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In this week’s episode of Hit Your Numbers, we sat down with Jonny Coleman, Global Head of Sales at First AML, to unpack the art and science of effective one-to-ones and sales coaching. With over 16 years in sales leadership across complex environments, Jonny brought a wealth of insights that are immediately applicable to frontline managers and aspiring leaders alike.
Here’s a breakdown of the key lessons from the episode:
One of the most common pitfalls for sales leaders is the inconsistent delivery of coaching. It’s not enough to rely on ad hoc sessions or one-off training workshops. Reps need consistent, structured coaching at regular intervals to embed new habits and behaviours.
The best leaders don’t leave coaching to chance, they systemise it. Weekly one-to-ones, real-time feedback, and timely reinforcement of skills are what drive performance improvement and behaviour change over the long term.
A major theme in the episode was the risk of one-to-ones becoming little more than glorified pipeline reviews. With data dashboards available at your fingertips, wasting precious face time running through figures is a lost opportunity.
Instead, one-to-ones should focus on:
It’s not about checking in, it’s about checking on the development of your people.
Jonny emphasized that effective coaching mirrors a great discovery call. The leader’s job is to ask open-ended, intentional questions that help reps self-identify their weaknesses, skill gaps, and blockers - rather than being told what to fix.
This method builds self-awareness, confidence, and crucially, ownership. If a rep can articulate the problem and propose a solution, they’re much more likely to implement and stick with it.
For coaching to be effective, both the manager and the rep must come prepared. Jonny uses a shared Notion doc template for each one-to-one where reps track metrics, reflect on what’s working or not, and outline areas for discussion.
This not only drives accountability but also reinforces behaviours like self-analysis and reflection, critical traits in high-performing sellers.
Trying to solve five problems at once never works. Use a mix of data and call analysis to identify the most critical skill gap impacting performance, and double down on improving that area.
Whether it’s weak discovery, poor qualification, or lack of follow-through, isolate the issue and co-create a short-term plan to work on it. Then, track progress and hold reps accountable for their improvement.
Feedback can only land if the environment supports it. Jonny stressed the importance of building psychological safety, where reps feel comfortable raising their hand and saying, “I’m struggling, can you help?”
That kind of openness starts with the leader. Sharing your own mistakes, showing vulnerability, and reinforcing that asking for help is a sign of strength, not weakness, sets the tone.
When delivering tough feedback, the goal is to help someone improve, not knock them down. Jonny still uses the classic 'feedback sandwich' to soften the delivery without diluting the message.
It’s not just about what you say - it’s how you say it. Be honest, specific, and outcome-focused, but do it in a way that leaves the rep feeling supported and motivated, not defensive or demoralised.
The end result of a great coaching conversation isn’t “good chat” - it’s a plan. Every identified skill gap or issue should result in a tangible next step, owned by the rep.
Jonny recommends:
No plan, no progress.
Before you even begin your one-to-ones, set the tone. Jonny uses a “mutual agreement” approach: clearly outlining what he commits to as a manager (e.g., never cancelling sessions) and what he expects in return (e.g., preparation, ownership, communication).
This creates a foundation of trust, accountability, and mutual respect that makes coaching more effective from day one.
Coaching can’t happen from a distance. To really understand what’s holding reps back, leaders need to listen to calls, sit in on meetings, and ride along during prospecting. It’s only by observing the behaviours up close that you can offer meaningful, personalised support.
As Jonny put it, you can't coach from a spreadsheet.
The goal of coaching isn’t dependency - it’s independence. Jonny encourages leaders to "retire themselves" from the day-to-day by building reps who are self-aware, proactive, and capable of diagnosing and fixing their own challenges.
When reps can come to a one-to-one and say, “I know what’s wrong and I’ve got a plan to fix it,” you know you’ve done your job right.
First AML is on a rocket ship trajectory with plans to dominate a market ripe for disruption. They’re hiring SDRs and AEs - so if you want to work for a leader who will truly invest in your development, follow Jonny on LinkedIn and reach out.
If you’re a sales leader looking to sharpen your coaching game or a rep looking to grow faster, this episode is a must-listen.
And don’t forget, you can sign up for a 7-day free trial of the Sales University!
