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Simon Jackson

@simonjackson.co.uk
41 followers 73 following 63 posts

Sales Leaders Coach | Author of Stop Managing, Start Leading | Helping you lead with clarity, purpose & a human touch | Book out now #StopManagingStartLeading #TheSalesLeadersCoach #SalesLeadership

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Simon Jackson @simonjackson.co.uk · 22/07/2026
open.substack.com/pub/thesales...
open.substack.com
"I Say It Like It Is." The Badge of Honour That's Quietly Costing You.
Where communication is actually judged — and why the responsibility to adjust sits with the leader, not the listener.
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Simon Jackson @simonjackson.co.uk · 04/07/2026
There is a 25% off my book until 31 August via my publisher – practicalinspiration.com/book/stop-ma... Code SMSL25 at checkout.
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Simon Jackson @simonjackson.co.uk · 19/06/2026
The Ladder Problem: If AI Replaces the Bottom Rung, What Happens Next? substack.com/@thesaleslea...
substack.com
The Ladder Problem: If AI Replaces the Bottom Rung, What Happens Next?
The Ladder Problem: If AI Replaces the Bottom Rung, What Happens Next?
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Simon Jackson @simonjackson.co.uk · 08/06/2026
thesalesleaderscoach.substack.com/p/your-role-...
thesalesleaderscoach.substack.com
Your Role Will End. The Question Is: How?
Most leaders plan for the beginning. Very few plan for the end.
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Simon Jackson @simonjackson.co.uk · 29/05/2026
open.substack.com/pub/thesales...
open.substack.com
Experience Isn't Enough. It's How and Why That Matter Most.
Job experience is one of the weakest predictors of future performance. Here's what to look for instead.
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Simon Jackson @simonjackson.co.uk · 27/05/2026
Hire Like It Matters (Because It Does) open.substack.com/pub/thesales...
open.substack.com
Hire Like It Matters (Because It Does)
Hiring is the first system in your culture. Most leaders treat it like an emergency.
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Simon Jackson @simonjackson.co.uk · 30/04/2026
open.substack.com/pub/thesales...
open.substack.com
The Trouble Is… There's No Accountability.
Why demanding accountability without building responsibility and ownership first is a losing strategy.
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Simon Jackson @simonjackson.co.uk · 13/04/2026
"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
linkedin.com
"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...
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Simon Jackson @simonjackson.co.uk · 30/03/2026
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.
thinkers50.com
Thinkers50 Booklists - The Most Influential Management Books
Explore Thinkers50's booklists highlighting the most influential management books, both timeless classics and groundbreaking new releases.
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Simon Jackson @simonjackson.co.uk · 30/03/2026
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:
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Practical Inspiration Publishing @practicalinspiration.com · 30/03/2026
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
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Simon Jackson @simonjackson.co.uk · 18/03/2026
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
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Simon Jackson @simonjackson.co.uk · 14/03/2026
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...
linkedin.com
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.
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Simon Jackson @simonjackson.co.uk · 09/02/2026
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...
linkedin.com
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...
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Simon Jackson @simonjackson.co.uk · 03/02/2026
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. 🙏
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Simon Jackson @simonjackson.co.uk · 02/02/2026
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...
linkedin.com
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,...
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Simon Jackson @simonjackson.co.uk · 29/01/2026
An overview of my work with CROs, Sales VPs, and sales leaders – from 1:1 leadership coaching to sales transformation and leadership facilitation.
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Simon Jackson @simonjackson.co.uk · 28/01/2026
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...
linkedin.com
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.
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Simon Jackson @simonjackson.co.uk · 19/01/2026
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...
linkedin.com
What a year 2026, huh?
Happy New Year – even if it feels a little late to be saying it. January has been full-on.
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Simon Jackson @simonjackson.co.uk · 07/01/2026
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!
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Simon Jackson @simonjackson.co.uk · 17/12/2025
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
linkedin.com
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 ...
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Simon Jackson @simonjackson.co.uk · 11/12/2025
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
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Simon Jackson @simonjackson.co.uk · 11/12/2025
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.
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Simon Jackson @simonjackson.co.uk · 11/12/2025
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.
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Simon Jackson @simonjackson.co.uk · 09/12/2025
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
linkedin.com
#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...
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Simon Jackson @simonjackson.co.uk · 08/12/2025
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
linkedin.com
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 ...
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Simon Jackson @simonjackson.co.uk · 04/12/2025
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
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Simon Jackson @simonjackson.co.uk · 01/12/2025
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
linkedin.com
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.
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Simon Jackson @simonjackson.co.uk · 01/12/2025
An offer from my Publisher... practicalinspiration.com/book/stop-ma...
practicalinspiration.com
Stop Managing, Start Leading – Practical Inspiration Publishing
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Simon Jackson @simonjackson.co.uk · 30/11/2025
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. 🙏
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Simon Jackson @simonjackson.co.uk · 03/11/2025
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
linkedin.com
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.
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Simon Jackson @simonjackson.co.uk · 28/10/2025
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...
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Simon Jackson @simonjackson.co.uk · 27/10/2025
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
linkedin.com
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...
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Simon Jackson @simonjackson.co.uk · 24/10/2025
"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 😄
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Simon Jackson @simonjackson.co.uk · 14/10/2025
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
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Simon Jackson @simonjackson.co.uk · 13/10/2025
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...
linkedin.com
“FORCECASTING”: When ‘Stretch’ Breaks the Forecast
Some of you won’t agree with this. And that’s exactly why I’m writing it.
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Simon Jackson @simonjackson.co.uk · 11/10/2025
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...
linkedin.com
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.
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Simon Jackson @simonjackson.co.uk · 10/10/2025
I’ll just leave this here then 😁 bsky.app/profile/simo...
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Simon Jackson @simonjackson.co.uk · 10/10/2025
Lat week I published the very first edition of The Sales Leader’s Coach, my new weekly LinkedIn newsletter. www.linkedin.com/pulse/why-im...
linkedin.com
Why I’m Launching The Sales Leader’s Coach
Welcome to the very first edition of The Sales Leader’s Coach. Every Sunday evening, I’ll share one idea to sharpen your leadership for the week ahead.
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Simon Jackson @simonjackson.co.uk · 01/10/2025
The buzz of launch day has just sunk in… and now comes the bit that matters most. If you do grab a copy of Stop Managing, Start Leading, I’d love to know what you think. Reviews, reflections, or even a quick DM, it all helps and means a lot. #StopManagingStartLeading #SalesLeadership #BookReviews
Simon Jackson holding his book, Stop Managing Start Leading.
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Reposted by Simon Jackson
Practical Inspiration Publishing @practicalinspiration.com · 30/09/2025
What a month! 😮‍💨 Here are the books we published in the month of September: 'What Next?' by Jane Moffett 'Smart Conflict' by Alice Driscoll and Louise van Haarst 'Stop Managing, Start Leading' by Simon Jackson Incredibly proud to have worked alongside these authors to bring their titles to life!
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Simon Jackson @simonjackson.co.uk · 29/09/2025
Day one and already #1 Hot New Release in Business & Sales on Amazon. Surreal. 🙏 Thanks to everyone who’s bought so far. If you read it, reviews help more than you know. Kindle’s still just £/$/€0.99 today.
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Simon Jackson @simonjackson.co.uk · 27/09/2025
Congratulations John, wishing you every success for your book.
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Simon Jackson @simonjackson.co.uk · 27/09/2025
Big week ahead… 📚 Stop Managing, Start Leading officially launches Tuesday, but the Kindle version is out Monday for just £/$/€0.99. Kindle: mybook.to/SMSL-eb Print: mybook.to/SMSL @practicalinspiration.com
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Simon Jackson @simonjackson.co.uk · 25/09/2025
Stop Managing, Start Leading lands Sept 30. The book I wish I’d had starting out in sales leadership, 30 years of lessons, wins, mistakes, and coaching conversations distilled into one book. Excited (and a little surreal) that it’s nearly here. #StopManagingStartLeading #SalesLeadership
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Simon Jackson @simonjackson.co.uk · 10/09/2025
Grateful. Inspired. Slightly tired. And yes, still nursing the Guinness. 🍺 #SalesLeadership #Leadership #PsychologicalSafety #StopManagingStartLeading
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Simon Jackson @simonjackson.co.uk · 10/09/2025
Loved working with a smart, seasoned group of revenue leaders over the past two days. Open. Engaged. Willing to challenge and be challenged. This is the work that matters.
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Simon Jackson @simonjackson.co.uk · 10/09/2025
When people go quiet—out of fear or apathy—you don’t get their best. Great leaders create safe environments where disagreement is seen as engagement, not disloyalty. That’s where the real work happens.
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Simon Jackson @simonjackson.co.uk · 10/09/2025
At the start of every session, I say: it’s OK to disagree. Leadership and sales aren't black and white. What matters is how we explore the grey. Different views = better thinking. And respectful challenge? It means they’re in.
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Simon Jackson @simonjackson.co.uk · 10/09/2025
✈️ At Dublin Airport, Guinness in hand, reflecting on a moment from today’s workshop… 🗣️ “Honestly, I don’t agree with any of that. I couldn’t disagree more.” A strong comment—but I welcomed it.
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