Coaching a seller you cannot out-sell

A founder said something to me recently that I hear often, in various forms: "I can't coach her, she's a better salesperson than I am."

It sounds like humility and it is usually an excuse to avoid an uncomfortable job. It also misunderstands what coaching a seller involves.

You are not teaching technique

If you hired well, they know how to run a meeting, handle an objection and ask for the business better than you do. Trying to teach them that is where founders get it wrong, and it is why the conversation feels awkward for both people.

What you have that they do not is context. You know the product, the market, the twenty deals that came before, why the last three customers actually bought and what the two that churned had in common.

You do not have to be better at selling than them. You have to be better at asking about this deal than they are.

Coach the deal, not the person

The unit of coaching is a specific opportunity, and the tool is questions rather than instructions. Six that work on almost any deal:

• What does this person actually want, personally? Not the organisation - them. Who looks good if this works?
• Who else has to agree, and have we met them?
• What would make them do nothing? Doing nothing is your real competitor, far more often than another vendor.
• What have they told us this costs them, in their own numbers?
• What is the next thing they have agreed to do, and when?
• What would have to be true for this to be signed by the date you have put on it?

You are not checking up. You are making them think about the deal in a way they were not going to on their own. A good seller will often answer question three and immediately know what to do next without you saying anything.

Separate the two conversations

The most common structural mistake is running coaching and forecasting in the same meeting.

The moment a conversation is about whether the number is going to be hit, honesty leaves. Nobody says "I think this one is soft" in a meeting where softness is a problem. So you get optimism, and optimism is useless to coach against.

Keep them apart. The forecast meeting is short and about numbers. The coaching conversation is longer, on specific deals, and explicitly not about whether they are on target. Say that out loud the first few times.

The listening half

Coaching runs in both directions and founders systematically undervalue this half. Your seller is in more buyer conversations than you now. They are hearing objections you have never heard, competitor claims you did not know existed, and the reason people say no this quarter rather than last.

Ask for it deliberately, because it will not arrive by itself: what did you hear this week that surprised you? What are you having to explain that the pitch should already handle? What are we losing to, and is it a competitor or is it inertia?

Then act on some of it visibly. A seller who sees their feedback change the pitch brings you the next thing. One who does not, stops.

When you should stay out

Two rules I would hold to.

Do not take over a live meeting. If you have to be in the room, be in it as the technical expert or the founder answering a specific question, and hand the deal back visibly at the end. A buyer who learns that the founder runs the important part will always want the founder.

Do not overrule a judgement call inside their authority. If you gave them a discount they can approve, let them approve it, even when you would have done it differently. Authority you take back once is authority nobody uses again.

The rhythm

Weekly, thirty minutes, on two or three deals rather than the whole list. Regular and small beats occasional and heavy, mostly because occasional and heavy only ever gets scheduled when something is wrong, which makes coaching feel like a symptom.

So this week, pick their biggest open deal and ask what would make the buyer do nothing. Then be quiet and see what you learn about your own product.