Webinar Summary: How to build personalized coaching paths for every rep

Sales coaching has always been one of the highest-leverage activities in a sales organization – and one of the hardest to execute well.

In our recent session with Mark Kosoglow (CRO at Docebo), Devang Agrawal (CTO at Glyphic), and Nicolas Galantini (Enso Connect), a few consistent challenges came up:

Managers are expected to coach across dozens of deals and hundreds of calls each week.
Most coaching is based on a small sample of interactions. And feedback, when it does happen, is often subjective and hard to measure.

As a result, coaching is often inconsistent, difficult to scale, and rarely translates into sustained behavior change across a team. That’s the real problem – not a lack of frameworks or intent, but a lack of a system that makes coaching repeatable.

The data reflects the same disconnect. 45% of reps now rate the coaching they receive as below average, up from 29% last year. And yet, 64% of sales leaders believe they are spending more time on coaching than 12 months ago.

Where Coaching Breaks Down in Practice

Most teams don’t necessarily lack coaching frameworks. Instead, they lack coverage, consistency, and follow-through. Mark Kosoglow described the reality most leaders face:

“You might have hundreds of calls in a week. Managers can only review a handful. So coaching ends up being based on a very small sample.”

That creates a distorted view of performance. Reps are coached on isolated moments, not patterns. Managers rely on what they happen to see, not what’s actually happening across the pipeline. On top of that, coaching is often disconnected from execution.

• Feedback is given after the fact
• Training is delivered outside of live deals
• There’s little visibility into whether behavior actually changes

Which leads to a familiar outcome: activity increases, but performance doesn’t move in a predictable way.

The Shift: From Coaching as an Activity → Coaching as a System

The most useful part of the discussion was how teams are starting to rethink coaching entirely. Not as something managers do occasionally, but as something the organization operates continuously.

Devang Agrawal framed it clearly: “The issue isn’t that teams don’t know how to coach. It’s that coaching isn’t built into the way work happens.”

When coaching is a system, three things change.

1. Coaching Starts With a Defined Problem

Instead of broad feedback (“run better discovery”), teams isolate specific failure points:

• Deals stall after first meetings → weak problem definition or stakeholder alignment
• Pipeline looks full but doesn’t convert → poor qualification or next-step clarity
• Deals slip late → lack of mutual action plans or buying process visibility

Nicolas Galantini shared how this changed their approach: “We stopped trying to improve everything at once. We focused on where deals were actually breaking – and coached that.” This creates focus and makes coaching measurable.

2. Leading Indicators Replace Gut Feel

Another consistent theme: most teams rely too heavily on lagging metrics.

Win rate and revenue tell you what happened. They don’t tell you what to fix.

The teams seeing progress are tracking behaviors inside deals and calls, such as:

• Whether a clear customer problem is defined
• Whether next steps are agreed and dated
• Whether multiple stakeholders are engaged

These indicators show whether reps are executing the right motions – early enough to intervene. This also removes some of the subjectivity from coaching. Instead of: “That call could have been better” It becomes: “There was no clear next step or buyer commitment. Let’s fix that.”

3. Coaching Moves Closer to Live Execution

Traditional coaching often happens outside the flow of work:

• End-of-week call reviews
• Quarterly training sessions

But the teams discussed are shifting coaching into:

• Active deals
• Recent conversations
• In-progress accounts

As Mark put it: “The most effective coaching happens inside a real deal. That’s where context exists, and where change actually sticks.”

This requires a different level of visibility – and is where most teams hit practical limits. Because reviewing enough real interactions, consistently, doesn’t scale manually.

Where AI Actually Changes the Model

AI didn’t come up as a replacement for managers. It came up as the infrastructure layer that makes this system possible.

Specifically, it allows teams to:

• Analyze every call, not just a sample
• Identify patterns across reps and deals
• Surface where coaching is needed without manual review
• Track leading indicators automatically

This changes coaching from:

• Periodic → continuous
• Sample-based → comprehensive
• Manager-dependent → system-supported

Or as Devang summarized during the session: “AI doesn’t make you a better coach by itself. It makes coaching scalable.”

What This Means in Practice

The takeaway from the session wasn’t to “do more coaching.”

It was to change how coaching is structured.

Teams seeing results are:

• Narrowing focus to 1–2 coaching areas at a time
• Defining clear leading indicators for those areas
• Embedding coaching into real workflows (calls, deals, accounts)
• Creating a cadence of inspection (weekly, not quarterly)

And importantly: They’re closing the loop between insight → action → verification. Because without that loop, coaching stays theoretical.

The Real Advantage Isn’t AI — It’s Learning Speed

One idea that came up repeatedly: the advantage isn’t access to AI. It’s how quickly teams can turn insight into behavior change.

The teams pulling ahead are:

• Instrumenting their sales process
• Identifying gaps faster
• Reinforcing behaviors continuously

Not perfectly – but consistently. And over time, that compounds.

‍