columnist Alison Green answers questions about workplace and management issues--everything from how to deal with a micromanaging boss to how to talk to someone on your team about body odor.

A reader asks:

I have a colleague who I depend on for data for a recurring project. Every time the update is due, I schedule check-in meetings weeks in advance and make it explicitly clear that I need X by [date] and Y by [date].

And every. single. time. my colleague slips the deadline, running us down to the wire, so I am scrambling to pull everything together last minute - and sometimes the data are wrong and we haven't had the chance to QA it and only discover the mistakes months later.

My colleague is always apologetic. He's a really nice guy, and I like him personally. 

It seems like a no-brainer that I need to surface this to my boss or to my colleague's boss, and it's stupid that I haven't done it yet. I'm just at war with myself over how to do this, even though I know that it's the right thing to do.

Should I have a conversation with him first and let him know that this is unacceptable and that I have to alert my manager or his manager the next time he misses a deadline? Should I just send an email to his manager, CC mine, and not tell him first? Or I could bring it up in my next 1:1 with my manager -- but my manager is very, very senior, and I worry that I'm coming to her with a problem and not a solution. 

Green responds:

Yes, you do need to speak up and loop in your manager. If this had just happened once, you could try working it out with your colleague directly. But it's a long-running pattern, it's causing real and ongoing problems, and the very reasonable steps that you've taken to try to address it haven't solved the problem.

And it is a problem that needs to be solved, so that means that you need to escalate it.

At this point, you need to do two things:

1. Talk to your colleague about your concern. You shouldn't have to do this -- your colleague already knows there's a pattern of him missing these deadlines and should be acknowledging it and coming up with a plan to fix it -- but since that's not happening, you need to raise it. Say something like this: "Cecil, I want to talk to you about the deadlines for the X project. I depend on you to get me the data in time twice every year, and it's causing real problems that the data is often late and contains mistakes, or doesn't come in time to QA it. It's become enough of a problem that I think I need to pull Jane (Jane is your boss here) and possibly Bob (Bos is his boss) in on this because I really need the next set of data to be on time and accurate. I wanted to give you a heads-up that I'm going to do that."

Alternately, you could change that last bit to say that you're going to bring Jane and Bob in in only if there are problems in the future. But that means accepting that there's a pretty good chance that the next data set is going to be messed up too. Are you willing to accept that high likelihood in exchange for giving him one final chance to handle this on his own? Whether or not that makes sense to do depends on how much of an impact his mistakes will have if it happens again.

2. Regardless of the timing, at some point, yes, you'll need to talk with your own manager about what's going on. You said you're hesitant to bring her a problem without a solution, but this is a problem where the solution isn't within your control. The solution here is that your coworker's boss needs to step in and more closely manage him, and you can't make that happen without escalating things.

Say something like this: "I want to loop you in to a problem I've been having with the data for X. I rely on Cecil to supply me with the data for X, and it's always late and often inaccurate. I've tried checking in with him weeks in advance and making it really clear what I'll need by when, but each time it's late and I've been left scrambling at the last minute, without a chance to QA it. At this point, I think I need to talk to Bob and get his help in resolving this. Does that sound right to you?"

(And actually, in this formulation, you are bringing her a solution -- your proposed solution is talking with Cecil's boss. But you might work somewhere where it would be more appropriate for your boss to be the one to do that, in which case you could change this wording to whatever's appropriate in your organization, like "I wondered if you'd be willing to talk with Bob about how we can get what we need from his team" or whatever.)

Does it suck to have to escalate something when it's about a coworker? Yes. But this is impacting your work, it's happened repeatedly, and your boss and your coworker's boss would almost certainly want to know this is happening and have the chance to step in and resolve it.

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