Recently my friend Billie was taking a walk down memory lane, reliving war stories from her jump into retail ownership. She laughed, “‘I don’t know what I don’t know’ was an understatement!” Have you had a similar year?
Billie thought all the pieces were falling into place when a local store came up for sale. She’d built quite a reputation in her friends’ circle for flower designs. So, owning a flower shop seemed like a natural match. There were two bonuses: She could leverage the store brand’s goodwill, and she negotiated a hand-off period, where the owner would teach her the daily ins and outs.
But gotchas started surfacing soon after the sale closed. First, the building tenants were stung by special assessment fees after a pipe burst. Then the roof went out. Running on a shoestring budget, she started pulling withdrawals from her old corporate 401(k), expecting to repay the money down the road.
There were also staffing hiccups. Billie thought she’d spend days designing show-stopping arrangements while others ran the front of house. However, the reality was that she frequently covered when employees or their families were out sick, had car trouble, or were attending to a family emergency.
Two years in, she did the unthinkable: She threw in the towel and sold the store. However, instead of forgetting about all the lessons learned, she uses them at her new job as the Events Manager at a busy Community Center. Her role allows her to capitalize on the design work she enjoys without the drudgery of balancing books.
In the November series, Pass the Masterclass, we’re discussing how soft skills can help you change common mistakes into empowering wisdom. Like Billie’s story, has this year felt like one battle after another? Don’t abandon your dream yet. You may just need to ask inconvenient questions, then fine-tune. Looking back, that was Billie’s challenge.
For instance, she was so enthusiastic about running the shop that she forgot to think through what abouts (such as ways to handle demanding, last-minute clients). She skipped past issues about the not-so-glamorous side of running a retail shop. Overall, Billie wanted answers that aligned with the picture in her mind’s eye. I’ve made similar mistakes—how about you?
But here’s the good news: With soft skills, you can transform those missteps into lasting insights. For example, if you had had a crystal ball, what essential people competencies might have turned that sticky situation around? Contingency planning? Calibrating your choices to a changing environment? Or maybe a partner with a different set of expertise or a mentor who could help you manage blind spots?
If you’re still skeptical about the value of inconvenient questions, reframe that idea. Rather than undermining your self-confidence, see taking a straight, no chaser mindset as your secret weapon to get equipped (and you won’t be equipped if you only have half the facts).
Conor Grennan, Chief AI Architect at NYU Stern School of Business, highlighted the value of this concept by saying, “The most successful leaders know how to question outputs, challenge assumptions, and apply human judgment. They use AI to amplify their strategic thinking, not replace it.”
So, here are three starter questions to consider. They work whether you’re hunting for a new job or opening a business:
And if you’re looking for a prompt to tailor to your situation, challenge AI’s false positivity with: “I’m interested in <goal>, but I have limited experience and capital. Show me where my reasoning is weak or how I might be fooling myself. Then give me a step-by-step plan to address potential mistakes before they happen.”
Let this be the year where you kept a high-minded approach but left over-idealized thinking in your rear-view mirror. Transform your results by passing the masterclass for asking inconvenient questions.