At the closing bell on Friday 29 February 2008, I grabbed my gym bag and darted toward the marble stairs off the Main Room floor of the NYSE. Out to Broad Street and onto JFK airport I hustled, to catch the shuttle to Boston to meet my then-girlfriend, Maria (foreshadowing). I arrived in Beantown just before dinner with friends, and asked Maria if she saw my stepmother’s email about Sadie Hawkins Day – a day misconstrued as both Leap Year and when women ask men on a date. In this case, the insinuation was: to marry. She replied “yes” to seeing the note, and smiled politely. Continuing the inquisition, I asked if she had anything she wanted to ask me. She replied “No” smiling more widely. I left it there for the night.

FFWD >> 24 hours and instead of overlooking a snowy Copley Square, we were now ice skating around Brooklyn’s Prospect Park rink. I resumed my marital inquiry, this time presenting a ring on awkwardly bent knee: “Vuoi sposarme?” (For those without Google Translate, Italian for: Do you want to marry me?) Excitedly, she responded: “Did you ask my father?” Indeed, I had.

Socrates contemplated a pragmatic approach to improve upon hypotheticals and arrive at satisfactory conclusions, or knowledge:

  1. Consider a hypothesis: Maria wants to marry me.
  2. Pose a question to stimulate critical thinking, identify weaknesses: Confirmed disinterest in asking me. Might consider my proposal favorably.
  3. Inquire again and again to strengthen the hypothesis: Ask directly in Italian.
  4. Arrive at the most refined conclusion, or knowledge: Confirmed interest – provided her father’s blessing. She’s mine!

High performing executives and teams expect similar patterns of inquiry to arrive at paths forward agreeable to all stakeholders. It is not about the inquisitor. It is all about the client (team, spouse or even child). Nurturing communicative relationships requires finesse. Diplomatic inquiry unlocks bias, exposes root causes, and guides progress toward the edge where the final knowledge leap may be taken. Trick is to avoid premature declaration of what appears evident from the outside. Fostering self-discovery of new wisdom galvanizes the learning. In the moment, we are tempted to point out that which is apparent to us – so restraint is key. True and lasting progress, or knowledge, cannot be achieved after a contentious interaction, regardless of logic presented. 

Said more plainly: people do not like to be “should” on.

should | shood |(verb) def: to direct someone to do something based on your wants for them; often done while pointing a finger. ex: Last night, my parents should all over me. They kept telling me how I should study more, clean my room, and do my chores.

IL PUNTO (the point): Diminishing the urge to press on with directives that appear logical from the outside will serve us well in our mission to stimulate positive growth and healthy communication. Investing in a few more thoughtful inquiries pays dividends of clarity, buy-in and prolonged support for intended outcomes.