"Representative!"

"Representative!"

When I think about my customer service experiences, I think about that word. Along with that word comes stress and frustration.​

I’ve yelled it into the phone too many times to count. I’ve lost patience listening to menu items, which seem to have always changed (so listen carefully!). I’ve rolled the dice and pressed “0” right away, hoping that it would get me to a human. I’ve waited on hold, been connected to a human, explained my issue and been hung up on, left to start from scratch.

I have pretty low expectations for customer service. I also have some insight into why they tend to be bad.

Early in my career, I somehow became responsible for setting up customer service for an online product. I was hardly qualified for the job, but I figured it out as best I could. I learned that there was a specific cost associated with every type of customer service interaction. The most expensive was speaking with a human. The cheapest was a self service option contained in the website FAQ's. In between were things like email support, social media support and early versions of online chat bots. The goal was to solve as many customer issues as quickly as we could at the lowest cost possible. Avoiding the high cost interactions and pushing people to the low cost ones even had a name. It was called "deflection".

We regularly looked at reports to see what new levers we could pull to “deflect” issues and keep costs down. Occasionally we looked at data related to customer satisfaction, but it rarely factored into any of our decisions. It was all about the money.

Eventually I moved out of that role and returned to my role as a frustrated customer. Having been on the other side of the curtain, I felt empathy for the people managing customer support experiences. I pictured someone in an office, staring at a spreadsheet, trying to figure out how to make me stop yelling "representative!".

Since then, Artificial Intelligence has grown and become more powerful. That growth gave me hope that soon I'd be able to get answers quickly. No more phone menu options or FAQs. Just a friendly, knowledgeable chat bot ready to help me out any time of day or night.

​But that didn't happen, at least it hasn’t yet. Aside from the most basic issues, I couldn’t get answers, many times being served up links to FAQ’s. I found myself typing "Representative!" instead of yelling it.

One day, I tried a different approach for a problem I was having.

I use email marketing software to manage this newsletter. I use a separate platform to manage my website. A newsletter sign up on my website was stored in a list managed by my website platform. Adding that person to my newsletter platform had to be done manually. Eventually the manual effort was enough for me to seek out a way to connect the two. I started by pouring through the FAQ's and help sections of both platforms. I couldn’t find what I needed. There was no phone number to call and email just felt like a black hole. I was spending lots of time on my problem and getting nowhere.​

At that time I was using AI to help me with all kinds of tasks. I thought “Why am I not using it for this???”

I typed in my situation and desired outcome. It returned the exact steps I needed. I followed them and minutes later my problem was solved. Since then, AI has become my customer support tool for just about everything. I only go to a company’s customer service for issues AI wouldn’t be able to handle, like checking on my specific account.

Why can't companies make it this easy?

I think part of it is that customer service is generally seen as a cost center, not a revenue driver. My guess is that customer service chat bots aren’t a big part of a company's AI investments. (If you have examples where CS is seen as a revenue driver, please share! I’m curious.)​

Another factor is complexity and the number of potential issues. A proprietary chat bot focuses on issues mainly within a company’s product. Many issues involve combinations of multiple products from multiple companies, like my newsletter sign up issue. The information is out there, just not in one place. Some of it may be in blogs or review sites. One company might have the info and another might not. Organizing all of that is a lot for a cost center and probably not high on the priority list. For AI, it’s easy. It can piece all of that together into a solution.

I think this is great. I just need my problems solved. How that gets done doesn’t really matter to me.

Thanks to AI, my customer service experience is so much better now. I’m hopeful again, but it didn’t play out in the way I expected.​

What about you? Have you had good or bad customer service experiences? Are you hopeful?

Last week I met with someone to discuss possible approaches for my book launch. During this meeting she asked me one of the best questions I've ever heard.​

"What's your favorite question?"​
​

To my surprise, I knew my answer immediately.

"How did you come to feel that way?" I said.​

That's it. That's my favorite question. Here's why.
​

It helps me get to the underlying reasons

When I'm interviewing a client or their customers, "I love that product" or "I hate that product" doesn't help me all that much. To figure out what to do next, I need the "why" not just the "what". If they love it, I can learn how to make it more lovable, or apply some of the same qualities to something they don't love. If they hate it, I can work on addressing the specific reasons for the hate.

​

The past is more reliable than the future

Asking someone what they would want isn't all that reliable. People might have an idea what they want, but that often changes if you put that thing in front of them. The past gets you the real story. You can work from there to address the bad and enhance the good.

​

It helps find common ground

This is a big one. Think about a time you disagreed with someone's point of view. Did you immediately share yours or start to tell them why theirs was wrong? Or did you just walk away and check that person off the list of people you will interact with? "How did you come to feel that way?" gives you a chance to find common ground. I'm a lifelong New York Yankees fan. The Boston Red Sox are the Yankees' arch rivals. I can see someone wearing a Red Sox jersey at a game and immediately tell them their team sucks (which they do, btw!). Or I can ask how they came to be a Red Sox fan. Maybe I find out that their dad took them as a kid and they got to meet a player once. Maybe that same thing happened to me. Now, despite our differences, we’ve found some common ground.

It builds connection

Similar to common ground, "How did you come to feel that way?" creates an immediate connection. Chances are, they've never been asked. There's likely a story behind it. You get to learn that story and maybe share your own.

The wording matters

As much as I'm a fan of them, questions that start with "Why?" are often viewed as accusations or criticisms. Most of it has to do with tone or familiarity. There's a big difference between "Why did you do that?" in an accusatory tone vs "Why did you do that?" in a curious tone. Pivoting to "How did you come to feel that way?" or even "What led you to that decision?" moves the question into curiosityville.

There you have it. That's my favorite question and how I came to feel that way. I have a friend who starts conversations with "What are you looking forward to?", which is another good one. Even a simple "How are you feeling?" moves past the almost rhetorical "How are you?" or "How's it going?".

What's your favorite question?

How many times have you entered a Monday morning meeting and been greeted with "Happy Monday!"?

I'm not sure where the phrase came from and ChatGPT didn't seem to know either. I've been on the receiving end of many a "Happy Monday" in my career. I've even delivered a few (though I'm not proud of it).

It seems like a relatively recent phrase, something that gained traction over the past 5-10 years. Maybe it started as a way to counter the feeling of dread some people experience at the start of a new work week. Maybe it's like smiling to force a mood change when you feel down. Maybe it showed up around the same time as the famous quote from the movie, Office Space "Sounds like someone has a case of the Mondays". Maybe it’s just something to fill in awkward silences, like talking about the weather.

However it started, I’ve always thought it was a strange thing to say. We don't say "Happy 4 o'clock!" or "Happy June!". Why Happy Monday?​

Monday isn't alone. Friday gets the happy tag too, but I kinda get that one. Friday is the kick off to the weekend and people generally look forward to weekends. “Happy Friday” feels just close enough to “Enjoy your weekend” that I can get behind it. I've also experienced the rare Happy Tuesday, Wednesday or Thursday. Those make no sense. We should stop those.
​

I never know how to respond to a Happy Monday.

​

"Happy Monday to you too?"

"Thanks?"

Usually I say something like “yep, here we are…”.

I know the person saying it has no ill intent. They mean well. I just don’t know what to do with it. I freeze up.

If I have time, I’ll try to strike first with a quick “How was your weekend?” or “How are you feeling today?”. I like those because they can lead to some conversation. We can connect a little. We can learn if our Mondays are, in fact, happy.

I’m not trying to knock the Happy Monday fans. We all say some strange things at work. We circle back and run things up the flag pole. We try to move the needle without boiling the ocean while we all think outside the box.

I’m not sure how to wrap this post up so I’ll need to take it offline while I get my ducks in a row.

I’ll just leave you with one question.

When did Monday become so Happy?

​"A wise old owl lived in an oak.

The more he saw, the less he spoke.

The less he spoke, the more he heard.

Why can’t we be like that wise old bird?"

​
The first time I heard this I was sitting in my living room, enjoying a glass of wine and good conversation with some family. My niece and nephew were two and three at the time and we had the "Little Baby Bum" youtube channel on to keep them entertained. The channel plays an endless string of mesmerizing musical nursery rhymes.

Most of the rhymes were just background noise to me, but one of them made my ears perk up. It was about the wise old owl - the one living in an oak. I stopped and replayed the song a few times. I was blown away by the wisdom and simplicity of it. "The more he saw, the less he spoke. The less he spoke, the more he heard." 🤯🤯🤯

It brought up images of Yoda and Mr. Miyagi, who both seemed to always be listening and paying attention to everything, occasionally offering wise old owl level insights.

​
It also reminded me of my father, who'd recently died. My dad was a world class listener. He’d ask a question and wait patiently for the answer, then listen to it. He was totally fine with silence. He never seemed to feel the need to fill it with anything.

Not everyone is like my father, Yoda or Mr. Miyagi. Most of us feel compelled to solve, story swap or disagree as soon as there's a millisecond of silence.

I've been guilty of politely waiting for the other person to stop flapping their lips so I can say my thing, which may or may not be related to their thing.

I bet the wise old owl would be a great innovator. Instead of raving about his ideas for upgraded nests, he'd listen and observe how nests are used. He'd learn about unmet owl needs. Then he'd design a nest that addressed real owl issues.

The nursery rhyme has been stuck in my head (again) ever since I thought about writing this post, and I'm constantly thinking about new settings where it would be a superpower.

What do you think? Did the wise old owl have it all figured out?

Btw, if you want, you can check out the nursery rhyme here. Warning, it might be stuck in your head for a while

An old colleague and friend of mine was an excellent photographer. One day, he showed me his website. He had beautiful photos of family, friends, nature. Every one of them looked professional.

“What’s your secret?” I asked.

“It’s all about the camera and the lens.” He said.

This was 2010 and the iPhone camera was still pretty bare bones - incapable of doing anything close to what he was showing me. I picked his brain some more. What kind of camera? What kind of lens?

He had a wealth of photography knowledge and recommended a sleek looking Nikon D5000 with a Tamron lens. I clicked the buy button and waited eagerly, thinking about all the amazing photos I would take.

When the camera arrived, I carefully opened the box and held the camera in my hand. It was heavy. The kind of heavy that means something is really good quality. I attached the lens and the shoulder strap. I put it around my neck and pretended to snap away like a fashion photographer.

I examined it more closely. There were dials, buttons and knobs. All of them were labeled in a language I didn’t understand. I couldn’t wait to learn how to use it. Excited about my new toy, I put everything into the travel case and placed it on a shelf in my closet. Tomorrow I’d start watching Youtube videos and taking practice shots.

A week went by. Then another. Every time I promised myself I’d start to learn, I lost motivation. Sometimes I’d take it out of the case and take some pictures. I adjusted the buttons and knobs, clueless about what they did. Along with not knowing how to operate the camera, I also couldn’t come up with a reason why I would operate the camera. Other than, “take better pictures”, I had no real use case to get me started. 15 years later, my Nikon D5000 is still sitting on my shelf, collecting dust. What happened?

What if I’d bought the camera for a more specific purpose? What if my main use case was something like taking photos of my kids during swim class at the poorly lit local pool? Surely there was a setting somewhere for low lighting that could capture action shots without being blurry. A use case like that would have given me specific motivation to start. I could have learned how to solve just that problem. I bet that would have led to me learning more.

That feeling of not knowing where to begin or why feels very similar to what I hear from many people about AI. People have been told by their companies to use AI to make things more efficient. “Find all the tasks you can do with AI!” Leaders have invested millions in new tools but remain quietly frustrated about low adoption rates amongst employees. People stare at the ChatGPT prompt box, unsure what to type.

Most companies attack this problem through training and mandates. Training is definitely important, but is there a missing piece? What if we found specific reasons and use cases first, then moved into targeted training to address just those use cases?

It seems overly simple to order things this way, yet the approach is often rejected. “Too time consuming” or “We’ll end up using AI anyway” are some common reasons.

What if there were a simple way to find the use cases? What if you could do it in 20 minutes?​

Here’s a method I’ve tried. It won’t help you merge millions of data points or develop powerful predictive models, but it will help people get unstuck.

Step 1: Unpack​
Write down all the tasks you do - individually or with a team. Use stickies or a virtual tool like Miro or Mural. One task per sticky. For this part, you can look at the calendar over the last week, project databases, to do lists - anything that helps you remember all the things.​

Step 2: Plot

Create a quick 2X2 grid that looks like this:​

Plot each task where you think it belongs on the 2X2. Work quickly and don’t worry about being perfect.

Step 3: Categorize

Once all the tasks have been plotted, overlay these categories on each quadrant.

Step 4: Review the grid

You should now have some tasks that can be eliminated, some that can be left alone and some that are prime candidates for AI. Instead of just finding tasks, you will have taken things one step further and found use cases.

An exercise like this might have helped me learn how to use my camera. Who knows? Maybe it would have shown me that I didn't really need a camera, but something else. Wherever it led me, it was probably worth 20 minutes of my time.
​
What do you think?

Think about a decision you made recently - something that didn't have an obvious choice.

For me, I had to decide if I would publish this post or not. I think it will be interesting to read, but I have no way of knowing for sure. I can only work with the information I have. People have told me they enjoyed reading previous posts. I enjoyed writing this one. Those are good indicators. Still, I'm taking a chance.

We make decisions like this every day without any way to know exactly how they'll turn out.

After I write this I'm going to do some work to help me see if it was a good decision. I'll send it through my newsletter. A few days after that, I'll post it on LinkedIn and Medium. I'll tag people I think might like it. I'll make sure to respond to any feedback and comments along the way.

The work I do after the decision has a lot more lasting impact than the decision itself. I might learn that it doesn't really resonate with people. Or maybe it does. That will be new information I'll consider when writing my next post.

I had a boss once who was very involved in the day to day. He always asked questions and wanted to know the latest information. He was also known to change his mind - a lot. One day something was the top priority and a week later it was something else.

Many of us would complain behind his back about all this zig-zagging. It was frustrating to work that way.

During a team meeting, that boss seemed to sense our frustration. He paused for a moment and said, with no anger or accusation in his voice, "I reserve the right to change my mind when I receive new information."

Since then, I've always questioned whether decisions on their own were that important. There's no way of knowing exactly how a decision will play out. It's a best guess based on the information available at the time.

Throughout my career, I've watched people and teams, including myself, overvalue decisions.

Many organizations do hierarchical decision making. Teams discuss something and gather information. After that they "run it by leadership". This involves getting a sliver of time in some upcoming "leadership meeting" which might be weeks away. The meeting eventually rolls around and the ship of leaders makes a decision based on incomplete information.

Decision in hand, the team forges ahead to carry out that decision. They'll do the work to make it a "right" decision, but they'll be closed off to any new information that might warrant a change in direction. If there is any new information, it means getting another sliver of ship time in some future meeting. The cycle of uninformed decisions repeats, with teams sitting around and waiting in between.

I've also worked with teams where decisions weren't the top priority. Instead, they were a way to figure something out - more like a hypothesis or experiment.

Those teams make faster, smaller decisions, using what they learn between each one to inform the next one. It's like dribbling a soccer ball across a soccer field to score a goal. They can course correct over and over and give themselves a great chance of scoring. Hierarchical ship decision making is like winding up at one end of the field and trying to blast the ball all the way to the goal at the other end. It might go in, but there's no chance to course correct if it’s offline.

Teams that dribble the ball usually have leaders that either get directly involved or get out of the way. They work faster and more efficiently, resulting in far more breakthrough ideas and goals reached. They lower the stakes on decisions and prioritize the work in between each one. They get closer to "right" much faster, through iteration and learning. To them, decisions aren't that important.

I'd love to know what you think about this idea so I can factor it into my next post.

Are decisions that important?

When I talk to clients, the number one thing on their minds is artificial intelligence. It’s in every roadmap, every mission statement, every agenda, every performance review. I even saw it on a water bottle label.

“Natural Spring water, infused with AI”.

Not really, but I bet you can see it, right!

Learning & Development teams are feeling pressure to upskill their workforce on how to use AI. Client facing teams are feeling pressure from their clients to figure out how they should be using AI. Leadership teams are conflicted about where to place focus and budget. People at every level of the organization are feeling it. It’s a race. For most companies, the starting line is in the form of investments, training, mandates or even job elimination. The desired finish lines include efficiency, faster times to market, higher margins, bigger innovations or just survival. The road in between is paved with conflict and uncertainty.

I believe that with a slight reframe of these challenges, clarity can be found.

What if we shifted our mindset from “What can we do with AI?” to “What problems or opportunities do we have?”

It seems small, but the words matter. “What can we do with AI?” starts with the solution and tries to work backwards into problems. “What can I do with a hammer?” starts with a solution and does the same. AI is infinitely more powerful and flexible than a hammer, but the principle still applies.

In April of 2025, Micha Kaufman, CEO of Fiverr sent an email to his employees.

“It does not matter if you are a programmer, designer, product manager, data scientist, lawyer, customer support rep, salesperson, or a finance person—AI is coming for you.”

AI will undoubtedly be able to do many of the jobs currently done by humans, but what if statements like this were problem focused? What is the current problem with the job a programmer does? What about the other roles? Are they doing a bad job? Are they making customers unhappy? Instead of job elimination, what if we focused on problem elimination? Cost, time and market competition might be problems, but what are the problems behind those problems? “AI is coming for you” implies that you are the problem.

Starting from problems and working outward doesn’t mean AI won’t be the solution. In many cases it will be. The reframe provides focus. It gives leaders a much clearer starting point for investment decisions. It gives teams clarity on what to work on. It meets AI beginners where they are.

AI can play a role in identifying those problems. Artificial Intelligence has the capacity to analyze more information than a human ever could. It can pore through years of sales data and find patterns a human couldn’t. The AI fluent can focus their problem finding efforts there.

Along with every other human, AI beginners have a lifetime of lived experiences. They can share specific interactions with customers and recall the tone, body language and behaviors of those customers.

This pairing provides important guardrails. Instead of searching for things AI could do, it puts the problem at the center, with AI in the pool of possibilities for solving that problem.

This reframe does require a little bit of patience, trust and courage, but I’ve seen it pay off. I’ve watched skepticism transform into relief during workshops with clients. It also allows everyone to participate. It moves from the subjective to the objective. If teams can agree on the problems, they can start to see all kinds of possible solutions, many including AI - just with more focus.

I heard a quote recently from an AI expert that I wanted to weave into this post, but it’s so concise, I think it stands alone:

“AI can write a sentence but it can’t read the room.”

My seven year old daughter recently asked me if anyone in the world could speak every language. I paused. I didn't think anyone could. That seemed impossible.​

Then I second guessed myself. Was it possible? I quickly scanned my mental file cabinet for some kind of clue. Maybe I saw something about it on Jeopardy? Maybe a spelling bee champ went on to learn every language? I found nothing in my mental files, but I didn't want to shoot down my daughter's question so I said I wasn't sure.

She looked at me and made a curious face. "Hmmm... how could we find out?" Her second question sent us off on a curiosity mission.​

How could we find out?

Instead of Googling it or asking ChatGPT, we started by thinking about how many languages there might be in the world and how we might figure that out. How many countries are there? How many languages might be spoken in each country? Could the United States be a good proxy since so many people speak so many languages in the US?

As we did this, I felt a little bit ashamed. I would never have had the courage to ask a question like that. Instead I'd be doubting myself.

What if the answer was too obvious?
What if someone actually could speak every language, and I'd somehow never heard about it?
Was it even possible to do?
Was it just too ridiculous to ask?​

My seven-year-old daughter had none of those concerns. She just wondered, so she asked.

I thought about times when I was in a work meeting and didn't understand something, but refused to ask, assuming I was the only one. I recalled conversations with people who referenced something I'd never heard of. Instead of asking, I just let it go, figuring I'd eventually get some kind of context that would tell me.

My daughter and I talked about her question for a while. We never really got to a definitive answer, but by the end of our mission we both agreed it probably wasn't possible for someone to speak every language.

I loved how genuine the interaction was. I also felt sad knowing that in a few years, her unfiltered curiosity would probably fade. Self consciousness will creep in during the teenage years. As an adult, she'll feel like she should already know the answers.
​
But, what if she kept that same childhood curiosity? What if everyone did? What if assumptions went away? What if experts asked instead of told?

What if...?

Think about someone cool. Maybe a friend, a classmate, a relative, a celebrity. What made them look cool?

I'd never really thought about this until I took my first surfing lesson.

I was at a work conference in, of all places, Hawaii. I generally find the big, convention center conferences a waste of time so I seek out smaller, more intimate ones where I can learn and discuss things directly with others in my field. This one just happened to be in Hawaii, so how could I not go?

The first day was everything I'd hoped for. Despite my jetlag, I was fully engaged and couldn't write fast enough in my notebook all the ideas I wanted to bring back after.

The morning of the second day was open and we were encouraged to explore the area. I decided to take a surfing lesson. I'd never surfed before. What better place to start than the white sand and blue water of Hawaii?

I showed up at the location with one other brave conference attendee. There was a tiny beat up shack near the beach with some sand covered surf boards leaning against it. It seemed like the meet up spot.

A tall, thin man in board shorts and a rash guard shirt emerged with a cup of coffee in his hand. "I'm Lenny. You guys doing the lesson?"

Aside from being a bit older than I expected, Lenny looked exactly the way I pictured a surfer. Long, sun bleached hair. Tan, leathery skin with faint, sunglasses-shaped stripes wrapped around his eyes.

He handed us our own rash guards and pointed us to two surf boards laid out on the sand. We told him neither of us had ever surfed before. "OK, let's go over the basics", he said.

"The most important thing to remember when you are surfing is to look cool."

We both laughed, figuring this was his go-to surf instructor joke. His face didn't change. He was serious.

Then he proceeded showed us the basics - how to lay down on the board, where to place our hands and feet and how to paddle. He showed us how to pop up on the board by placing one foot forward and swinging the other through. Then came the "look cool" part.

"When you pop up, keep your eyes on the shore and your knees bent. Do it cool."

There was that word again. I wanted an actual lesson, but he kept talking about looking cool. What did that even mean? Why would I worry about looking cool as a first time surfer just trying not to fall off my board?

I ignored the cool part and focused on the handful of actual surfing advice he gave.

We walked our boards out to knee depth, hopped on our bellies and paddled out. He swam effortlessly alongside, talking about everything but surfing. He'd been in a band. He moved here from San Diego a few years ago. His son had just graduated from college.

I wondered how that information would help me surf.

He spotted the first wave and pointed me toward the beach. When it got closer, he told me to start paddling, then gave my board a firm push. I paddled as hard as I could.

"Pop up!"

I tightened every muscle, swung one leg forward under me, the other leg in front of that one. I gritted my teeth and tried to lock my body to the board. Then I fell off. The board flipped over my head and the strap attached from the board to my ankle pulled me in every direction. I'd failed my first attempt. I gathered my board and proceeded to paddle back out to Lenny.

"You gotta do it cooler, man!"

That's it? That's what you tell me?

I was annoyed and wondering how I could get my money back or find a different instructor when Lenny pushed me into the next wave. Same result. I fished my board out and paddled back to Lenny.

"Look man, when you pop up, keep your eyes on the shore and do it cool."

I ignored him and stuck with my approach of trying to muscle my way onto the board, falling off every time.

Finally, mostly out of muscle fatigue, I tried it his way. I let my body relax, sunk into my stance, totally present in the moment, pretending to look cool. I cruised all the way to the sand and looked back at Lenny. He was pumping his fists in the air.

I paddled back out. "That was cool!" I said. Lenny high fived me and pushed me into the next wave. Another success.

After many more successful pop ups, I walked back to my hotel, trying to unpack what had just happened. I thought about cool people. Denzel Washington was cool, but why? The Fonz from Happy Days was cool, but why? Ken Griffey Jr. was. cool, but why?

Every cool person I could think of had three qualities. They looked relaxed, confident and fully present in the moment. They didn't seem to be worrying about the past or the future. Could it be that simple?

Supposedly if you smile, you instantly feel happier. Maybe coolness worked that way?

I've thought about Lenny a lot over the years. Every time I felt nervous about speaking in front of a crowd or trying something new, I've tried to do it cool. It helps me stay in the moment. It gives me confidence. It helps me relax. It's a surprising hack that's served me well.

Next time you are nervous about something, take Lenny's advice.

"Do it cool!"

I've had a roller coaster relationship with questions.

Sometimes I used them to show off what I knew, what someone else didn't know, or just to check the box of having said something. Early in my career I just didn't ask, figuring I was too junior. Mid career, I asked questions, but usually not my own, opting instead to regurgitate what the bosses were asking. As I became more senior, I felt compelled as a leader to have all the answers. Instead of questions I made statements, sometimes made up ones.

Throughout these ups and downs I had breakthrough moments where I let my guard down and just asked. Regardless of my level, I asked to go from not knowing to knowing. The collection of those moments led me to a career I absolutely love.

Here's one example of how a senior leader let their guard down and asked a question he didn't know the answer to. It was one of the moments that changed my career trajectory.

"I sat across the table from the CEO. His office was like a large living room with couches and paintings on the wall. I turned to page two of my roadmap for the year. As I began to speak, he asked me calmly, with no accusation in his voice, “Is this what our customers want?”

I froze and quickly realized that I had no idea what our customers wanted. I’d never asked. I’d never even considered the question. I couldn’t tell him why this thing was a good idea, except that other people said it was. Exactly what problem or need was it addressing? I had no clue.

At first I wasn’t sure what his motives were. He could have known the answer and wanted to see if I knew. In my experience, when someone reached the highest levels at a company, they seemed to have all the answers, always able to provide clear direction to the rest of the organization. I viewed that as great leadership. In my mind, saying “I don’t know” wasn’t part of the job description of a leader. Surely his question was a trap, but I took a chance and walked right into it, sheepishly admitting I didn’t really know if our customers wanted this. I could have made something up, but for some reason I didn’t. As I braced for the consequences, he followed with another question. “How can we find out?”

He didn’t know either.

I thought about how rarely I’d encountered this sort of pure curiosity from a high-ranking leader like him. Admitting to not knowing something requires a mix of self-confidence and vulnerability. I certainly hadn’t displayed that mix with teams I managed. When I didn’t know something I either made it up or talked around it enough to hide that I didn’t know.

The CEO had done something I couldn’t. After his question and my confession of not knowing, we discussed how to find out if our customers actually wanted this. The whole interaction could have easily been a him versus me situation, but instead it was him and me versus the problem. He said he appreciated my honesty and told me to do my homework next time."

Questions like his can be the doorway into new thinking. He simply wanted to go from not knowing to knowing, so he asked. It's something we all did as kids, but can slowly be engineers out of us as we enter the working world.

I've heard dozens of stories just like this from people at every level. Some who were like me, some who were like the CEO. What are your stories?

“Great news, I found an expert!” said Nancy. “Yes! Can’t wait to meet this person!” I said.

We’d been working on a large-scale website project that included a redesign of the way the website looked as well as an overhaul of the systems running behind the scenes to make it work.

I’d worked on projects like this before, but nothing of this scale. I was nervous about what I didn’t know and not all that confident in my ability to deliver. The team and I were discussing a few of the key decisions we’d need to make in the project and couldn’t agree on a direction.

“We need an expert.” I’d said. Everyone agreed. Then we each scanned our networks for someone who’d done something like this before. Nancy was the first to find someone, Steve. Steve was our expert.

Nancy reached out to Steve to ask if he might be able to join our next meeting and share some of his expertise. He said yes. I breathed a sigh of relief. Steve to the rescue!

A few days later, Steve was scheduled to show up to our meeting. He was late and I was feeling concerned. What if he didn’t show up? I had so many questions and very few answers. Steve suddenly burst into the room, tossed his bag on the table and looked towards Nancy. Nancy quickly introduced Steve to the team and thanked him for coming.

Then, as if someone pushed a button in his back, Steve began to tell us exactly what we should do on this project. At first, I thought, “This is great! Steve doesn’t mess around!” But the more he spoke, the more troubled I felt. What Steve was telling us made sense, in theory, but very little of it was related to our project. Maybe he just needed some context. I attempted to interject, but Steve was leaving no room for questions or comments. He plowed ahead relentlessly for 15 more minutes, scooped up his bag, and abruptly exited.

Steve hadn’t asked us a single question. His advice was totally disconnected from our situation. He may as well have been telling us how to bake a cake.

I felt a pit in my stomach. We’d brought in an expert and it hadn’t helped at all. Now what?

I’d just learned a valuable lesson. Sometimes an expert isn’t what you need.

It’s not always the case, but in my experience, experts are more likely to be closed off to new information. They are less likely to ask questions. And they are less likely to be able to put themselves in your shoes.

They are suffering from the curse of knowledge. They know their particular area so well, that they’ve lost the ability to remember what it was like to not know it.

This happens a lot in sports. Sometimes the best players make the worst coaches. Wayne Gretzky is widely regarded as the greatest hockey player ever, yet his greatness did not translate to coaching. After his playing days, he coached for four years with little success. Why does this happen?

I believe it is because some experts struggle to relate, to empathize. They forget what it was like to not be one of the best. Like Steve, they don’t ask questions because they know exactly what to do. They lose the curiosity that made them experts to begin with.

Expertise, on its own, isn’t enough. Expertise + curiosity is the secret to success.

I got to see this amazing combination at work in, of all places, a ski shop. I became a skier much later in life than most people. I never skied as a kid and only got into it because of my kids. I found myself simultaneously teaching them to ski while learning how to ski myself. I’d reached a point where repeatedly renting my skis was cost-prohibitive and it was worth it for me to buy.

I went to the ski shop I’d rented from many times with a new goal — to walk out with a brand new pair of my very own skis.

I was nervous. Having been in this ski shop many times, I knew how knowledgeable they all were. They’d skied everywhere, knew every mountain, knew every detail about every ski. The carbon plating, the width, the length, the weight, the brands. I knew nothing. I’d always just taken the rentals they gave me without a thought. Skis were skis, right?

Though the staff had always been nice, but I was prepared to feel stupid. I was prepared for an onslaught of expertise and recommendations for skis that were “top of the line” and likely very expensive.

That’s not what I got. I walked in and said I was looking to buy skis. Rick smiled and said, “Great, follow me!”. But Rick wasn’t walking towards the endless rack of shrink-wrapped skis. He was walking over to a couple of benches on the opposite side of the store. He sat down. What was happening?

Rick says, “Tell me about a day of skiing for you.” Still unsure why we were sitting there, I told him how I’d start by gathering my young kids and all our rental equipment. Then we’d load everything up and head to the mountain where I’d spend the day trying to learn and teach at the same time.

He asked about the kids. “What are they like when they ski?” I told him how both were pretty good. Easy Greens and a few more challenging Blue trails. One kid was more fearless than the other and often took off down the mountain. The other was more cautious. I’d try to stay behind both of them because I routinely had to stop to scoop one of them up from a fall, get their skis back on, and point them in the right direction — a very challenging process for me as a novice skier.

He asked about my goals as a skier. I told him how, for the foreseeable future, I just needed to be able to keep track of the kids. I needed to be able to stop myself on just about any trail and remain steady enough to help whoever had fallen down. I needed to not fall because if I got stuck somewhere, they were too young to help. I wanted to be competent. Later in life, I’d think about getting really good.

Rick listened intently to all of this. He even had a tattered little notebook where he was jotting down notes and doodles.

Then he finally said something that wasn’t a question. “Given your goals and current situation, I have a few ideas. Let’s head over to the ski rack.”

Rick showed me skis that he felt would give me lots of control, stability, and the ability to stop and stand in any spot. Skis that would take a beating and stand up to most east coast ski conditions, where we’d be. He assured me that I wasn’t going to win any downhill races in these, but he knew that wasn’t a goal of mine. He was honest that once the kids got older, I’d probably want a different kind of ski, but these would work well for now. He also picked reasonably priced skis, having heard about how expensive a ski day is with the kids.

We settled on a pair. I felt good about my purchase. Then the next ski day came around and I felt lots of control, stopping power, and stability. Things I’d never felt on the rentals. Rick was right.

Rick was a curious expert and I’d benefited greatly. I was grateful for our encounter.

I’d argue there is nothing more valuable when facing a challenge than a curious expert.

The expert who knows what they know and seeks to know more. They seek out new information, new viewpoints. They combine that new information with their lived experiences to offer true expertise. They do this on purpose.

Thinking back, I bet Steve could have helped us. Had he asked a few questions or just left some room to learn, he could have better understood our situation. And I bet he would have had valuable insights to share with us. But he wasn’t a curious expert. And therefore, he really didn’t add any value.

Everyone has expertise in something. You do. I do. To be valuable to others, be a curious expert!