Prospecting tips from a founder who does it

Most prospecting tips are really channel advice. Try LinkedIn, try cold calling, try video. That's a different question from the one that decides whether your pipeline fills: what small habits you keep up when the week gets ugly.

These are the tips for prospecting I'd give someone starting outbound tomorrow. I do my own at LiveDocument, I ran growth at a couple of data startups before that, and every tip below is something I learned by doing the opposite first. If you want the channel list, I've written up 13 prospecting methods. This one is about how you run whichever two you pick.

Write the target down before you open a tab

Before any list building, write one sentence: who, at what kind of company, with what problem right now. If you can't, you'll spend the morning collecting names that feel productive and aren't.

I used to build lists first and decide fit later. I'd end up with 400 contacts and no way to say why any of them should care. A sentence on a sticky note fixes that. The longer version is in my post on the ideal prospect.

Cut the list before you grow it

Everyone adds. Almost nobody subtracts. Take your list and remove anyone you wouldn't be thrilled to land. What's left is smaller, and it's the only list worth your attention.

A short list you work properly beats a long one you skim. I go deeper on this in strategic prospecting, but the one-line version is that deciding who not to call is most of the skill.

Spend two minutes of research on one specific thing

You don't need a dossier. You need one true, specific thing about the person or their company that changes what you'd say. A new hire, a product launch, a post they wrote that you disagreed with a little.

If the research doesn't change the message, it was decoration. Skip it and send something plain rather than something that pretends to be personal. Readers can tell the difference within a sentence.

Make the first message about them and short enough to read on a phone

Four or five sentences. One idea. One easy question at the end. Not "do you have 30 minutes for a call", which asks for a lot from a stranger, but something they can answer in a line.

My own rule: if I wouldn't send it to someone I'd met once at a conference, I don't send it. Cold doesn't have to mean stiff.

Put prospecting in the calendar, not on the to-do list

A to-do list gives prospecting the leftovers of your day, and there aren't any. Block ninety minutes, same time, most days. Phone away, inbox closed.

This is the unglamorous truth of doing outbound as a founder. Nobody cancels it for you, so you have to protect it from yourself. A consistent small block beats a heroic Friday that happens twice a month. I've written about turning this into a repeatable routine in prospecting workflow, and about the one-page version in your prospecting plan.

Follow up more than feels polite, and add something each time

Most replies come after the first message, not to it. That's the part that surprises people, and the part that gets skipped because following up feels pushy.

The fix isn't to nag. It's to give each touch a reason to exist: a relevant link, a short answer to a question they probably have, a note about something that changed. "Just bumping this" adds nothing and gets treated accordingly. If a proposal is already out, how to follow up after sending a proposal covers the cadence in more detail.

Send the thing as a link, and be there when they open it

At some point a prospect says "send me something". This is where a lot of good conversations die. You attach a PDF, it lands in an inbox, and you have no idea whether anyone looked.

This is the one place I'll talk about our own product, because it's the problem I built it for. With LiveDocument you attach a recorded walkthrough to a PDF or image and send it as one link, so the prospect gets your face and voice talking them through it instead of a silent file. You also see which pages they spent time on, via PDF tracking. It won't write the proposal for you, it isn't a CRM, and it can't make someone care. But a two-minute video walkthrough on the PDF does a lot of the explaining you'd otherwise hope they'd do themselves. If you sell for a living, the sales use case shows how that looks in practice.

Plain alternatives work too. A short Loom and a linked document is fine. The point is to stop sending files into the void.

Read signals as hints, not verdicts

Someone opened your document three times. Great, but that doesn't mean they're buying. Maybe they forwarded it, maybe they were looking for something else, maybe they're comparing you with three others.

Use activity to decide who to contact sooner, not to decide what they think. I've over-read a lot of signals in my time and been wrong in both directions. A view is a reason to send a useful follow-up. It isn't a reason to ring them and say "I saw you looked at page four".

Keep a note of why each person said no

"Not now" and "not for us" are different answers, and your CRM, spreadsheet or notes app should know which one you got. Add a date to revisit the first kind.

Some of my better conversations have come from people who said no eight months earlier, because things changed on their side and I was the only one who remembered the context. Reviewing your losses is also the cheapest market research there is.

Prospecting tips, quick answers

What are the best prospecting tips for beginners?

Pick one narrow target, one channel and one daily time block. Write short messages, follow up properly, and keep notes on every no. Add a second channel only once the first is working.

How many prospects should I contact a day?

There's no honest universal number. It depends on your channel and how much research each contact needs. Start with a volume you can personalise properly, then raise it only if replies hold up.

How do you prospect without sounding pushy?

Make the first message useful and easy to answer, and give every follow-up a new reason to exist. Pushy usually means repetitive. Tips for prospecting that feel natural all come down to adding something each time.