Over the years I have developed five questions that I ask myself, other leaders, and my team all the time.

They are so simple. They are also so profound.

Can it really be that simple?

I have come to believe that just about every problem worth solving can be discovered through these five questions. Almost every blind spot. Almost every friction point. Almost every thing you wish you had known six months ago. Five questions. That is it.

Just about every problem worth solving can be discovered through these five questions.

If you are leading a team and you want to know what is actually going on under the surface, these questions get you there. If you are coaching another leader who is stuck, these questions get them unstuck. If you are sitting alone in a clarity break trying to figure out what to do next, these questions will surface the answer.

Here they are.

1. What has you excited.
2. What has you scared.
3. What has you frustrated.
4. What tools do you need to do your job.
5. What do I need to know.

That is it. Five questions. They will save you years.

Now let me tell you how I got here.

How I got to these five

I did not invent them. The people who shaped them deserve the credit.

The first three came to me through my friend TJ Christensen, who picked them up from an Andy Stanley marriage study. Andy Stanley has used them time and time again. Then I had the privilege of having dinner with Jeff Henderson, and I was asking him for advice. He told me he runs a quarterly advisory board meeting that he has held for over a decade, and the entire agenda is built on three questions. What has you excited. What has you scared. What has you frustrated.

The next two are the ones TJ added, because he had found they worked when he was a manager. What tools do you need to do your job. What do I need to know.

When I first started using them, I used them because they sounded good. Andy Stanley said them. Jeff Henderson built a board agenda on them. TJ said they worked. That was enough for me to try them.

But over six years of asking them, in some way, shape, or form, almost daily, the more I have used them, the more convicted I have become. Not because they sound good. Because of the results. The conversations they unlock. The blind spots they surface. The relationships they deepen. Every time I ask them, I become more emboldened by them. The more I share them with other leaders, the more their feedback confirms what I already believed.

Not because they sound good. Because of the results.

These might be the five most important questions any leader can ask. The insight you get and the way they make people reflect, including yourself, are that valuable.

Why these questions actually work

These questions do not ask you to think. They ask you to feel.

These questions do not ask you to think. They ask you to feel.

That is the whole key. When I figured that out, everything changed.

If I ask you how you are doing, your brain goes to work. It runs through a list. It edits. It picks the safe answer. By the time you open your mouth, you have already filtered out the real thing. You will tell me good or busy or hanging in there, and we will both move on, and neither of us will be any closer to the truth.

But if I ask you to tell me about a time you were scared, something different happens. You do not think. You feel it. You feel it in your chest before you can even put words to it. The fear surfaces first, and the words come second. Your brain is not making something up. It is finding language for what is already there.

The specific feeling is the key. Not how are you feeling, which is abstract and easy to deflect. But what has you scared, which is specific, and you cannot dodge it without lying. Most people will not lie when you ask them like that. They pause. They sit with it. And then they tell you.

When the feeling shows up, the walls come down. Not all the way. But enough. Enough that the conversation can finally get somewhere.

When the feeling shows up, the walls come down.

That is also why the order of the five matters.

The three feeling questions go first. Excited. Scared. Frustrated. Those get the person into reflective mode. By the time you get to what tools do you need to do your job, the person has already been feeling for ten or fifteen minutes. They are not in their analytical brain anymore. They are in their reflective brain. Reflective brain has real answers. Analytical brain has spreadsheet answers.

Reflective brain has real answers. Analytical brain has spreadsheet answers.

If I asked what tools do you need first, you would probably say nothing, I am good. Because your analytical brain has not been put on notice. It is still in default mode, which is to deflect and move on. But if I have already asked you what you are scared of, you have admitted something real. You have warmed up. The next question lands in a different place.

The fifth question lands deepest of all, because by then everything else has been said. By the time I ask what do I need to know, the person has emotionally cleared their throat. They are ready to tell me the thing they almost did not tell me.

Five questions. Three feelings, then a practical reset, then the deepest one. In that order. Every time.

What has you excited

Ask someone to describe what retirement looks like and most of them cannot do it. It is too hard. It is too far away. But ask someone what has them excited and they can answer that fundamentally. It is not off-putting. It is not confusing. They can feel it in the fiber of their being. No matter how hard life is going for someone, they can still point to something that has them excited.

Excitement is hope for the future. That is why this question goes first. You want to start from a positive place. Dan Sullivan says to start every meeting with a positive focus. Gino Wickman teaches us in EOS to start with one positive business and one positive personal. The psychology is heavily weighted here. Putting people in a positive mindset changes the way they think for the rest of the conversation.

Excitement is hope for the future. That is why this question goes first.

And notice the question matters. If I just said how are you doing, or what is going great in your life, I would not get the same answer. The specific words make people stop and actually reflect on what is exciting them, which most people never do.

What has you scared

Same idea. If I asked what challenges do you have, or is anything bothering you, I would not get as rich of an answer. Scared is an emotion we all share. Sometimes we cannot even name what scares us, but we can feel it, and when we name the feeling the answer comes.

If you want to know what your team is really struggling with, this is the question. If you want to find insights on how to lead them better, or how to protect and support your spouse, what a thing to ask. And what a thing to reflect on for ourselves.

What has you frustrated

This is completely different from scared. Scared lives on the threat and weakness side of a SWOT analysis. It is the thing being exposed. The thing you do not have an answer for.

Frustrated is the friction. The pain points. As leaders our job is to remove obstacles and barriers for our team so they can be the best version of themselves. The frustration might be a person problem. It might be technology. It might be that you forgot to give someone a raise and they feel undervalued. It might be that they simply have too much on their plate. Imagine the insight you would have about your team if you just knew, plainly, what was frustrating them.

Frustrated is the friction. Our job as leaders is to remove it.

What tools do you need to do your job

I always think about when my wife was working at a company. She would come home frustrated and say can you believe the CEO lets this happen. And I would ask her, are you sure she even knows this is happening. Have you actually had the conversation. No. Then how do you know.

Leadership is one of the loneliest things in life, because people do not want to share the pains and struggles they are carrying. I do not know what tools my team needs unless I ask them directly. We have to be very direct with this one. The answers always amaze me. Sometimes it is a day off. Sometimes it is access to a program they did not know they were missing. You will never guess it. You have to ask it.

Leadership is one of the loneliest things in life, because people do not want to share the pains and struggles they are carrying.

And remember the order. By the time you get to this one, the person has been feeling for ten minutes. They are not going to say nothing, I am good. They are going to tell you what they actually need.

What do I need to know

This is my personal favorite. Because leadership is lonely, and we genuinely do not know what is going on.

I cannot tell you how many problems I have solved through the answer to this question. People mistreating other people. Tasks not getting done. Things I never would have seen on my own. The answer to this one often takes time. People have to build trust before they will say it. Sometimes they have to be asked the same question many times before they are comfortable enough to tell you.

You can stretch it further. What do I need to know that I do not already know. What do I need to know that is going on in your life. I will often explain it to my team rather than just asking it, so they understand the door is genuinely open.

Three directions

I told you at the top that I ask these in three directions. Of myself. Of other leaders. Of my team. Let me show you what each one actually looks like.

With my team

This is where I started. Every quarterly review with every team member, these are the questions. I also use them in monthly touch bases with my integrator. I have built them into our rhythm so deeply that people on my team now expect them. They come prepared. And the answers I get in the third or fourth time I have asked are deeper than the answers I got the first time, because trust compounds.

With other leaders

I was just helping a leader work through an issue. He was stuck. He could not see his way through. And I realized in the middle of the conversation that the most helpful thing I could do for him was not to give him advice. It was to hand him a better question.

I use these questions two ways with other leaders.

The first way is to gather insight. When I am sitting across from a CEO at a nonprofit, or making small talk at an event, or having coffee with another business owner, these questions get me past the surface fast. Most leaders are not used to being asked what they are scared of. Most are not used to being asked what they are frustrated by. The moment you ask, you can watch them shift. They lean in. They tell you the real thing. You learn more about a leader in fifteen minutes with these five questions than you do in a year of standard small talk.

The second way is when a leader is stuck. I will hand them the questions and tell them to go ask themselves. Not me. Themselves. Because most of the time, the answer they need is already inside them. They just have not been asked the right question to surface it. What has you frustrated about this situation. What are you scared of here. What tools do you need that you do not have. What is the thing you are not telling yourself. The questions do the work.

Sometimes the most helpful thing you can do for another leader is not to give them advice. It is to hand them a better question.

With myself

Once a month I take a clarity break. If you have read Traction, you know what I am talking about. I get out of the office. I get out of email. I sit down with a journal. And I work the same five questions on myself.

What has me excited. I write it down. I want to see the hope I am carrying into the next month.

What has me scared. I write it down. I want it on paper, because once it is on paper it stops running the show from the back of my head.

What has me frustrated. I write it down. And then I ask myself what I am going to do about it. Because if I can name the friction, I can usually do something about the friction. Sitting in it is the problem.

What tools do I need to do my job. This one is humbling. Sometimes the answer is that I have been white knuckling a workflow that needs a real solution. Sometimes the answer is that I need help. Sometimes the answer is that I need to actually use the tools I already have.

What do I need to know. This is the hardest one to ask yourself, because you have to be honest. What is the thing I have been avoiding seeing. What is the truth I have been working around. What do I already know in my gut that I have not let myself say out loud yet.

When I am alone in my clarity break, I do not just ask myself this one. I ask God. God, what is it that I need to know that I do not know. What is it I need to search my heart for. Reveal it to me.

That is the question that surfaces the deepest stuff. Because the things I have been quietly ignoring are the things I cannot find on my own. I need help. Every time I sit with this question, something comes up. Not always something dramatic. Usually something I had been working around. But sometimes something I never would have seen without asking the One who already knew.

I started by asking these questions of other people. Over the last six years, the most valuable place I ask them is on myself. And the deepest one is the one I ask God.

None of this works without a safe space

Every one of these questions is useless if there is not a safe space for the answer.

With your team, that means they have to know you, like you, and trust you. They have to believe you have their best interest at heart before they will be vulnerable with you. And you have to show them an ROI. If they tell you about a tool they need, follow up and tell them why you could or could not get it. If they tell you something you needed to know, go back, thank them, and show them the action you took. If they share what has them excited, remember it, and share the reward and the success when it comes.

With other leaders, the safe space is your posture. You cannot ask another CEO what scares him while you are looking for ammunition. You have to ask it because you actually want to know, and because you actually want to help. Leaders can smell the difference.

With yourself, the safe space is harder. You have to give yourself permission to write down hard answers. You have to give yourself permission to be scared. You have to give yourself permission to be frustrated with someone you love or something you built. And then you have to do something with the answer. Otherwise the clarity break is just journaling. The break only works if you act on what surfaces.

These questions are useless if you do not ask them consistently, if you do not ask them with genuine interest, if you do not listen, and if you never follow up. That is true with your team. It is true with other leaders. It is true with yourself.

These questions are useless if you do not ask them consistently, if you do not ask them with genuine interest, if you do not listen, and if you never follow up.

Show your team an ROI on the answers they give you and they will give you better answers. Show other leaders that you are safe to be honest with and they will let you in. Show yourself that you will act on what you find in your clarity break and the clarity break will start to actually change your life.

How to make them even better

Once you have been asking these questions for a while, there is an upgrade.

Have you read Never Split the Difference by Chris Voss? Around our office we call it the Gospel According to Chris Voss, tongue in cheek. He was an FBI hostage negotiator. He spent his career figuring out how to get people to tell him the truth in the highest-stakes conversations on earth. And one of the things he teaches has stuck with me for years.

Voss says you should not ask questions when you can make statements instead. Questions put people on the defensive. Their brain hears a question and immediately wonders if it is being tested, if there is a right answer, if they are being judged. A statement does the opposite. A statement is an invitation. It says I am ready to listen. You decide what to tell me.

Stop asking. Start telling.

So once you have gotten comfortable with the five, try this. Stop asking. Start telling.

• Tell me what has you excited.
• Tell me what has you scared.
• Tell me what has you frustrated.
• Tell me what tools you need to do your job.
• Tell me what I need to know right now that I do not know.

Same five questions. Different posture. And the answers change.

When I ask what has you scared, there is a tiny part of the person's brain that hears a question and gets ready to perform an answer. When I say tell me what has you scared, that part of the brain quiets down. It is no longer an interview. It is an opening. The person leans in a different way. The walls come down faster.

Try it for a quarter. Compare the answers you get. I think you will see what I see.

Your turn

Have you used these questions before? I would love to hear how. Have you developed your own set of questions over the years? Tell me about them. Have you tried turning them into statements the Chris Voss way? Tell me what happened.

The whole point of these questions is the conversation they open up. So let's start one.

Live Intentional.

Greg Furer, Founder and Visionary