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Welcome to My New Meta, where I share hard-earned wisdom (and humour-filled faceplants) from 30 years of corporate real estate development. Like Patrick Lencioni's business fables, I tell real stories (as I remember them) that reveal powerful lessons.

⚠️ Warning: Like all good storytellers, I may occasionally embellish for dramatic effect. While the lessons are real, some scenes have been enhanced for entertainment value but no spreadsheets were harmed in the making of this newsletter.

Here’s what I’ve got for you today:

TLDR (The No-BS Version):

• Charge by value, not time—double your income.

• Get comfortable with awkward questions—they lead to big wins.

• Silence is a power move—just don’t overdo it.

• Asking tough questions can save or make millions.

• Use the "Awkwardness Framework" to turn discomfort into profit.

Let’s get into it.

Small Talk: The $20k Awkward Conversation

Last week, I nearly made a classic rookie mistake with my new client, Terry. He wanted help with a development proforma, and I immediately quoted my hourly rate like a corporate drone on autopilot.

Then it hit me - I was about to trap myself in the time-for-money game. Again.

SCENE: Coffee shop downtown. I'm sweating through my second americano, about to have that awkward pricing conversation.

ME: "Actually Terry, instead of billing hours, let's talk about the value this proforma brings to your project."

TERRY: "Go on..."

ME: "This analysis could save you six figures in development costs and months of headaches. How about we price it based on the project's complexity instead of my time?"

Terry didn't just agree - he doubled my original estimate because now we were talking results, not timesheets.

Lesson learned: When you charge for value, clients invest in outcomes, not hours.

On to the main event…

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From Corner Office to Corner Booth

Ever wonder what happens when a former real estate president has to work a wedding show booth? This weekend, I found out - and it wasn't pretty.

Picture this: The Calgary Wedding Show, packed with excited couples planning their big day. There's Kirsten, confidently showing how chargeFUZE keeps phones charged during those late-night dance parties where Instagram is mandatory. 

And then there's me - the guy who used to run multi-million dollar deals, now hiding behind our fancy display table whenever someone walks by so I don’t make that awkward eye contact.

Here's how one chat went:

WEDDING PLANNER: "Oh, this looks interesting! How does it work?"

KIRSTEN: "Let me show you! Your guests just scan this QR code, grab a portable charger, and—"

ME: (pretending to adjust our perfectly working display unit) "Uh, technical difficulties over here! Very important... adjustments...voltage off by 1 nanobyte or so."

KIRSTEN: (continuing smoothly) "As I was saying, no more dead phones during speeches or first dances..."

ME: (now completely behind the station) "Just making sure the unit leveled perfectly! Very crucial stuff!"

WEDDING PLANNER: (to Kirsten) "This is brilliant! How many venues are using these?"

ME: (suddenly remembering I used to be important) "Did you know I once had a corner office with THREE windows? Big-time executive energy, right?"

KIRSTEN: (saving me, again) "Let me show you our venue list..."

Walking home that night, something hit me: Back in my early development days, I was the king of being awkward and asking those uncomfortable questions.

I'd stop meetings cold to ask about numbers that didn't add up. I'd call out problems others ignored. That awkwardness made my career.

But somewhere between that corner office and this corner booth, I forgot a crucial lesson: Business isn't about looking important - it's about helping people solve problems.

And sometimes, that means being awkward enough to ask the right questions.

Looking back at my behaviour at the wedding show, I have to wonder: Have I gotten too proud to do the basic work? Too worried about my image to connect with potential customers?

Too far removed from the simple art of asking questions and really listening to answers?

Maybe it's time to get awkward again…hence the very uncomfortable selfie below…

The Silence Master: When Awkward Goes Pro

Ever had lunch with someone who treats conversation like a zen meditation? Meet Dave, one of my first real estate development bosses and the undisputed champion of awkward silences.

SCENE: 1999, Alice Fazooli's in downtown Oakville (because nothing says "important business lunch" like unlimited breadsticks and career anxiety).

Dave has invited me to discuss my first major project.

ME: "So what did you think about the site plan?"

DAVE: (methodically twirls pasta)

ME: (waiting politely)

DAVE: (examines single noodle with scientific interest)

ME: (still waiting)

DAVE: (stares intently at breadstick)

ME: "Should I revise the..."

DAVE: (raises finger slightly, returns to pasta contemplation)

[15 minutes pass. My fettuccine gets cold. Three different servers ask if we're okay.]

DAVE: "Good pasta."

ME: "The site plan?"

DAVE: (begins architectural analysis of tiramisu structure)

Looking back, I learned two things from those lunches with Dave:

1. Silence can be a powerful tool in business

2. But maybe not 15 minutes of pasta-contemplation silence

That experience taught me something crucial about awkwardness in business - it's all about finding the right balance.

Too little (like me hiding from wedding show customers), and you miss opportunities.

Too much (like Dave's pasta meditation), and you create confusion instead of clarity.

Which brings us to the story that changed my entire approach to business...after an important word from our generous sponsor…

The $50 Million Question: How Awkward Conversations Create Real Estate Fortunes

Watching Dave master the art of silence taught me something important: Awkwardness can be a tool if you know how to use it. While Dave might have taken it to extremes with his pasta meditation, he showed me that being comfortable with uncomfortable moments could be powerful.

I put that lesson to use sooner than I expected. Just three years later, in a moment that would change my career forever...

The Meeting That Changed Everything

Picture this: Toronto, 2002. A room full of senior executives nodding along to clearly flawed numbers on a $50 million mixed-use development.

The financial assumptions were wrong. Everyone knew it. No one said anything.

Finally, my desperate need to avoid future embarrassment overpowered my fear of immediate awkwardness.

"Sorry, but..." I squeaked, channeling Dave's silence for courage while my dress shirt betrayed me with rapidly expanding sweat circles. "These numbers seem..." (voice crack, because timing is everything) "...way off?"

The silence that followed was so complete you could hear Karen's diet Coke fizzing three rooms away. Someone coughed.

Someone else studied their shoes like they held the secrets of the universe.

I started calculating how many cardboard boxes I'd need to clean out my desk.

Seventeen eternal seconds passed. I counted each one while planning my next career move: professional dog walker.

Bill, the CEO, tapped his pen once, twice… then stopped.

That's when I deployed my secret weapon - pure, unfiltered, Dave-inspired silence. Just me, sweating through my new suit while mentally drafting my LinkedIn update: "Seeking new opportunities, specializing in awkward meeting moments."

But then something magical happened. The CEO set down his pen, leaned back, and did something I'd never seen in my three years at the company.

He smiled.

"Finally! Someone said it. Greg's right - these numbers are garbage. Let's fix them."

That moment launched my career. Within a year, I was leading major projects. Why? Because I was willing to be temporarily uncomfortable to prevent permanent problems.

The Awkward Questions That Built My Career:

• "What if these projections are too optimistic?"

• "Could we structure this deal differently?"

• "Have we considered what happens if the market drops?"

• "Why are we really doing this project?"

Each question felt awkward.

Each answer made millions.

…The Awkwardness Framework and Template after more ads and some curated links help with your awkward communication..

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Curated Links: Let’s Communicate

Conversation Starter and Support Apps

1. Slowly – A modern twist on pen pal letters, this app connects you with like-minded people around the world. But there’s a catch—messages take time to deliver, just like real mail. Choose topics you care about and build thoughtful, meaningful connections, one delayed message at a time.

2. Party Qs - – Say goodbye to awkward silences! This free app packs over 2,000 hand-picked conversation starters, covering everything from deep debates to lighthearted laughs. Perfect for couples, friends, and even those dreaded work icebreakers.

3. LongWalks - – More than just small talk, this app sparks meaningful conversations with daily prompts on gratitude, joy, and mindfulness. Whether with friends, family, or yourself, it’s like a guided walk for your thoughts—minus the blisters.

4. Awkward Silence - – Your secret weapon against dead air. This weekly email delivers fresh conversation starters, giving you 500+ topics for work chats, family dinners, or even nerve-wracking first dates—all for less than a buck a month.

5. Fabriq - The ultimate cheat sheet for keeping in touch. This app tracks your contacts' interests and important dates, nudging you with reminders to reach out—because meaningful connections shouldn’t rely on “Oops, I forgot your birthday” moments.

The Awkwardness Framework

Over 30 years of development deals, I've created a simple system for turning awkward questions into profitable answers:

1. The Setup

• Write down the awkward question

• List potential positive outcomes

• Identify worst-case scenario (usually just embarrassment)

• Channel your inner Dave (but maybe 30 seconds of silence, not 15 minutes)

2. The Delivery

• Ask directly but respectfully

• Let the silence work for you

• Stay quiet until they respond (Dave taught me this one, believe it or not)

• Resist the urge to fill the void with nervous chatter

3. The Follow-Through

• Document the response

• Schedule next steps immediately

• Follow up within 24 hours

• No pasta-contemplation required

Your Awkwardness Toolkit

Here's a simple template to help you harness the power of productive awkwardness:

Question Planning Snake:

Real Estate Translation:

Every major deal I've closed started with an awkward question.

"Would you consider selling?"

"Did someone die in this house?"

"What if we structured this deal differently?"

“Can I pour out this bag of marbles to see if the floor has any low spots?”

“Have you ever let a beaver loose in a pine furniture factory?”

"Mind if I give the cupboard under the sink the old sniff test?"

Business Translation:

Your next promotion, raise, or breakthrough probably lives on the other side of an uncomfortable conversation.

Salary Impact: Being known as someone who constructively addresses elephants in the room is worth $10-15k in additional salary per year. Companies pay a premium for people who prevent expensive mistakes by speaking up early.

Tomorrow's Action Items:

✅ Identify one awkward question you’ve been avoiding.

✅ Use the template to plan your approach.

✅ Ask the question within 24 hours. (Yes, actually do it.)

✅ Document what happens.

✅ Practice strategic silence. (But keep your pasta warm.)

THAT’S A WRAP

Remember: In real estate and in life, the biggest risks often carry the biggest rewards.

But sometimes, the biggest risk is simply being willing to ask the question everyone else is afraid to ask.

Stay awkward and keep closing,

Greg "new baby deer with awkward legs" Mills

P.S. Want to practice? Start small. Next time you're buying anything, ask "Is that the best you can do?" Then sit in silence until they respond. The savings will fund your "dealing with awkwardness" therapy.

P.P.S. Just don't pull a full Dave and silently stare at your shopping cart for 15 minutes. We're going for productive awkwardness, not performance art.

If you liked what you read and are not a subscriber yet, join the crowd:

Here are some back issues if you are just not sure yet:

Issue #22: Adding Value At $30k Per Minute 

Issue #21: How To Lose A $500,000 Sale In A Matter Of Minutes 

Issue #20: How Three Months of Silence Became a $5 Million Mistake 

Issue #19: $2,295/Month To Avoid Talking To Humans 

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