One of the first things I do when I join a startup as a fractional VP of Sales is sit in on a pipeline review.
Usually, there isn’t one.
Most often, there is no pipeline review.
The founder checks the CRM, scrolls through deals, and asks the rep: “So, what’s closing this month?”
The rep says, “Good. A few things are moving.”
Nobody learns anything.
Nobody makes a decision.
Then, at the end of the month, the number is missed.
Everyone is surprised.
But nobody should be.
Turning it into an interrogation. By far the most common.
The moment the meeting becomes stressful, your team starts hiding information.
They won’t show you the deals they are confident about, scared about your reaction if things don’t go as planned.
They tell you what you want to hear.
Hold pipeline reviews for 30 minutes, weekly, on the same day and time.
Always start with deals closing this month.
These are the most urgent to tackle.
For each deal, I look at one thing first:
Is there a clear next step? Agreed and booked?
Not “they said they will get back to me.”
Not “I will follow up next week.”
A real next step.
A meeting on the calendar.
Something critical has happened, or it’s about to happen.
If the next step is vague, the deal is stuck.
And we fix it right there.
If we need to, we can review the call, emails, and everything that has happened.
Sometimes a rep walks me through a deal, and something feels off.
The answers are vague.
They are not sure, and I can feel it.
That is when I ask some follow-up questions:
Close date, amount, next steps. Everything is up to date, or the meeting is aborted.
Pick 5 to 8 deals per rep. If it lasts more than 30 minutes, you are going too deep or too wide.
And remember, never punish honesty.
If a rep tells you a deal is dead, say thank you and move on.
Look at the backup pipeline or have a plan to create a new pipeline for the lost deals.
Cleaning the pipeline is more valuable than inflating it.
But only killing deals won’t bring you to the goal.
If you discussed a blocker on Tuesday and never mentioned it again, the team stops trusting the meeting.
Follow up on the actions.
Every single week.
Takes time, but it’s worth it, and the trust from your team is all you've got.
I have been using Claude with my CRM for some time. Now, most of the above can be handled by AI.
How?
It’s straightforward.
→ Connect your CRM to Claude Cowork
→ Connect the “sales” plugin
→ There is already a native prompt called “health pipeline check”
→ Claude will deliver to you an HTML file with the whole pipeline review.
Add to your prompt this newsletter as an .md file and reference it in the file.
You are going to have a complete pipeline review in a few seconds.
Now.
The earlier you build this habit, the stronger your culture will be.
When you eventually hire a Head of Sales, they will walk into a team that already has discipline.
And trust me - I have been there, and my job was way easier.
Thanks for reading. See you next week!
