Five Life Lessons from 30,000 Cold Calls

In my 20’s and 30’s I wanted to save the world with the work I did. As an aerobics instructor, I helped students feel good in their bodies. As a flight attendant, I calmed over-stressed passengers. As a movement therapist, I helped patients struggling with mental illness connect with others. As a personal coach, I supported individuals to overcome insecurities in pursuit of goals.

But there was one problem, I wasn’t fulfilled.

When I was an aerobics instructor, I struggled with bulimia. While working as a flight-attendant, I was going to college full-time and held myself to such high standards that the one time I got a bad grade I actually punched a hole in a wall! While I was a movement therapist and personal coach, I judged myself so harshly that I held myself back from opportunities for professional development and advancement.

Something had to change and not knowing what, I accepted a job in sales. It was radically different from what I’d done up to that point. And as much as I had past bad experiences with sales people being pushy, manipulative, etc. I was equally inspired by good sales people. At its best, sales provided a win-win match between needs and resources. Nothing wrong with that. And in any event, it didn’t really matter because my plan was to get in and get out. Sell stuff. Make money and then go back to trying to change the world.

But that’s not what happened. I ended up staying in sales for about 10 years or approximately 30,000 cold calls. Here are just five of the lessons I’ve learned:

1. Face adversity with all ya got

My first sales job was at a tech company that sold website localization services. Basically, we sold a service that gave websites the look and feel of the culture of our customers’ target market. At the time, not a well-known topic. Selling it was hard and required months of educating potential customers before they’d buy.

I had no sales experience so I started out in a Business Development role, which in sales vernacular translates to: picking up the phone, smiling and dialing over and over again, all day long. My success at sales boiled down to whether or not I could pick up the phone. I loved people and enjoyed communicating, so I assumed it would be a breeze.

It wasn’t.

I was given a list of names to call and a script and a paragraph explaining the service that the company provided. It wasn’t expected that I make my way through the 100 names on the list because I was a newbie, but eyes were on me to make a gallant effort. So, I did. And after a couple of days memorizing, practicing in front of the mirror and role playing with a sympathetic Outside Sales rep named Chuck, I felt ready.

Feelings can be deceiving.

My first call went terribly. I was terrified that a real person would answer the phone and, as luck would have it, a real person did. I said my name but forgot the company name; I talked so fast that the person I called asked — Who are you? Who are you with? And then the most dreaded question, What do you want?

With each word, I spiraled deeper inside myself until a loud voice from the other end of the line shouted: “Take me off your damn list, loser!”

I spent the last hour of the day hiding in the bathroom, sitting on a toilet seat, and muffling my crying bouts with toilet paper anytime someone came in. I didn’t count on the fact that being in the role of calling another person unsolicited, automatically put me, the caller, in the unenviable position of being avoided at best and more likely, hated.

My most recent job had been as a personal coach and while clients didn’t necessarily agree or even like what you told them, they paid for your services and so half expected you to confront them from time to time. But in a cold calling situation, not only is a person not expecting it, but they may not even need what it is that you’re selling and even if they did, they don’t want some stranger telling them that they do. Either way you’re the intruder.

That’s a whole different thing.

Going home that night I had one question. How was I going to muster the courage to start calling that list of a hundred names that would most assuredly be facing me the next morning?

7:00 AM came fast. I got ready for work with the heaviness one has when getting dressed for a funeral. Actually, it felt worse. I was getting dressed for my own execution.

Then it struck me. What if I thought of cold calling as a challenge to be overcome in order to reach an important goal — one that really mattered to me. I’ve had plenty of those in my life — many of which I’ve overcome. Why should this be different?

This would mean that I diverted from the script I was given. That’s not a bad thing…is it?

On my way to work, I sensed the slightest change inside from dread to less dread.

I’ll never forget walking through the giant double door entrance that morning. It was as if I had a super hero cape on under my crisp white blouse and blue pencil skirt.

From that day on things were different.

2. Counter negativity with smart sensitivity

After my first sales job, I went to work for a couple of software companies that sold speech self-service. You know, those automated agents you have to interact with when calling the airlines or bank to get to a real person.

At one of these jobs, I was calling on the biggest company in the country at the time that provided transportation to outpatients for dialysis, doctor appointments and hospital visits. I knew they had a lot of calls coming in to their non-emergency medical call center. I also knew that the agents had the difficult task of having to handle everything from reservations and scheduling to responding to complaints when drivers were late or didn’t show up at all. The worst calls were when patients were picked up but left at the wrong location.

One such call was recorded and put on YouTube. It was the worst customer service call I’d ever heard. I was angry just listening to it not only because the agent came across as dismissive and harsh, but also because the caller was clearly distraught and scared. After listening to this painful 20-minute conversation between the call center agent and patient I wanted to hit someone.

I spent much more time than usual researching that company. I discovered the main decision makers, how many complaints they got, their customer service ratings and how they trained their agents. At first, I was unsuccessful in reaching anybody let alone a decision maker. The company seemed as secretive and impenetrable as the CIA. Leadership from the CEO to Director level had no contact information other than the same 800 number. LinkedIn and other online business sites listed no names with titles of Director or higher. And the poor souls who did answer the phone — assuming you had the patience to wait through the most convoluted call routing tree in existence — were unable to give you any information. They didn’t know how to find out anything and wouldn’t transfer you if they did. In other words — their job wasn’t just to be a gate keeper, but to be the gate to a dead end. After all this work, all I had was a name of THE person who controlled the quality of customer service. (I’ll use a fictional name, Peter.)

Then something wonderful happened. I came across a post written a year earlier about internal efforts being made to improve Call Center Operations. Peter was quoted as saying that he was “focusing on improving quality across all call centers.”

Bingo. I had my motive and I knew his; all I needed was a cell phone number.

Inspired by this new information, I called the office manager in the city where I suspected Peter worked. I’d spoken to her once before, so I was hoping she’d be more receptive. When she answered, I told her that I needed to return a call to Peter but didn’t have his cell phone. Could she help me? She did.

Double Bingo!

When I called, Peter answered.

Me: “Hi Peter I’m Robin. It’s been hard to find you. Do you have a quick minute?”

Peter: “Who are you? How did you get my number?”

Me: “I’m a sales guy on a mission to make your life easier.” (I almost said, “I’m Robin, and I’m on a mission from God!” inspired by the 80’s hit film, The Blues Brothers, but thought that might be coming on too strong.)

Peter: “What?? I don’t take cold calls!”

Me: “Whether or not this is a cold call, which it is, what does it matter if I have something that can help you do your job better,” I said with righteous indignation. The fact that I had listened to that painful call on YouTube, made me fearless.

Peter: “Look, I don’t have time for this bullshit. I’ve got blah, blah…”

Me: Interrupting him I said,” Peter, I’ve seen the video on YouTube; I have an idea of the challenges you’re facing and the stakes involved. That’s why I took the chance to call at the risk of you slamming me. I get it.”

Peter: After a long pause he replied, “Yea, the stakes are high.”

Me: I must have hit the right chord because his demeanor changed. But not just with him. His tone made me change too. “So, let’s talk when you’re not on your way to a meeting, and I’ll tell you how we’re helping call centers reduce wait times and improve customer care. Sound good?”

Peter: “Sounds good. Thank you for calling, Robin.”

Me: “Thanks for listening to a cold caller, Peter,” I said, both of us chuckling as we hung up. I was happy that I reached him and got a commitment for a follow-up call, but I was also bewildered. I started-off angry at this guy, but after the call I was just wanting to help him. What changed? What made me more sensitive? I was able to connect with the human being behind the role.

3. Know that rejection and failure do not define you

My first few years in sales I learned to overcome my own resistance to picking up the phone. And more importantly, I could do this over and over again, day after day. I had plenty of rejection, of course, but it was worth it thanks to the minority of times that I was able to make a connection with people, and sometimes even close a deal.

I was good at what I did, and I enjoyed it, until I worked at a tech company selling project management software to architectural design firms. Up to this point, the closest I’d been to the industry was an Architectural Drafting class I took in high school which I barely passed because I skipped class so much. I did so to avoid the flirtatious teacher who lingered annoyingly by my desk when I was working. This was embarrassing enough but the fact that his pathetic attempt at small talk came in an invisible cloud of halitosis made class unbearable.

Suffice to say, I had a negative opinion, however irrational and unfair, of architects. This made calling on them day after day inordinately unpleasant. But I needed the job so I stuck it out.

Then one day I managed to get a key decision maker at a high-profile firm to agree to see a demo. Bob (fictitious name) was responsible for overseeing a huge multi-unit design project. Bob said that he had to do an RFP (request for proposal) because it was a public project, but that he was willing to listen to what I had to say before putting it out there. This was great news! It gave me a head start over all the other bidders. We chatted a bit before ending the call. I was elated.

That night, I researched everything I could about Bob’s company, including the types of projects they did, what their strengths were as well as their challenges. By the time I was finished I was clear about his project needs and how our software could help manage the entire thing. On top of it I had a really good feeling about Bob. He was a straight shooter and told me upfront what he was looking for. I was ready and I knew I’d nail it.

Ten minutes before my online presentation, I sat in the conference room going over my notes. At exactly 1 PM Bob arrives along with his entire technical team. After a swift round of introductions, their questions ensued, which came at me in rapid fire. I adjusted accordingly and was able to respond to most of them pretty well. Reading the room as best I could in light of the fact that I could only hear their voices on the phone, and even that was curtailed by their use of the mute button, I was confident that things were going well and asked, “Does anybody else have any questions?”

Silence.

Then Bob said, “Yes, I do.”

“Oh, great Bob,” I said anticipating a positive wrap-up and maybe even an invitation for next steps, “What is it?”

I don’t remember his exact question only that it was so far beyond my knowledge of what I’d researched including what I knew about my own product. Whatever it was it set off my fight-flight response. Mentally, I was frantically searching for an answer. Physically, I was in the jungle about to be attacked by a lion. I needed help. But no one was available. My boss was out that day; the senior sales rep was on a call. There were two other people in the office but they were more on the customer management side and also didn’t have the technical background. The techies, or solution consultants as they were referred to, were out to lunch.

Bob must have sensed my overwhelm and fear because before I had a chance to give a response he said, “You’re a joke. Next time, try studying up on your solution. This has been a waste of our time,” click.

Stunned and ashamed I sat there stung by his words. It felt like they were making their way through me like poison. I questioned my work and my worth.

I went outside to get some air. There was a beautiful water fountain across the street. I crouched beside it and felt it’s spray on my face. After a while I stood up and did a cartwheel into the fountain. Sounds silly but it did the trick.

It reminded me that life is bigger than any role or job. Move on.

It took about an hour to get back on the phone. But it took even more to not leave that day.

4. Think outside the box and ACT on it

Around the same time that I had this negative experience at work, I started a passion project called Peace Puppets.

Peace Puppets was an initiative to get hundreds of cuddly puppets into the arms of children traumatized by the war that was raging between Israel and Gaza in the Fall of 2014. Our goal was to send 1,000 puppets from the United States to kids ages 2 through 10 living in Southern Israel and Gaza. Some would be taken there in suitcases by my project partner, who had family there. But we had hundreds more and so we needed to find another way to send them. I asked myself:

• Are there organizations based in the San Francisco Bay Area (where I lived at the time) that help children in the Middle East?
• Are there organizations based in Israel and/or Gaza that have partner organizations in the Bay Area?
• Are there people in my network who have contacts at these organizations?

My mission for the next few weeks was to answer these questions. I had no idea how I’d do it. I just knew that it had to happen.

I started with large organizations like UNICEF, Save the Children and The Red Cross, but soon learned that no “in-kind” donations were accepted due to the fact that the cost to transport was prohibitive. Calling them was pleasant, and I learned a lot, but nothing came of it.

Next, I called smaller organizations. In some cases, they were able to accept in-kind donations, but the priority was for items that met basic necessities like medicine, water purifiers and portable lights. I had some inspiring conversations with people who wanted to help but couldn’t. But there were also many who reacted with cynical dismay when I told them about the project and our goal to send puppets into a war zone. The most common response was some version of That’s impossible, you’ll never be able to do it — why even try?And then there were several whose responses felt like veiled accusation, Puppets…in a war zone? That’s the last thing they need.

Even though this latter type of response wasn’t the norm, it took the wind out of me. At the same time, it was these kinds of comments that allowed me to practice not taking things so personally. It helped that I had a clear picture in my mind of children holding puppets even if hell was in the background. I got to a point where I could listen to their response, take it in and say with calm assurance that while they had a very important point (and they did), that it was equally important to protect and nurture joy. When I responded this way the tone of the conversation shifted from what wasn’t possible to what was.

In one such conversation the person I was talking to stopped mid-sentence and said, “Wait, I think I know someone who can help you!” She gave me the name of a small non-profit in San Mateo, California called Rebuilding Alliance.

Rebuilding Alliance was a nonprofit providing living supplies to uprooted Palestinian families.

I called and the Founder herself answered the phone. I told her my goal and what I was looking for, bracing myself for hearing no. But she didn’t say no. She said yes! She told me that they were planning to send a container from San Francisco bound for Israel, the final destination being a mental health clinic for children in Gaza. She said that although most of the containers would be full of clothing, bedding and medical supplies, there would be enough room for our puppets. She’d make sure of it. She went on to say that puppets would be a welcome and perfect addition. Bursting with excitement, I thanked her but in my elated state forgot her name! Not missing a beat and with a smile in her voice she said, “My name is Donna, and I’m so glad that you called.”

Right after the call I opened one of the many boxes full of puppets that crowded my cozy apartment, placed them on the couch and did a happy dance.

5. Listening is its own reward

It’s amazing what’s possible when you question your certainties. Up to this point my confidence was based on what I knew and could prove. But having success with Peace Puppets validated what I’d learned from similar experiences earlier in life. As a result, I had the wherewithal to navigate uncertainty like never before. It freed me up in a wonderful way. Here’s an example.

I took a job selling financial software to car dealerships. In hindsight, it probably wasn’t the best fit since I’m terrible at finances and I don’t have much interest in cars. But, in my defense, the company was a start-up — which I loved — and the owner was smart and super cool.

I was tasked with calling the owners of dealerships that sold cars for cheap. Ever heard the phrase Buy Here Pay Here? Well, it’s not just a slogan, it’s a culture rich with passion for cars, hunger for making sales and toughness when it comes to keeping their businesses alive.

I called 40–60 dealerships a day and spoke to individuals who didn’t give a rat’s ass about what I was selling. At the same time, there was an honesty to the rejections that was oddly refreshing. There was one shop in particular that I knew was struggling. I had already called the owner many times with no luck. I was persistent because he actually answered the phone. But each time it was never a good time — he’d be driving to a car auction or he had a customer in front of him. And even though the last reason was a common response from most of the dealers I called; when he said that he was too busy, it seemed sincere. That plus the fact that his dealership was the right kind of customer for the CRM software I was pedaling. I knew it was just a matter of time before I’d get him to watch a demo.

So, I kept at it, trying different times of the day, on different days of the week. No luck, until one Friday afternoon:

Me: “Hi, Ken, guess who? It’s Robin, I hope this time is the right time to show you a demo. What do ya think?”

Ken: “Robin…Hi. How are you? he said apprehensively, “Actually, it’s not a good time at all.”

I didn’t know Ken at all beyond a few quick back and forth conversations on the phone. He was always nice but this time his tone was different.

“Are you okay?” I asked.

With characteristic sincerity he said, “Oh, you don’t want to hear this, trust me,”

I know we don’t know each other but that doesn’t matter, “What’s going on?

“I just found out that I’m going to be deported,” his words barely audible.

Shocked, I asked, “What? …Why?”

“I came to this country with my parents from El Salvador when I was thirteen. We left because life there had become unsafe and deadly.”

“I know, I’ve read about it and have a friend from there who left at about the same age,” I said trying to relate as best I could.

He continued, “President Bush had created a humanitarian campaign to provide temporary citizenship for people seeking asylum. It saved me and my family. We were planning to return when an earthquake devastated the entire region where our home was.”

“What happened then?” I asked.

He paused, “Are you sure you have the time?”

“Yes, I have the time,” I said wanting to be a friend on the one hand, but not wanting to invade his privacy on the other.

“Well, for one thing, you called to sell me your CRM,” he chuckled.

“That’s absolutely true. But some things are more important than CRM’s, just don’t tell my boss I said that!” I laughed.

“I was twenty when this whole thing went down. It was unsafe to go back home and so I decided to make a life for myself here in the United States. Because I love cars, I saved up to buy a car dealership,” Ken said with a spark of enthusiasm.

“It hasn’t been easy, but today I can say that I’m responsible for ten employees working full time. And on top of that, I’ve personally financed car loans for customers in need of a vehicle who have bad credit.” There was a long pause before he added, “And I pay taxes!”

Sincerely dismayed, I asked, “So why are you being deported?”

“I’m not sure. Every president before the one we have now has continued the humanitarian initiative started by Bush. As long as I pay taxes and keep a clean record (which is checked every year), I’ve been allowed to stay and work. I intended to apply for citizenship but got involved in building my business. I didn’t do it and now everything’s at stake.”

“When do you have to leave by?”

“January…I have 6 months.”

“My heart really goes out to you Ken. I can’t imagine what you’re going through. I wish I had a solution,” I added, not knowing what else to say.

“I appreciate that,” he said. Then after a long pause, “So, tell me about your software.”

“You’re kidding, right? You want to hear about a CRM after getting news like this?”

“Yeah, I’m sure, it’ll get my mind off things for a minute, and besides, I owe ya.”

Hearing this made me stop inside. So often bad news makes us focus in on ourselves, and only ourselves — I know it does for me — and here was this guy willing to give a minute of his time.

“Yes, you sure do, my friend!” I said jokingly which made him laugh with me. “But I warn you — this CRM will blow your mind — it’s best in class. Just like you.”

Nothing wasted. Everything gained.

When I consider all of the people I’ve cold called and the associated experiences — positive, negative and everything in between — I am struck by how much I learned, especially given the fact that it was a role that began with a state of dread. Wonderful things happened and often in the least likely moments. Not just during a conversation, but before and after a conversation.

Yes, it’s about attitude. But it goes deeper than that. It’s about being willing to approach something that scares the jingles out you, but that you are, for reasons true to you, drawn to do.

I think that that is where opportunity lives, between hope and uncertainty. And not necessarily the opportunity to make money or close a deal or whatever it is. That’s small in comparison to the bigger opportunity of showing up with your whole self to face what calls you even if that thing that calls you, scares you.

Having that kind of courage is what work means to me. I’m not changing the world like I planned to do but I’m changing and maybe that’s the better plan. And maybe it’s what the world needs.