Why your sellers aren't ramping
I've onboarded a lot of sellers. Over time, the way I think about it has narrowed down to two questions. How do we get them to do the job immediately? And how do we make the feedback loop as tight as possible once they are? Everything else is noise.
It's easy and tempting to get both wrong. New joiners spend their first two to four weeks reading internal documentation, sitting in on calls, and not actually doing anything themselves. When they finally get started, they realise they learned almost nothing. Then, once they are doing the job, you want to systematise and automate the process, and the feedback is too slow, too generic, or too detached from the actual work to be useful. The result is long ramp times, bad habits, and sellers who never fully develop — not because they lacked potential, but because the system failed them.
Training, when done well, is the highest-leverage activity in any organisation. Anyone who trains effectively is doubling their own output. But most onboarding attempts to teach everything a seller might need at some point while neglecting what they desperately need today.
Full speed, no mistakes
There are a million new things to learn when you start at a new company. Most companies mistakenly create a seemingly infinite list of things for new joiners to learn. The problem is that new hires get lost and end up spending their time on a bunch of things they won't immediately need.
The biggest risk early on is getting lost trying to learn things that you won't need, which doesn't stick.
The finish line for a new seller — hitting target, owning a territory, closing large deals — is real, but it's distant and hard to navigate toward on day one. So most organisations default to preparation. Read the handbook. Shadow some calls. Absorb everything you might possibly need. Then, eventually, start.
The result is that new joiners spend weeks not moving. And when they finally do move, they're disoriented anyway, because reading about sales and doing sales are completely different things. The preparation didn't prepare them.
The better approach is to identify the nearest landmark and run at it hard. For a new seller, that landmark is simple: book a meeting on the first day.
Action-mode
We consume information fundamentally differently depending on whether we're just about to use it (action-mode) or whether we're just passively observing (consumption mode). The nuances are almost impossible to internalise unless we're doing the work.
This is exactly what's wrong with front-loaded onboarding. Two weeks of reading documentation and shadowing calls is consumption-mode. You can sit through ten demos and not notice the moment a prospect's tone shifts, because you're not the one who has to respond to it. You can read the objection-handling guide cover to cover and retain none of it, because no one is objecting to you. The information washes over you. Nothing sticks, because nothing has to.
But put a new seller on the phones on day one, and suddenly everything changes. The ICP document isn't abstract anymore, it's the difference between a productive call and a wasted one. The product positioning isn't a slide deck, it's the thing you're fumbling to articulate while a prospect decides whether to give you another thirty seconds. Every piece of information the company has to offer becomes vivid and urgent, because you have an immediate reason to use it.
This is why starting early isn't reckless. Every week you spend "preparing" a new joiner is a week where they're seeing the job in muted grey instead of colour. The fix isn't a better training deck. It's the willingness to put someone in motion before they feel fully ready, and then to be there when they need you.
Be there when they need you
Getting someone into action-mode is the first half. The second is what happens once they're moving. And this is where most companies fail even harder.
The best way to learn is to do something to the best of your ability while an expert adjusts what you're doing in real time. Not generic coaching. Not "here's what typically works." Direct, specific feedback on exactly what you just did, tailored to how you work, delivered in the moment when it actually lands. When you're shoulder-to-shoulder, corrections are instant. The wrong approach gets fixed before it becomes a habit.
The difference in speed is staggering. If you sync with a new joiner once a month, you're barely giving them a chance to improve at all. Feedback arrives so late that the habits formed in the gap are already hardened. Once a week is better, but you're still wasting most of their learning time. Once a day is meaningfully better. But ideally? You sit down and do the work with them. You will be blown away by how much someone can develop in a single day under those conditions.
I see this most clearly in challenge interviews. In the span of a single session, I'm effectively onboarding a candidate on our approach to sales, showing them the framework, letting them try it, adjusting what isn't working, letting them try again. The improvement within that one interview is often remarkable. To me, it's a clear demonstration of what short iteration loops actually means.
This is not a radical idea. It's the oldest model in the book. You learn by working next to someone who already knows how to win, absorbing how they think in real time, and gradually taking on more of the work yourself. Shadow, then lead, then own. The structure isn't new. What's new is that high-growth tech companies have convinced themselves they've found a more scalable alternative, and in doing so, they've stopped developing elite sellers altogether.
The usual objection is that this doesn't scale. "We hire smart, self-sufficient people. They don't need to be hand-held." This gets it exactly backwards. The best people aren't the ones who need the least coaching. They're the ones who benefit from it most, because they can actually absorb it, act on it, and compound it. The more raw ability someone has, the higher the return on every hour you invest in them. If you hire someone exceptional and then leave them to figure it out alone because you trust them, you're wasting their potential.
The information flows both ways
Here's something that rarely gets said out loud: leaders who sit with their team become dramatically better at their own jobs.
When you're not in the trenches, you lose touch. You build processes without knowing which ones create unnecessary friction. You set expectations without understanding what actually takes time. You make decisions about what matters without knowing what's genuinely hard.
I've seen it over and over. A sales leader builds an outreach playbook, rolls it out to the team, and moves on. Six months later, the team is spending hours on steps that don't move the needle and the leader has no idea, because they haven't done the work themselves since they wrote the playbook. The process made sense in theory. In practice, it's full of dead weight. You can't see that from a dashboard. You can't fix what you can't see.
Sitting with an SDR and going through the full outreach sequence — selecting accounts, finding contacts, writing copy, making calls — is one of the highest-leverage things a sales leader can do. Not just for the SDR, but for you. You'll learn which parts of the process are unnecessarily painful. You'll see where the tools fail. You'll notice the gap between what you think is happening and what's actually happening. The best leaders never fully leave the floor. They don't manage from abstractions. They manage from current experience.
This is the real reason the apprenticeship model works. Teaching forces clarity. Doing the work alongside someone forces honesty about what your processes actually look like in practice, not what you wish they looked like. The new joiner gets developed. The leader stays sharp. The information flows both ways.
Get points on the board
Ramp time isn't a fixed cost. It's a symptom. It exists because companies delay motion, front-load information people can't yet use, and keep new joiners away from the feedback that would actually develop them. Change those conditions, and ramp time shrinks — not because you've optimised the onboarding checklist, but because the new joiner is genuinely learning from the moment they start.
The goal on day one is to book a meeting. Get the ICP right. Get on the phones. Get something in the diary. You're on the board. You're moving. You're learning things that no internal documentation could teach you, and you're doing it without getting lost.
Full speed. No mistakes.