Learning to Learn and Confronting the Uncomfortable

When I graduated college, I got promoted from my job waiting tables to being a manager for a new restaurant the company was opening.

At 22, I was beyond excited to get an opportunity to be in a leadership position. Like most young folks getting promoted, I had a lot of confidence in myself.

At 22, I knew I had a lot to learn, but I assumed I would be great right off the bat.

“It doesn’t look so hard,” I thought.

As many of us are at 22, I was very wrong.

I remember my first dinner shift like it was yesterday. I was wearing a brand new suit and was projecting a lot of confidence. In reality, I had a solid stream of sweat dripping down my back. Brand new restaurant, brand new employees, brand new everything, and the staff was looking to me for help and guidance. If a customer asked to speak to a manager, they were getting a baby face 22-year-old trying to get his sea legs in a new position.

As we picked up steam in the middle of the shift, I remember the kitchen not getting orders out on time, I remember servers not being able to get drinks from the bar fast enough, I remember the brand new computer system not working smoothly. In the world of restaurants, it was a nightmare.

Every server needed help, every host needed help, everyone seemed to need help. So, I helped. I started helping servers take orders, bring drinks to tables, refill waters, run food from the kitchen. I was grooving, my confidence was on the rise. I thought I was really making a positive impact.

In the middle of this mayhem, I remember one of the members of the corporate team, Shane, asked me how many tables I had visited. I started listing all the things I was doing to support the staff. He was not impressed with my list of accomplishments. He told me I needed to go to every table in the dining room and make sure they were happy.

I went to a couple of tables as instructed. My goodness it was awkward. I had gotten used to chatting with guests as a server, but walking up to a table cold scared the ever-living shit out of me, even when things were running smoothly. Anyone who has opened a restaurant or started a  business knows that things do not run smoothly on opening night. After a few visits, and more sweat, I fell back into helping all the servers and busboys running around the dining room.

Shane came back a little later and asked how all the tables were that I went to. I told him I was so backed up helping everyone and that I had only gotten to a couple of tables. He reminded me – in no uncertain terms – that my job was not to be an extra set of hands, but to make sure the guests are happy and the only way to be sure is to talk to every table.

At 22, I took the critique and carried on. I went to more tables, but I was annoyed. I remember thinking that I had been working my ass off, but that clearly that was not enough. I was helping get all these guests fed, and if I weren’t there, it would have gone slower! How did he not realize how much I was doing?

I still remember this first shift vividly, not because it was a messy opening night. Not because I had my confidence knocked down a peg by a superior. Not even because I had a harsh realization that I knew far less than I thought. I remember that night because Shane was 100% correct. My job was to support the staff, but that was only one part. As a manager, I needed to see the big picture, not get bogged down in the weeds, and get comfortable dealing with customers who are having less than a stellar experience.

When I was overwhelmed, I fell back on what was comfortable for me. In an effort to look like I knew what I was doing, I focused on the easier tasks I knew I could handle. Shane helped push me out of my comfort zone and I have learned that what makes you the least comfortable is probably where you need to focus your energy the most.

“Fear cuts deeper than swords.” – George R.R. Martin

This lesson plays out in business and in life, far beyond the restaurant industry. It took a lot of awkward table visits before I felt any type of confidence in a crucial part of my new job.

We all fall victim to reverting back into comfortable habits when things get tough. We might even have the attitude I had to start. We think we know everything, we think it’s easy. The reality is, sticking to tasks that seem easy to us doesn’t promote learning and it doesn’t encourage growth. Often we don’t surround ourselves with people who will give us blunt feedback the way Shane gave it to me.

We also fall into the habit of feeling accomplished because we feel busy. I was pissed that Shane seemed to be busting my balls while I was busting my ass trying to please guests.

The reality was that I did not know how to best serve the guest and fell back on what I was comfortable with instead of developing new skills.

These are not easy lessons to learn, 22-year-old Jeff certainly did not internalize this lesson for some time.

Maybe you are very well tuned to your own strengths and weaknesses. Maybe you know which areas in your life need some attention and improvement. However, I personally, had no idea how much I didn’t know and was patting myself on the back for a job well done in my state of oblivion.

So, what can we do about this?

It is good to have confidence in our abilities, trust that we will do the right thing. But, it is just as important to recognize where we can make strides to become well-rounded in the work place and outside of it.

If I could go back in time, I wish I had sought out someone like Shane to ask for advice about the components of what makes a good manager. It’s not easy to ask for someone to critique you, but if we leave it up to ourselves, that lack of constructive criticism can lead to staying busy with menial tasks and patting ourselves on the back (like I did) for not pushing ourselves to be the best we can be.

In case it isn’t obvious by now, I learned a lot from that early professional experience. It was humbling.

I learned I needed to seek out feedback and mentors since they are fewer and further between when we leave the safe confines of college.

“True intuitive expertise is learned from prolonged experience with good feedback on mistakes” – Daniel Kahneman

And, just like how you have to lift weights that are a little heavier than you are used to to get stronger, I learned that I needed to push myself out of my comfort zone and tackle situations with challenging customers to get better at it.

These are lessons that can be applied right away and that I wanted to share with you.

When was the last time you asked a supervisor, friend or colleague to give you some honest feedback about your performance?

When was the last time you pushed yourself to do something that caused the sweat to run down your back the way it did for me during the restaurant’s opening night?

Drop a line in the comments. I’d love to hear about it.

Are you listening?

“You know, in marriage, the most important thing is you’ve got to listen.  A lot of wives complain their husbands don’t listen.  I’ve never heard my wife say this.  She may have.”

That is one of my favorite jokes by Jerry Seinfeld.  While that bit makes me laugh every time I hear it, the message really isn’t funny.

Whether talking to my boss, brother, father or friends, I hate the feeling of having what I say fall on deaf ears.  I know my girlfriend loves it when I don’t remember a detail from our conversation the previous day.

Now, you are probably thinking, “I don’t need to read this, I am a great listener!”

You are not alone.  Accenture published a study in 2014 of 3,600 business professionals worldwide.  The subjects were evenly distributed by age, gender and salary. 

Guess what percent of those subjects said they were “good listeners?”

Seriously, stop reading for a second and take a guess.  I’ll wait…

Okay, ready?

96 percent claimed to be good listeners.  96 percent!!!!!

Did you hear that?

Of course you did, 96 percent of you are such great listeners.

I don’t know about you, but far more than 4 percent of the people I know could use some work on their listening skills (myself included).

It’s important to examine why we are not as good listeners as we think, and develop skills and tools to improve.

Let’s begin with the why.

Daniel Kahneman, Nobel Prize winner in Economics, sheds light on this problem in his book Thinking, Fast and Slow.  Kahneman explains that our brain has two modes of thinking: “System 1” thinking is instant, unconscious, emotional and intuitive, while “System 2” thinking is slower, rational and more deliberate.

We face so many situations throughout our day and make judgments constantly.  We rely on System 1 to make up our mind on things like, not even thinking to order tuna for lunch because you hate tuna, or not walking down a poorly lit alleyway at night while you are alone because it doesn’t feel safe, or thinking the new guy at the office, Sam, is mean because he was not friendly when you were introduced.

Wait a second. System 1 leads us to believe that Sam is a dick because of one bad interaction?

Maybe Sam was having an off moment, maybe Sam was overwhelmed with his new surrounding, maybe Sam is under the weather.  The possibilities are endless.

System 1 is capable of betraying us if we are not careful.  System 1 wants to make quick decisions, often without complete information, and can lead us to conclusions that are unsubstantiated.

What does this have to do with listening?

In conversation, System 1 does a great job of making us think we have everything figured out.  This is illustrated by the fact that we are rarely stumped.  System 1 allows us to have intuitive knee-jerk reactions to everything.  When was the last time you or someone you know said, “I really don’t know enough about this topic to have an opinion.”

Not often, right?

This can be very dangerous when it comes to conversation and reaching any kind of understanding with people who don’t share the same feelings we do.

What can we do about this?

We can start by not immediately judging what someone says to us.  This is not easy.  Kahneman goes to great lengths to explain how powerful System 1 is in our lives.  It is often difficult to see how irrationally we react to things without a complete set of information.

Imagine someone asking you, “Do you know everything there is to know about everything?”  You would probably laugh in their face.  Of course you don’t know everything, none of us do.

“The more I learn, the more I realize how much I don’t know.” 

That was Einstein, by most accounts, a pretty smart dude.

Keep your ears and eyes open. Every moment is an opportunity to see the world from a new perspective.
Keep your ears and eyes open. Every moment is an opportunity to see the world from a new perspective.

If it is so obvious that there is so much we don’t know or understand, why do we frequently act like we do in day-to-day conversation (or online banter)?

This is where System 2 comes in handy.  System 2, the analytical part of our mind, needs time to process information to reach a conclusion.  We can practice paying attention to situations where System 1 is jumping to irrational conclusions, exercise restraint, and allow System 2 do it’s thing.

Truly hearing someone through is becoming harder and harder in our world of bite sized information, tweets, headlines and Facebook arguments.  With such limited information, all of our System 1’s are racing to judgment and making assumptions left and right, while our analytical System 2’s are getting lazy.

It is easy, and even feels good, to follow your intuitions as opposed to confronting them.

Don’t get me wrong, System 1’s intuition can be valuable and makes navigating this ever more complex world of ours a whole lot more manageable.  However, if we blindly trust our intuition without ever questioning our own assumptions (or of those around us), we miss out on the opportunity to learn and find common ground.

How can we help ourselves accomplish this?

Shut up.  Seriously, shut up and listen.  Stop interrupting and try to withhold judgement until you have heard someone through.  They may be completely wrong, but more often than not, the truth lies somewhere in the middle.

When I say “listen,” I do not mean simply wait your turn while you are formulating your response.  Really hear what the person is telling you and respond to what they are saying.

Make eye-contact.  Besides helping you focus on the person you are interacting with, this is a simple sign of respect.  We have all been there, talking to someone while their eyes wander all over.  It is frustrating to be on the receiving end, and quite frankly, it’s pretty rude.

Maintaining eye-contact can be a bit awkward at first.  However, it is amazing how much more you retain and how improved the connection between the person you are talking to is when you look them in the eye. 

If you struggle with this, try focusing on one of the person’s eye at a time.  Sounds a little weird, but it has worked for me and is a good trick.

Ask a question.  Sounds obvious, but asking a follow-up question about what the other person just said is a great way to retain information and show you are paying attention.

Summarize.  This is similar to asking a follow-up question.  As we have established, our System 1 (quick, reactionary part of our brain) likes to jump to conclusions.  It is so easy to misunderstand someone and miss their message.

To avoid this mental landmine, summarize what you have taken away from the conversation and let the person confirm.

“So, you are saying….?”


“Would I be right to say your point is….?”

Being an active listener and being open-minded are skills that require practice.  Our brains like to play tricks on us and love when we stick to our guns.  Luckily, we have opportunities all around us to practice.

There is a consistent message that our society has never been more divided and stratified.  Regardless of your point of view, becoming a better listener can make you more approachable, likable, connected and most importantly informed.  Really hearing and understanding each other can begin to bridge this societal divide.  Better listening can help us be a better friends, mothers, bosses, sons, employees and better people in general.  And that is something worth striving for.

So, just one more question.  Are you listening?