Leadership Questions
I have heard this conversation in organizations for years. A leader passes their employee in the hallway, catches them before a meeting, or sits down for a one-to-one and says:
“How’s it going?”
“Fine.”
And too often, that’s end of the conversation.
There is nothing wrong with asking how someone is doing. The problem is, if the answer is always “fine,” it doesn’t tell us very much.
Years ago, I created an image around the word FINE because I had heard it used so often when talking about stress and mental health. “Fine” could mean frustrated, insecure, nervous, exhausted, isolated, fearful, inadequate or any number of other emotions. Sometimes, people really are fine. Sometimes, it is simply the easiest answer for them to give.
The same thing is true when leaders ask, “Any concerns?”, “Does everyone understand?”, or “Do you need anything?” – not bad questions, but they are just broad enough that they make it easy to give a short answer.
If you really want to understand what is really going on with your people, you need to ask a different kind of leadership question. One that elicits a longer response and invites the employee to explain. The question will depend on what you want to know, so let’s take a look at several different scenarios in which you may want to probe more deeply.
When You Want to Know How Someone Is Really Doing
Most leaders genuinely want to know how their people are doing. But asking “How are you?” has become such a meaningless social pleasantry that the answer is often just whatever the employee feels like giving. It may be that they are having a hard time, but the truth is they don’t know how to explain it, or they don’t want to sound negative, or they haven’t stopped to truly analyze the situation.
A more useful check-in gives them somewhere to go.
Some of the leadership questions I sometimes use in my mental health, resilience and burnout work are::
- What has been taking the most energy from you lately?
- What is feeling harder than it normally would?
- What has been going well for you lately?
- How manageable does your workload feel right now?
- Is there anything making it harder for you to do your best work?
- Where could you use more support?
Note that I am not assuming a diagnosis, just creating the space for the person to give one.
While some of the issues raised may be personal, others are likely to be work-related and both are important for the leader to know.
When Stress or Frustration Is Building
One of the issues I sometimes see with leaders is that we ask how people are doing before we really understand what may be causing the issue.
“How are you managing?”
“Are you okay?”
“Can you handle this?”
Asking these questions can make the employee feel as if they have to defend their need for help.
In fact, in my S-O-S Principle™ — Situation, Ourself, Support — I encourage people to first examine what is causing the stress, rather than how they are responding to it.
These Leadership Questions might be:
- What is creating the most pressure for you right now?
- What part of this situation is creating the greatest frustration?
- What is making your work harder than it needs to be?
- What feels within your control, and what doesn’t?
- What would make this more manageable?
- What support would be most helpful from me?
You may discover that the issue is not a lack of resilience at all.
Perhaps there are several competing priorities and nobody has clarified which is more important or a process that makes everyone do hours of paperwork that isn’t necessary. Sometimes people need to strengthen their coping skills. Sometimes leaders need to ‘remove the rocks from their shoes’…removing the irritations.
When Your Team Is Going Through Change
Change is one of those times when asking a better leadership question can make a big difference.
A plan is unveiled, people see the presentation and leaders explain why the change is important.
Then the leader asks:
“Everyone okay with this?”
Silence.
It is easy to interpret that silence as acceptance.
It may not be.
In my H.U.M.A.N.I.Z.E. Change Pathway™, I encourage leaders to treat resistance as information rather than automatically seeing it as negativity or unwillingness to cooperate.
Resistance often tells us something about the employee experience.
They may be concerned about the workload or how the change will affect their ability to do their work, their competence and status within the organization or they may not understand why the change is happening. They may feel that decisions are being made without regard for what’s actually going on the front lines.
Rather than asking if people are “on board,” try these leadership questions:
- What about this change still feels unclear?
- What concerns you most about how this is going to work?
- What do you feel we may be underestimating?
- What part of this feels outside your control?
- What do you feel you may be losing as we make this change?
- What are we asking you to let go of that worked well before?
- What would help you feel more confident moving forward?
- What could we do differently that would make implementation easier?
One of the principles I use in my change work is that two things can be true at the same time, The old way of doing things may have had real value and there may still be good reasons to move to something new. Allowing the employee to discuss both can be much more revealing than asking if they are “on board.”
When Conflict, Negativity or Toxic Behaviour Is Emerging
Leaders also hear a lot of frustration about other people.
“She never listens.”
“He is impossible to work with.”
“They don’t respect me.”
The temptation is often to agree, defend the other person, or jump quickly into solving the problem.
I would rather slow the conversation down.
This is something I work with extensively in my Difficult People and Toxicity programs, my 3P™ Assessment Model — Person, Payoff, Plan, and my work around difficult conversations.
The first step is always to separate the person from the behaviour.
Ask these Leadership Questions:
- What specifically happened?
- What behaviour are you concerned about?
- What impact is that behaviour having on you or the team?
- Is this something that happened once, or is there a pattern?
- What have you already tried?
- What outcome would you like to see?
- What needs to change for you to be able to work together more effectively?
- What part of this situation can you influence?
These questions get us past the labels (“Difficult.” “Lazy.” “Negative.” “Disrespectful.”) and closer to the facts of the situation. It’s important that leaders understand legitimate concerns without being pulled into the frustration themselves.
There is a difference between empathizing with someone and joining them in their anger.
A good question encourages curiosity that leads you to the facts of the situation without leaping to conclusions.
When You Need to Understand What Is Getting in the Way
Sometimes there is no obvious conflict or crisis.
Work just isn’t flowing as it should. Deadlines are slipping, people seem frustrated, decisions take longer than they should and the same problems resurface again and again.
This is when some of the simplest questions can be the most enlightening.
In my 10 Essential Employee Engagement Needs™, several needs speak directly to this: Knowing What’s Expected, Leadership Support, Resources to Do the Job and Periods of Calm.
One of my favourite leadership questions is simply:
What is getting in your way?
Followed by these Leadership Questions:
- What is harder than it needs to be?
- Where are expectations unclear?
- What competing priorities are making your job difficult?
- What information or decision are you waiting for?
- What resource do you need that you don’t currently have?
- What could I remove, clarify or help resolve?
- What are we overlooking?
Leaders see the workplace from one perspective. Employees experience the systems, customers, workloads, policies, technology and relationships from another.
Sometimes the question uncovers a major issue.
Sometimes the answer is surprisingly small.
Either way, you cannot respond to something you do not know is there.
When You Want People to Speak Up and Contribute Ideas
Most leaders tell me they want employees to bring forward ideas and concerns.
Many will say:
“My door is always open.”
But an open door still puts responsibility on the employee to decide whether it is safe and appropriate for them to walk through.
One of the 10 Essential Employee Engagement Needs™ is Freedom to Speak Up. That doesn’t simply mean employees are allowed to speak; it’s about creating the conditions in which they feel that speaking up will be heard and their concerns addressed.
That means more than words. It means asking Leadership Questions like:
- What do you think I may be missing?
- What are we not talking about that we probably should be?
- Where do you see a risk that we haven’t addressed?
- What are people struggling with that may not be reaching me?
- What would you challenge about our current approach?
- If you could change one thing about how we are doing this, what would it be?
- What is one idea we haven’t considered?
- If you were in my position, what would you be paying attention to right now?
Curiosity is an important leadership behaviour. So is responding appropriately to what you’ve been told. If someone finally opens up to you and you respond by explaining how they’re wrong, becoming defensive, or dismissing their concern altogether, they won’t be likely to speak up again. People learn very quickly whether they are genuinely welcome to speak up or simply encouraged to in theory.
When You Need to Move From Frustration to Action
There are also times when the employee has had plenty of opportunity to explain the problem, they are frustrated and you understand why, but now you need to decide what to do.
This is where I draw on my C.L.E.A.R. Conversations™ work and the difference between Speaking Up and Sounding Off.
Speaking up is intended to improve something. Sounding off is primarily intended to release frustration.
Once the employee has been heard, you can move the conversation to what comes next.
Ask these Leadership Questions:
- What would a good outcome look like?
- What would you like to see change?
- What options have you considered?
- What is within your control right now?
- What would progress look like?
- What is one step you could take next?
- What do you need from me?
- What can you take ownership of?
Note the last question. Supporting someone doesn’t mean doing everything for them. Sometimes the leader needs to act, clarify something, make a decision, get resources or address inappropriate behaviour on someone else’s part. Other times, the best support is helping the employee realize what they can do for themselves. We are often much more likely to accept help with something if we feel we did it ourselves.
The Question Is Only Half the Conversation
You could collect 100 excellent leadership questions and still have ineffective conversations.
Because your team is also paying attention to how you respond.
Are you looking at your phone while they answer?
Do you interrupt because you think you know where the conversation is going?
Are you formulating your response instead of listening to theirs?
Do you jump in with advice?
Do you sound annoyed that they’ve raised an issue you didn’t want to hear?
Do you give them enough time to think about what they want to say?
One of the things I teach through C.L.E.A.R. Conversations™ is that listening is not simply waiting for the other person to stop talking.
It’s about hearing what the other person is really saying to you. Sometimes that means asking a clarifying question. It may mean saying very little at all. And occasionally, it means hearing something you don’t want to hear.
You Don’t Need the Perfect Leadership Questions
Leaders do not need to walk around with a list of perfectly crafted questions , but they do need to become more thoughtful about what they want to know.
If someone says they are “fine,” perhaps the follow up question is:
What has been taking the most energy lately?
When someone says, “This change will never work,” maybe you ask:
What are you seeing that I may be missing?
When someone complains about a coworker:
Tell me specifically what is happening.
When work keeps getting stuck:
What is getting in your way?
And when someone brings you a problem they have talked about several times:
What would you like to see happen next?
The leadership questions will always depend on the conversation, but the intention remains the same. You want to understand what the person is experiencing, what may be getting in the way and what needs attention next “How’s it going?” might be a good opening question, but don’t assume that “Fine.” is an adequate response.
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Contact Beverly about hosting a Leadership workshop for your leaders. Discover tips to deal with build engagement and encourage positive well-being!
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If you have some strategies to share – comment on this posting!
Additional Reading:
Humanizing Change: A Leadership Pathway for Supporting People Through Change
Leading Through the Chaos: Navigating Change with Confidence
Effective Communication For Leadership Success
How to Build a Positive Workplace Culture | C.U.L.T.I.V.A.T.E. the Culture™
What Is Adaptability Quotient (AQ)? A Leadership System for Navigating Change
Managing Complexity and Change: Lessons In How To Foster Resilience
How To Deal With The Stress Of Change
Humour Can Help You Thrive In Change
Be On Purpose Month: Life Requires Some Stress and Change
What Is the S-O-S Resilience Principle ™ – A Practical System for Managing Stress in Real Time
7 Reality Anchors™ for Dealing With Difficult People
Dealing With Difficult People At Work: A Leader’s Guide to Toxic Behaviour and Conflict
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Frequently Asked Questions About Effective Leadership Questions
What are effective leadership questions to ask during an employee check-in?
Good leadership questions go beyond “How are you?” and help uncover what may be affecting the employee’s work or well-being. Questions such as “What has been taking the most energy lately?”, “What is getting in your way?” and “Where could you use more support?” often lead to more useful conversations.
How can leadership questions help employees speak up about concerns?
Leadership questions can make it easier for employees to raise issues they may otherwise keep to themselves. Asking “What do you think I may be missing?”, “What are we not talking about that we probably should be?” or “Where do you see a risk we haven’t addressed?” signals that different perspectives and concerns are genuinely welcome.
What leadership questions can help during workplace change?
During change, useful leadership questions focus on uncertainty, concerns and barriers rather than simply asking whether people are “on board.” Questions such as “What about this change still feels unclear?”, “What do you think we may be underestimating?” and “What would help you feel more confident moving forward?” can help leaders understand what is underneath resistance and respond more effectively.