Seeing through Silence, Foaling Around, and What Would You Do?

A fresh serving of Bob's Bites

Welcome back to The Workaround. I’m Bob 👋

You’re in good company with fellow entrepreneurs and innovators who follow my stories from a career in tech startups and corporate innovation.

I’m here to make you think, smile, and discover a shortcut to success or a trap to avoid.

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Giant puppies (a.k.a. foals) love the winter. Why don’t you?

This is another round of Bob’s Bites. Every couple of weeks, I serve up a handful of short stories and lessons…

What Would You Do?

Here’s a real-life situation someone shared with me recently—with encouragement to post here. It’s not uncommon in today's business world, but it’s rarely discussed.

Put yourself in my friend’s shoes and let’s play What Would You Do?

Picture this scenario…

You’re a year into your new job at a small but growing marketing agency. Thanks to your and others’ hard work, the agency is growing quickly and has a bright future.

As the new year begins, the founder/CEO pulls you aside to say he will grant shares in the company he owns to you and a handful of senior leaders. Before the details are in your hands, he tells prospective clients that “his senior team is locked in with shares.”

Eventually, the legal paperwork arrives in your inbox. You’ve never seen an agency ownership agreement, and want to make sure you know what you’re signing up for and what you might get out of it.

So you drop the contract into ChatGPT, asking for a simple summary, the odds of how much you’d make on a future sale, and how this compares to similar agreements in the marketplace.

In less than 30 seconds, you’ve got its opinion: Yuck.

The agency would have to thread near-impossible needles for you to see a payout; you get nothing if you leave before a sale; and these shares can be withdrawn at any time for any reason. Your odds of seeing a nickel are near zero, and this structure is far worse than market norms.

You ask a good friend who has been an agency owner (that’s me) for a second opinion. He agrees with the AI’s assessment and tells a story of a CEO who fired multiple exec team members who were similarly granted shares while negotiating the sale of his business. The CEO simply didn’t want to pay them, and the share agreement, like my friend’s, made this perfectly legal.

Armed with this knowledge, what would you do now?

Do you share this assessment and try to negotiate with the CEO?

Do you tell your fellow executives to get a similar review, even though they seemed to be excited before?

Is it time to get your resume ready?

My friend is still processing it. If you have thoughts, please put them in the comments below.

My takeaway is that we have another way AI can help level the playing field and add transparency where it is sorely lacking.

Before you give loyalty to a company, make sure you’re not buying into make-believe.

Employee shares come with so many limits and issues that they almost never pay out. Put your faith in annual performance bonuses and profit-sharing instead.

Seeing through Silence

My little story last week about George and his over-use of the Sh*t/Compliment Sandwich earned more reactions in one day than most of my posts get in a month.

Why? Well, in part, its brevity is a better fit with the time allotted for email triage. But more than that, I think people recognized a common workplace annoyance.

Here’s another one: The Silence Tactic. It’s when you are negotiating with someone about, well, just about anything, and when it is their turn to speak, they choose to go silent.

The purpose of this move is to exploit our human nature to not let the silence between people go unfilled. Silence triggers our social fears that we said something offensive or that the person no longer likes us. So we tend to fill the space—often by giving the other side more of what they want in the deal in order to please them.

It’s the kind of thing we need pointed out to notice it the first time. For me, this was twenty-something years ago, when a peer at my corporate job bragged about how he got a supplier to give up a ton of concessions. I can still hear the excitement in his voice as he cracked the code on partner manipulation:

“I just sat there silently on the conference call, and they kept adding more free stuff!”

I didn’t like it then, and I didn’t like it last week when a friendly catch-up chat turned into a sales pitch for an investment.

This seasoned seller filled our discussion with multiple silent spots, I guess hoping I’d fill the gaps with a desire to learn more or ask for wire instructions to get in on the ground floor.

Now that I see this tactic, I do two things:

First, I make a mental note to ignore this person next time they reach out. I don’t hate the player, but I hate getting played. And I find that people who regularly use even small manipulations have turned off ethical guidelines more generally, and worse behavior is lurking around the corner for you, their mark.¹

Second, I try to have fun with it. Sometimes I make it a contest and just keep the silence going until they fill it. You can check a lot of email during those pauses. Or I’ll fill the space with a completely random non sequitur. “Huh, just heard my stomach growling. What are you having for lunch today?”

Now that you know, please pay this lesson forward to someone else👇

If you like my writing, feel free to click the ❤️ or 🔄 button on this post so more people can discover it on Substack 🙏

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1. People who play this way usually turn off all ethical rules because it’s much less stressful than trying to have ethics in degrees. For more on this, check out The Confidence Game, which tells many stories of Con Men and Women along with their methods and madnesses.