Avoid Boring People

I have discovered the best book title of all time.  

It’s James Watson’s Avoid Boring People.

It also happens to be one of the best ways to have better conversations.  

Avoid boring people.  It’s a useful mantra with a powerful double meaning.  The first meaning is as simple as seeking out the people you find interesting.  To avoid spending time with boring people sounds harsh, but it’s a valuable practice in how we invest our time.  Jim Rohn famously wrote, “we are the average of the five people we spend the most time with.”  If that is true (and it is) then we are the average of the five people with whom we talk most.  If we surround ourselves with interesting people with which to talk, our conversations, and ultimately our lives get better.  

The real magic is in the second meaning--in reading “boring” as a verb. 

Do not bore people.  That might sound high pressure, but it’s table stakes for having better conversations. There are many ways to avoid boring people, but here are five techniques you can use immediately to avoid boring people.

1. Be interesting

Choosing interesting people to have most of your conversations with is a great first step.  It increases your chances of having a better conversation, but it’s not enough.  We must take personal responsibility for not boring the person we are in conversation with.  People often struggle with calling themselves interesting, but it remains crucial to lifting our conversations.  

The most direct path to being interesting is to begin with being interested. It’s difficult to fake curiosity.  If you want to know more about your partner, you will ask questions.  By leading with curiosity and practicing asking high-velocity questions, your conversations will improve steadily day after day.

Another way to be interesting is to tell stories. By now you have no doubt read about the power of storytelling to stick in the minds of our audience.  Sharing brief stories in a conversation adds life and memorability to your conversation.

One final way to be more interesting is to utilize the power of specificity.  Provide details.  To understand the power of adding specifics, it is helpful to imagine a conversation with none. 

Partner: I had this amazing wine last week.

You: Oh yeah, what was it called?

Partner: Ugh...I don’t remember.

You: How did you discover it?

Partner: The man at the wine store recommended it. 

You: zzzzzzzzzzzz

I don’t know about you, but that is not the kind of conversation I want to have.  I want my conversations to crackle with life.  That conversation was boring because of the lack of specificity.  No wine name.  No tasting notes.  No description of the store.  I could go on and on.  You have had a conversation like this, and I am certain that it was brief.  

2. Listen better

Let your partner hear you listening. That’s right, when you are not waiting for your turn to talk, or redirecting the question back to you, the person in your conversation can hear you listening.

This is subject for an entire blog post, but for now, just listen--you don’t need another question at the ready until the person with whom you are speaking is done talking.  Often, by the time my guest is finished talking, I will ask an entirely different question than I originally thought I might.  Sometimes the final words or even the inflection of someone’s voice prompts me to ask a certain question.  This is only possible when we listen fully to what our partner wants to share. 

3. Make your conversation a performance

The best meals, the best dances, the best romantic experiences of our lives, all take on some level of performance.  A heightened form of reality.  A wonderful conversation should be no different.  On a podcast, the presence of the microphone automatically raises the stakes because you know an audience will eventually hear your conversation. I want to encourage you to have conversations where there is an invisible microphone in front of you.  At first this might sound inauthentic or like pressure.  I want you to think about it more like play.  Author Cathy Salit describes this idea as “being who you are and who you are not yet.”  I love this idea for helping to transform our conversations.  

Most of your conversations will not be recorded and played on a podcast for the world to hear, but I bet that when you think back on some of the most fulfilling conversations of your life, you wish they were. 

To avoid boring people:

1. Find interesting people

2. Be more interesting 

3. Listen better

4. Make the conversation a performance

High-Velocity Questions

One of the most effective ways to transform conversations and supercharge learning is to get in the habit of asking what I call high-velocity questions.

A high-velocity question asks one thing but accomplishes multiple things. It can set a tone, make the guest think, and even add an element of surprise for the guest and the audience.  

By its nature velocity is urgent; it’s on its way somewhere and fast.  Velocity does not rush, it simply moves with purpose. When an object moves with velocity and meets something on the end of its path, dramatic, often surprising things can happen. That’s the life I want crackling through my conversations.  

Unfortunately, I do not hear a lot of high-velocity questions.  What I have found in listening to thousands of interviews in the last 10 years  is that very few hosts ask questions that demand urgency, and even fewer ask questions that go somewhere fast. 

Here’s an example that will illustrate velocity differences:

Recently I heard a host open his podcast conversation with this question: “how did you go from working on Wall Street to becoming a professional miniature golfer?” 

This is a low-velocity question. It can be argued that this question is going in a direction, but it will not get there anytime soon. In effect the host is asking for his guest to tell the story of his entire professional journey. Depending on the detail the guest wants to use in telling that story, the entire conversation could contain this one question only.  Paradoxically, the host initially might be pleased because he is getting his guest to talk, but in reality he has lost control of the conversation. When it will be his turn to ask another question remains unknown. 

The question above is not a bad question.  It invites the guest into the conversation with very low stakes.  It gives him freedom.  It will never fail.  But we can do better.  

Imagine what would happen if this same conversation opened with a high-velocity question such as: “what did your wife say when you told her you have decided to become a professional miniature golfer?” There is no expecting this question, and yet it travels in the same direction that the host hopes the conversation will go.  This question is creative and original, but it’s more than that.  This question cannot be prepared for.  It demands that the guest go to his memory and pull out an anecdote that will often surprise and delight him. It gets the guest to think about the situation in a new way while getting right to the center of the journey that the host hopes to take the guest and the listening audience on. 

If your first reaction to this question is that it is too artsy, too abstract, too something,  I understand. This type of question takes time to craft, and it must be scripted.  Since it is the first question of the interview, fortunately it can be.  If it still feels too daunting though, consider a high-velocity version of the host's original question that alters just one section: “When did you know that you were going to go from Wall Street to becoming a professional miniature golfer?” You can hear the difference in the question.  Imagine the difference it will produce in the guest’s answer.  A why or how question is more common in this situation, and admittedly it will allow more elaboration, but it is not better.  Asking when in this spot creates a focused lane for the guest to travel with his answer, and that’s a good thing.  Creativity and discovery flourish in situations where constraints are carefully placed.  

I would like to share an example of a high-velocity question I asked recently on my podcast.  It too opens our conversation.  The first question of a conversation is not the only time to ask a high-velocity question, but it is the best time.  Opening with a high-velocity question lets the guest know that this will not be the typical conversation and forces the listener to sit up a little straighter in his or her chair. 

Graphic design by Stewart Hillhouse

1% Better with guest Michael Gervais March 29, 2020

I began our conversation by asking:  “I'm 42 years old and in 15 days, Mike, I will be skiing for the first time. I'm in reasonable shape. Some people will blink at that. What do I need to know about skiing for the first time at the age of 42?”

This was the first question I asked Michael Gervais.  He would later tell me that he’s never been asked that question on air.  The fact that he had never been asked it before is not enough to make it a great question, but with limited time on microphones and on Earth, I believe that questions need to do more.  Let’s look at what this question does.

1. It’s unexpected.

2. I call him Mike.  The only reason this is worth mentioning is that prior to hitting record I asked him what he likes to be called.  This is a simple move to build rapport that would shock you to learn how many skip it.  I do it in my classroom, “Do people call you Alli?”  and I do it when I interview someone. 

3. It’s related to his expertise.  If I asked him about paintball or bowling, he would be seasoned enough to provide value in his answer, but it would not layer our conversation.  It would not cause Mike to audibly giggle and say “That’s a GREAT place to start because…” As I uncovered in the research prior to our conversation, Mike is an avid skier and outdoorsman. Giving advice on skiing isn’t directly related to getting better, but the mindset and techniques needed to survive the slopes is related. 

4. The question adds comedy. “I am in reasonable shape...some people will blink at that.” This self-deprecating jab will let regular listeners smile while not detracting from the actual question.

5. Leaves an impression on the guest.  With one question, look at all that he learns:

   1. I am 42

   2. I have a sense of humor

   3. I care enough to ask his preferred name 

   4. I did my research

   5. I asked a question he’s never been asked before

   6. I’m curious

The question has velocity.  For a question to have velocity, it needs to have speed (ideas per word) and direction (an idea that heads in a desired direction).  

And we still have 50 minutes left in our conversation.  That’s velocity.