Friday last week, I jumped on a phone call with a founder who reached out to me after checking out my blog. In my deep fascination on how she found and learns from her mentors, she shed some light as to why she feels safe to ask stupid questions. The TL;DR of her answer – implicit trust, blended with mutual respect and admiration. That her mentors know that when she does ask a question, it’s out of curiosity and not willing ignorance – or naivety.
But on a wider scope, our conversation got me thinking and reflecting. How can we build psychological safety around questions that may seem dumb at first glace? And sometimes, even unwittingly, may seem foolish to the person answering. The characteristics of which, include:
- A question whose answer is easily Google-able;
- A question that the person answering may have heard too many times (and subsequently, may feel fatigue from answering again);
- And, a question whose answer may seem like common sense. But common sense, arguably, is subjective. Take, for example, selling losses and holding gains in the stock market may be common sense to practiced public market investors, but may feel counter-intuitive to the average amateur trader.
We’re Human
But, if you’re like me, every so often, I ask a ‘dumb’ question. Or I feel the urge to ask it ’cause either I think the person I’m asking would provide a perspective I can’t find elsewhere or, simply, purely by accident. The latter of which happens, though I try not to, when I’m droning through a conversation. When my mind regresses to “How are you doing?” or the like.
To fix the latter, the simple solution is to be more cognizant and aware during conversations. For the former, I play with contextualization and exaggeration. Now, I should note that this isn’t a foolproof strategy and neither is it guaranteed to not make you look like a fool. You may still seem like one. But hopefully, if you’re still dying to know (and for some reason, you haven’t done your homework), you’re more likely to get an answer.
Contextualizing your question
Preface your question with context as to:
- Why you’re asking;
- And, especially, what you’re reasonably confident the person answering would be thinking when asked.
In other words, defuse the tension by addressing the elephant in the room before the elephant even arrives in the room.
For instance, I preface the beginning of all my cold emails, and many of my regular emails that include calls-to-action (CTA). How long will this email take to respond? How much work do I have to put in to read this email? To answer your CTA? What do you really want?
On a more literal sense, the contextualization I usually regress to is:
I apologize for having lived under a rock until this conversation…
Why?
You’re asking because you know what you don’t know and you admit that there are others who do know, namely the person who you’re talking to. In a sense, it’s like asking for a favor. A favor for knowledge. You can find plenty of literature and discourse on the interwebs – both in academia and from influencers – why asking for a small favor helps makes people like you more. But I won’t intend to dive into that rabbit hole, at least for the scope of this post.
Admit what you don’t know. And be frank. You don’t always have to give a reason as to why you don’t know. But don’t try to hide it.
While I only have a few in my personal toolkit, I’ve learned from many who are smarter than me.
- Hostage negotiators,
- People who serve on the other side of suicide hotlines,
- Salespeople,
- Podcasters,
- Talk show hosts,
- Investors,
- And people who have and continue to spend time in the ecosystem of asking and answering questions.
Here are just 3 examples…
From people smarter than me
From Chris Voss
Chris Voss‘s, former FBI hostage negotiator, strategy for negotiating with difficult people works in a similar way. He prefaces with any 1 of the 3:
- “I’m here to sign-up for the stupid American of the day award.”
- “I’m about to make your day incredibly difficult.”
- “Bless me father for I have sinned.”
… each ending with an effective pause. 1-Mississippi. 2-Mississippi. 3-Mississippi. In preempting the elephant in the room, it “innoculates [them] from possible negative reactions”. As Chris puts it, “denials plant negatives – labels diffuse them.” Label yourself before others do so.
If you’re interested in learning more about negotiation and tactics to master conversation, I highly recommend checking out either (or both) his Masterclass or his book, Never Split the Difference: Negotiating As If Your Life Depended On It. The latter really changed my life – both when I was an operator and how I build friendships with new people. And don’t worry, he didn’t pay me to say that.
From Jason Calacanis
Jason Calacanis, early investor in Uber, Calm, and Robinhood, shared his hack to get into a packed restaurant without a reservation on his recent podcast episode with Joel Montaniel, founder of SEVENROOMS. Right after walking into the restaurant he usually says:
“I’m so sorry I didn’t make a reservation, or my assistant might have, maybe you can check. But if there’s anything you can do to help me, I would really appreciate it.”
The takeaway is that he starts off with apologizing, instead of acting confrontational or pretending he did make a reservation. Whether it’s your fault or not, you want to diffuse the tension before any can accumulate. The goal isn’t to prove who’s right, but to get the help you want.
From Tim Ferriss
On a similar note, Tim Ferriss, brilliant podcaster, in his recent interview with astrophysicist Janna Levin prefaced one of his questions with:
“I’m going to ask you a question that you’ve no doubt been asked many, many times, and I apologize, but I want to ask it anyway.”
He admits that Janna probably gets asked this question more times than she can count. And indubitably, has answered the question more times than she’d care to remember. Whether it’s true or not. Defaulting on the worst case scenario. If it’s not true, no harm no foul. If it is, just like Chris Voss, he’s defused the tension before she can even think of it.
Later, in the same interview, he prefaces another question with:
“… this is going to be a third-grade question.”
Well, the beauty of his question is that it’s not really elementary at all. But the tactic still holds.
The Venture Parallel
In closing, the same is true when founders pitch to investors. Before the pitch meeting even starts,
- Why now? What makes now the opportune time for your product to take the market by storm? And, what market (economic, technological, social, political, etc.) trends make it so?
- Why you? What makes you the person/team to take this to market? Why are you better than anyone else to do so?
- What do you know that others don’t or are overlooking and underestimating?
- Do you have a compelling narrative as to why you do this? Is this a personal vendetta? Or a product of pure market research?
Pricing the Risk
And once, the investor has enough context, the next step is to price the risk. What is and how much is the…
- Execution Risk?
- Team Risk?
- Do you/your team have a track record of entrepreneurship?
- What has your journey through the idea maze looked like?
- Are you industry/category leaders?
- What do you know? What do you still need help with?
- Product/Technological Risk?
- Is the product still in tech dev?
- Pre-traction? Have you launched? Have you done market testing to see if you have a minimum lovable product (MLP)?
- Pre-revenue? Do you have letters of intent (LOIs)? Do you have a business model?
- What does your roadmap look like?
- Team Risk?
- Market Risk?
- What is the margin that we’ll be off on timing?
- Am I/are you wrong on our underlying assumptions?
- Where is the market now? Where is the market likely to head?
Naturally, if you, as a founder, can do the legwork for an investor before they sit down with an excel sheet, then you’re one step ahead of the curve.
Photo by Hello I’m Nik ? on Unsplash
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