Uncover 31 Mighty Leadership Questions for Employees & Employers
Updated: Nov 14
LEADERSHIP QUESTIONS GOT YOU STUMPED? YOU TOO CAN ASK MORE EFFECTIVE ONES!
First off, every one of us is a leader, whether we have a formal position of leadership or not. We can choose to lead others regardless of our title or position. First, we need to learn how to lead ourselves, which starts with self-awareness and reflection on how we can approach people and situations from a position of humility.
With that in mind, there are many leadership questions we wonder about.
What questions about leadership do top-notch leaders ask their team?
What questions should we ask interviewees?
We’ve compiled a list of the best questions about leadership for you to digest and implement. Feel free to use the list wholesale or pick and choose ones to your liking.
Here’s to your continued leadership success!
9 STELLAR QUESTIONS ABOUT LEADERSHIP TOP LEADERS ASK THEIR TEAMS
Ever wondered what questions top leaders ask others? Here are nine of them to satisfy your curiosity.
1. WHAT CAN I DO TO LEAD BETTER?
True leaders know that they have shortcomings and need to continually grow. Even those who are pretty self-aware in this area actively seek out feedback to see what they still may be missing.
2. WHAT SHOULD SUCCESS LOOK LIKE?
When someone is presenting something for approval, ask them this question to get the specifics on what the outcome should look like. And drill down with follow-up questions to make sure there is a strong agreement on this before moving forward.
3. WHAT THINGS ARE HOLDING THE ORGANIZATION BACK?
It is way too easy to get comfortable with the status quo, even for those who are driven by the need for change. Regularly ask this of people inside and outside of the company to get new insights into how things might be stale or behind the curve.
4. WHAT IF THIS CHALLENGE IS REALLY AN OPPORTUNITY FOR SUCCESS?
If someone has a setback, encourage them to view this as an opportunity to grow and turn the challenge into a win. Sometimes all they need is a shift in mindset that asking this question can prompt.
5. WHY OR WHY NOT?
I love this follow-up question to probe a bit further on any statement. Michael "Vsauce" Stevens has a great take on why we should ask questions more regularly. Be sure to watch him in the video above.
6. WHAT THINGS SHOULD WE STOP (OR START) DOING?
There are usually things we could stop doing, and it wouldn’t have any negative impact on the organization (or might even have a positive one). Then there are others that we should start doing (in place of the things you’ve stopped) that could have a much bigger impact on achieving your company’s goals.
7. WHAT ARE PEOPLE THINKING BUT AFRAID TO SAY?
Maybe there are some fresh ideas people want to implement, but they are afraid to mention a sacred cow for fear of ridicule or reprisal. Ensure them that it is okay to bring these things up and that they won’t be ridiculed for it. Then discourage any bad behavior amongst your team if it arises.
8. DO WE HAVE THE NECESSARY RESOURCES TO ACHIEVE THIS GOAL?
If we make a decision and go down that path, do we have the people, money, and tools to cross the goal line?
Perhaps we haven’t counted all of the costs. It’s much better to take a little time to nail these down before moving forward, rather than finding out that you can’t finish the project after you’ve wasted a ton of time and money.
9. WHAT ARE THE WEAKEST PARTS OF YOUR PLAN AND HOW WILL YOU DEAL WITH THEM?
If you don’t identify the weaknesses in your strategies and make plans to avoid them, they will come back to haunt you. It’s always better to plan ahead so you can anticipate and mitigate any issues.
13 FIRST-RATE LEADERSHIP QUESTIONS TO ASK PROSPECTIVE EMPLOYEES
I’ve had interviewers dominate the conversation, trying to intimidate me as a candidate, as if that would make the cream rise to the top. This only serves to discourage many people. I’ve found it’s just the opposite that works best in getting to know more about the real candidate.
It’s better to break the ice with candidates and do your best to make them feel comfortable . This is already a stressful event for them. No need to add more. You want to witness who they really are, not see how they would perform under the hot lights of an interrogation.
Answers to these questions can be taken from personal or work life, so tell the candidates that either is acceptable to place their mind at ease.
And consider asking some of these same questions to a candidate’s references to double check their truthfulness.
1. TELL ME ABOUT A TIME WHEN YOU FAILED AND HOW YOU OVERCAME IT?
We have all failed.
There, I’ve said it. It’s true, even of those who seem to have a high level of success. It just comes with life, so let’s try to uncover how they deal with failure. What are the ways they try to avoid and overcome it when it does come?
2. WHAT ARE THE THREE MOST IMPORTANT VALUES YOU DEMONSTRATE DAILY?
We lead ourselves and others by the values that we keep. Are the candidate’s values a good fit with your organization? And are those values borne out when you talk to their references?
3. WHAT IS THE ONE THING THAT SEPARATES YOU FROM ALL OTHER CANDIDATES?
Making them boil it down to just one thing is crucial. If they give you several, they might not be good at following directions. And if they do supply just one, you now know what they firmly believe is their best offering to the organization.
4. WHO WAS YOUR WORST AND BEST MANAGER AND WHY?
These are two separate questions really. Ask them to talk about their favorite boss. Then see how they chat about their least favorite.
Was he or she a tyrant or a trusted mentor? Usually, you don’t want to hear someone badmouth their previous manager, but rather provide an objective view of what they learned from the situation, good or bad.
5. IF YOU KNEW YOUR BOSS WAS 100% WRONG, HOW WOULD YOU HANDLE IT?
Now, most of us wouldn’t go over our boss’s head to their boss or the board of directors, but how far would we go?
Most leaders want their team members to feel comfortable challenging them, but in a professional way. If candidates say they would have no problem confronting a superior, they may be overly direct, lying, or even a jerk. Even when we know something would be bad, it’s hard to push back on someone who holds the power of hiring and firing.
6. WHO IS YOUR HERO AND WHY?
I ask this all the time, and most people are surprised. They’ve never had someone ask this, and some of the answers I get are all over the board. One of the most interesting responses I’ve heard is that their hero is Tony Stark (Iron Man). When I asked him why, he said it was because he wanted to be a billionaire playboy.
Needless to say, I passed on his candidacy. Not because he said “Iron Man,” but because his values clearly didn't align with ours.
7. HOW DO YOU GET OTHERS TO VOLUNTARILY FOLLOW YOU?
If they lead mostly by telling people what to do, they might not be a good fit. While every role has some telling others what to do, most people want to be led rather than told. They want a voice, and we need to hire people to encourage others to high performance.
8. HOW WOULD YOU DESCRIBE YOUR LEADERSHIP STYLE AND WHY DID YOU CHOOSE IT?
As an example, my personal style is servant leadership. I believe in it wholeheartedly and have written about it, so it's easy and exciting for me to talk about when I'm asked. Asking your candidates can generate a lot of insight into how they think.
What you're looking for is a credible answer and a good fit with your culture.
9. HOW DO YOU PRAISE OR ADMONISH PERFORMANCE?
Generally, it is better to praise people for their exemplary performance in public and admonish in private. The key here is to identify how they give feedback to others around them. Are they thoughtful in delivering constructive feedback?
10. WHAT TYPE OF LEADER WOULD YOUR TEAM SAY YOU ARE?
This makes them think about how others view and describe them, which is a different question than how we view ourselves. Often, they may try to say they are the same, but given a little more probing, they may reveal more about their true selves.
11. WHAT MOTIVATES OR DEMOTIVATES YOU?
Most people have no trouble answering what motivates them. For some it’s money, for others it’s power or position. But whatever it is, you will identify what you need to motivate them should they be hired.
On the flip side, there are things that demotivate each of us. For me, micromanagement is a huge drain on my energy.
12. WHAT IS THE MOST DIFFICULT PART OF BEING A LEADER?
Being in charge is rough at times; you have to make tough, often unpopular, calls. Plus, the buck stops with you. You want to see a humility and understanding in their answer. Have they been in a leadership role? Do they have sympathy for someone they know who has?
13. WHAT DO YOU EXPECT FROM YOUR LEADER?
The answer will help you manage this person and determine how you can step up your game. It is a great conversation starter for setting expectations for the role. If there is some disagreement or misunderstanding brewing, wouldn’t you rather know it right out of the gate?
2 CHIEF TIPS FOR ANSWERING INTERVIEW QUESTIONS
For those of us going on interviews, here are a couple of tips to keep in mind when crafting your responses.
1. STAR METHOD
There are four elements to this method that many interviewers use, and its best to use all four when answering those questions.
Situation: Provide specific context about a particular instance that highlights the area they are asking about.
Task: What was your responsibility in that situation?
Action: What did you actually do yourself (not what others did)?
Result: How did it turn out, and what did you learn?
Be careful about displaying negativity, dishonesty, inflexibility, arrogance, or making excuses; sometimes we can demonstrate these in the way we say something.
But above all, be honest in your answers. Lies have a way of catching up to you eventually.
7 INQUISITIVE QUESTIONS EVERY INTERVIEWEE SHOULD ASK
When a recruiter gets to the end of their questions and asks you, “What questions do you have for us?” that is not the time to say, “None for me, I’m good.”
Even if they have already answered all of your questions, come up with a few more. The best way to approach this is to come prepared with a list of questions.
Here are seven main questions to ask:
1. WHAT IS THE REASON FOR THIS POSITION BEING OPEN?
With this question, it’s important to understand if this is a new or existing position. If new, why are they creating this role and what are its goals? What is the business pain driving this? If it’s an existing position, what happened to the previous employee?
Now, they won’t always tell you, but you can gently ask some probing questions to see how much info they will give you. And you might even be able to reach out to the person leaving to get the lowdown on the role. But take any input with a grain of salt, because it’s only one person’s viewpoint. If you talk to multiple people inside and outside the company, there might be a pattern there.
2. WHAT IS YOUR CULTURE LIKE?
Pay attention to how they answer this question.Their answer will give you some indication into their culture, but it’s usually best to try to independently verify this with others in the organization. Ask if you can talk to a potential coworker or contact people who work there via LinkedIn to get another point of view.
3. WHAT PERCENTAGE OF THE JOB IS DOING VERSUS LEADING?
The answer to this depends on what you prefer.
Do you like leading a team or being involved in the execution? Or maybe it is some of both. The bottom line is to identify whether or not the job is a good fit for you and the company.
4. WHAT KEEPS YOU UP AT NIGHT?
This question gives you ample opportunity to dig into their main business pain, so you can demonstrate how you can solve it for them. Hopefully, they aren’t so overwhelmed that they don’t sleep due to stress—that it’s just a metaphorical question and answer. If it is literal, you might want to avoid this job.
5. WHAT ARE YOUR WORKPLACE PET PEEVES?
It’s best to find out what they hate or what drives them crazy and avoid it like the plague. No need to find out the hard way. Just ask and avoid a bad situation before it arises.
6. AM I TAKING OVER A SUCCEEDING OR STRUGGLING JOB OR DEPARTMENT?
They may tell you a lot or a little when you ask this question, but the answer will reveal some clues as to what you are getting into. Watch to see if they are hesitant in their answer. They may want to hide something bad or just protect a sensitive situation.
And don’t be afraid to take a job that is challenging. You have only one way to go … up! Relieving someone who has done a remarkable job will be tough shoes to fill. If given a choice, take the job that will challenge you. It will give you greater growth potential long-term.
7. OVER WHAT PERIOD OF TIME WILL I BE MEASURED INITIALLY?
Will you only be given 90 days to turn things around when it will take 9 months or more? This will help you have those conversations to set expectations early and get any unrealistic goals out in the open for discussion.
QUESTIONS ARE GREAT, BUT SOMETIMES...
Some questions are better not asked too early in the process. Hold off on questions about pay, benefits, working remotely, etc., unless you’re at the point where they are ready to make you an offer. You don’t want to get ahead of the process and give the impression that you are all about the money and benefits before they are sold on your candidacy.
HAVE OTHER PRESSING LEADERSHIP QUESTIONS? LET INITIATIVEONE BE YOUR GUIDE
We know you have gained new insights and leadership questions to ask others on your leadership journey. If you are looking to take your team’s leadership to the next level, InitiativeOne can come alongside to help increase the effectiveness of your team.
There are several parts to this leadership transformation process provided by InitiativeOne, including a personal profile assessment, cognitive learning, group sessions with real-world challenges, personal discovery, and a toolkit to empower leaders to perform at their best.
There are really only two things stopping good teams from being great. One is how they make decisions and the second is how they solve problems. Contact us today to grow your team’s leadership performance by making decisions and solving problems more swiftly than ever before!