A sales team assessment a busy CEO can do in an hour
Most assessments end as a slide deck nobody opens. This one is a list of things to look at, and what each one tells you about where deals leak.
Assessment · 8 min read
What a sales team assessment looks at
A sales team assessment looks at four things: whether your pipeline stages describe something a buyer did, how a rep actually runs a live deal, what the manager does with their week, and the gap between your two best reps and everyone else. You get those answers by watching real deals and comparing what you saw against what the CRM claims. Surveying the team tells you almost nothing, because people describe the process they think they should be following.
An assessment is not a survey. Ask a sales team how the process is going and you will get a description of the process they believe exists. Watch them work a deal and you find out what they do when nobody is looking.
Everything below can be observed in two or three weeks. None of it requires new software, and none of it requires anyone to fill out a form.
1. Whether a sales process exists in practice
Almost every company has a process written down somewhere, usually in a slide deck from a sales kickoff two years ago. The real question is whether two reps working the same kind of deal would take the same steps. Usually they would not.
Fastest way to find out: pick five open opportunities sitting at the same stage and ask each rep what has to be true for that deal to move forward. Five different answers means the stage is a label.
What to look for
- Stage definitions that describe buyer behavior instead of seller activity
- Exit criteria a manager could verify without taking the rep's word for it
- Deals parked in one stage longer than the average close cycle
- Opportunities that skip stages on the way to closed won
2. Pipeline honesty
A forecast is only worth something if the pipeline underneath it is honest. Take the last two quarters of closed lost deals and check when each one was last touched before it died. If a deal was marked commit three weeks before it went dark, that is not a forecasting discipline problem. Nobody knew what the buyer was actually doing.
Four numbers that tell you most of it
- Average days in each stage, compared rep to rep
- Win rate by stage entered, not just overall win rate
- Share of closed lost deals that had been forecast to close
- Open deals with no buyer activity in the last 30 days
3. Discovery quality
Discovery is where B2B deals are won and lost, and it is the easiest thing to assess because you can listen to it. Recorded calls if you have them. Ride-alongs if you do not.
Shallow discovery has a shape you can recognize in the first four minutes. The rep asks about the problem, gets one sentence back, and goes to a demo. Nobody finds out what the buyer already tried, what it cost them, who else signs off, or what happens if they do nothing at all. Those four things are the deal. Everything else is context.
If a rep cannot tell you in one sentence why this buyer would spend money this quarter instead of next year, the discovery was not deep enough.
4. Objection handling
Every team hears the same six or seven objections. Ask each rep to name them and explain how they respond. The answers vary more than anyone expects, and one or two reps will not have an answer at all. That is a training gap. It is not a talent problem, and treating it as one is how good reps get managed out for something a manager never taught them.
5. How managers spend their week
This is the finding that surprises people most. In a struggling sales organization the manager is working deals, not coaching reps. It feels productive. It hides everything, because the manager closes the quarter and the team learns nothing they can repeat.
Pull up the manager's calendar for last month. Count hours spent one on one on a real deal with the rep doing the talking. In most teams the number is close to zero, and the manager is genuinely surprised when they see it.
6. Whether the team shares a goal
Individual quotas are normal. What is not normal is when nobody on the team can describe what the group is trying to do beyond adding those quotas together. You can spot it fast. Reps hoard what works. Pipeline review turns into a round of status updates. Nobody offers help on a deal that is not theirs, because there is no reason to.
What comes out of it
A useful assessment ends in a written document that says what is broken, roughly what it costs you, and the order to fix it in. Three or four items, sequenced, with the reasoning visible so your sales leadership can argue with me about it. Twenty recommendations is a way of avoiding a decision.
The order matters more than the list. Training a team on a process that does not exist yet wastes everyone's week. Redesigning a process before you understand why the current one gets ignored just produces a second ignored process.