“It depends.”
A phrase we should hear more often from advisors, consultants, and colleagues.
There’s no universal fix for every business problem. If someone claims there is, they don’t understand how business actually works.
Should you adopt MEDDICC? It depends.
Should account managers sell back...
Most teams skip one of the most valuable habits in sales: the post-deal debrief.
Not just for losses — for every deal.
Ask:
- Why did we win?
- Why did we negotiate?
- Why did it take so long to close?
- Why did we lose?
When you deconstruct deals, you:
- Raise win rates
- Speed up cycles
- Level ...
Sales isn’t complicated.
It’s just often done backwards.
Most reps rush to pitch before they understand the problem.
Slow down.
Dig in. Ask until you fully grasp what’s broken and what it’s costing them.
Then restate it in plain language:
“It sounds like…. Did I get that right?”
Only after that...
Paul Olean taught me a lot early in my career.
Some lessons were about marketing. Some about sales.
But the best ones were about leadership.
Here’s one I’ve carried with me ever since:
If you’re the employee — don’t just bring your boss a problem.
Think it through. Bring ideas for how to fix it.
The greatest asset to any cold caller is…
(sorry, couldn’t resist the dramatic pause)
Research.
Drop a nugget of insight in the first 10–20 seconds and suddenly you’re not “another random caller.” You’re the interesting one.
The best teams either:
- Dig it up themselves and keep it handy (in a ...
AI can send emails.
It can’t save you from your own reply-blackhole.
If you’re using AI to prospect, you need a bulletproof reply-monitoring process.
Speed matters more than most teams think:
- Positive replies: Hit fast → book more meetings.
- Negative replies: Hit fast → win referrals, occasion ...
If you’re a frontline manager, you probably feel buried under rep questions. Most days. Instead of coaching or strategy, you’re stuck in reaction mode.
Reps can be lazy (sorry, reps). When they don’t know something, their first instinct is to ask you.Â
Not to think. Not to check the playbook. Not ...
Culture is defined by how you behave in hard times.
You say you value transparency, then cancel the town hall when numbers drop.
You say positivity matters, then protect the top performer who poisons the team.
You say you don’t discount, then slash prices in Q4 to hit the board target.
Values do...
I said to my wife, “Heads up, I’m probably getting fired today.”
She offered some encouragement. I hung up, sweating, and walked to the CEO’s office.
Back up.
I was a marketer at a startup. I had pitched a massive direct mail campaign—$200k+ on one bet. The CEO approved it. I ran with it.
Months o...
Scaling sales teams often make the same mistake:
They try to manage behavior instead of building a system.
Endless one-on-ones, activity policing, skills oversight—it all piles up. Leaders get overwhelmed. Reps feel micromanaged. And performance stalls.
The fix isn’t tighter management. It’s a sys...
It’s not new. But it’s never been more important.
Why?
Because distractions are relentless:
Slack. Teams. LinkedIn. Email. Pop-ins. Notifications. Noise.
Time blocking is how you fight back.
Here’s how to make it stick:
- Coordinate with your team—everyone blocks the same time
- Leaders: Make the ...
If you're an SDR Leader or a leader of a leader of SDRs, you're going to want to join this webinar.
We'll be talking SDR KPIs. What metrics matter and how to use them, so your team drives revenue.
I'll be joining Greg Casale, Kevin Kelly, and Richard Lane.
It's hosted by durhamlane.
Date: Thursd...
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