how do I train my team to do my job without making it obvious I’m planning to leave?

A reader writes:

The company I currently work for was perfect for me when I started in the corporate world — low-key, the owner is very hands-off, and my bosses let me work without micromanaging. But recently we’ve become a lot bigger while still keeping that “small business” mindset.

Our profit has more than quadrupled in the past seven years, but the number of employees in headquarters has not increased in response (we’re still fewer than 20 people). A daily catch phrase is, “It’ll slow down eventually … right?”

It’s wearing me down to a point where I need to find another job, and I have started to activity job search. My concern is, I honestly do the job of three people (with three different managers) and I know they won’t be able to hire and train someone between me putting in my notice and leaving. No one else at the company is currently able to do the majority of my work.

How can I start prepping and training my coworkers to do my jobs without making it obvious I’m planning to leave? Or potentially putting my job in jeopardy before I can get a new job?

Or this a situation where I just need to let it go and say, “Not my responsibility”?

The latter.

If your employer were as concerned about this as you are, they would be creating time and structures for you to cross-train your colleagues. They’re not, so you don’t need to.

There are some limits to that: the more senior your job gets, the more it’s your responsibility to ensure things like that are taken care of. If you’re a department director saying “no one will be able to cover even the basics if I’m buried in an avalanche tomorrow, oh well, too bad,” that’s a problem. That kind of planning is part of that job. And even if you’re not that senior, at a certain responsibility level in some cases it would be part of doing the job well to identify the must-do areas that other people need to be trained in and ensure that happens, or point it out to someone who can — or to say to your own boss, “Here’s a major point of weakness in our coverage, here’s what the consequences could be if I were suddenly not here, and here’s what I think we could do about it — but I don’t currently have any time to do it.”

So if you haven’t done that last part, you should. You don’t need to make it obvious that it’s because you’re thinking about leaving; frame it as thinking about what would happen if you were suddenly hospitalized, won the lottery, got eaten by a wild boar, etc.

But if they don’t make it a priority — which means carving out actual time for you to do it by moving back other priorities and doing the same for the people you want to train in your areas — then you don’t need to either. You’ll have flagged it for them, and the next steps are up to them.

All that said, if you have time to work on some transition documentation that you can leave behind, that’s a good thing to do … but it doesn’t sound like you have a ton of spare time for that, and it’s not something you should work extra hours to get done (since again, if it were that important to your employer, they’d ensure you had time to prioritize it). Moreover, when people leave behind detailed and beautifully organized documentation for their work, it often never gets looked at by anyone — so it’s definitely not something you should contort yourself to achieve if it’s not easily doable. (For that same reason, if you do it, aim for a couple of pages of bulleted info, max. The idea isn’t to write a detailed manual to how to do your job — again, unless you’re asked to and given enough time for it — it’s to leave the most key info for whoever needs it when you’re gone.)

But it’s very normal in office-type jobs not to be able to hire and train someone before a person leaves. Most people give two weeks of notice, which isn’t enough time to advertise the job, interview candidates, make an offer, and then wait for that person to give their own notice. So it’s not unusual that they won’t be able to do that; that’s how it normally goes and companies muddle through.

“Muddling through” can mean that they back-burner projects you were working on out of necessity, or half-ass them in ways you wouldn’t have, or kill certain projects altogether, or bring in outside help. Or sure, occasionally a team will crash and burn because someone leaves, but it’s surprisingly rare for that to be the result. More often, their solutions just might not look like how you’re doing everything now, but they’ll figure it out.

Regardless, it’s not yours to solve because this is not your company! Flag the concern, and then leave it to them to decide what to do about it.

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