“This is just stupid!” I roared from inside my boss’ windowless office. Thankfully no windows meant good acoustics for rage-Nate.

Debra, my boisterous, blond boss had been trying to teach me the lost art of cold calling. After surviving the third hardest college program in the world, and eking out a short but high-impact career in the Air Force, then managing a rapidly growing small business, I had tripped headlong into the lowest point in my professional career: calling strangers and asking them for money.

Our cookie-cutter cubicle jungle in Bellevue, Washington had been an easy ride up to that point. Reviewing piles of resumes, interviewing geeks and up-selling them to local companies’ tech departments. Some days I even got to play with gnarly advanced Google search strings to scratch my own nerdy itch. But this … this felt like punishment. An exercise in embarrassment. Miles away from any sort of authenticity. Dialing for dollars.

But my boss’ boss has made it clear that everyone on the floor had to sell or risk a jobless existence in 2008. For those that don’t remember, ’08 marked the second largest depression since the greater one before WWII.

Anyways, back to rage-Nate. My boss – in her 50s – had seen it all, and never stopped smiling throughout my tirade.

“Nate, who’s next on your call list?” Debra asked. I mumbled out a name and gave her the contact’s phone number.

She wrote it down and picked up her phone and started dialing.

“Whoa, you can’t call him. I’m not even sure if it’s the right person.” Her smile remained steady as the phone rang.

Then I got a master class in phone sales in the span of 4-minutes. It was like watching Jackie Chan in the Drunken Master, a raw unscripted ramble of words, bobbing and weaving around two gatekeepers and eventually onto the calendar of John … or was it Jake. Debra messed up the guys’ name twice with one of the receptionists and again with the actually guy. And she still got the meeting.

Rock bottom me immediately started my own self-deprecating ramble. “I can’t do that.” “Of course you’re better at it – you are my boss.” “I don’t belong here.” “Can I just have my old job back? You know I’m good at that.” Blah, blah, blah. Excuse, excuse, excuse.

Debra’s advice was simple.

  1. Just pickup the damn phone.
  2. Smile when you talk … they can tell if you aren’t.
  3. Be genuinely curious.

The first two are common to nearly every sales training program in existence. That third nugget has changed my life … well … in some curious ways.

Now I eventually got fired from that job. I started my business in the wake of that experience, and it has supported my family and the families of 100+ freelancers over the past 8-years. And those three commandments have fueled much of my survival and success since then. But it wasn’t until the past year that the power of curiosity really rocked my world.

When applied to interacting with people, curiosity can elevate your level of connection rapidly. In the now classic film 40 Year Old Virgin, Andy’s work buddies coach him to “Just ask questions” – it worked a little too well, and hilarity ensues. Point is, it works. Of course when conversing with socially savvy folks, faux interest in their problems, fears, happy’s and sad’s can be spotted a mile away. That’s where *genuine* curiosity comes into play.

Now here’s the rub. People can be bland creatures. Average Joe’s and Jill’s rarely reveal the interesting bits about themselves. It’s kinda hard to blame them. Uncovering the unique aspects of yourself can feel like emotional nudity in the wrong environment. How can you be genuinely curious about someone when they are the human equivalent of a generic brand of white bread?

Here’s the deal. There is always something. It may take a well crafted question to tease out enough material to trigger genuine curiosity. And often those well-crafted questions will make you feel uncomfortable yourself. I make an effort to put in reps in this area at grocery stores. Checkers are trained to ask, “How are you today sir/ma’am?” And I’ll always answer with uncomfortable honestly. Here are my back-pocket answers to that generic question for cracking open a chance at an unapologetically human, gritty conversation:

Whenever I drop one of these odd little guys, I get one of three responses:

  1. [awkward silence]
  2. Oh, I’m doing good. [an awkward laugh for effect]
  3. Me too. [and if I’m lucky, a mini story about why]

This year, I learned a way to take genuine curiosity a step further, a few inches deeper, a few grains grittier. Meditation practitioners teach the importance of transforming fear of you own thoughts into curiosity. Why am I sad / depressed / scared / lonely / dejected / anxious / etc… ? It’s an unsettling exercise, and to be brutally honest, I still have a hard time examining my own internal landscape in this way. However, my initial gains have been large enough to keep me going down that uncomfortable path.

More curiosity brings more clarity. And for me, that clarity creates quiet, a rare sensation in such a noisy world.

Get a weekly jam delivered to your inbox chock full of ‘in the trenches’ lessons in productivity, habit breaking/forming, human expert interrogations and gritty anecdotes.