Booked. Issue #03 - June 2026

- Booked.  ·  The honest conversation

This week we're saying the stuff nobody wants to say out loud.

Your ICP might be a comfortable lie your stack keeps telling you. Your pipeline review is probably a group exercise in wishful thinking with an audience. And something very good is coming later this week - keep an eye out.

Tuesday 3 June 2026

Quick thing before we get into it.

This week I kept coming back to the same idea: most of the problems I write about - the activity trap, the weak CTA, the ICP built from vibes and a LinkedIn filter - they're not really about tactics. They're about what happens when nobody stops to ask whether the thing we're doing is actually connected to the result we want.

We're very good at being busy. Significantly less good at being honest about whether the busyness is working. And the conversation where someone looks at the dashboard and says "wait, none of this is connected to pipeline" - that's the one that almost never happens until it's too late to do much about it.

That's what this issue is about. Also Cynthia Handal says something later this week that will make you want to forward it to your entire leadership team. Keep an eye out.

✦ This Week on the Blog

Post 04 - Targeting

Your ICP Is a Lie.

Marcus has 9 tools telling him who his ICP is. He has zero opinions about it. Last quarter: $340K pipeline, 0.4% reply rate, 6% meeting-to-opp. The stack is working perfectly. The problem is the human stopped doing the part the tools can't do.

Read the full post ->
 

Free Tool - Frameworks

The Pipeline Health Diagnostic

A 12-signal scan that tells you exactly where your pipeline is leaking - and what to do about it. Covers the four things that actually matter: Coverage, Velocity, Conversion, and Source Mix. Built for leaders and reps. Takes about two minutes. Considerably more useful than your last pipeline review.
Coverage Velocity Conversion Source Mix
For Leaders For Reps
♦ Featured Interview - Vol. 01
 

Coming later this week

An interview with Cynthia Handal

Sales leader. Enablement coach. The person who said the quiet part loud about micromanagement, women in sales, and why the title everyone's chasing might be the thing that makes them miserable. She added that last part unprompted. I'm glad she did.

She didn't give me packaged answers. She gave me real ones. Keep an eye out - it's worth the read.

Dropping later this week
⚙ Run This Monday - ICP Audit

The ICP audit - run this before you build another sequence

Pull your last 20 closed-won deals. Pull your last 10 churned accounts. For each one, answer these three questions - not from a dashboard, from memory. If you can't, that's already the answer.

01

What triggered the buying decision?

Not the industry or the headcount. The thing that changed at the company in the 60 days before they took the first call. That trigger is your ICP. The firmographics are just the wrapping paper.
02

Why did the churned accounts churn?

Churn data is ICP gold and almost nobody uses it. The segments that keep churning at six months don't belong in your ICP. Your scoring model doesn't know this. Your renewals team does. Talk to them.
03

What signal would have told you the timing was right?

Funding, hiring spike, leadership change, competitor churn. That list of signals is your ICP's signal layer. Feed it into your scoring this Monday and watch what changes about who you're actually calling.

73%

Of B2B buyers say outbound messaging feels less relevant than two years ago. More tools. More automation. Less signal. The answer isn't more infrastructure.

Gartner B2B Buyer Report 2026
↗ Unsolicited Recommendations
01

Podcast

The Revenue Builders Podcast

Sales leadership, GTM strategy, hiring, operating models. More executive than tactical - which is exactly why you should be listening. If you want to sound like you understand the whole revenue engine and not just your lane, this is the one.

Apple Podcasts
02

Book

Gap Selling - Keenan

Stop pitching. Diagnose the problem. This book is essentially the manual for everything we talked about in the urgency post - finding the gap between where a buyer is and where they want to be, then making that gap impossible to ignore. Required reading if you coach reps on discovery.

Amazon
03

Website

Cynthia Handal

Our interview drops later this week - but go follow her now so you're not behind. She says the things most people in sales edit out before they hit publish. Her website is worth a proper browse too.

cynthiahandal.com
😐 One Bad Joke - Except It's Not

😐

This is not a joke. This is a pipeline review. Same thing.

Know someone who needs the honest conversation?

Forward this. It costs nothing and might actually make their next pipeline review less of a group exercise in wishful thinking.

Forward to someone who needs it ->

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© 2026 Smarter Outbound  ·  Written by a human who's lived it.