I run my sales org on Brevity. Here’s the guesswork that it saved me.

Every week I send my CEO a report. What’s going well, where the risk is.

One of last week’s risks was a deal where the buyer had never actually agreed to a signing date. That risk is a common one. How I found out about it was not.

I wasn’t on the call where the risk surfaced. It wasn’t my rep who told me. Brevity did.

It listened to the call, picked up that the date had been assumed rather than agreed, and put it in front of me. By the time I read the notice, Brevity had already built a role play around that exact moment, and my rep was running it, so he was ready to address it in his next call.

I’ve sent that CEO report, or one like it, every week for twenty years.

Until three months ago, every one was built based on what my reps told me… Open-ended storytelling about a pipeline.

A risk made it into the report if a rep thought to mention it, or if I’d happened to be on the call.

Then I started at Brevity, and for the first time the team I lead runs on the product I sell.

The job hasn’t changed. It’s still my responsibility to know the state of the pipeline, coach the team, and, ultimately, deliver the number.

What’s changed is that every one of those is faster and better than it has been at any point in twenty years.

Knowing the true state of the pipeline

I’ve made a career out of coming to companies built on founder-led sales and an informal motion and building a GTM engine to unlock the next stage of growth for them.

I’ve done it enough times to know what I’ll find when I walk in: Inflated pipeline, commoditized deals, and reps selling to the wrong person.

The CRM shows me a lot of pipeline and a lot of close dates, and no way to tell which of them mean anything.

Brevity was running here before I arrived.

But it wasn’t tuned to the playbook that I want my team to follow. My first job was getting Brevity ready to judge my team my way: what counts as a compelling event, who counts as power, what every call has to establish before the next one.

From then on, every call was scored against that.

Within the first few weeks I saw what I’d normally wait half a year for.

Which deals were real. Which ones had a compelling event with a consequence attached.

Whether the buyer on each call understood what the call was for, and what had to be true before the next one.

I came in and found that our pipeline was overinflated by roughly 5X. We quickly removed the junk and focused on the deals that realistically would get us to our number.

I ended up forecasting our Q3 number within 2 points of what actually happened.

Let me use a specific example to illustrate something that we caught early on.

A prospect needed their sales team trained ahead of a product launch that was gated on regulatory approval, and the training had to be in place by January. Our rep was working to close the deal in September because the deal was critical for him to hit his number.

But based on the January timeline, the real decision was an October decision. It was a Q4 deal sitting in his Q3 pipeline.

Clearly, that’s not the right way to sell. But in previous roles, I would’ve missed it because I would’ve relied on the close date my rep put in CRM and whatever relevant information my rep decided to raise to me.

It’s a lot harder to coach when you don’t have full information.

Speaking of which…

Coaching the team

No two reps need the same coaching. A new hire has to learn the product, the method, and how to position, all at once. A veteran has always done it their way and doesn’t want to hear otherwise.

And then there’s a whole range in between like a rep who is good at the hard parts of selling (selling to power, finding champions), but they suck at pinning down the evaluation timeline.

To coach each seller where they are, I need two things:

1. A real read on each rep’s strengths and weaknesses
2. To know when a deal is at a critical moment and needs my intervention

Before Brevity, this was the most difficult part of the job. Sure, I had a call recording I’d listen to at night if there was time, and a 1:1 built from what the rep remembered, but the moment that needed me usually went by before I knew it existed.

Too often, I was finding out about deals in danger too late, after the best moment to save them had passed.

Thanks to Brevity, I know where each rep is strong and where they’re weak based on what they do on calls, which is a different thing from what they tell me afterward.

And when a moment needs my attention, it comes to me. It’s raised the week it happens, with the rep and the deal attached, and I decide the appropriate action to take.

That signing date gap example from earlier is what that looks like.

But even better, after receiving that flag, the system told me the pattern went past one call.

Across that week, the whole team only scored around 60 percent on confirming the compelling event and the timeline in their calls.

So Brevity proposed a drill: a role play built around that exact moment, getting a buyer to commit to a date and finding out what happens to them if they don’t.

I know where my sellers stand, and I know when deals need my attention, while there’s still time to do something about it.

And because the reps see the same read I do, our 1:1’s are incredibly productive.

Running the 1:1

Getting reps to run their own 1:1 is what I’ve worked toward on every team I’ve led. It’s the clearest sign the culture has turned: the rep owns the deal, and I’m there to help.

It usually takes me the better part of a year.

A 1:1 starts out as me inspecting each rep’s book, which puts them in a naturally defensive posture, and it takes months of those before a rep trusts the meeting enough to lead it.

Here, it took weeks.

The reps come in already knowing the feedback from the week’s calls, because the system has already told them the same things I would. There’s nothing for me to inspect that we both haven’t already seen. So they lead.

Our 1:1s consist of the rep telling me: here’s what’s going on, here’s where I’m stuck, here’s where I need your help and at what point. Once we get past this, I can tell you the deal comes in at this price around this date.

Each rep runs their book like a line of business. They’ve gone from being on defense to offense. They already have great visibility on the risks for each of their deals and the gaps they need to overcome. So our meetings become strategy sessions about the best way to do that.

Delivering the number

Everyone thinks a tool like Brevity is tactical.

Flag the risk, run the drill, move some revenue from the left column to the right. And to a certain extent, they’re right. That is part of the value.

But the biggest thing it does is empower culture change and force accountability. In my experience, change like that takes at least a year.

I know what that year goes to.

Assessing everyone and finding the problems. Deciding whether I have the right people, then hiring and ramping the ones I don’t. Lining up process and reporting. Going through the stack.

With Brevity, all of that happens faster than ever before based on real insights from real calls.

Culture change takes a year. Here, it took a quarter.

This week I’ll send the report again. What’s going well, where the risk is.

The risks in it came off real calls. The reps already know about them, and the fixes are already running.

For twenty years I sent that report hoping it was right. Now I know.