#023: Black Swans


Hey, 👋 Scott from The Sales Mastermind here.

Today’s edition only takes 3 minutes.

Advanced Warning: There will be no newsletter next week as the 24th is Christmas Eve. I'll return to your inbox with a New Year trick on the 31st.


"Never, on cross-examination, ask a witness a question you don't already know the answer to." - Harper Lee, To Kill a Mocking Bird.

The sales translation is "Never answer a question if you don't already know the motivation."


I led a webinar on Friday for junior to mid-level sellers: SDRs, AEs, and other individual contributors.

The talk is basically:

  • If you're getting bad outcomes, learn to ask better questions
  • Ask bad questions, get bad answers
  • Ask good questions, get good answers
  • And most of all, be aware of Black Swan Questions from your buyers.

Black Swans

Nassim Taleb coined the term "Black Swan" to mean a rare event with dramatic consequences, which is obvious in hindsight.

It comes from the idea that Northern Hemisphere swans are (almost) exclusively white.

And, to the shock of the "Old World," black swans were discovered in Western Australia in the 1600s. In hindsight, nothing stopped swans from evolving black feathers.

Treat every question like a gun. Assume it is loaded

Black Swan Questions are when your buyer asks a question that often isn't intended to catch you out but ultimately does.

The reason they are called Black Swan Questions is that 99 times out of 100, the apparent answer is fine. Yet, 1 time in 100, the apparent answer is a colossal mistake.

Safe owners treat every gun as if it is loaded, so they never accidentally fire an "unloaded" gun.

Great sellers treat every question as a Black Swan Question so they never accidentally fall into a trap.

Example

Imagine you're selling a CRM that includes a dialler.

Buyer: "Does the dialler record the calls?"
99/100 Sellers jump in: "Mrs Buyer, not only does it record calls, you can listen to them by clicking this option here. Our AI will automatically transcribe the calls and pick out key words… blah blah blah."
Buyer: "That won't work for us."
99/100 Seller: "Oh…."

Or...

Buyer: "Does the dialler record the calls?"
1/100 Seller (assuming it could be a Black Swan Question). "Do you want to record the calls?"
Buyer: "I wish, but I can't. We have clear instructions from our legal team never to record calls in case we break privacy."
1/100 Seller: "Gotcha. In that case, we won't record the calls."

Hence, "never answer a question if you don't already know the motivation."

Get-out-of-jail questions

When you need clarification on what the buyer is asking, be like a doctor, lawyer, or engineer. Be a professional.

In a call on Monday, about 15 minutes, my wife made a statement to which our Paediatrician replied, "And… why do you make that point?"

When a buyer asks a question, find out why. The onus is on them to explain what they are talking about.

Good examples:

  • "When you say XXX, what does that mean to you?"
  • "Help me understand, you've just said XXX. I'm not sure I follow how that relates to ABC"
  • "And why do you make that point?"

Or, the ultimate get-out-of-jail question:

  • "What do you mean?"

When you put the question back on the buyer, they'll often rephrase it —buying you time to form an answer. Or it could be a more straightforward question the second time around.

Be aware of Black Swans and use your get-out-of-jail questions to keep the conversation flowing.


Let me know what you think! it to a friend


Until next week,
Scott Cowley

PS Did you like what you read today? Consider forwarding it to a friend, colleague or team member.

Did someone forward you this email and it seems like something you want more of: Link to subscribe

Hi! It's The Sales Mastermind

I help founders who sell, but aren't "sales"people. Are you open to one hyper actionable sales tip per week, useful for your very next sales meeting and consumable in 4 minutes or less?

Read more from Hi! It's The Sales Mastermind
people in black jacket taking photo

Hey, 👋 Scott from The Sales Mastermind here. Today’s edition only takes 2 minutes. To close a deal, you have to be in the deal. That is why every seller and every business should strive for Fame. Today we’ll cover: Storytime What is Fame Some Stats Make it Real Storytime I was recently watching a YouTube channel about Pokémon card collecting called "DeepPocketMonsters" (DPM). DPM has over 2 million subscribers and is run by Pat Flynn. Pat also runs a business/podcast called Smart Passive...

Train travels through a sunny mountain valley at sunset.

Hey, 👋 Scott from The Sales Mastermind here. Today’s edition only takes 3 minutes. Selling is about helping buyers desire what you're selling. Then moving them from emotion to logic, and nothing does this better than a proprietary named system, process, or method. Today we’ll cover: Storytime Why Naming Works Visuals Make it Real Storytime An agency I work with sells websites, local SEO, and lead-generation services to micro-trade businesses (think your local plumber, arborist, electrician,...

person in blue long sleeve shirt using black Surface

Hey, 👋 Scott from The Sales Mastermind here. Today’s edition only takes 2 minutes. Storytime In the last 30 days, I have audited six sellers across three businesses. More on the audit product here. If you want to learn your strengths and weaknesses, benchmark them against others at a similar stage and hyper-specific ways to improve right away - reply to this email. I have one opening at the end of July. And a consistent mistake that has an easy fix is optimising your video meeting setup. Best...