
The fastest way to learn how a company buys is to ask the person buying. Get them to walk you through the last thing they bought like this: who was involved, what each person needed, and where it got stuck. One good question does more than a month of guessing from the outside.
Studying your own past deals tells you how companies like this one usually buy. That is useful. But it is an average, and you are not selling to an average. You are selling to one company with its own rules, its own finance team, and its own bad memory of the last tool that did not work out.
The buyer already knows all of that. They have been through it. Asking them costs you one question and gets you the real path instead of a typical one.
This is the worry that stops most people, and it is backwards. Asking how a decision gets made does not sound junior. It sounds like someone who has done this enough times to know the paperwork is where deals go to die.
What sounds junior is the opposite: promising a date you cannot possibly know, then going quiet when it slips. Buyers notice which one you are within about two questions.
People are vague about the future and specific about the past. Instead of asking how they will buy, ask how they did buy, the last time they brought in something similar. You get names, steps and timings.
Last time you brought in a new tool for the team, what did that actually look like? Who had to get involved?
A list of names is not a map. What makes it useful is knowing what each person wanted to see before they were happy. That tells you what to prepare and when.
When it got to your finance director, what did she want to see before she was comfortable?
Every company has one step that always drags. The buyer knows exactly which one it is, and will usually tell you with feeling, because it annoyed them too. Then you can start that step early.
Where did that one slow down? If we hit the same thing here, can we start it now rather than at the end?
Repeat the path in your own words and let them correct you. People fix a wrong summary far more readily than they volunteer a right one, so this is where the missing step usually appears.
So it is you, then your boss, then security review, then procurement. Have I missed anyone?
What does your decision making process look like? Asked cold, in process language, this gets you a shrug and the word 'standard'. Nobody thinks about their own company that way.
Last time you brought in something like this, how did it go? Who else got pulled in, and where did it drag? This gets you a story, with names, steps and one very specific complaint about procurement.
Ask about a real thing that happened, not about a process. Stories come with detail attached. Process questions come back empty.
You have got this when your close dates stop moving. Before a call, you can name every person who still has to say yes and what each one needs to see. When something slips, you saw it coming a fortnight out because you knew the step was there. And your buyer treats you a little differently, because someone who asks how the money actually gets approved is clearly not on their first deal.
Ask about the past, not the future. Say: the last time you brought in something like this, what did that look like, and who got involved? People describe things that actually happened in detail, but answer process questions with vague words like 'standard'. Then ask what each person needed and where it got stuck, and say the path back to them to check you have it right.
Almost never, if you ask about their last purchase rather than reading out a checklist. Buyers find approval steps annoying too, so they are usually happy to warn you about the one that drags. What does annoy them is a seller who promises a date, misses it, and blames a step the buyer could have flagged in ten seconds.
That is useful information on its own. It means your contact is not the one who has done this before, so someone else in the company has. Ask them who did it last time and whether you can get five minutes with that person. A contact who cannot describe how buying works is also a contact who cannot push it through alone.
Earlier than feels natural. Once the buyer is interested but before you have talked pricing is ideal, because it is a calm question at that point rather than a panicked one. Ask it in the last two weeks of a quarter and it sounds like you are chasing a signature, which changes how the answer comes back.
They answer different questions and work best together. Looking at deals you already won tells you how companies in your patch usually buy, which helps you forecast before you have met anyone. Asking this buyer tells you how this one company buys, including the quirks no average would show you. Start with the pattern, then confirm it with the person.
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