The Sales Mastery Podcast · Episode 17

The Onboarding Gap

With James Denny · Sales Geek

A new seller takes anywhere from three to nine months to reach full productivity. The difference is rarely the person you hired, so build a sales onboarding plan that proves competence rather than a timetable that just moves people along.

In most business to business companies, a new salesperson takes somewhere between three and nine months to reach full productivity. Three to nine. That is quite the spread, and the gap between the fast end and the slow end is almost never about the person you hired. Instead, it is about what you did with them once they arrived.

A new salesperson starts on a Monday. You give them a laptop, a login and a target. Somebody walks them round the office, they sit with a couple of people for an hour each, and by Wednesday afternoon they have run out of things to read. So they start making calls, because making calls looks like work and sitting still does not. Nine months later that same person is under review, and everyone in the room is talking about their attitude.

The fortnight that undoes the hire

Last time we spent half an hour on how to hire properly, or at least how to start doing it properly. How to see past the person who is brilliant in the room, how to audition them rather than interview them, how to score the things you cannot train. Today, though, I want to talk about the fortnight that can undo all of that good work.

Think about that three to nine month range and what it really means. Two businesses hire similar people into similar markets. One has a productive seller in twelve weeks, while the other is still waiting eight months later. Same raw material, so the difference is not the hire. It is what happened to them in the first month, and that part is completely within your control.

In almost every business I walk into, these two words are tangled together, and it causes real damage. So let me pull them apart, because they are not the same thing at all.

The day and a half that belongs to somebody else

Induction, first of all, is a HR job. Contracts, policies, where the fire exits are, how the expenses system works, who to ring when the laptop will not connect. All of it matters, obviously. But it takes about a day and a half, and somebody other than you owns it.

The job that cannot be delegated

Onboarding is a commercial job, and a completely different thing. It is the process of taking somebody from knowing nothing about your market to being safe in front of your customers on their own. That, ultimately, is sales leadership work. So it cannot be handed to a folder on a shared drive, and it cannot be handed to HR or to a junior member of the team either.

The gap between knowing where the toilets are and being able to hold a proper commercial conversation unsupervised, closing that gap is the whole job.

Can I see the document?

When leaders tell me they have a good sales onboarding process, I ask them one question. Can I see the document? And nine times out of ten what comes back is an induction checklist with a bit of product training bolted on at the end. Week one is systems, week two is product, week three is sitting with somebody, and week four is off you go.

Systems, product, shadow, go. That is a timetable, and a timetable is not a plan.

A plan has proof points in it, meaning things the person has to demonstrate before they are allowed to move forward. A timetable just carries them along whether they are ready or not, and then acts surprised in month six when it turns out they were not.

Smaller businesses often tell me they have not got the resource for formal onboarding. We are too small, we do not need it. I understand the instinct, but it is exactly the wrong way round. The smaller you are, the less you can afford a seller running at half speed for eight months while you slowly find out they were never right for the job.

There are plenty of reasons sales onboarding is the thing that slips, but three of them are worth naming.

Nothing external is pulling on it

Onboarding is the only management job with no deadline attached. Nobody rings you demanding it. No customer is waiting on it, and there is no board paper about it. So it competes for your time against pipeline reviews, escalations and quarter end, all of which do have deadlines, and it loses every single time.

Skip a forecast meeting and nobody notices that week. Skip the session where you were going to teach your new starter how buyers in your sector really make decisions, though, and nobody notices for a year.

Most of us were sellers, not teachers

The second reason is less comfortable. Most sales leaders got the job because they were good sellers, so of course they know how to do the work. But they have never once had to describe how they do it.

Teaching somebody means breaking your own instinct down into steps you can hand over, and that is genuinely hard. It is much easier to sit the new person next to you and tell them to listen in, which feels like training but is mostly useless, because they do not yet know what they are listening for or why it matters.

The pressure to see activity

A new person costs money from day one. Watching them sit and read for three days is uncomfortable, so we push them onto the phones early. They have forty bad conversations, they learn that the phone is a painful place to be, and we have accidentally trained the exact behaviour we will be trying to correct in month five.

So let me say this plainly. Early activity is not progress. In the first couple of weeks, activity is usually just noise you will have to unpick later.

Most onboarding plans never answer that question. There are four things a new seller needs to be able to do, and we call them the four competencies. They are not equal in effort and they do not happen one after the other, so you work on all four from week one. But nobody goes in front of a customer alone until all four have a tick against them.

The one that gets over-taught, and the one that matters

Notice what is missing from those four. Nowhere did I say knows the product decks by heart. Product knowledge is the easiest of the four, and yet it is the one businesses spend most of their onboarding time on, for the simple reason that it is already written down somewhere. It is in the brochures, on the website, in the prospectus.

Customer, by contrast, is the hard one. It is also the one that separates the seller who can hold a room from the one who can only recite features. So if you fix a single thing after reading this, fix that one. Get your new starter in front of your existing customers in the first fortnight, not to sell them anything, but to listen.

Cadence, meanwhile, is the one people skip because it feels like admin. It is admin. But cadence is where the habits you can see get set, and there is a rule here that should worry you slightly.

Whatever you tolerate in a new starter’s first month becomes their standard for as long as they work for you. It sets a little like concrete, which is exactly why that first month is worth more of your attention than the next six put together.

Most businesses already have a sales onboarding plan of some kind, usually a thirty, sixty, ninety day version, and most of them are useless for one reason. They are full of activities instead of proof.

A typical plan says complete product training. Fine, but complete it how? To what standard? And who decides it is done? What you have written there is a to-do list with a development plan written on the front. So instead, make every milestone something the person demonstrates in front of somebody who signs it off.

How to onboard a new salesperson in ninety days

Across ninety days, that might look like this.

1. Day 10. They can explain what you do and who you do it for, in their own words, in under ninety seconds. Proof is that they deliver it live to two colleagues who did not help them write it.
2. Day 20. They can describe the buyer’s world, the pressures, the budget cycle and how a decision gets made. Proof is a one-page buyer profile plus notes from two real customer conversations they have had themselves.
3. Day 30. They can run a discovery call from start to finish. Proof is a recorded role play, scored against your discovery standards.
4. Day 45. They can handle your most common objections without a script. Proof is a role play where you are being deliberately difficult.
5. Day 60. They own a small number of live opportunities and keep the CRM clean. Proof is that their pipeline gets reviewed in the normal weekly meeting with no special treatment.
6. Day 90. They can work unsupervised and call a deal straight. Proof is that they call one and the call is right, or better still, they tell you a deal has slipped before you have had to ask, and the reasoning is rational, real and relevant.

Two rules that make it work

First, if somebody misses a proof point, they do not move on. You go back and teach it again, because the plan is a gate rather than a calendar. It exists to stop people, not simply to carry them forward.

Second, the sign-off is always a person and never a system. Somebody has to watch them do it, because if nobody watched it happen then as far as you are concerned it did not happen. That second rule is getting harder to hold, incidentally, as more companies hand the whole process to AI agents and let them work it out. Useful as those tools are, they still get plenty wrong, and a competence you have not seen with your own eyes is not a competence.

One more note on that final milestone. I have deliberately made day ninety about forecasting rather than about revenue. A new seller who tells you a deal has slipped before you chase them has understood how your business works. One who has closed something big but cannot tell you why it closed has not, or at least not yet.

Plenty of people reading this will be thinking that their team started eighteen months ago, so none of it applies. You cannot re-onboard everybody, and that is true. But you can find out what you never taught them, because it always shows up as a pattern in how they sell today.

We call that onboarding debt. You did not pay the cost in month one, so you have been paying interest on it every month since. In practice, five patterns come up more than any others.

Run those five across your team and be straight with yourself about what you find. Most of what gets labelled a performance problem in month nine is a teaching problem from month one, and the conversation you need to have is completely different depending on which one it is.

That does not mean underperformance is always your fault, of course. Sometimes it genuinely is the person. But you owe yourself the diagnostic before you have that conversation, because if you skip it you will exit somebody, hire again, and get exactly the same result in a year.

Most of what gets called a performance problem in month nine is a teaching problem from month one.

So that none of this sounds theoretical, let me describe a business that does it properly. First, the sales onboarding plan exists before the person starts. Their first three weeks are already in the diary, and the leader has blocked out the time to be there. They meet four customers in the first fortnight. Somebody watches them do the job live at least twice a week during the first month. Nothing moves on until it has been proved. Then at day ninety there is a proper two-way conversation about what is solid and what still needs work.

All of that costs the leader around three hours a week for twelve weeks, so a little over thirty-five hours in total. Set that against a salary, a whole territory and the six months you would otherwise spend wondering whether the hire was a mistake.

Get it wrong instead and you go into onboarding debt, which you will be paying off for months. Multiply it by the two, three or four people you are adding while you scale, and the debt becomes overbearing.

1. Induction is HR and onboarding is commercial. One takes a day and a half and belongs to somebody else. The other is a sales leader’s job, and it decides what kind of seller you end up with.
2. A timetable is not a sales onboarding plan. Systems, product, shadow, go just moves people along whether they are ready or not. Put gates in it instead, and make them show competence.
3. There are four competencies, not one. Company, customer, conversation and cadence. Most businesses teach the first and hope the other three turn up on their own.
4. Customer matters most and gets taught last. Get your new starter in front of real customers in the first fortnight with good questions and no slide deck, even if they are only shadowing.
5. Every milestone needs proof and a name against it. Something they demonstrate in front of somebody who signs it off, because if nobody watched it happen you have to assume it did not.
6. Whatever you tolerate in month one becomes their standard. Cadence sets early and then it sticks, which is why that month is worth more of your time than the next six put together.
7. Most performance problems in month nine are teaching problems from month one. Run the debt diagnostic before you start any performance process, or you will hire the same problem again next year.