If you spend any time in the sales communities on Reddit, you start to notice the same questions repeating. Usually from someone who is new to sales.
They have a list of a few hundred companies, a quota, and a sequence they are supposed to fill. And in one form or another, they’re asking: “who am I actually supposed to reach out to? What am I doing wrong? Pretty sure I’m getting put on a PIP –what do I do?”
The answers they get are often overwhelming. Send more. Personalize everything. Follow up 15 times. Most of the advice is about the message and the volume and very little talks about the actual list.
A little bit about me:
I’ve worked in sales since I was 16 and can tell you that right now is the hardest it’s ever to been to actually sell something.
Why?
Inboxes are fuller, everyone has access to AI and messages all sound the same. So what do we do?
The reframe
Most of us, when outbound isn’t working, assume the problem is what we’re saying. So we rewrite the subject line, refine the body and add another follow-up. But the harder truth is that a lot of the people and companies in the sequence never belonged there in the first place. No message can fix a list of the wrong people.
Hear me out. Because there’s a number that makes this concrete. At any given moment, only about one to two percent of a market is actively looking to buy. That holds across nearly every kind of B2B selling.
Sit with that for a second. If only one or two accounts out of a hundred are ready to buy this quarter, then the list of companies your new boss just gave you is all noise. That means your job isn’t to reach everyone who could buy. It’s to find the few companies and people who fit and have a reason to move now.
That leads to three simple questions to ask before anyone goes into a cadence.
Question one: does the business actually have the problem?
Most descriptions of an ideal customer are really just a description of who a rep wants to talk to. “Marketing leaders at software companies with 50 to 500 employees” is not a real target. It is a demographic. It says nothing about whether that company actually struggles with the thing you fix.
The better test is almost too simple: can you look at a company and say, in a sentence, why they specifically have the problem you solve? If you can’t, they do not belong on the list. Not because they are the wrong size or industry, but because you have no evidence of the pain.
Two things save you a lot of time here. First, don’t trust the filters in your prospecting tool. A company can match every box — right industry, right size, right region — and still have no real use for what you sell. Pull up their site or their product for a minute and check if what your selling would actually fit into how they already work. Second, be honest about which accounts deserve your best hours. There’s pressure to chase only the big logos, but a middle logo deals that closes this month is often what keeps your numbers alive while large deal drags across two quarters. Keep those smaller accounts nurtured with a lighter touch rather than overlooking them.
Question two: can this person buy, or open a door to someone who can?
The first question gets you the right company. This one gets you the right person inside it.
New reps often stress over whether to reach out to the decision-maker or to someone lower down. The honest answer is that it depends on your goal, but it’s rarely only the decision-maker who makes a decision. I like to split my outreach between C-Suite and someone closer to the actual work – who really feels the problem. They’ll make the case for you in rooms you’ll never be invited into.
The one person to skip is the one with no authority and no path to it. A pleasant conversation that leads nowhere is still nowhere. So the test is straightforward: this person passes if they can buy, or if they can credibly carry you toward someone who can.
Question three: is there a reason to reach out right now?
This is the question that most reps skip, and it’s the one that fixes reaching too wide.
Fit tells you a company is a good match. Timing tells you they are a good match today. The strongest outreach almost always points to something happening in the prospect’s world right now. If your message could have been written a month ago, it’s already stale.
So what counts as a reason to move now? A few of the clearest signals, strongest first:
- A decision-maker changes jobs or gets promoted. This is the single strongest one — people rethink what they buy soon after stepping into a new role.
- The company recently raised funding. ( Yes, everyone knows this one)
- They are hiring for roles that point to the work you support.
- They use a tool yours works alongside, or they are swapping tools in that stack.
- They engaged with content, attended an event, or asked publicly about the exact problem you solve.
- They left a critical review of a competitor, on the weakness you happen to be better at.
You do not need all of these. You need one, and it needs to be current.
The whole thing on a sticky note
Before anyone goes into a cadence, they should clear all three: the business has the problem, the person can buy or open a door, and there is a reason to reach out now.
And for everyone who does not clear all three, the answer is not “delete.” It is usually “wait.” A good-fit account with the right person but no trigger yet doesn’t get a sequence; it gets patience, and your attention the moment something changes. Most sales are made on the follow-up, when a good fit finally meets a real need.
It feels backward, but the reps with the steadiest pipeline are usually sending less, not more. A smaller list of the right people, reached at the right moment, beats a giant list of the wrong ones every time.
Why I wanted to write this down
I’m writing this down for the person on Reddit with three thousand accounts and no idea where to start. When I began, no one handed me a simple way to decide who was worth the effort.
Qualify hard. Be patient with the rest. And put your best hours into the few who have actually earned them.