Most phone system rollouts don’t fall over because of the technology. They fall over on a Tuesday morning in week two, when the receptionist can’t work out how to transfer a call, gets flustered in front of a customer, and quietly goes back to using her mobile.

That happens a lot more than people admit. The system works. The handsets are plugged in. The number has moved across without a hitch. And somebody is still telling customers “hang on, I’ll ring you back from my own phone.”

A few things tend to help.

Teach the three things people do all day

Nobody uses every feature. Almost everyone does the same handful of things: answer a call, put it on hold, transfer it. Add checking voicemail and you’ve covered most of a normal working day.

Teach those first, and teach them with people actually pressing buttons on a real handset or app. Watching someone click through slides doesn’t stick. Transferring is the one that trips people up, because there’s usually a choice between sending the call straight across and speaking to the other person first. The difference isn’t obvious until you’ve dropped a customer into someone’s voicemail by accident.

Let everybody try both a couple of times while it doesn’t matter.

Call queues, reports, recording and the rest can wait. If you cover all of it on day one, people remember none of it.

Look after the person who dreads it

Every office has one. Maybe it’s the receptionist who knew the old system inside out. Maybe it’s the owner who has never opened a settings page in his life. Sit with that person first, not last. If the most nervous member of the team feels looked after, the others tend to relax. If they get left until the end, you’ll hear about it for months.

It also pays to find the one who actually enjoys this sort of thing and make them the person to ask. It takes pressure off whoever set the system up, and a ten-second question gets answered at the next desk instead of waiting in a support queue.

The workarounds will show up fast

People are resourceful, and within a week they’ll have found a way around anything they find fiddly. The usual suspects are handing customers a personal mobile number because it feels easier, forwarding the main line to one person “just for now,” and leaving the old desk phone plugged in “in case.”

A few days of that is harmless. Beyond that it undoes the reason you switched. Be straight with the team and pick a date. After that date, the new system is the phone.

What a sensible two weeks looks like

Before go-live, run one short, hands-on session covering the basics, and hand out a cheat sheet. One page. How to transfer, how to hold, how to get voicemail. Stick it up next to the phones.

On the first day, have someone around who can answer questions all day. Not someone on the end of a queue, someone physically there or properly reachable. Most of the questions will take about ten seconds to answer, and that’s exactly why you want a person close by.

At the end of week one, spend fifteen minutes with the whole team. What’s annoying? What did nobody expect? You’ll hear things you’d never have thought to ask, like the headset being too quiet, or not being able to see whether a colleague is already on a call.

In week two, add one extra feature, whichever will save people the most time. For a lot of teams that’s voicemail to email or the mobile app.

Check what your customers hear

Regular callers notice changes before you do. A new greeting, different hold music, a slightly different pause before someone picks up. Most of it won’t bother anyone. What does bother them is when something they relied on stops working: a direct number to a particular person, an extension they’d memorised, the number they ring after hours.

Ring in yourself, from outside the office, on a few different days and at a few different times. It’s dull and it catches things.

What your provider should be doing

Posting out handsets and emailing a login isn’t a rollout. A decent provider helps set up the call flows around how your business actually runs, hands over properly, and answers the phone when something’s unclear in the first couple of weeks. That’s the stretch where nearly all the problems turn up.

That’s the approach we take with Yabbit. If you’re weighing up providers, ask what happens in week two. The answer tells you a lot.

Last thing. Write down the three things everyone needs to know how to do, and put it on the wall by the phones. It’s boring, and it works.