Short answer
Start with the symptoms you can already see: deals stalling after the first meeting, proposals going out without discovery, discounts on every deal, forecasts that collapse late in the quarter. Each symptom points to a specific gap. Then check each seller across four areas (Mindset, Skills, Tools and Knowledge) on their own live deals, not in a test. Fix one gap at a time and reinforce it weekly.
Pipeline problems are usually skill problems
When a pipeline is weak, the usual responses are to hire more salespeople, add more leads or push harder in reviews. Sometimes that’s right. More often, the existing team is losing deals it should win, and the cause is a small number of skills that were never built.
Most tech companies train their people on products, technology and solutions. Very few train them on the skills that decide whether a deal moves: discovery, qualification, controlling the conversation, objection handling and negotiation. Those gaps don’t show up in a product test. They show up in the pipeline.
Step 1: Read the symptoms
You don’t need an assessment platform to start. Your pipeline already shows you where the gaps are.
| Symptom you see | Likely skill gap | Where to check |
|---|---|---|
| Deals stall after the first or second meeting | Discovery: the real problem was never found | Ask the rep to explain the customer’s business problem in their own words |
| Proposals go out quickly, then nothing happens | Qualification: the deal was never real | Check the deal against all five MANT-C factors |
| Discounts on almost every deal | Objection handling and negotiation | Listen to how price objections are answered |
| Meetings end with “we’ll get back to you” | Controlling the conversation; next steps | Was there an agenda? Was a dated next step agreed? |
| The forecast collapses in weeks 9–10 | Qualification and forecasting discipline | Compare commit deals with the evidence behind them |
| Reps can’t explain the customer’s industry | Knowledge of the customer’s business | Ask what pressures the customer’s industry faces this year |
| Good reps go quiet after a bad month | Mindset | How do they talk about targets and rejection? |
Step 2: Use MSTK to see the whole seller
In B2B Tech SalesOS, every seller is built on four pillars, which I call MSTK:
- Mindset: how they see selling, targets, pressure and rejection. Do they own their number?
- Skills: discovery, qualification, meeting control, objection handling, negotiation.
- Tools: how well they use the CRM, AI assistants and other tools to prepare and follow up.
- Knowledge: the product, yes, but also the customer’s business and industry.
A gap in any one of these limits the others. A seller with excellent product knowledge and a fearful mindset will still discount. A confident seller with weak discovery will still chase deals that were never real.
Step 3: Check on live deals, not in a classroom
The most reliable way to find a skill gap is to look at how a seller handles their own current opportunities:
- Pick two or three live deals per seller.
- Ask them to walk you through each one: the customer’s situation, the problem, its impact, who decides, the budget, the timing, the competition.
- Notice where the answers get vague. Vague answers point to the gap.
- Before their next meeting on one of those deals, ask what they plan to ask and what next step they want.
- After the meeting, ask what happened.
Within a few weeks, the pattern is usually obvious.
Step 4: Fix one gap at a time
The temptation is to fix everything in one workshop. That rarely works, for the reasons I explain in Why sales training is a waste of time (unless it’s reinforced).
Instead:
- Choose the gap that costs the most. Usually discovery or qualification.
- Give a short orientation on that one skill.
- Reinforce it on live deals every week.
- Review it until it’s habit, then move to the next.
Two quick self-checks
If you’d like a starting point, these take two minutes each and need no sign-up:
- The Revenue Predictability Check shows where your sales system is weakest.
- The Stalled Deal Rescue Check helps you decide which silent deals are worth recovering.
Common mistakes
- Testing product knowledge and assuming that covers selling skill.
- Blaming the individual when the whole team shows the same symptom.
- Fixing everything at once, so nothing is reinforced.
- Ignoring mindset, which quietly undermines every skill.
- Hiring before diagnosing, adding new people to the same gaps.
Frequently asked questions
How do you identify skill gaps in a sales team?
Start from pipeline symptoms (stalled deals, heavy discounting, late forecast collapses), then review each seller’s live deals to see where their answers become vague.
What are the most common skill gaps in tech sales?
Discovery, qualification, controlling the conversation, objection handling and negotiation. Most tech companies train on products instead.
What is MSTK?
The four pillars every seller builds on in B2B Tech SalesOS: Mindset, Skills, Tools and Knowledge.
Should I hire more salespeople or fix skill gaps first?
Diagnose first. If your existing team is losing winnable deals, more people will often repeat the same gaps.
Want an outside view of your team’s gaps?
We review live deals with your team and show you where the pipeline is leaking.
