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📄 Accidental manager to leader—this is the transition most high performers and founders struggle with, and it’s exactly why so many businesses fail to scale.
In this episode, we sit down with John Mason, Founder & Chief Revenue Officer, to break down what really happens when top performers are thrown into leadership roles without a playbook—and how that creates bottlenecks in both revenue and team growth.
If you’ve ever felt overwhelmed trying to grow your business, lead a team, or figure out where to focus next… this conversation will give you clarity.
We dive into:
Why most founders fail to scale due to lack of focus
The real difference between management vs leadership
How to transition from individual contributor to leader
Why narrowing your ICP is critical for how to scale a startup
The truth about AI in sales and why it won’t replace great salespeople
How to avoid becoming the bottleneck in your own business
John Mason shares practical insights from working as a fractional CRO, helping startups build sales pipeline strategy, develop teams, and implement real chief revenue officer strategy that drives results.
Whether you're stepping into leadership for the first time or trying to fix a struggling team, this episode is packed with actionable frameworks around: 👉 Leadership for new managers 👉 How to lead a team for the first time 👉 Sales leadership training 👉 How to build a sales team
If you’re searching for answers on how to grow without chaos, lead without burnout, and scale without losing control—this episode is for you.
⏱️ TIMESTAMPS (20:12 VIDEO)
00:00 – Intro: Why growth breaks without clarity 01:00 – Meet John Mason (CRO & founder) 02:30 – Founder struggles: lack of focus & ICP 04:00 – Biggest pain points in scaling a business 05:00 – AI in sales: opportunity vs illusion 08:00 – Midroll: leverage vs complexity 09:00 – Accidental manager → leader transition 11:00 – Is middle management dead? 13:00 – Bottlenecks & scaling mistakes 14:00 – Traits of great leaders 17:00 – Using sales skills to lead people 18:30 – Marketing, mindset & Carlsberg analogy 19:30 – Outro + final insights
If you're building a business or you've recently stepped in the leadership and you feel like things are starting to get messy,
this episode is going to hit home because here's the truth most people don't talk about.
Growth doesn't break because they lack of effort and breaks because of a lack of focus and lack of clarity.
You build something that works and now you're trying to sell to everyone.
You get promoted because you're great at your job but now you're responsible for people and no one ever taught you how to lead.
So you end up stuck in this in-between phase where the old way of doing things no longer works but the new way hasn't fully clicked yet.
And that's exactly where today's guest John Mason comes in.
John works with founders who have a product but don't know how to take it to market and with high performers who suddenly find themselves leading teams without a label.
In this conversation we break down what actually creates clarity in a business why most people struggle with a move in the leadership and how to stop being the bottleneck in your own growth.
We also get into the real role of AI in sales and business and why it's not going to replace what actually drives results.
If you've ever felt overwhelmed trying to scale whether it's your revenue team or yourself, this episode will give you a much clearer path for it.
So let's get into it.
Welcome to another episode of the financial freedom podcast where we showcase business owners and entrepreneurs and today we have John Mason founder and chief revenue officer of people in pipeline consulting.
He's had sales leadership positions business development really happy to have him on John welcome.
Thanks Chris pleasure to be here briefly introduce yourself and what you do in your current role.
I'm founder and chief revenue officer at people in pipeline consulting that a business I set up going solo on my own my whole chief revenue officer positions on a fractional basis for startup companies helping them with their pipeline eventually helping them with their people.
I provide sales training and leadership to new managers whether that's through my own company or through a company that I'm affiliated with called my sales coach 12 years experience and business development throughout my life I've built my own business.
This is the real deal. What is your customer and client avatar that you help?
On the revenue side of things startups tend to be typically two people one of those might be the product person and one of them might be this operational business person.
If that operational business person doesn't have the natural born sales that human the natural born charisma to put themselves out there and take the product to market.
Then they can struggle that's where I come into help third person you've got the person delivered in the product and SAS.
The person operation we run on the company and myself putting those ideas together to take them to market by turning it up to companies that pilot financial systems in the UK CRM for financial advisors and the QL a data federation company which is going to be global wide wide we have staff already in the UK and Europe taking them forward.
On behalf of my business is the people side my typical avatar would be myself back in 2020 take when I became the head of business development I was an accidental manager.
I was given the role because I was good I had people skills and it was a case of can you make those guys as good as you are and get us to our number off you go those are new to management roles coming into leadership because they were good individual contributors now find themselves in charge of others that's where I can help them figure out what they got to do.
What are the top questions problems pain points of frustrations that clients are coming to you with.
On the setting up company side of things being able to focus in on your niche a lot of people create something new that can solve many problems if you try and take them all to market at the same time you can run into trouble.
But if you focus down on who you're helping focused on your ICP you're able to take that product to market where do we start who do we target helping business identify there why which translates into the people side of thing why am I a manager what kind of manager do I want to be.
Where do I start I've got to deal with things that are outstanding from the previous manager things that have been brought to my attention now and things that are going to be planning for the future.
How do I put those fires out where do I start the main question translates on both sides of course there two different avenues.
How are you viewing artificial intelligence how are you using it to stay abreast keep ahead and help solve clients problems.
Yeah AI where to begin AI has a place in business has a place in training and sales as well I think it can help the automation side of things the fact we call it artificial intelligence is too forward thinking a lot of people are using your automation side of it to do heavy lifting so the human input can be added and accelerated later it's the next digital wave we had computers tablets mobile phones.
We're back further we had the worldwide web Microsoft Excel being the next big thing for the last 40 years AI is the next thing on that if we think it's going to solve all of our problems we're going to fail if we learn to use embrace and leverage it to our advantage will succeed.
It can help you digest data come up with ideas you have to put the guard rails on like when Wikipedia came out that was an open source in cyclopedia but you needed moderators you need moderators in your own use of AI you need to put the guard rails on to make sure it's being used correctly.
Where do I think it won't have success is replacing at frontline salespeople SDR sales representers people on the phones that's not going to cut it.
I received a few phone calls on the business to customer side as a potential customer from these AI agents they make really good content for LinkedIn they do not make really good AI agents I think those that learn to embrace it to assist with what they're doing to help.
The cat apartment sells for it will do well those that think it's going to do their job for them not going to do well those that ignore it and come late to the party will fall behind and have to catch up.
Being a chief revenue officer being in sales and leadership how have those two roles helped with you solving current problems what are the problems that require both the skills from a chief revenue officer and the skills of a sales and leadership coach.
It's important to understand it comes down to people whether you're dealing with a company of three or 150 people you have to have those interpersonal skills that help you navigate through those conversations.
The further you go up the career ladder in a business the more exposure you get to other aspects of the business rather she forever your officer i'm going to get exposure to the other sea sweets in the company.
And what's important to them on a daily basis what's important to me isn't necessarily important to them but we've got to pull together to collectively move forward with the businesses desire purpose understanding how things in my world affect things in operations product finance so we can stay on the same page and move forward if you're used to leading people as a head of business development and move into a CRO position.
Then you've got some of those skills sets to make sure that you're all in the table move forward together it's the same with sales training you can't need a horse to water as an adage of course when you're trying to train somebody trying to get them from a to be meet them on their terms find out what their goals and help deliver it going through that position of going from frontline work and manager to being in charge of department skills that help you build the ability to navigate.
Future situations and help the company solve it problems how do we as a business get from a to be I have the ability to chip in with the idea on finance product operations having the exposure to the wider company helps solve those problems any good head of department chief officer is good to have.
Quick pause here if this episode is making you rethink how your income is structured that's intentional information doesn't create freedom structure does at the end of this episode I'm going to show you how to diagnose whether you're building leverage or just scaling complexity let's get back into.
Continue the conversation what I found interesting was former team leader you got promoted on the merit of selling and people skills you said not your desire to manage how is management and leadership different from your perspective.
It's something I've spoken to quite a lot recently is what really helped me decide this is what the direction I should take people in public consulting foremost it's not a bad thing that my previous company promoted me the way they did.
It's the way a lot of companies promote people industries roles it's not unique to me and sales it's everywhere happens in the NHS all the time in the UK I thought my career trajectory was to go from sales to senior consultant to enterprise development director.
Lone wolf roles look after myself maybe do a buddy in mentoring ultimately I'm responsible for my target the opportunity of leadership came about I kept my feet in both camps I've been doing the work necessary to continue as a lone wolf in lane foundations without realizing to be a good leader and not just manage people.
When I was promoted I was very lucky that the person that promoted me the CRO at the time and the CEO of the company believed in putting the right people in the right post they must have seen something in me that I hadn't yet realized and it very quickly became
I'm also having children if you're single you're responsible for yourself and if you have children you're now responsible for others the development of those others also make your life better.
The development of my sales team means they bring in more money I'm compensated on the team success it's no longer about me myself and I it's about we putting others before yourself one of the biggest things I sales people going into leadership need to be able to get their head around is
I have to put other people before myself now because in the short term I may not make bonus this quarter but in the long term I make a lot more bonuses by investing in my people I treated it like my own business.
You were talking about how you believe the best managers aren't the loudest or people pleasers they're the ones empowered to lead with intention my question for you is middle management a thing of the past given that artificial intelligence is eliminating excess why would you need managers if you have algorithms software or artificial intelligence.
I think it's a good question organizations all over the world UK US Europe APAC Africa you're going to find that situation where you end up with first second third level managers where that has its true benefit is there's only so much capacity a sales person has to manage other people if I'm going to conduct really effective one to ones with my team.
There are only so many people I can manage because I have to do the day job might be selling as well if you're going to invest time in running through individual pipelines and time running through individuals aspirations and careers and individual coaching all of a sudden you could be spending 20 30% of your week most things let alone group huddles your one to one with your boss you're a forecast meetings things that you always get pulled into I think middle management
is great when people aren't promoted to manager just because they want more responsibility and it's a pay rise and it's to tick a box and it's good when it's a case of your managing nine people you're drowning let me promote people under you to take responsibility so they can manage to each and you can manage three so you'd have two people managed by one two by a second two by a third there are your nine direct reports you've now only got three people to manage they've got to each that's where I've been all management will help even with AI
if you start stripping out people because cost saving exercises or because of AI being great you can definitely make mistakes a lot of businesses have big layoffs that have to go back and hire more people happens frequently if you're a small business not an Amazon that can be detrimental I think middle managers are important if you focus on how much of their time they can give each of the people they manage in a week a month.
They're really interest film itself by Southwest recently were the corporation got rid of all of the middle managers except one that one person was overseeing a fleet of robots software and artificial intelligence really fascinating one thing I wanted to ask you mentioned the middle management question I didn't realize the person you were thinking of from that film with documentary was everyone was gone except him and he was managing a fleet of autonomous robots I can imagine the type of companies that would be for
that person's ill you know there's a bottleneck there right if they get hit by bus tomorrow who's going to train them to do his job or her job that happens a lot in business we strip things back so much that we become dependent on certain people when they become a bottleneck a single point of failure any business out there whether you're growing or cutting make sure you don't create bottlenecks and single points of failure because if you leave and people don't know how to do their job afterwards you were the single point of failure.
What are the central mindsets skills traits for accidental managers that become leaders I think they are the traits they would look to hire people with they are willing to be coached willing to listen the ability to wear more or more hats probably got them into position in the first place they're good at doing more than one thing you have a new set of hats where when you're a manager the way to make it more purposeful when it's accidental is to be able to have conversations with your team.
You may be managing people that you are friends or you never got on with now you have to find new level of ground where you can trust me I will go and back for you I have your best interests are heart if there is something coming down from the top table I will put my shield up and whether that storm for you I will pass on a more constructive message rather than beating down if you have things you want to pass up we can talk about them so we make sure if we put our head above the parapet we're doing it for a legitimate reason.
Being able to say let me take off my I'm your boss hat I'm your I'm a person with empathy hat we are my human being hat what's going on your world I've had it before where someone comes means that I need to leave I'm very stressed out I said okay leaving is not going to make you any less stressed because you'll have no job in here a long time you're allowed to take time off for mental health being unwell that's not a problem you're allowed to do that then if you take that time off and reflect while still being paid.
You can decide whether or not is it the job or is it the company is the job you can change teams if you don't like being in sales go to customer success go to marketing go to products if it's the company it don't matter which team you go in you're going to be unhappy I've been there in the past and had to decide whether I want to leave a company for what reasons if you're really good at your job people may try to keep you.
Once in my career was offered anything to stay I realized it nothing could offer me want me to stay my mind was made up I'd fell out of love with the company outside of our office our office was fine moving me to a different team in the office would have been better a different manager may have helped one or two little things but the big overarching thing outside our physical location I didn't want to go back for this massive corporation anymore.
I want to go back for my manager and our office our regional hub but I didn't want to go back for the big bad giant I didn't have faith that they could deliver the things I promised our customers and had to move on.
Being able to swap those hats and understand what's in the best interest of this person as human and the company you have a for this responsibility as a manager to the company.
Somewhere in that list towards the bottom is what's best for you none of those things are best for you if someone goes off sick you've got to cover their work if someone leaves you got to find their replacement none of these outcomes are going to help me.
What's best for you and what's best for this company so we can move forward and I would have to pick up the mess so take that ability to wear multiple hats and suddenly apply it to.
This is what the company messages but let's dive into you let's get off the surface level and dive into it because in sales we ask questions to do discoveries to probe beyond the surface level I don't have any money no budget if you find a problem big enough that needs fixing you find budget so you start diving into those layers take those sales skills you have those multiple hat wearing skills and you'll go from accidental manager to a purpose for one very quickly.
Last question is what do you mean by if carlsberg did podcast guess callsberg as a Danish beer popular in the UK it's lower strength for below 4% alcohol not necessarily the most popular one of their advertising campaigns were if callsberg did this thing it would end up being the greatest thing in the world so if callsberg did cars i'm a BMW driver for example you know for those in the UK that was seeing that campaign.
They get that in joke if you will it's a really cover piece of marketing similar to the Guinness campaign in the 90s which was good things come to those who wait lovely campaign horses running across a beach with waves it was in black and white because Guinness is black and cream.
The whole point is Guinness takes longer to pour therefore it's worth the weight they've turned the negative into a positive free reframing which any marketer would think is genius.
i'm a big fan when marketing campaigns go well I think that's important to see our own I have to look after customers people I have to look after marketing I have to look after sales so if callsberg the podcast guests apparently it would be me according to me.
How can people connect with you find me on LinkedIn john Mason feel free to add me i'm more than happy to add anyone that wants to see my content on me to see theirs or join for the spirit of debate more than happy for that.
What a fantastic way to end the conversation thanks so much for coming on I really enjoyed talking with you like wise bring it pleasure I really enjoyed your questions thank you for your time Chris.
Let's zoom out if you're a physician founder or high income professional and you feel like you're working harder every year but not structurally fear you're not alone.
The mistake is an effort its architecture this show exists to help you convert expertise into scalable leverage faster and with fewer expensive missteps here's the diagnostic I mentioned before if your income requires your constant presence if your capital isn't compounding outside your profession if your highest value talent is doing low value tasks you don't have a growth problem you have a leverage design problem and if you want to fix it with clarity instead of guesswork.
I offer a limited number of one-on-one leverage strategy sessions each month we audit your income model capital deployment 30 positioning and structural bottlenecks and design your highest return.
If you're serious about compressing years into months going to apply is below.
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