Managing (someone else's) deadlines
April 13, 2018 10:17 AM   Subscribe

Someone I'm supervising has trouble with deadlines (as in a lot of trouble with deadlines). I've been tasked with "helping her out" with them. I could use some help myself.

So I was just promoted up to a position where I supervise other people's work as well as doing my own; this entails editing their written work for content and style, and addressing problems with the reasoning or conclusions, if any. We work on extremely tight deadlines, and the deadlines are constant, i.e., it's not a situation where you'll have a very tight deadline for a project and once you're done, there's a bit of breathing room for a few weeks. The pace is pretty relentless. (I'm deliberately being a bit vague about the work itself, but the important part is that people are writing reports that are anywhere from 15 to 35 pages long, but usually on the shorter side of that.)

I'm supervising a woman I'll call Tracy. Tracy is smart, competent, pleasant to work with, and her work product is generally excellent. Only problem is, she's chronically very late finishing her work. Using somewhat random days that will give you an idea of the scope of the problem: let's say our deadline is that we have to be finished with a report 30 days before a date certain; she generally finishes 15 days before the date certain. So we're talking significantly late -- she gives us half the days we need to do what we need to do.

My boss (who's actually a friend of mine) has directed me to help Tracy timely complete her work. To be honest, I had problems with my own timeliness in the past, and often still do, so this is a bit outside my area of expertise. The other problem is that I'm just not sure how to address this in an effective way. We're all professionals (all lawyers, to be exact), and I intend to treat Tracy like a professional, not like an unruly child under my care. So my inclination is to sit down with her and say, "Ok, Bossman has asked me to help you get more timely. How do you think we can accomplish that?" Only problem with that is, as I mentioned above, Tracy is smart and competent, so if she's late with her work, it's not because she's recalcitrant or doesn't give a damn; quite to the contrary, the reason she's late is that in this job, smart and competent gets rewarded with the more difficult work, whereas people who are not especially competent and have a poor work ethic get the easy work. You see the problem.

There was once a manager here who was a nice person but a dreadful manager; his method for keeping his people timely was to call them at 11 am on the day of the deadline and say, "Bob, it's 11 am. Where's your report??!! I want it on my desk in the next five minutes." He would then show up in Bob's office and literally stand there glaring until Bob finished. I swear to Christ I am not making this up. That's just...out.

So, management-type Mefites -- how should I proceed here? I realize this question is kinda basic, along the lines of "How do I office?" but I'm really at a loss.
posted by holborne to Work & Money (23 answers total) 9 users marked this as a favorite
 
Start with, "Ok, Bossman has asked me to help you get more timely," and then ask, "what do you see as the reasons you have trouble meeting deadlines?"

She's smart; she knows she's late; she knows why.

Adjust your offer of assistance accordingly - if she just gets caught up in the work and loses track of time, offer to send her weekly reminders. If she works on several projects at once and doesn't get any of them finished until after a deadline, offer to meet with her to discuss the one that's most pressing - maybe reviewing progress with another person will put it at the top of her internal "gotta do this next" list.

If she's prone to being a bit lazy because hey, she's smart, she can do most of this in her sleep, so she just lets it slide until there's a blinking red DUE YESTERDAY notice on her calender (which she's not going to admit, and nor should you try to pressure her into it, but you might be able to tell that's what's going on), ask if she'd do better with reminder emails/calls, or with progress reviews, or with an initial project setup that gets her fired-up to focus on it.

Does she need an outside nudge, or someone to bounce ideas around with, or a way to be more emotionally invested in the projects?

There are ways to provide any or all of those, but you need to know which one is hanging her up. And she knows. Ask; as long as you're clear that "you're awesome! We love your work! We want to see more of it sooner; how can we make that happen?" she'll be less likely to be defensive about it.
posted by ErisLordFreedom at 10:26 AM on April 13, 2018 [4 favorites]


I'm not a manager, but I am a Tracy, maybe.

One thing that helps me a lot is having someone else really engaged. To borrow from a Scrum framework, the idea of a daily check-in where I can honestly discuss progress and proactively discuss any "blockers" with someone else is pretty transformative. Being - or running - late on something can create a big ol' anxiety thing that makes it much harder to go outside myself for support on the project as that would mean exposing exactly where I am on it so I just avoid things and run farther and farther behind. Proactive check-ins keep that anxiety at bay and allow me to address the things that ultimately impede my own timely delivery.
posted by mosst at 10:29 AM on April 13, 2018 [13 favorites]


Best answer: 1) Interim deadlines! The best thing you can do is help Tracy break down a report into smaller chunks and come up with days when she needs to have those small chunks done. A couple days before the day when they need to be done, you'll meet with her and check in on her progress, then remind her of the deadline. To manage these, you should become awesome at Microsoft Outlook, if you use it. Set up calendar reminders (i.e., an all-day or zero-minute appointment) and Tasks for each interim deadline and share them with Tracy.

2) Prioritization. Most likely, since Tracy is a high performer, she's missing deadlines because she's busy working on other tasks, not because she's slacking off. Working with Tracy, lay out all of the tasks she works on, and help her develop a hierarchy and rules like "I will not work on X until my report is done" or "I will not spend more than one hour per day doing Y". Outlook also helps with this--a lot of my colleagues block out times on their own calendars to work on specific tasks.

3) Tips to make tasks faster. She may not know that it's okay to copy-and-paste a certain section of a report from previous documents, or use your editing software to automatically format things, or that certain sections don't need to be as long as she's making them.

You do also want to be open here to the idea that Tracy is just under unreasonable expectations. If you've exhausted everything you can think of in steps 1-3 and she still has way more than 40 hours a week's worth of work to do, then your job shifts to helping her make the case to your shared manager that she needs to stop doing certain tasks, or that she can't actually get the reports done in the time allotted. As a caveatt, something I have seen with people who are dedicated, talented high performers is that...they think they are required to do something that is actually above and beyond expectations. This may not be that difficult a conversation, because your boss might say "oh wow, Tracy, I had no idea you were trying to handle this thing by yourself, you should delegate that to the interns" or whatever.
posted by capricorn at 10:32 AM on April 13, 2018 [17 favorites]


the reason she's late is that in this job, smart and competent gets rewarded with the more difficult work, whereas people who are not especially competent and have a poor work ethic get the easy work

It is good that you have identified the main problem here. Part of management is managing your employees but the other part is managing UP. So, letting YOUR boss know that expectations are unreasonable. Is there some type of metric that sets the deadlines according to the complexity of the work? Or is it more "we have three reports that need to be written: one 20 pages on a simple topic that Roop will do, one 15 page on a more complex topic for Robin and a 20 pager on a super complex topic for Tracy - you all have one week to do it. Tracy, make sure yours isn't late AGAIN."

So have a look at the process itself, as well as the equitability of the workload. If your boss isn't happy with your feedback and refuses to make changes that tells you they don't really care about the work or the workers, in which case, why should you?
posted by saucysault at 10:35 AM on April 13, 2018 [15 favorites]


Is there any sort of existing system for tracking assignments, deadlines, and ownership? Can the work be estimated in advance in even a remotely meaningful way? If possible, I'd hope to make it not be about Tracy but rather search for process improvements that help everyone in some way or another. Like, for Tracy, it's deadlines. For someone else, maybe it's planning vacation. For your boss, it's advance warning that something is just going to be late no matter what. Your example may be intentionally simplified to the point where we can't tell what would help, but for the given example, I'd wonder if something like a spreadsheet sorted by deadline, a column for expected days of work that remain, and a reasonably frequent progress sync (less than 5 minutes) to update the status would help the group.
posted by Wobbuffet at 10:40 AM on April 13, 2018


Smart competent people can also be perfectionists - and this is a powerfully paralyzing force that leads to procrastination. It's almost the exact opposite of laziness although it looks the same.
The solution to this type of deadline missing starts with accepting that nothing is perfect and that 'Done is the engine of more'
posted by Heloise9 at 10:42 AM on April 13, 2018 [19 favorites]


You do also want to be open here to the idea that Tracy is just under unreasonable expectations.

This is where I would start. I manage in an entirely time dependent industry; the first thing is always examining feasibility or labor hours vs task. That feels off here.

For me being "excellent" and "15 days late" are just incompatible. From my management point of view those two things can't be simultaneously true unless the work load is wrong. Because time management is an important part of any job.

So supposing the problem is in part Tracy the steps I would take is clear set interim deadlines, frequent progress reports. If those don't cut it i'd move to Start of day / End of day rundowns either written or verbal.

If she's managing time well, working diligently and still behind and upper management can't/won't change the deadlines or workload than she's going to need to start doing lower quality work. This can be a hard conversation to have but it's one that needs to happen sometimes. "you need to do B+ work fast, not A+ work super late" Some people really struggle with that adjustment but the best you can do is set clear expectations and communicate that after a certain point quantity/speed tops quality/precision in many things.
posted by French Fry at 10:46 AM on April 13, 2018 [6 favorites]


I am a Tracy, and while I also believe I'm relatively bright, I am terrible at managing deadlines. I have really, really high anxiety which makes it difficult to start projects, but also REALLY hard to finish them, because then I have to pass them off to my boss to review, who is very, very smart and capable and ugh. I fought really hard to keep my knowledge of my anxiety to myself, but I chose to disclose some limited information to my supervisor because I felt like it was the best choice at the time. I think I still believe it was the right choice, but hey, you can't put the kittens back in the cat. Tracy may or may not have similar struggles, but as someone upthread noted, she knows she's late, and it probably is very stressful to her (given the way you've described her otherwise conscientious work). It may be workload, it may be she's got a sick kid/sick parent/financial difficulties and maybe she's having a hard time managing.

Informal check-ins with my supervisor have been the most successful thing for me to stay on track. While I'd prefer to avoid them entirely (see: anxiety referenced above), but I need that accountability. I'm a professional with advanced degrees, but deadlines are my kryptonite. (Btw, this became 1000% worse for me when I entered the workforce in my field. I never, ever missed a deadline in my almost 27 years of school.)
posted by heathergirl at 10:59 AM on April 13, 2018 [4 favorites]


Sounds to me like this is a workload problem mislabeled as a deadline problem by the upper management who'd rather stick their head in the sand about staffing. In my industry (software engineering which is similar to law in the sense that it's knowledge based "technical" type work) it is widely acknowledged that the most effective managers are shit umbrellas who catch all the nonsense raining down and let their best people get on with actual work. I am sorry but to solve this you need to manage up, not down.
posted by rada at 11:00 AM on April 13, 2018 [4 favorites]


There's always the "let's work backward from the deadline" approach. Suppose it's due in 30 days. Can she send you an outline in 15 days? Can she send you a rough draft in 20? Or can she send you the first half in 15 days? ... You know your work better than I do, so I don't know what'll work for you, but setting internal deadlines for interim milestones seems like one possible approach.
posted by salvia at 11:11 AM on April 13, 2018


It might also help to ask her to outline a typical process for you. Maybe you'll learn she spends 20 days just [researching pertinent case law or reading every page of the administrative record - am I using these terms right?] or otherwise doing something far more thoroughly than most people do.
posted by salvia at 11:15 AM on April 13, 2018


Going back to basics, has anyone ever told Tracy that there is a problem with her missing deadlines? Different workplaces have different approaches to deadlines, so if she's chronically behind but nobody has ever directly told her that this is a problem, she may be operating under the assumption that it's ok to miss them.
posted by radioamy at 11:31 AM on April 13, 2018 [2 favorites]


Fake dates. It's the only way.
posted by libraryhead at 12:22 PM on April 13, 2018 [2 favorites]


In 10 years of supervising people who had no interest in being actual team players the only thing that kept me from filling my sleeves with stones and walking into the sea was:

- lying about deadlines, which stops working after 3-4 times
- doing most of the work myself on 3h of sleep the day of deadline
- doing most of the work myself from the get go

Absolutely none of the other frankly excellent managerial suggestions mentioned above ever worked for me. Flat out offering bribes as incentives did nothing. Even doing the work myself and sending it to them and saying "make enough changes to make it look like you did this" did fucking nothing.
posted by poffin boffin at 2:32 PM on April 13, 2018 [1 favorite]


Tracy is smart and competent. If she's missing deadlines because she has harder work that takes longer, then she is not the issue. The person setting the deadlines needs to account for this and allow her a longer timeframe, instead of throwing it back on her and making it her problem when it sounds like it can't possibly be achieved in the allotted time. In short, management needs to sort their shit out.
posted by Jubey at 3:06 PM on April 13, 2018 [3 favorites]


Response by poster: Thanks for all the answers so far. Just to clarify: the deadlines are not only set in stone, but known before the project is assigned and they correspond to the court calendar. So fake deadlines aren’t possible (although I know from being behind the scenes for a few years that the deadlines we have are a bit soft, with a day or so of wiggle room). And it is definitely a staffing problem; they’re in the process of hiring three new people. It will eventually get better, but it will take a while to get the new people up to speed.
posted by holborne at 4:07 PM on April 13, 2018


Response by poster: Oh, sorry, one more thing: there are a few people on staff who have work as difficult as hers, and those people are generally timely. And I used to do what she’s doing; I had some problems with timeliness, but they weren’t as severe as hers. So although it’s not entirely her fault, it’s most definitely possible for her to not be turning her work in so late.
posted by holborne at 4:11 PM on April 13, 2018


Until recently in my own job, I was turning in work according to my personal standard of quality and I was killing myself to do it. I wasn't late, but I was working a ton of hours without being paid extra for it and it was making me grumpy as hell.

Recently, I've allowed the quality of my work to drop by a notch and a half or so, and I feel much better about the amount of my life that my job is eating up. Absolutely nobody has said a peep about it, if indeed they've even noticed.

Possibly the best thing you can do for Tracy is help her identify areas where she's expending effort in ways that nobody will care about. Help her find the places where she can cut corners and have it not matter, the places where she's killing herself for things that nobody will ever notice or reward her for.

Help her see what "good enough" work looks like, where "good enough" means not the bare minimum, but the point beyond which only she will ever know the difference. Help her see that a good enough product turned in on time is better than a perfect product turned in late.
posted by Anticipation Of A New Lover's Arrival, The at 8:18 PM on April 13, 2018 [4 favorites]


I have so many questions!

If Tracy got behind by 15 days at one point, has there been an opportunity for her to catch up?

Does she take on a lot of the emotional labour at the office? What is she doing instead of the project-driven work? Does she carry more of the client-facing load?

What’s her mental health and health like?

Why haven’t there been any consequences for the lateness? What could be some or rather could there be early finishing bonuses?

Has Tracy had a vacation lately? Vacations can be a great reset point.
posted by warriorqueen at 9:11 PM on April 13, 2018


> Thanks for all the answers so far. Just to clarify: the deadlines are not only set in stone, but known before the project is assigned and they correspond to the court calendar. So fake deadlines aren’t possible

I still think you can set fake deadlines. "Hey Tracy, Bob told me he wants your piece by May 15 instead."

Or, you break it up into smaller deadlines. "Hey, can you sent me the first half of your draft by April 30? I want to make sure we're on track, so please have at least half of it done by then." If these written reporters and divided into sections, then say you need certain sections done by an internal deadline.

Or do regular check-ins to monitor her progress. When I know I need to talk to my boss, I make sure I have some shit done, whether it's formally expected or not.
posted by AppleTurnover at 1:09 AM on April 14, 2018 [1 favorite]


You can't set fake deadlines, but you can set interim deadlines. My department does this around a recurring meeting – the deadline to submit the report to the committee chair is five days before the meeting, but that's mostly irrelevant to us because we're actually working to an earlier deadline of reviewing it with my manager ten days before the meeting.
posted by Lexica at 10:22 AM on April 14, 2018


The comment from Anticipation Of A New Lover's Arrival, The is really good. It will be hard for you to point out where exactly those areas are, but you can help her prioritize timeliness over that last 10 percent. And via frequent check-ins you can hear her say that next she's going to do XYZ+10% and tell her that doing XYZ is good enough or that the section looks good enough already.
posted by salvia at 1:44 PM on April 14, 2018


Response by poster: Don’t want to threadsit, but to answer warriorqueen’s questions:

If Tracy got behind by 15 days at one point, has there been an opportunity for her to catch up?

They have given her opportunities to catch up; she catches up and then the problem recurs.

Does she take on a lot of the emotional labour at the office? What is she doing instead of the project-driven work? Does she carry more of the client-facing load?

No to all these questions (she’s not doing anything other than the project-driven work).

What’s her mental health and health like?
To the best of my knowledge, these are both fine. We do have a bunch of people reassigned to lighter duties because of health problems, so she knows that would be an option.

Why haven’t there been any consequences for the lateness? What could be some or rather could there be early finishing bonuses?

There have been consequences: the reason she’s still on the level of supervision she’s on is that she’s always late. It’s considered a bit embarrassing to be supervised this closely when you’re a senior as she is. Bonuses are not an option.

Has Tracy had a vacation lately? Vacations can be a great reset point.

I’m not sure when she last had a vacation but it was probably several months ago.
posted by holborne at 6:22 PM on April 14, 2018


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