-value/dismiss the colleague’s point of view? Does s/he stress who turned out to be right and who was wrong? -this also goes to humility. For the last two questions, leave them open ended. You want to know how the candidate interprets the question. What is top of mind for them?

Learning Capacity (Type 1)

DQ - Estimate for me how much do you rely on your own instincts, experience, research vs. utilize others’ instincts, experience, research to make decisions? (you're looking for a ratio/percentage)

DQ - Tell me what was the most valuable lesson you learned at work in the past year? What was valuable about it? Who or what contributed to your education?

DQ - Tell me about a valuable lesson you were able to teach another person at work?

DQ - Describe a significant mistake with consequences that occurred on your watch by your team?

Look for leaders who know how to leverage external information, intellect, and data. Look for leaders who want to learn from others. Can s/he easily admit knowing less or being incorrect prior to the learning event? Is s/he more comfortable talking about learning from someone or teaching someone? You’re looking a comfort level with the possibility that at any point in time, s/he will be making the wrong move, the ability to quickly recognize it when it happens and take  and take mitigating action.

Insight (Type 1)

(These questions should be traditional interview questions which address depth of technical or industry knowledge and experience the candidate possesses)

Self Awareness  (Type 2)

DQ - What part has luck played in your ascent? Or “What is the cost of being right?”

DQ - What offends you at work? How do you deal with it?

DQ - How often are you demotivated? How do you deal with being demotivated?

DQ - Do you have a role in the motivation of your team?

Your first two questions should be anything provocative. By this time you should have a good sense of this person’s EQ and Self awareness. What you’re looking for here is for him/her to share insight, to pause and think, to be able to go deep without trying to sell himself. This is about the ability to question yourself on the fly, which is vital to lead others. The final 2 questions are a simple test. Everyone everywhere is demotivated more than they are motivated. Does the candidate recognize that in him/herself? Does s/he recognize and address it in the people s/he leads?

Humility  (Type 2)

DQ - What do you think about the statement “Achievement is often anonymous?”

DQ - When we talked about your disagreement. You mentioned… Why was it important for you to tell me that?

DQ - How often are you wrong?

This set of questions is an ego check. You want find a balance of a confident leader with one who has the ability to defer, motivate and contribute to the evolution of those in his/her charge. The second question should pick up on any previous set of questions that smacked of either egotism or controlling characteristics and go deeper. This set of questions will also test for patience, focus, and commitment to the process.

For more information on this Deep Interview Tool Kit or to discuss others, contact me at Change Ethic.



bottom of page