📄 The simple psychology of repeat purchases

There’s something really simple and effective you can do to get more sales, and it doesn't get nearly enough airtime:

Generating repeat purchases.

Here’s the deal.

I happen to be lazy, in that I’m always looking for the best, fastest, easiest way to get results - also known as: being efficient and effective.

And the fastest and easiest way to generate sales, is very often as simple as talking to past buyers, and seeing if they need any more help.

But you don't want to show up needy, and instead of tuning you out and ignoring you, you want them to engage.

And to do that, you need to sit and reflect for a moment, on what things must be like from your past buyer's point of view.

And so, you need to ask yourself two types of questions.

First, the 'before-questions'.

Things like:

Why did they buy in the past?

What problem were they looking to solve?

How urgent was it, and how costly to not solve the problem?

In other words: what were the psychological and practical motivators that initially drove them to buy?

Next, once you’ve reviewed those motivators, you move from ‘before questions’, to:

The ‘now questions’.

Here, you're trying to project what you know about your buyer, historically speaking, into what life must be like for them at this moment.

Where are they at?

What could be going on in their world?

What problems might they be facing, that you could solve?

What could have shifted in their business, what might have broken?

What would motivate them to buy your solution again, or another solution, or a solution you could provide through a partner or ally (i.e. cross-selling)?

How urgently would they want to?

What specific, precise, measurable outcome would they like to achieve by getting more help from you, or a partner?

Doing this exercise will give you a hypothesis - a theory as to which people would need help, for which reasons, and it informs you on which questions to ask these people.

That way, you don't blindly ask "Want some more?", but you'll have relevant, thoughtful, and specific topics and questions to bring to the table.

Which brings us to the next stage:

You get on a call and you talk to them.

Not to pitch or sell, mind you.

No, you talk to them in order to ask questions - the kind of questions that tell you whether or not your theory was right.

For instance:

"I imagine that at this rate of growth, your team's cohesion and productivity might be suffering. Is that a fair assessment?"

"All that publicity must get you a ton of traffic - have you considered improving you conversion rates, to get more returns from the increase?"

"Do you find it a challenge to stay on top of projects, now that you raised that investment round, and there's all these new inititiatives getting started and new employees getting on-boarded?"

When you ask questions like that, and you're correct, then very often something funny happens:

They’ll sell themselves on getting more of your help.

They themselves will turn a friendly, informal conversation, into a sales conversation.


Because if your theory was right, you asking the questions demonstrates that you get them, that you understand what they’re up against, that you have a grasp of what it’s like to be them.

And who better to ask for help, than someone who really gets us, who gets our challenges and reality?


The easiest sale is from a past buyer.

Go talk to them and ask them about their problems right up until the moment that they ask you about your solution.

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