Asking for the business

For anyone whose income depends on somebody saying yes — commission, retainers, referrals, a quote you sent on Tuesday.

There is a moment near the end of a good conversation where the work is done and somebody has to decide. You have listened well. You know what they need. And then the sentence that would move it forward does not come out, and the conversation ends with “let me think about it” and a follow-up that never happens.

I do not think that is a confidence problem, and I do not think the fix is a closing technique. I think most people are working from a bad estimate of what the other person is doing.

You are probably wrong about how likely they are to say yes

Francis Flynn and Vanessa Lake ran six studies on direct requests, published in the Journal of Personality and Social Psychology in 2008. In the first three, people underestimated by as much as 50 percent how likely others were to agree to a direct request for help. That held in the lab and out in the field, across a range of different asks.

The sixth study explains why. The person doing the asking is adding up the cost of yes — the time, the money, the inconvenience they are about to hand over. The person being asked is also weighing the cost of no, which is social and immediate and sits right there in the room. Askers do not price that in. So they brace for a refusal that is less likely than it feels, and some of them stop short of asking at all.

Read that back as a business fact. If you are systematically overestimating rejection, you are systematically under-asking. That is not a personality flaw. It is a forecasting error, and you can correct for it.

What earns the ask is questions, not talking

The other half of this is what happens before the ask. Karen Huang and colleagues at Harvard studied live conversations and found that people who ask more questions, and particularly follow-up questions, are better liked by the person they are talking to. It was published in the Journal of Personality and Social Psychology in 2017. The mechanism they identified was responsiveness: a follow-up question is proof you were listening, and it reads as care rather than technique.

The part worth sitting with is the last finding. People do not anticipate this. We expect to be liked for what we say about ourselves, so under pressure we talk more, and the pressure of an impending ask is exactly when that instinct fires.

If you advise for a living, there is a companion finding. Alison Wood Brooks, Francesca Gino and Maurice Schweitzer found that seeking someone's advice raises their view of your competence rather than lowering it. Asking a client how they would want the next step to go does not cost you standing. It tends to buy some.

The shape of an ask that works

Three parts, in this order, and none of them are clever.

1. Say back what you heard. One sentence, in their words, not yours. “So the problem is that you are turning work away in October and you do not want to hire for it.”
2. Name what you propose, once. One option, a price, a date. Not three tiers. Three tiers moves the decision from yes-or-no to a comparison exercise, and comparison exercises get postponed.
3. Ask a closed question with a date in it. “Do you want me to start the week of the sixth?” A closed question can be answered. “What do you think?” cannot, which is why it produces “let me think about it.”

Then stop talking. The silence after an ask belongs to the other person, and the most common way people undo their own ask is to fill it — usually by discounting, or by listing an objection the client had not raised yet.

The three habits that undo it

• Pre-discounting. Cutting the number before anyone pushes back tells them the first number was not real, and invites a second cut.
• Apologizing into the ask. “I know you are busy, and this is probably not the right time, but…” You have just written their exit line for them.
• Sending the ask instead of making it. Email is where a decision goes to wait. If the conversation is live, ask while it is live.

Where this research is thin

Flynn and Lake studied requests for help, not commercial proposals. Huang's work was on get-to-know-you conversations and speed dating, not sales calls. Neither one tells you your close rate will move, and I am not going to tell you that either. What they do establish is a direction of error: people expect no more often than they get it, and they talk more when they should be asking. Both of those are correctable in the next conversation you have.

If you want to put a number on it

The calculator has a branch for exactly this. Give it one deal you did not close and it will show you the arithmetic on a year of them. What one more close is worth →

The workshop that covers this ground is Daily Influence and Negotiation, and the piece next to it is why practice is the part people skip.

Common questions

Why is it so hard to just ask for the sale or the close?

Not temperament. Research on requests for help found people expect no far more often than they get it, which makes asking feel riskier than it is. Most people also keep talking past the point where they should stop and ask, because silence after the ask feels exposed.

What are the most common ways people undercut their own ask?

Three habits: cutting the price before anyone pushes back, apologizing into the ask instead of making it directly, and sending the ask by email instead of making it while the conversation is still live.

Does asking directly improve close rates?

The research behind this piece was on requests for help and get-to-know-you conversations, not commercial close rates specifically, so no one can promise a number will move. What it does establish is a direction of error worth correcting: most people under-ask and over-explain.

Sources

• Flynn, F. J., & Lake, V. K. B. (2008). If you need help, just ask: underestimating compliance with direct requests for help. Journal of Personality and Social Psychology, 95(1), 128–143. Peer-reviewed.
• Huang, K., Yeomans, M., Brooks, A. W., Minson, J., & Gino, F. (2017). It doesn't hurt to ask: question-asking increases liking. Journal of Personality and Social Psychology, 113(3), 430–452. Peer-reviewed.
• Brooks, A. W., Gino, F., & Schweitzer, M. E. (2015). Smart people ask for (my) advice: seeking advice boosts perceptions of competence. Management Science, 61(6), 1421–1435. Peer-reviewed.