How ASK BOSCO's founder gave his sales team the coaching he couldn't make time for

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ASK BOSCO sales coaching case study at a glance

What coaching challenge was ASK BOSCO trying to solve?

John Readman is the founder of ASK BOSCO, a marketing AI platform for digital marketing agencies and brands that helps them save time and work out exactly where to spend their money on online marketing. As a commercial founder, John also runs sales. John says:

"As a commercial founder, I've struggled to find the time to support my sales team, and a normal sales one to one would end up just being talking about pipeline and deals and actually not talking about developing their skills."

"When you're a founder-led sales leader and you're talking to the salespeople, it's very easy to just get distracted into the day to day of deals, pipeline activity, which is all an important part of sales management, but it's often the coaching element, or listening to calls or giving feedback or trying to work on the softer skills around questioning or prospecting tactics that often get forgotten."

That frustration was personal. John says:

"I've been a sales professional my life. I know how important that is, which makes it even more frustrating when you can't find the time to fit it all in."

"I used to do it all, and realistically, I wasn't doing it well enough."

The risk was bigger than missed coaching. John explains:

"It just wasn't happening. And then what you're in danger of is you're not developing your team. If you worst case, they may end up leaving. They're not developing their skills. They're professional people. They want to improve what they're doing."

John also believes an outside coach brings something a leader can't:

"Parents aren't necessarily the best people to teach people to drive or teach people a musical instrument. Having someone else, externally, who's got a better lens on the professional elements of sales, rather than the nitty gritty detail, I think is a really good benefit."

Why ASK BOSCO chose 1:1 sales coaching over sales training

ASK BOSCO had tried online training, classroom seminars and group sessions. John Readman says:

"Everybody's at different stages in their sales career, and they need different levels of support. So MySalesCoach gives us that personal one to one coaching, without that huge overhead of someone having to be in the business."

"We were doing other forms of sales training, I suppose, rather than coaching. And now we've moved that budget into MySalesCoach."

Training hasn't disappeared. Internal team training now focuses on the product: how to position it, the ICPs, the pains ASK BOSCO solves and the questions that help position it best. MySalesCoach's coaching complements it.

ASK BOSCO is a people-first business, and John wanted to invest in the sales team's development. He says:

"We realised we wanted to make our sales team more professional."

The coaching gives the team skills for their time at ASK BOSCO, and for their careers if they move on in future.

How MySalesCoach's Sales Coaching Operating System worked for ASK BOSCO

After a successful trial, ASK BOSCO moved onto the monthly programme of MySalesCoach's Sales Coaching Operating System. Every salesperson uses it, and John Readman has told them they can book in as many sessions as they want.

Reps choose their own coach

Each rep picks their own coach and works on an individual plan, based on where they are in their sales career. John says:

"They're picking their own sales coaches, and they're putting in their sessions, and they're all working on individual skills, and then it becomes part of my one to one process with them."

John's one-to-ones now start from the coaching: what are you working on with the coach, how's it going, what have you learned?

Reps learn from each other's coaches

Because the reps have different coaches, they bring different ideas back. John says:

"What's been really nice, actually, is they're also sharing with each other what they're working on with their sales coaches, because they have different coaches."

Each rep works on what they need

• One rep is working on outreach messaging: avoiding getting ghosted and making sure follow-up is better.
• Another is working on asking better questions and better qualification.

Isabel came from a business consulting background and joined from an agency where she sold agency services, not software. Her coach has helped her ask better discovery questions, qualify opportunities and come up with better prospecting ideas. She has also been working on time blocking for prospecting. John says:

"Everybody talks about it, and then, oh, an opportunity comes in. This comes in. We've got to respond to that email. I've got to do this. And then suddenly you get to the end of the day and you haven't done any prospecting."

"Not just chatting about it, giving practical tools and advice of how to do it, and really holding her to her own goals and accountability of blocking out her time, so she has time to do all her prospecting."

Isabel sent John a WhatsApp after one session. John says she told him:

"I've just had the best call of my life with my sales coach. It's going to revolutionise what I'm doing."

A team that wants to be coached

ASK BOSCO's salespeople are senior, with seven or eight-plus years' experience and past qualification training such as MEDDIC. They see themselves as sales professionals, and that matters. John says:

"Someone's got to want to be coached and want to be coachable."

What results has ASK BOSCO seen from sales coaching?

John Readman is honest that coaching is hard to isolate in the numbers. ASK BOSCO recruited a new team, they all used MySalesCoach, and sales improved. John says:

"I don't know whether it's the new people, or it's the coaching, or it's also the product's got better, but it's definitely part of the mix."

What he can see clearly is the effect on the team, on his own time, and on hiring.

A motivated team that books its own sessions

John says:

"Because this team are excited about meeting with their sales coach, it's not a hassle, it's not a chore. I think they really appreciate the fact we're investing in it for them. So the value in having a happy, motivated sales team is huge."

"I regularly get WhatsApps from the team after they've had their coaching session, saying, I've just had a really good coaching session. We're working on this, this and this, it's been brilliant. I'm not having to force anybody to do it or remind anybody to book it in."

The team's feedback is why ASK BOSCO stayed on the programme: they were getting a lot of value from it, enjoying it, learning new things, and felt it was a good use of their time.

More time back for the founder

John says:

"As a founder who's running sales, it definitely freed up a lot of my time and gave me the reassurance and confidence that my team have somebody to ask and get support from when they're trying to improve themselves in sales and improve their sales techniques or their sales process."

Reps also ask a coach things they wouldn't ask the boss:

"It's a bit almost like sales therapy. They might feel awkward asking me the question, because they might think that I think they should know the answer, whereas if you've got an external coach, it's a lot more anonymous and less of a risk asking those questions."

A reason to join, and to stay

John used MySalesCoach as a positive when recruiting ASK BOSCO's latest salesperson, Chris. John says:

"I used it as a positive in the recruitment process, saying, we invest in a professional sales coach. This is it. Have a look."

Chris was excited to get stuck in. John sees it as a positive for both retention and recruitment.

How long has ASK BOSCO worked with MySalesCoach?

ASK BOSCO started with a trial in August or September 2023, then signed up to the monthly programme. When it rebuilt the sales team in October 2023, the two new salespeople started using MySalesCoach straight away, and so has every hire since. Coaching is now part of how ASK BOSCO supports its salespeople from day one, and the team will keep growing.

What other sales leaders can learn from ASK BOSCO

• Founder-led sales one-to-ones drift into pipeline and deals. Skills coaching needs its own time and its own person.
• An external coach sees the professional side of sales more clearly than a leader buried in the detail.
• Letting reps choose their own coach builds ownership, and different coaches bring different ideas back to the team.
• Coaching works best with people who want to be coached, so it's worth hiring for coachability.
• Coaching is a recruitment advantage: it shows candidates you invest in their development.

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