How to Diagnose Sales Team Performance Gaps When You Join as a New Leader

The biggest diagnostic mistake new sales leaders make is trusting the dashboard. It shows you what is happening. It rarely tells you why. And in a new role, acting on symptoms rather than causes is how you spend your first month fixing the wrong things.

The Problem With Starting From the Dashboard

Pipeline is down. Conversion has dropped. Activity looks inconsistent. These are the signals a new sales leader reads first, and they are all real. The problem is that each of them could have a dozen different causes — and the dashboard does not distinguish between them.

What looks like a prospecting gap might be a messaging problem. What reads as a conversion issue could be a comp structure incentivising the wrong behaviour. What appears to be a will problem might be a skill gap no one has addressed. Acting on the headline number without tracing it to a root cause leads to interventions that solve for the symptom and leave the actual cause intact.

Richard Bounds, Sales Coach at MySalesCoach, puts the sequence plainly:

“Your first 90 days aren’t about proving you’re the smartest — they’re about deep listening and asking the smartest questions. Avoid the need to fix and start by diagnosing.”

It is also one of the most expensive mistakes new sales leaders make in their first 30 days — the ones that cost the most time to undo.

MySalesCoach's State of Sales Coaching 2026, drawing on 1,050 sales professionals, found that 64% of sales leaders believe they are spending more time on coaching than the previous year — while 45% of reps rate the coaching they receive as below average.That gap is not a communication failure. It is a diagnostic failure. Leaders are acting on what they assume the problem is rather than what it actually is.

What Walking the Floor Actually Means

Walking the floor is not a metaphor. It is a specific four-step diagnostic process.

Alex Olley describes it directly:

“I would do what I call ‘walking the floor’ and go deeper. Shadow calls, review CRM notes, listen to historical calls and review email communications. Run debriefs with reps to uncover whether gaps stem from skill, will, or structural misalignment.”

In practice, this means:

Shadow live and recorded calls. Do not just read summaries or look at win/loss data. Listen to how reps actually open conversations, handle objections, and establish value. The patterns you hear on call are the raw material for every coaching decision that follows.

Review CRM notes. What reps log — and what they don’t — tells you a lot about how they understand the sales process and where deals actually stall. A rep who consistently logs detailed discovery notes is different from one who logs “spoke with prospect, following up.”

Read outbound communications. Pull a sample of emails and sequences. You are looking at message quality, personalisation, and whether anyone is actually following a consistent approach or freelancing.

Run one-to-one rep debriefs. Ask each rep to walk you through a recent deal — one that closed and one that didn’t. How they explain outcomes reveals both their understanding of what drives results and their self-awareness about where they struggle.

As Alex puts it:

“Clarity comes from triangulating data, behaviour, and context. Great sales leaders don’t just spot what’s missing. They uncover why it’s missing and prioritise what’s fixable first.”

How to Identify Whether a Performance Gap Is Skill, Will, or Structural

The Walking the Floor Diagnostic produces raw material. The Skill-Will-Structure framework is how you interpret it. Every underperformance gap you find sits in one of three categories:

Skill gaps

The rep is not capable of doing the thing — not because they lack effort or motivation, but because they have not been taught how. This shows up as: inconsistent discovery questioning, weak objection handling, inability to establish differentiated value, or poor outbound sequencing. Skill gaps respond to coaching and practice. They require patience, not pressure.

Will gaps

The rep has the ability but is not applying it consistently. This can come from low motivation, unclear expectations, a disconnect between effort and reward, or a personal situation affecting performance. Will gaps are more complex to address because they are rarely just about performance. The first 1:1 questions — understanding personal goals, development aspirations, and what someone is working towards outside work — are your primary diagnostic tool here.

The sales 1:1 questions that surface motivation issues are different from the ones that surface skill gaps — getting this right in that first conversation is where diagnostic accuracy starts.

Structural misalignment

Neither the rep’s skill nor their motivation is the problem. The problem is in the system around them: a comp structure that incentivises the wrong behaviour, a sales process that creates friction at the wrong stage, a messaging framework that does not resonate with the market, or a territory assignment that makes success mathematically unlikely. Structural issues require management action, not coaching.

The distinction matters because applying the wrong intervention to a gap makes it worse. Coaching a rep who has a structural problem teaches them the system is broken and leadership doesn’t understand it. Applying management pressure to a skill gap demoralises someone who is already trying.

Misreading the category is one of the most common sales coaching mistakes — and one of the most demoralising for the rep on the receiving end.

What to Do With What You Find

By the end of your diagnostic phase, you should have a clear picture of which gaps are skill, which are will, and which are structural. Two things come next.

First, share what you found. Not just with leadership, but with your team. Richard Bounds’ sequence applies here:

“Listen, learn, then share the plan and thoughts.”

The diagnostic earns you the credibility to make changes. But only if you communicate what you found and why it points to specific actions rather than announcing decisions without context.

Second, prioritise what is fixable first. Not everything you find will be addressable in the next 30 days. Structural problems — comp redesigns, territory changes, messaging overhauls — take time and require buy-in beyond your own role. Skill gaps that compound fastest — outbound quality and discovery depth — are where your early coaching focus belongs.

For how to structure that coaching once you know where the gaps are, the guide on how to coach your sales team covers the methods.

For the full framework of what happens once your diagnostic is complete, the First 90 Days as a Sales Leader guide covers how phases two and three build on the diagnostic work done in phase one. On the sales coaching techniques needed to address skill gaps once identified, that post covers the core methodology.

Frequently Asked Questions

How long should the diagnostic phase take when you join a new sales team?

The first 30 days. This phase — shadowing calls, reviewing CRM data, running rep debriefs — should be completed before you implement any significant changes. Moving faster risks acting on incomplete information. Moving slower delays the coaching work that compounds performance. Thirty days gives you enough breadth to identify patterns without paralysing your ability to act in month two.

What is the Skill-Will-Structure Diagnostic?

A three-category framework for identifying the root cause of a sales performance gap, developed by Alex Olley. Skill gaps mean the rep lacks the capability. Will gaps mean the rep has the capability but is not applying it. Structural gaps mean the process, comp, or messaging around the rep is creating the problem. Each category requires a different management response — coaching, motivation, or systemic change.

What does “walking the floor” mean in sales leadership?

It is Alex Olley’s diagnostic methodology for new sales leaders: shadowing live and recorded calls, reviewing CRM notes, reading email communications, and running one-to-one rep debriefs. The purpose is to build a ground-level picture of what is actually happening in the team — not what the dashboards summarise — so that interventions target root causes rather than symptoms.

How do you diagnose a will gap versus a skill gap?

Shadow the rep on calls and listen for capability: can they execute the skill when they focus? If yes, it is a will gap. If they cannot execute it reliably regardless of effort, it is a skill gap. The first 1:1 conversation — asking about personal goals, development aspirations, and what they want from the role — surfaces motivation issues that pure performance data will not reveal.

What should I do if I find a structural problem rather than a coaching gap?

Flag it, quantify it, and escalate it with evidence. Structural problems — comp misalignment, poor territory design, broken messaging — cannot be solved through coaching and require broader organisational action. Document what you found during the diagnostic: which reps, which patterns, what the data shows. Present it to your management team with a recommended fix. Then make sure your coaching programme is focused on the gaps it can actually address.

Work With a Coach Through Your Diagnostic Phase

The diagnostic process is methodologically straightforward. The difficulty is holding the line on observation when you are under pressure to show results. An experienced sales coach who has navigated a new leadership role before can help you stay in diagnostic mode long enough to find the real problems — and act on the right ones.

MySalesCoach matches sales leaders with expert 1:1 coaches through our sales coaching for teams service — matched to your role, team stage, and the specific challenges you are working through. Book a meeting to explore how a coach could support your transition.