The Diary of a Sales Leader 😱

The Diary of a Sales Leader 😱

You might have seen me on LinkedIn today getting a sneaky look at what a sales leader's calendar looks like in 2025.

A look inside Mark's calendar

Spoiler: It was just as horrific as I thought it would be.

As the Head of Sales at MySalesCoach, Mark Ackers is a busy man.

He described his calendar to me as “very colourful.”

Translation? Jam-packed.

It's MAD to me just how many meetings sales leaders are in every day and it's the same story, right across the entire industry.

From one-on-ones to forecasting calls, pipeline reviews to internal syncs, every inch of space is spoken for.

It's colour-coded calendar chaos and it gives me anxiety just looking at it.

What that can mean is that reps aren’t getting help when they need it most.

The Sales Coaching Gap

Let’s face it... When a make-or-break moment comes up on a deal, reps often can’t wait until next week’s coaching session. They need help right now.

But most sales leaders, buried under back-to-back meetings, simply can’t be everywhere at once. That leaves reps to figure it out alone or worse, lose the deal altogether.

(Which I HATE to see happening!)

Coaching shouldn’t be a luxury. It should be accessible, instant, and integrated into how modern teams work.

Enter: Same-Day Deal Coaching from MySalesCoach

This week, we launched Deal Coaching:

🚨 Same-day coaching for your most critical deals.

Here’s how it works:

  • A rep submits a deal they’re stuck on.

  • One of our expert coaches picks it up that same day.

  • The rep gets tailored advice, specific to the challenge they’re facing... Whether that’s dealing with pricing pressure, re-engaging a stalled buyer, or navigating procurement hurdles.

The result? Fewer stuck deals. More revenue. Greater confidence.

This isn’t generic feedback or delayed guidance. It’s rapid-response coaching, from a proven sales leader, delivered exactly when your team needs it.

Early user feedback has been strong on this one:

“We’re no longer waiting to debrief losses. We’re preventing them in real time.”

Wait, are you trying to replace sales leaders?

With markets tightening and quotas rising, the margin for error in sales is shrinking. A single lost deal can define a quarter. And yet, most sales coaching today is reactive, retrospective, or rushed.

Deal Coaching flips that on its head. It’s built for the speed and complexity of modern B2B sales.

We’re not replacing sales leaders. We’re supporting them.

helping them scale their impact, and giving their teams the edge when it matters most.

🎉 GET complimentary Deal Coaching! 🎉

To celebrate the launch, we’re giving three sales leaders complimentary Deal Coaching for their team.

👉 Enter here: https://lnkd.in/ePaAE5dP

P.S Filling in this form will be the best use of your time all week.

(If you can find room in your calendar!) 😉

Laiba Maqsood

Senior Marketing Specialist @Success.ai | Empowering 30,000+ Companies to Automate Outreach, Personalize Engagement, and Boost Conversions with Scalable, AI-Powered Strategies

2mo

Fully agree

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Ollie Whitfield

Fractional Marketer for B2B Sales businesses needing to get known & build leadflow. Marketing Agency owner. Creative content 📈📈📈

2mo

Quick one....

Volker Ballueder

🏆 I coach senior leaders and SLTs to grow personally and organisationally. | 🧬 EQ, NLP, Mindfulness, Therapy | 📕Best Selling Author | 🎙️Podcast Host

2mo

This post dives into the chaos of a sales leader’s calendar and introduces Same-Day Deal Coaching by MySalesCoach—a fast, responsive way to support reps in critical deal moments without waiting for the next coaching session. Comment: Blimey, I’ve seen less colour in a packet of Skittles than some sales leaders’ calendars. And I’ve coached a few execs who wore that busyness like a badge of honour... until we unpacked how little real leadership was actually happening between Zoom hops. Coaching at the moment it matters? That’s a game-changer. I helped a CRO recently by simply getting her to listen instead of leading every call—deal velocity shot up in a fortnight. Funny what a little timely intervention can do, eh? Curious though... what’s getting cut from the calendar to make room for this kind of real-time impact?

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