B2B Sales & Marketing Blog | Growth Insights | Brickwork

How to Find Gaps With a Sales Skills Assessment

Written by Jennifer Hogberg | Jun 1, 2026 3:43:40 PM

Key Takeaways

  • A sales skills assessment measures how well reps can apply key selling skills, not just whether they hit quota.
  • By the time skills gaps show up in pipeline data, they’ve likely already cost you revenue.
  • Micro-topics like active listening, objection handling, and asking the best questions allow go-to-market (GTM) leaders to focus on the areas their reps need most guidance in.

Why You Need a Sales Skills Assessment

When did you last assess your sales team’s strengths and weaknesses?

Not whether they hit quota. Not whether they have pipeline. Whether they have and can apply the specific skills needed to be successful.

For most revenue leaders, the honest answer is not recently, if ever. They need a way to uncover gaps before they show up in business results.

What Is a Sales Skills Assessment?

A sales skills assessment is a structured evaluation of a salesperson’s competencies across the full range of behaviors that drive revenue, from attitude and mindset to tactical selling skills to how consistently they execute. It replaces gut feel and anecdotal manager feedback with a clear, scored picture of where each rep stands and what needs to change.

When building or scaling a revenue team, it answers a question that pipeline data can’t: Do we have the right people doing the right things the right way? And where can our existing team grow?

What Pipeline Data Alone Won’t Tell You

Most GTM leaders rely on outcomes such as closed revenue, win rates, average deal size, and pipeline coverage to evaluate their teams. These are lagging indicators. By the time a skill gap surfaces in your metrics, it has already cost you deals.

The more dangerous problem is self-perception. Salespeople tend to rate themselves higher than they perform, especially in areas like relationship management and strategic selling, where the definition of good is fuzzy. Without an objective framework, managers are coaching to perception, not reality. And hiring decisions get made on interviews and intuition rather than evidence.

A structured assessment changes that. It creates a baseline that makes every coaching conversation, hiring decision, and team-design choice easier to make and to defend.

The 4 Dimensions of a Sales Assessment

Our people and training assessment at Brickwork evaluates reps across four dimensions, each scored on a 1–5 scale, where 5 represents mastery of the skill or competency. Together, they give GTM leaders a full picture not just of what reps know but of whether they show up and execute.

1. Attitude

This is the foundation. No amount of skill development helps a rep who isn’t coachable, doesn’t believe in what they’re selling, or folds under pressure. Attitude competencies include:

  • Coachable: Receptive to critical feedback and willing to adjust behavior based on it
  • All In/Adheres to Company Values: Genuinely believes in the company’s mission, not just going through the motions
  • Passionate: Displays real enthusiasm for the product and inspires that in buyers
  • Resilient: Stays composed through rejection and adversity; bounces back without a performance hit
  • Competitive: Has a genuine desire to win, not just to participate
  • Customer Loyalty/Customer Service: Acts with the client’s interest in mind, not just their own number

2. Skills

The core selling competencies. This is where most pipeline gaps originate:

  • Pre-Call Preparation: Does the rep arrive with a plan or improvise?
  • Client Development: Are they expanding existing accounts or staying comfortable with the initial contact?
  • Communication: Can they deliver a clear, compelling message and champion the opportunity internally?
  • Relationship Development: Are they building trust and retention, or just staying visible?
  • Client Strategy: Do they understand what the client is trying to achieve at a business level and position accordingly?

3. Activity

Skill without consistent execution is just potential. This dimension looks at whether reps are doing enough of the right things repeatedly.

  • Prospecting: Are they actively hunting new business through multiple methods?
  • Proposal Activity: Do they generate enough proposals to sustain pipeline?
  • Sales Calls: Are they in front of enough buyers often enough?
  • Follow-Up: Do they stay disciplined about re-engaging?
  • Networking: Are they building a referral and lead ecosystem beyond the CRM?

4. Knowledge

Even the most motivated rep can’t win without the right context:

  • Product: Deep understanding of what they’re selling and how it delivers value
  • Market/Industry: Fluency in the buyer’s world, trends, and pressures
  • Competition: Understanding who the customer buys from, who you’re up against, and how to sell on value instead of price

The Micro-Topics That Make Coaching Actionable

Broad dimension scores tell you where to look. Micro-topics provide hyper-specific areas, challenges, or best practices your team needs guidance on. Brickwork’s assessments pull out these topics from the results, so you see exactly what to fix and how to make measurable improvements.

Here are some micro-topics that surface most often as gaps:

Active Listening

When a rep isn’t truly listening, they miss buying signals, misread objections, and pitch solutions to problems the customer never confirmed. Active listening is the foundation for rapport, trust, and every conversation that follows.

Asking the Best Questions

Reps who don’t ask the right open-ended questions to surface symptoms rather than root causes and propose solutions that don’t stick. This micro-topic builds the questioning framework that helps buyers articulate what they care about most.

Sales Cadence and Contact Management

Most reps know they should follow up; they just don’t have a structured system for doing it consistently. A strong cadence balances calls, voicemails, social touches, and email in a sequence that keeps opportunities moving instead of going cold.

Elevator Pitches and Value Propositions

When reps can’t quickly articulate why a prospect should care, they lose the room before the conversation starts. This module addresses both the elevator pitch and the value proposition, with practice on real buyer personas.

Presentations: The Do’s and Don’ts

Most reps walk through slides rather than lead a conversation. Coaching includes live delivery practice against a real company deck, scored on confidence, opening and closing statements, and overall impact.

Social Selling/LinkedIn

LinkedIn is a pre-call planning tool as much as a prospecting channel, and reps who use it strategically show up to client conversations with more context and credibility. This gap compounds, as reps can steadily lose ground to competitors who show up consistently on social media.

Objection Handling

Reps need to uncover what’s actually behind the objection before attempting to address it. A rep who hears “we don’t have budget” and pivots immediately to pricing has misread the situation. Coaching focuses on curiosity-first responses that surface the real blocker.

From Assessment to GTM Decision-Making

The real value of a skills assessment isn’t the scores but rather what the scores enable. For GTM leaders, that means:

Smarter hiring. When you know what mastery looks like across your best performers, you can interview against a trusted standard. Assessment data from your existing team defines the profile you’re hiring for.

Faster onboarding. New reps have known gaps before they start. An assessment in the first 30 days surfaces those gaps early, so you’re not waiting 90 days to realize someone needs help with prospecting.

Targeted development. Group coaching raises the floor. Individual coaching raises the ceiling. Assessment data tells you exactly what each rep needs so that development is specific, and your managers’ time goes where it will have the most impact.

Honest team design conversations. Sometimes an assessment confirms that a role, a territory, or a coverage model needs to change, not just the rep in it. That’s a harder conversation, but it’s the right one.

The Bottom Line

Missed pipeline targets don’t start at the end of the quarter. They start weeks or months earlier in calls that weren’t planned, questions that weren’t asked, or follow-ups that never happened.

A sales skills assessment gives GTM leaders the visibility to get ahead of that by knowing specifically, measurably, and early enough to do something about it.