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Posts by Simon Jackson

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"That Feels Like Micromanaging." Does It? I try to write these newsletters in real time based on conversations I'm having, patterns I'm seeing in clients, things that keep repeating until I can't ignore them. It isn't the most efficient way t...

"That feels like micromanaging."

Three clients. Same word. Same fear. Same retreat from the very things that make leaders effective.

My newsletter unpacks why the label is doing too much work.

www.linkedin.com/pulse/feels-...

#StopManagingStartLeading #TheSalesLeadersCoach #SalesLeadership

4 days ago 1 1 0 0
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Thinkers50 Booklists - The Most Influential Management Books Explore Thinkers50's booklists highlighting the most influential management books, both timeless classics and groundbreaking new releases.

The @thinkers50.com Best New Management Booklist is open for nominations (peer-led, so I can’t nominate it myself).

If the book has been useful to you or your team, I’d really appreciate you considering a nomination.

thinkers50.com/booklists/

Thank you for the support, it genuinely means a lot.

2 weeks ago 0 0 0 0
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Six months ago today, Stop Managing, Start Leading was published.

Grateful for the feedback, reviews, and, most importantly, how people are using it in practice.

It’s also been put forward for the Business Book Awards 2026.

A small ask:

2 weeks ago 2 1 1 0
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Happy 6-month book-aversary to Simon Jackson and Stop Managing, Start Leading! 🥂🍾

The ultimate guide for sales managers and leaders ready to elevate their game.

#businessbook

2 weeks ago 2 2 0 0
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A small milestone I’m pleased to share.

Stop Managing, Start Leading has been entered into the Business Book Awards 2026.

Great to be alongside so many strong titles and authors.

If it helps sales leaders build better environments for their teams, it’s doing its job.

#BBA2026 #SalesLeadership

4 weeks ago 2 1 0 0
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Eighteen Months. Is That Really All a CRO Gets? I recently had the pleasure of being a guest on the next + future podcast with Joel and Matt . One of the questions they asked me has stayed with me since.

The average CRO tenure is 18 months.

It isn’t a performance problem. It’s a structural one, accountability for revenue without control of the drivers behind it.

This week’s newsletter explores why, and what shifts the odds.

#SalesLeadership

www.linkedin.com/pulse/eighte...

1 month ago 1 1 0 0
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Your Role Will End. The Question Is: How? | Simon Jackson Every February, LinkedIn fills up with two very different stories. People delighted to be starting new roles. And others quietly navigating a tough job market. Both are real. And both got me thinki...

Every role ends.

This isn't being pessimistic, it’s just how careers work.

The more interesting question is how it ends… and what you leave behind as a leader.

I’ve shared a few reflections on that in this week’s newsletter.

Over to you once you’ve read it.

www.linkedin.com/pulse/your-r...

2 months ago 1 1 0 0
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If you’ve read Stop Managing, Start Leading, I’d genuinely love to hear what resonated, or even what challenged you.

Reviews and comments help bring the book to leaders who might benefit from it, so if you’re open to sharing your thoughts, I’d really appreciate it.

🙏

2 months ago 1 1 0 0
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The Ladder Problem: If AI Replaces the Bottom Rung, What Happens Next? I try to write these newsletters in real time, based on conversations I’m having, things I’m seeing in clients, and the quiet patterns that keep repeating. It isn’t the most efficient way of doing it,...

A couple of things I saw and heard last week made me stop and think.

If AI starts replacing entry-level roles, where do future senior salespeople and leaders actually come from?

This isn’t a scare piece. More a reflection, and an open question.

www.linkedin.com/pulse/ladder...

2 months ago 1 2 0 0
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An overview of my work with CROs, Sales VPs, and sales leaders – from 1:1 leadership coaching to sales transformation and leadership facilitation.

2 months ago 1 1 0 0
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Employee Engagement Isn’t Soft. It’s a Leadership Responsibility. January is always an interesting time to be a sales leader. Sales Kick-Offs are happening everywhere.

Sales attrition. Engagement. Leadership pressure.

I’ve shared some thinking in this week’s LinkedIn newsletter – what the numbers might really be telling us, and why engagement deserves far more attention than it gets.

Link below 👇

www.linkedin.com/pulse/employ...

2 months ago 2 1 0 0
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What a year 2026, huh? Happy New Year – even if it feels a little late to be saying it. January has been full-on.

January doesn’t always unfold the way the deck said it would.

That doesn’t mean the plan has failed – it means it needs adjusting.

This week’s newsletter is about staying focused, adaptable, and human as a sales leader.

Read it here 👉 www.linkedin.com/pulse/what-y...

2 months ago 1 1 0 0
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Contrary to popular belief, it isn’t always raining in Manchester. Although it was a bit gloomy and wet when I arrived in town this morning (all windswept).

Had the privilege of talking at the Supporting Women in Sales event — the first of many inperson events this busy January.

Happy New Year!

3 months ago 2 1 0 0
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The Trouble Is… There’s No Accountability. I remember a sales leader saying that to me in a moment of real frustration: “The trouble is… there’s just no accountability.” He’d spent a US holiday weekend on the phone with his AVP trying to land ...

Who’s accountable when things don’t go to plan?

I’ve published a new LinkedIn newsletter exploring responsibility, ownership, and accountability, and why accountability shouldn’t feel like a threat, but a natural outcome of good leadership.

www.linkedin.com/pulse/troubl...

#TheSalesLeadersCoach

4 months ago 2 1 0 0
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It’s a theme I build on in Stop Managing, Start Leading: leaders shouldn’t carry the load alone.

Which type of support do you already have, and which one do you need more of right now?

#StopManagingStartLeading #SalesLeadership #Resilience

4 months ago 0 0 0 0

Rob Cross & @kardillon.bsky.social’s work on microstress nails it: we need different people for different moments – listeners, inspirers, reframers, surge-helpers, the ones who make us laugh, the navigators, the people who help us unplug. No single mentor can do all that.

4 months ago 1 0 1 0

Who’s really in your corner?

I wrote this week about the quiet isolation many sales leaders feel – and why the smartest move isn’t pushing harder, but building the right support around you.

4 months ago 1 1 1 0
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#stopmanagingstartleading #thesalesleaderscoach #salesleadership | Simon Jackson I'm thinking of launching a new monthly webinar series for Sales Leaders – but I’d love your input. I’m planning to run a free 45-minute live webinar at the start of January, as a companion to my boo...

I'm thinking of running a monthly sales leadership webinar – live, short, and practical. First one in January.

Which topic would you find most useful?

Details, and vote for the first topic on LinkedIn 👇

www.linkedin.com/posts/simonj...

#StopManagingStartLeading #SalesLeadership

4 months ago 1 0 0 0
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Who Do You Turn To When You’re the One in Charge? It’s early December, which means my feed is full of “Top Sales Challenges for 2026”. Most of them say similar things: economic pressure and cautious buyers AI reshaping the way customers research and ...

I’ve been thinking a lot about the reality of leading sales, especially the parts we rarely discuss.

This week’s newsletter explores the personal side: support, isolation, and who we turn to when it counts.

Read it here 👉 www.linkedin.com/pulse/who-do...

#StopManagingStartLeading #SalesLeadership

4 months ago 1 1 0 0
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Early’ish start and a coffee at Piccadilly. Edinburgh next.

Catching up with a client I normally see on Zoom - and a few others flying in. Finalising January’s Atlanta RKO.

Funny how a quick in-person chat can unlock more in 10 minutes than an hour online.

#StopManagingStartLeading #SalesLeaders

4 months ago 2 1 0 0
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Quotas Change. Your North Star Shouldn’t. Last week we explored why standards beat expectations, and why clarity beats corporate speak. This week, we move to another pillar of the Vision, Clarity & Culture system.

When a team loses its direction, everything starts to wobble.

This week’s newsletter is about building a North Star your people can steer by – especially when you’re not in the room.

Read it here 👉 www.linkedin.com/pulse/quotas...

#StopManagingStartLeading #TheSalesLeadersCoach #SalesLeadership

4 months ago 2 1 1 0

An offer from my Publisher...

practicalinspiration.com/book/stop-ma...

4 months ago 1 1 0 0
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My book Stop Managing, Start Leading was published two months ago today.

Thank you to everyone who’s picked up a copy.

If you enjoyed it, a short review would really help others discover it too.

Grateful for all the support so far. 🙏

4 months ago 2 1 1 0
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Hire Like It Matters (Because It Does): Building the People System The great American philosopher, Homer Simpson, once decreed that alcohol is the cause of, and solution to, all of life’s problems. Tempting as that sounds, I think he’s wrong.

Most business problems are people problems.

That’s why the People System – how you hire and who you hire – shapes everything.

This week’s edition: Hire for Attitude. Train for Aptitude.

Read it here 👉 www.linkedin.com/pulse/hire-l...

#TheSalesLeadersCoach #StopManagingStartLeading

5 months ago 1 1 0 0
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Ange Postecoglou lasted 39 days at Forest. Different philosophy, same players, no alignment. In leadership or sales, it’s the same truth: you can’t build a new system on old habits. Culture doesn’t change in 39 days.

I unpack this idea in my latest newsletter: www.linkedin.com/pulse/you-do...

5 months ago 2 1 0 0
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You Don’t Get the Culture You Want. You Get the One You Build. | Simon Jackson If culture really eats strategy for breakfast, why do so few leaders spend time feeding it? Most can tell you their strategy, KPIs, and quarterly goals, but struggle to describe what their culture fe...

If culture really eats strategy for breakfast, why do so few leaders feed it?

My latest newsletter explores how intentional culture design separates high-performing teams from the rest.

👉 Read the full piece here: www.linkedin.com/posts/simonj...

#StopManagingStartLeading #SalesLeadership

5 months ago 1 1 0 0
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"I really enjoyed reading this book"

"Amazing book 📖"

"Helpful book"

5-Star reviews all-round on Amazon. But don't just take my Mum, my eldest daughter, and one of my nephew's word for it, check out my book for yourself.

Have a great weekend everyone 😄

5 months ago 3 1 1 0
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Unashamed plug for my book.

Too many leaders still dread their forecast calls - endless prep meetings, more scrutiny, less impact.

We don’t need more pressure. We need better leadership.

That’s what Stop Managing, Start Leading is all about.

#StopManagingStartLeading #SalesLeadership

6 months ago 2 1 0 0
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“FORCECASTING”: When ‘Stretch’ Breaks the Forecast Some of you won’t agree with this. And that’s exactly why I’m writing it.

Lately I’ve seen too many managers turning forecasting into FORCEcasting - telling people what number they must call, rather than asking for their best read of reality.

I get the intent: stretch people, push for more, create urgency.
But here’s the problem...

www.linkedin.com/pulse/forcec...

6 months ago 2 1 0 0
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The Hidden Quarter: How to Escape the Q4 Panic It’s the 80th minute, you’re one–nil down. You need at least a point to save your season.

The last 10 minutes of a football match.

One–nil down. Panic mode. Long balls, the big striker thrown up front, even the keeper wandering into the box.

For many sales teams, Q4 looks exactly like that. Check out my latest LinkedIn Newsletter.

www.linkedin.com/pulse/hidden...

6 months ago 2 1 0 0