I was let go from my job today.
But I don’t see it as a termination. I see it as my company choosing to churn early, before realizing full value.
That happens in sales. Not every customer is ready for what you bring to the table. Sometimes what you bring to the table is a jet ski expensed as “prospect entertainment,” and the customer doesn’t understand that’s an investment.
Out of respect for the relationship, I’ve already added my former manager to a nurture sequence. The first email went out this morning. Strong open rate so far.
Excited for what’s next. And for my former employer, who I believe will be back.
I accidentally emailed a prospect my private notes on him today.
Some highlights: “Easy mark.” “Cries at dog commercials.” “Wife makes the real decisions, go around him.”
Most reps would see that as a disaster. I see it as radical transparency.
Buyers are tired of being kept in the dark. This prospect now knows exactly where he stands in my process, which is more than most buyers ever get.
He replied asking to speak with my manager. That tells me he’s ready to bring more stakeholders into the conversation.
I’ve also reached out to his wife directly, per my notes.
Proud to be building trust in an industry that needs more of it.
#RadicalTransparency #Multithreading #BuyerEnablement #Trust
I fell asleep during a sales call today.
I was out cold for about 25 minutes.
But here’s what nobody tells you: silence is the most powerful tool in sales.
While I was out, the prospect talked uninterrupted about his goals, his budget, and his frustrations with his current vendor. Best talk-to-listen ratio of my career.
He said he could hear me snoring. Wrong. That's called active listening.
By the time I woke up, he’d asked to be reassigned to a different rep on my team. Some people would call that losing the deal.
I call it a warm handoff.
Grateful for the rest. Grateful for the lesson.
My wife filed for divorce this morning.
After 11 years, she’s decided to go with another vendor.
It stings. But every closed-lost deal is a learning opportunity, so I did something most reps are too scared to do. I asked her for feedback.
She said I treated our marriage like a pipeline. I respectfully disagree. I’ve never let a pipeline go 11 years without a check-in.
Honestly, I’m proud of the tenure. Our average customer churns in 9 months.
Her lawyer is one of the toughest negotiators I’ve ever sat across from. I’ve already invited him to a demo.
Wishing her and her new vendor nothing but success, and a seamless implementation.
A prospect punched me in the face today.
Most reps would call that a lost deal. I call it the most honest feedback I’ve received all quarter.
Buyers spend all day hiding their objections behind “send me some info” and “let’s circle back next quarter.”
Not this guy. When I showed up at his daughter’s birthday party to follow up on my 14 unanswered emails, he communicated his concerns with total clarity, directly to my jaw.
That’s what real buyer engagement looks like. You don’t get that over Zoom.
I’ve already sent a follow-up thanking him for his candor and proposing 15 minutes next week to align on next steps. Hoping to reconnect as soon as the swelling goes down.
Grateful for prospects who aren’t afraid to be direct.
Always leave a voicemail.
Most reps hang up when it goes to voicemail.
Because they're scared.
That’s a missed touch.
I leave one every time.
And I don’t do the quick name number after the beep crap.
I do the full pitch. Discovery. Demo. Pricing. Next steps.
If voicemail box cuts me off at 3 minutes, I call back and keep going.
You must OWN the prospects voicemail, leave no room for other sales reps to pitch.
The prospect's own mother shouldn't even be able to leave a message.
Discovery is everything.
Most reps ask surface-level questions. “What tools are you using?” “What’s your timeline?”
Weak.
I ask what keeps them up at night.
Then I ask why.
Then I ask about their father.
Is your father proud of you?
Did you have a good childhood?
If they start crying I know I've got them.
I don't stop. You never interrupt a prospect when they’re opening up.
Buyers don’t trust salespeople.
So the best thing you can do is be brutally honest.
A prospect asked if we integrate with HubSpot.
I say no.
Asks if we’re SOC 2 compliant.
No.
Asks if anyone’s ever renewed.
Not yet.
Asks if the product works.
Some days.
He sat there stunned.
He said I was the first honest salesman he’d ever met.
Signed that afternoon.
That’s the power of trust.
It’s why I could charge him double.
Never sell the product. Sell the outcome.
Nobody wants a drill. They want a hole.
So I stopped talking about our software completely.
I talk about how their life will feel after.
Promotion. Bigger house. Hotter wife. Kids who call them back.
The prospect asked what our product actually does.
I said, “Does it matter? You’ll be happy.”
He said yes, it matters.
I said that’s the old you talking.
He signed.
Six months later he called to cancel.
He said his wife left him.
That’s not a product issue.
That’s an onboarding issue.
Locked myself out on the balcony yesterday morning. 27th floor. Phone in my pocket, laptop inside. The door locks behind you, apparently.
So I worked from the balcony. 90 degrees, no shade.
The lady on the next balcony asked if I was okay. I said never better and asked what she does for work. She went inside.
Her husband came out and asked if he should call someone. I said I'm good, I've got a list. He went inside too.
Around noon a window washer came down past me on his platform. I pitched him the whole way down.
Booked 2 meetings by lunch.
The building manager finally let me in around 4. He asked why I didn't just call him.
He's not in my territory.
Went to a playoff baseball game last night and the kiss cam landed on me and the guy next to me.
Quarter zip, Apple Watch, definitely a decision maker.
40,000 people watching, so I shook his hand on the jumbotron and the whole stadium booed.
He laughed and asked what I do, so I pitched him until the next inning started.
He took my card.
Biggest room I've ever pitched.
ABC. Always Be Closing.
Most reps think that only applies on sales calls.
Wrong.
This morning the barista at Starbucks asked if I wanted a large.
Rookie mistake. Never ask a yes or no question.
So I stopped her.
I said, “Don’t ask if I want a large. Assume it.
Say: "I’ll get that large started for you."
She said okay.
I said, "Now create urgency. ‘We’re almost out of pastries.’”
She said, “We have a whole case of pastries.”
I said, “The customer doesn’t know that.”
She looked at the case. Then at me. Then back at the case.
“We’re almost out of pastries.”
I said, “Good. Now upsell.”
She said, “Would you like oat milk?”
I said, “Don’t ask. Assume the sale.”
“I’ll add oat milk.”
I said, “Bigger.”
“I’ll set you up with our 12-month bean subscription.”
Now she’s cooking.
Walked out with a large oat latte, four croissants, and a year of beans.
I don’t even own a coffee maker.
Best rep I’ve ever trained.
You have to create urgency.
“Price goes up at the end of the month” is the oldest trick in the book.
My price goes up every day the prospect doesn’t sign.
I sent a quote for $20k in June.
It’s $85k now.
He still hasn’t signed.
My manager says I priced us out of the deal.
No. I priced HIM out of the deal.
He’ll come crawling back.
And when he does, it’ll be six figures.
Follow for me sales tips.
Always ask for referrals.
Closed deal? Ask for referrals.
Lost deal? Ask for referrals.
Most reps only ask happy customers. That’s leaving money on the table.
The best time to ask is when people are emotional.
Weddings. Graduations. Funerals.
Especially funerals.
Everyone’s in a suit. Everyone’s networking. Everyone’s talking about how short life is.
You know what else is short? Your sales cycle with a warm intro.
Mirroring is the most powerful tool in sales.
Repeat the prospect’s last few words, match their energy, match their posture.
People buy from people who remind them of themselves.
So I take it further.
Prospect leans back, I lean back.
Prospect crosses his arms, I cross my arms.
Prospect scratches his nose, I scratch my nose.
Prospect asks why I’m copying him, I ask why he's copying him.
He asked me to leave. I asked me to leave.
Didn’t get the deal.
But for 30 minutes we were the same person.
You can’t put a price on that.
But I am on a PIP.
Every great salesman finds the pain.
But what if the prospect has no pain?
You have to create the pain.
Think of window salesmen who throw rocks through windows.
Sometimes bringing the prospect a solution isn't enough.
You need to bring them the pain AND the solution.
Oldest rule in sales: after you say the price, shut up.
First one to talk loses.
I sent a quote to a CFO two months ago.
We haven't spoken since.
My manager wants me to follow up.
He doesn't know shit.
I'm holding steady.
The thing about sales is your customer needs to feel close to you.
I hug every prospect the first time we meet.
Handshakes are too impersonal.
A handshake says “vendor.” A hug says “family.”
And I never let go first.
Last week I hugged a prospect for two full minutes in a Marriott lobby.
He tried to squirm away, but I wouldn't let him go.
Security came. I kept hugging.
He agreed to a follow-up meeting just to make it stop.
Some people would call that a hostage situation.
I call it a mutual action plan.