The weekly deal inspection that works
There are two kinds of deal review, and they look almost identical from the doorway. In one, a manager interrogates a rep, extracts a status, updates a spreadsheet, and moves on. In the other, the deal gets better and so does the rep. Same meeting on the calendar, opposite outcomes. The difference is entirely in what the manager is actually trying to do when they sit down.
Inspection versus interrogation
An interrogation is about the manager's comfort: give me a number I can put in the forecast. A real inspection is about the deal: what's true, what's missing, and what we do next. The tell is the questions. 'When is this closing' is interrogation. 'What has the buyer done that tells us they'll close' is inspection. The first extracts a guess. The second surfaces the gaps you can still do something about.
There's a discipline to this that's harder than it sounds. When a rep gives you a thin answer, the temptation is to fill the silence, supply the missing step yourself, and move on so the meeting stays on schedule. Resist it. The rep who is handed the answer learns nothing. The rep who has to sit in the discomfort of not having one learns to go get it before the next review.
Inspect the deal to make it better, not to make yourself feel better about the forecast.
Coach and qualify in the same breath
The best deal inspections do two jobs at once. They improve the specific deal on the table, and they build the rep's judgment so the next ten deals need less help. You get both by asking questions that make the rep think rather than just report. Steer every review toward substance:
- What is the customer's compelling reason to act, in their words rather than yours?
- Who actually signs, and have we been in a room with them?
- What's the single biggest risk to this deal, and what are we doing about it this week?
- What's the next concrete step, and what has the buyer agreed to do to move it forward?
Questions like these do double duty. They expose whether the deal is real, and they teach the rep what good looks like, so that over time they start asking themselves the same things before you ever do.
Keep it short, specific, and forward-looking
A weekly inspection is not the place to relitigate the whole pipeline or rehash last month. Focus on the few deals that matter most this quarter and on the next move for each. Keep it tight, keep it about what happens next, and end every deal with a clear owner and action. Done consistently, this is where coaching actually happens, one real deal at a time, which is the only way coaching ever truly sticks.