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The Sales Mastermind · Issue No. 12

TPSO - Tactical Pessimism, Strategic Optimism

By Scott Cowley3 min read

In this issue (9)
  1. Storytime
  2. TPSO - Tactical Pessimism and Strategic Optimism
  3. "Nothing is ever as good or bad as it seems."
  4. During discovery
  5. During the pitch
  6. During closing
  7. Final Thoughts
  8. LinkedIn Post of the Week
  9. Sales Tear Downs

Hey, Scott from The Sales Mastermind here.

Today's edition is only 3 minutes.


More committed deals are lost from miscommunication than anything else.

Miscommunication happens when someone gets "happy ears" and forgets to apply Tactical Pessimism and Strategic Optimism.


Happy Ears?

"Happy ears" means we hear what we want, accept our interpretation and don't question to confirm.

It's an easy trap to fall into as it's a vital part of our social life. We listen and make assumptions. Otherwise, you become the asshole constantly questioning and stirring people up.

While no one wants to be that asshole in a social setting, when selling, the rules change.

Storytime

Imagine you have been working with a prospect for months.

It's a business you admire and a "grow in public" CEO you have followed since he launched.

Your primary contact emails you, "OK, send a contract."

(Happy ears incoming...) Obviously, they mean the final contract.

You send a DocuSign to the agreed signatory (the CEO, not your primary contact) and include everyone in CC.

Within 5 minutes, your primary contact emails you ENRAGED.

How dare you send a contract to the CEO without speaking to them first...

This happened to me early in 2023.

Not long after sending the contract, I was ghosted because of my happy ears

This one hurt.

TPSO - Tactical Pessimism and Strategic Optimism

Sales is an enigma. You have to be strategically optimistic to keep going. Otherwise, you'll quit.

Yet, to avoid happy ears, you also need to be tactically pessimistic. Always questioning:

Tactical pessimism means staying grounded until it is impossible to misinterpret your buyer.

It means never getting ahead of their buying journey.

"Nothing is ever as good or bad as it seems."

Avoiding happy ears goes the other way, too. You need to prevent sad ears as well.

On average, a buyer who becomes a customer will have TWICE as many questions as a buyer kicking tires.

So when you're emailed the below, remember, it's not as bad as it seems:

  • "In light of the above, we regret we will not be able to move forward."
  • "I don't believe there's much we can do with *product*."
  • "Unfortunately, I didn't get the acceptance to go over my budget. Therefore, I need to suspend further steps."

Quotes like these are why you need strategic optimism to keep going.

They are all actual quotes from buyers who did become customers. Collectively, this list represents ~$140,000 worth of signed contract value.

Applying TPSO Tactical Pessimism and Strategic Optimism.

When applying TPSO, it's all about questions.

NOTE: I have covered an alternative method, The Question Stack™, before. Check out Newsletter #003 here.

During discovery

(You're trying to answer: is there a chance to do business here?)

1. Have you given up trying to solve this?

2. Based on our discussion, which strategic business objective does this align with?

3. How can you see yourself using this feature/idea/whatever?

During the pitch

(You're trying to answer: do they believe this is a problem deep enough to invest time, money and effort?)

1. If you were to take this to your leadership right now, what do you think they would push back on?

2. Is this a big enough problem for you/your stakeholders to invest in now?

3. What happens after I send you an email/some collateral/a proposal?

During closing

(You're trying to answer: How can I support the buyers to sell internally?)

1. Now that you want to start, who else must we get on board?

2. When you're satisfied, what happens before we sign a contract?

3. How long and what's involved to get legal/security/procurement/whoever to sign off?

Final Thoughts

Happy ears kill too many deals. Focus on your tactical pessimism and strategic optimism. Or another way of saying the same thing: "Trust but verify."


LinkedIn Post of the Week

Here are two top posts, one from me, one from someone else.

11 years in sales, 7 years helping founders who sell - here are the 9 most common mistakes
From Me

Speaking of Happy Ears
From Chris Orlob


Until next time,
Scott Cowley

PS If you're ready, I have just started conducting:

Sales Tear Downs

Is your business closing some deals, but not enough? I work with many sales leaders to do a top to bottom tear down of what is working, what isn't and what to do about it. Sound interesting?

Book a Call

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