Selling when you dislike selling

A large share of people who sell their own work describe themselves as bad at selling, and usually mean that they dislike a particular performance they associate with it. That performance is not required and mostly does not work.

What is actually being avoided

Worth separating, because the discomfort usually attaches to two or three specific things rather than to the whole activity.

• Asking for money. The most common, and the most improvable with practice.
• Being rejected personally, which is what makes follow-up feel exposing.
• Pretending to be certain about something you are not.
• Pressure, applied or received.
• Talking about yourself, which many competent people find genuinely unpleasant.

Only one of those is actually necessary, and it is the first. The other four are features of a style of selling, not of selling.

The version that works without any of it

1. 01Ask rather than tell. A conversation made of questions about their situation is not a performance, and it produces more than a pitch does.
2. 02Be the one who says it will not work when it will not. This is a comfortable position to occupy and it builds more trust than enthusiasm.
3. 03Put the price in writing, where you do not have to say it with your face. Transitional, and it works.
4. 04Make follow-up a schedule rather than a decision, so it stops being an emotional act.
5. 05Let the work be the argument: show something you made instead of describing what you are like.

The parts you cannot avoid

Two, and pretending otherwise is why some people never sell anything.

You have to say a number and then be quiet. There is no arrangement in which somebody else does this for you at this size, and the only remedy is repetition until it stops feeling like a confession.

And you have to ask for the work. Not aggressively: a sentence. Shall we go ahead. Would you like me to start on the fourteenth. A conversation that ends without anybody asking usually ends.

Reducing the number of times you have to do it

A legitimate strategy, and the better one for most people who dislike this. Raise the proportion of work that arrives already half-decided, so there is less persuading to do.

• Write publicly about the work. People who arrive having read something have pre-qualified themselves and need convincing of much less.
• Publish prices, which removes the most uncomfortable conversation from the call entirely.
• Be specific enough to be referred, since a referred prospect arrives with the trust already supplied.
• Say plainly what you do not do, which filters out the conversations you would have found unpleasant anyway.

None of that removes selling. It moves most of it into writing, done once, where somebody uncomfortable in conversation has the advantage.

Making the call itself easier

Small practical things, which sound trivial and do most of the work for somebody who finds this uncomfortable.

• Have the four questions written down in front of you. Reading a question is easier than inventing one while nervous.
• Book calls in a block on one day rather than scattered. The first is always the worst, and the fourth is noticeably easier.
• Decide the one thing the call has to achieve before it starts. A call with an objective ends; a call without one drifts and leaves you uncertain whether it went well.
• Keep them short and say so at the start. Twenty minutes, agreed in advance, is less daunting to run and easier for them to accept.
• Write the follow-up immediately afterwards, while it is fresh, rather than leaving it for a day when the words have gone.

And the one that matters most: do not rehearse what you will say. Rehearse the questions you will ask. Preparing answers makes you wait for your turn to speak; preparing questions makes you listen, which is both better and considerably less stressful.