how can I make sure my team meets deadlines?

by Alison Green on March 1, 2016

A reader writes:

If you’re a (much younger millennial) project manager contractor managing non-contractor long-term (much older) folks, and they say they’ll get something done but the deadline’s in less than 48 hours and they have nothing sent to you yet (after an earlier reminder), how do you remind them and get things done without:

1) panicking
2) nagging them
3) getting neurotic?

This is my first time managing folks on a large team project on a high scale effort, and while I’m excited (and happy that AAM helped me get to this point, even), I’m also silently terrified that I’ll miss even one deadline and my head’ll be on the chopping block so to speak. Another person used to be on the team but missed some deadline(s) and was sacked awhile ago.

I find myself sending frequent project updates to remote employees, asking for updates, and doing lots of collaboration. Another thing that worked was finding a snippet of a presentation, paraphrasing it, and getting it approved by its writer–ie. giving them the info, and they edit/add/or ok it. Is there anything additional I can do?

Well, do you have any reason to think they’re likely to miss the deadline unless you keep following up?

If these are responsible people with a track record of performing well, give them the space to do their jobs. They know the deadline, and you’ve already reminded them once. You should be able to trust people to meet deadlines unless they’ve already given you reason not to. (And if they have given you reason not to trust them to meet their commitments, then that’s the problem, and the one you need to address.)

The fact that the deadline is in less than 48 hours and they haven’t sent anything to you yet just means that it’s not the deadline yet. They are assuming that the deadline you gave them is the real one. If you secretly are panicking when you don’t get anything earlier, that’s not fair to them. If you truly need it earlier, or if you need some kind of check-in from them earlier, tell them that you’re first assigning the work. Don’t tell them the deadline is Wednesday but then get antsy when you haven’t heard anything by Monday.

Otherwise you will annoy the crap out of them, make them feel you don’t trust them to do their jobs, and make them wonder if all your deadlines really have secret deadlines that they’re supposed to figure out on their own.

Now, that’s not to say that you should just delegate work and then disappear and just hope that when it comes back to you in a month, it looks the way you wanted it to. Particularly on on large or important projects, you should stay involved along the way — to spot problems, give input, and course-correct if needed. But you want to build that into your project plan from the beginning so that everyone is clear on what that will look like and how it will happen. For example, you might ask for an initial outline or a piece of a section of a written product by X date, or for a progress report by Y date, or to look at a small sample of the whole by Z date. That’s smart to do because it will help you know early whether a project is on track and allow you to make any needed adjustments before tons of work has been done, and it will cut down on the angst you’re now feeling.

Build those check-ins into your schedule from the start and then you shouldn’t be panicking and wondering what’s going on with the work, because you’ll have a clear system to make sure you stay appropriately in the loop. (Of course, don’t go overboard on that either — calibrate the level of your engagement based on the skill and track record of the people on your team, and the difficulty/newness/importance of the project.) With an experienced staff member who you know does good work, you might just need a single interim check-in on a month-long project. With a newer staff member or one whose work you’re not confident in, or on a high-profile, high-stakes project, you might schedule more reviews/check-in’s along the way.

It’s too late for that on this project, of course, because you’re 48 hours away from the deadline. You’ve already issued one reminder, so at this point, you probably need to just sit tight and give people room to do their jobs.  At most — at absolute most, and only if you do have some cause for concern — you can say to people, “Is everything looking in good shape to meet our Wednesday deadline, or would it be helpful to touch base before then?”

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  1. Dovahkiin*

    I have really struggled with getting coworkers and contractors to make deadlines.

    So I give myself some wiggle room and make sure the deadline I give is a couple days before I actually need it. Just don’t let anyone know that the deadlines you give out have some wiggle room.

    1. Former Retail Manager*

      Yes, this! Is it possible to issue an artificial deadline to your team to ensure plenty of wiggle room? If you can without tipping them off, I would. All of the managers I currently work with do this to account for the couple of individuals who wait until the last minute to submit everything. Everyone knows the deadlines are artificial but respects them nonetheless.

      1. TootsNYC*

        It’s not even an artificial deadline.

        It’s “This is the day *I* need it, so I can have time to be sure it’s all here, and review it, before I pass it off to meet *their* deadline.”

        1. fposte*

          Yup. It was hard for me to realize that a deadline I chose was still a real deadline. (It didn’t really occur to me that deadlines were manmade, to be honest.)

    2. Ama*

      Yes, this is essential. I deal regularly with my org’s expert volunteer group, which means I have no real authority and also need to tread lightly with reminders (some of them interpret reminders as an implication that they won’t do it, and some just object to any time they are getting a high volume of emails from us). So instead of sending “hey it’s a week before deadline” reminders, I set the deadline for (at least) a week before, and then I can follow up with anyone who misses that deadline with “hey, just following up because you didn’t turn in your thing.”

      A couple people occasionally notice that I’m asking for material by the end of February that they know I’m not using until the middle of March (or later), but reminding them that staff needs time to compile and prep the responses usually covers their objections.

  2. Cat*

    I am wondering if the deadline is an external deadline and the OP had, reasonably, wanted it in advance of that to review. Which raises the question of whether there was a well-defined internal deadline, which can help.

    1. afiendishthingy*

      Sounds like that might be the case. There’s also a possibility that the OP and the contractors just have different outlooks on deadlines – some people make a habit of getting things done well before the deadline, while others take the more literal “Don’t tell me it’s due on Wednesday and then ask for it on Monday” viewpoint. (I fall firmly into the latter group.) So yes, set the deadline for when you actually want the work – don’t make them guess.

      1. MsChandandlerBong*

        I fall into the same camp. I am self-employed, so I juggle a lot of clients and have deadlines all over the place. I schedule my work based on when it’s due, how long it will take, and how much wiggle room I have. If you come to me on Monday and ask to see something due Thursday, there’s a good chance I haven’t even started it yet.

      2. BananaPants*

        My manager likes to say things are due on Wednesday and then pester me about it via email three or four times a day on Monday and Tuesday. Dude, you need to trust that if I hit roadblocks I will come to you and we can work out next steps, but until then leave me alone and let me do my job. If you really wanted it Monday so you can prep for a Thursday meeting, then SAY SO rather than giving me a Wednesday deadline and bothering me for two days straight to see if it’s done yet.

        (can you tell this makes me nuts?)

        1. OhNo*

          I mean, I can kind of tell where people like that are coming from. If your boss needs the info to prep for their meeting on Thursday, but the only time they have available to prep is on Monday and you still haven’t finished, I can see how their minds would switch over to “is it done yet? how about now? how about now?” mode. But that just means they’re really bad at planning their own work, and nothing you’re doing.

          (I also have a manager that likes to do this, and while I understand that she has her own deadlines to hit that depend on me to hit mine, I wish she would plan better so she’s not changing all my deadlines at the last minute to fit her workflow, and thereby throwing mine out the window.)

    2. Sadsack*

      I wonder about that, too. When I need input from others on my projects, I tell them the date I need to receive their work so I can have a reasonable amount of time to review it and address any issues or ask questions before the actual deadline. I often tell them exactly that, too.

    3. INTP*

      I thought this too. OP, it’s perfectly reasonable to request that your reports turn in work a few hours or days before your deadline, depending on the scale of the project, so that there is some wiggle room for last minute emergencies on their part and checking everything out on yours. I work in a deadline-heavy business with PMs, and I take for granted that they’re doing this. It doesn’t bother me, but them giving me one deadline and then asking me to turn it around early when I’ve carefully balanced out my schedule to take on a maximum of work while meeting all deadlines does.

    4. AnotherHRPro*

      This is what I came to say. If the OP isn’t establishing deadlines that gives her time to review the final product and edit it if needed then she needs to do this. I work with highly autonomous professionals but if I have a deadline to send something out, I ask to receive the work from my team by at least 1-2 days prior.

  3. AFT123*

    I love Alison’s advice. Please take to heart that not everybody works the same way that you might, and that doesn’t make them more or less likely to be successful. Some people will chunk out a hour each day for a few months for a project, some people prefer to arrange their schedule to chunk out larger portions over just a few weeks, etc. I think this can really be a struggle because a manager can have perfectly legitimate reasons for preferring reports to work in their “style”, but it may backfire and become more work for the employee to change their whole style vs. letting them do things the way that they work best (as long as they consistently churn out quality material on their deadlines).

    An example of this – a former manager of mine mandated that we use an electronic “tasks” system instead of or in addition to our own preferred method of keeping organized. I live and die by OneNote, Outlook, and Excel, and I’m VERY electronically organized, never missing dates or deadlines. My system worked very well for me, and many of my colleagues had also formed their own very effective systems. We were a very high performing team. When manager decided to mandate logging tasks, it slowed many of us down and became an administrative nightmare, and we started missing deadlines. We all ended up keeping our own systems as well as logging tasks so we didn’t get fired for not using tasks. I’m still not sure why manager insisted on tasks, or why she didn’t choose to only mandate it for people who were missing deadlines. She had assumed because her system worked well for her, that it was the best and only way to be successful.

    Long story short, unless there is a really good reason for it, try and let your high performing folks work how they’ve identified they work most effectively, and let them succeed or fail before intervening. Just be clear with your deadline expectations, and if you need or want things earlier, just set your deadline earlier.

    1. MsChandandlerBong*

      Good point. It’s difficult to switch from your own system to someone else’s. So much so that you may even end up being *less* efficient under the new system. I’ve mentioned here before that I once had a boss who would get mad if I typed “Let me know” instead of “LMK” when we were chatting online. He was obsessed with efficiency. However, typing LMK actually made me slower because I had to stop and think about doing it.

      1. Kate M*

        The thing is, he probably spent more time talking to you about using LMK than the whole amount of time typing LMK instead of “let me know” would have saved you in your entire career.

        1. Mallory Janis Ian*

          Some acronyms are like second nature to me (MIL, FIL, WTF, etc.), but some just will not stick (ITA, IANAL*, WFH) and I have to think about them every single time, no matter how long I’ve known about them. I think LMK would be one of the doesn’t-stick ones for me. It doesn’t look like anything that should be stored in my easily-retrievable memory.

          *I Am Now a Llama is what I always think.

          1. Kelly L.*

            I can’t seem to pick up “WRT,” especially if it’s in lowercase like wrt. Trips up my eye every time.

        2. MsChandandlerBong*

          Pretty much. I type 120 WPM, so it’s not like typing a few extra letters really slows me down!

    2. TL -*

      I do a lot better work when I work in chunks rather than spread out over a longer period of time – not pushing right up against the deadline, but I do like to get in “the zone” and stay there for a while. So doing an hour a week for three weeks is not as good for me as doing three hours in a row.

  4. Amtelope*

    I see two issues:

    1) If you want check-ins, or partial deliveries at various milestones (a third of the chocolate teapots at the end of week 1, a third at the end of week 2, and the rest at the end of week 3), you have to tell people that. They can’t guess.

    2) Your internal deadline shouldn’t be the date you have to submit the work to your boss or your client. Set an earlier deadline to give yourself time to chase down any missing work or correct any problems you identify.

    Otherwise, yeah, people are likely to assume that the deadline you set is when you need them to deliver, and if they’re busy people who are expected to set their own priorities for their work, they’re not going to prioritize delivering things before they’re due.

  5. Artemesia*

    A rookie mistake in managing is not realizing that the internal and external deadlines are different because the manager needs to review and edit and fine tune work before it goes out. When I managed work that involved client presentations, I would set a dress rehearsal session of the presentation several days in advance. People tend to be responsible to deadlines when it means they will make a fool of themselves if the work is not in shape and it gave us a chance to tweak the materials which was ALWAYS necessary. Before that there would be milestones built into the timeline e.g. the presentation stack would be due and sent around the team for review well before the run through. Early there would be a deadline for an outline of the content.

    For grant proposals, we would schedule milestones for various pieces of the project and a team sit down to review the complete proposal a couple of days before the internal review outside the department (grand proposals involved a lot of sign offs and so the due date at a corporation or agency was not the due date for us — we needed it to the internal bureaucracy well in advance of that.)

    If you make a set of milestone deadline clear on the front end and build a bit of performance in when appropriate it makes them easier to manage without additional nagging.

    1. KH*

      Very much in agreement with Artemesia.

      When I have a deadline for presentation to leadership, I set my team a deadline the day before if possible – and at least 4-5 hours prior. If it’s a longer term project than a couple of days, I set a deadline for a “check in” about 2/3 of the way through the timeline.

      That’s properly managing your resources. Never let their deadline be your absolute deadline as well.

  6. BRR*

    This would be difficult for me to do but you have to remember that a deadline is a deadline. If you need (or want but in that case you need to be realistic) something completed sooner, than the deadline should be moved. Unless there is an issue of not completing things on time, then I think it would be helpful to do the check ins.

    1. Doriana Gray*

      It would be difficult for me, too – I’m an Anxious Annie by nature. If I sent out a reminder about a deadline and got no response back, I’d quickly slip into panic mode.

      I feel for you, OP.

      1. neverjaunty*

        But rather than a reminder, wouldn’t it be better to simply ask for a status update? “Don’t forget the deadline is Friday” doesn’t really merit a response. “Since the deadline is Friday, I wanted to make sure everything is on track, and to see if you needed anything from me on this” does.

        It’s not fair to expect your employees to play Guess How to Fix Anxious Boss’s Anxiety.

        1. Judy*

          In the software world, even if our main deadline is March 1, either the project manager or the software engineer should have broken down the features required, and each would have a delivery date. This is project planning, and most companies want the project tasks planned so that each task takes no more than a week.

          I’d expect the same from writers if this project is their only project and takes more than 2-3 weeks, there should be a plan for Bob to work on the chapter on the history of spouts first, and ready for review by noon on Feb 5, and Jane to work on the history of lids first, that chapter would be longer, so the first draft is due Feb 10. If you’ve not estimated and planned the project, how will you know it will be done?

        2. Doriana Gray*

          Oh, I agree, neverjaunty, which is why a) I’m not a manager, b) will never be a manager, and c) never told OP her Anxious Annie ways were okay. I just get where she’s coming from.

          And from my experience in non-managerial leadership situations, status update requests can still yield no answer from the people/person you’ve addressed. Drives me nuts.

          1. OhNo*

            I think it’s all in the way you phrase the status update request. Even the phrasing from neverjaunty would not yield much information from someone like me. If there’s specific information that the manager wants, they’ve got to actually ask for it.

            Do they really just want to know if I need anything from them? Or, do they actually want to know exactly where I am in the project, what’s done or not done, and when I expect to finish by? Because that’s a laundry list of questions I would never think to answer unless they were explicitly asked.

            1. Doriana Gray*

              Very good point. It could be my questions weren’t clear to the recipient and that’s why the response rate was nil.

            2. neverjaunty*

              Definitely. But if it’s a situation where the manager just wants to be sure nothing is getting gummed up, ‘checking in, do you need anything’ is fine. Agree completely that if the manager wants to hear anything more than ‘no, thanks, I got this’, she needs to be specific.

          2. KH*

            I think a lot of people will send an email saying “Just checking to see that we are still all on track on the updated teapot report.” and then freak out when there’s no response. But that’s not necessarily an email I’d respond to – figuring that if I wasn’t in the weeds, she didn’t need to hear about it.

            People need to REQUEST ACTION when they send out emails if they want a response.

            “Can everyone send me a quick one-sentence update on where they are with the teapot report this afternoon?”

            “Can everyone please check in and tell me if you’re on track for the 2p.m. deadline.”

            “I would like an update from everyone on the team before noon today so we’re prepared for the 2p.m. deadline.”

            Too many people assume that a “just checking in” will elicit a response – and for many people it won’t. Be specific in what you want.

  7. Snarkus Aurelius*

    A couple of jobs ago, I was responsible for a monthly publication, which means there were a few deadlines throughout the process.  One of those deadlines was for my boss to have content by noon the second Friday of every month.  In my performance review, she told me to avoid “sending things at 11:50 AM on Friday” and “send it a bit earlier” so as not to look like I did something last minute.

    I can’t even…what?

    Do not be my ex-boss, OP.

    1. Allison*

      It reminds me of the pieces of flair thing from Office Space. Don’t tell people the minimum is 15 and then expect everyone to have at least 25, and don’t tell someone the deadline is noon but expect everyone to submit first thing in the morning.

      1. One of the Sarahs*

        Or the opposite thing, where managers ask you to prepare 3 ideas to a meeting, but there’ll only be time to talk about one….

  8. AnonEMoose*

    Please, please don’t do the “secret deadlines” thing. And definitely don’t do the equivalent of standing over someone’s shoulder, repeatedly asking “Is it done yet? Is it done yet? Done yet? How about now?” Because what it would inspire from me is a strong desire to punch you in the face. Not that I would, but I’d want to.

    I can completely understand feeling antsy about this, and I love Alison’s advice. But if they haven’t given you reason to think they’ll miss the deadline, trust them to do their jobs. In my volunteer life, I’ve seen the assumption in both directions that just because I don’t personally see things happening, nothing is happening – and that’s usually not the case. But that can be a good catalyst for a conversation about wanting more visibility to how things are progressing, what that might look like, and what’s feasible for the team to provide without interfering with their ability to get the work done.

    1. Snarkus Aurelius*

      Although I didn’t know it at the time, one of my bosses at my first job suffered from severe anxiety.  Another VP had given me a project, that my boss had nothing to do with, that was a big deal. My boss literally stood over my shoulder to simultaneously remind me that I was on deadline AND “supervise” me doing some minor edits.  Variations of “This has to be done in the next hour!” and “Did you get remove that comma from the bottom of page six?” all while she’s standing next to me behind my desk, watching me make the edits.

      This was also a woman who wouldn’t let me do anything beyond admin tasks and would get visibly anxious if she thought I was doing more but would openly bemoan that no young people wanted to get involved in our organization’s mission.

  9. KT*

    Yeah, if you told me I had until Friday to get something done, then emailed me Wednesday asking for an update, I would be confused/annoyed. If you needed a draft Wednesday, you should have told me that, otherwise my update will be “I’ll have it to you Friday like we agreed”.

    If they’ve given you reason to believe they won’t deliver on deadline, that’s a much bigger issue.

    1. Shell*

      I think it’s okay to ask for one update a little before a deadline, in the “Friday’s the deadline, how’s everything going? All good? Great” vein. It can still be a little obnoxious if the employees are all well-seasoned veterans who are quite capable of managing their own schedules, but it might be helpful for newer employees and/or if there are a lot of moving parts to this project. If it’s delivered in an off-the-cuff manner, I don’t think even most veterans would mind too much (it may be annoying, but not outrageously so).

      But the whole “it’s due Friday why haven’t you submitted it before Wednesday?” is excessive, unless Friday is an external deadline and hence the internal deadline should be sooner. And if that was the case, that should’ve been communicated up front.

    2. Persephone Mulberry*

      I’m okay with a request for an update. In this case, though, the OP “sent a reminder” and it sounds like is now a little panicky because no one acknowledged the reminder. To me, a reminder and a request for update are two different things. If you say “Don’t forget, the deadline’s Friday” I’m going to think “yep, sure is” and keep plugging away. If you say “Don’t forget, the deadline’s Friday. Please confirm that your piece is on track,” then you’ll get a “yep, all good here!”

      1. AnotherAlison*

        A lot of language in the OP’s letter made me think she is trying to do most of her PM tasks by email. (I could be reading too much into it.) If that is the case, she needs to think about doing some walk-bys if her contractors are in the same office. Spending 2 minutes stopping at someone’s desk and seeing how things are going is a lot better way to get a feel for how things are going then asking for an email update. Much easier to really get a feel for how people are doing with their tasks face-to-face.

        FWIW, I’m not sure I agree with Alison that silence can be interpreted as being on track. I guess I work with a lot of people who miss their deadlines!

  10. Allison*

    I do understand the unspoken rule that you should submit things before they’re due, because it makes you look like you’re on top of things and/or going above and beyond, BUT I don’t like it when people communicate one expectation, hold a different expectation in their head, and then get mad when people don’t meet the silent expectation. If you say a deadline is Wednesday, it’s great if people submit before that, but you can’t get mad at people who actually wait until Wednesday. If you want something completed and submitted by Monday, say that.

    If these people haven’t earned your trust yet (but haven’t really proven themselves untrustworthy either) it can be easy to borrow worry and constantly think “what if??” But try not to. If they don’t make the deadline, then you can get mad and find ways to prevent it from happening in the future.

  11. CaliCali*

    I’m a older-end millennial doing a type of project management, usually working with teams of all ages. What’s worked for me:

    1) Status meetings to check on progress of deliverables. I don’t demand things are done before the deadline, but I ask how things are progressing, if they anticipate any issues with meeting the deadline (in a non-judgmental, collaborative way), and if there’s anything I can do to expedite progress, if required. This gives me both reassurance that things are on track and gives the team room to voice any problems before they become PROBLEMS.
    2) Sandbag the schedule (as others have mentioned). Always give yourself a few hours/days/weeks of margin, dependent on the length of your projects. It’s not that you assume people won’t meet deadlines; it’s giving breathing room in case something comes up (someone gets pulled off your project, someone has an unexpected absence, someone quits). Don’t TELL people you’re doing this — not that you have to lie, but just tell them “I need by X date.”
    3) Emphasize the collaborative approach. You all have a common goal of getting things completed on time. Make sure they know that deadlines are focused on meeting that common goal.

    1. Washington*

      re your #2 – I would argue that planning for unexpected things to occur (like people being human) isn’t really sandbagging, it’s being a pragmatic project manager. Sandbagging would be knowing that a project would realistically take 4 weeks to complete and planning it for 6 months.

      1. AnotherHRPro*

        Actually, as a project manager, part of the job is reviewing the deliverable so it would be expected that you have a deadline for when it is due to you to give you sufficient time to review and modify as needed.

      2. CaliCali*

        True, I used the word too loosely :) My type of projects tend to take about 1.5-2 months (with hard deadlines), so I’ll work backwards, incorporate time for reviews and changes, but also keep an extra day or two in there for reserve when shit (inevitably) happens. It also keeps the team more relaxed, in that steady check-ins and staggered intermediary deadlines keep everyone progressing and aware of what’s happening. We all know the real “final” deadline but I communicate all the things I mentioned above, and sometimes people take advantage and push it, but most of the time, people want to make sure I have time to do my work at the end.

        1. Cafe au Lait*

          Yes! This is what I do! I handle a pretty time sensitive, highly detailed project twice a year. While there’s no firm “end” date, there is an expectation that most of the project will be completed by the first day of the semester. What I do is I look at which day the first day of the semester falls on (Tuesday or Wednesday), and if I’ll be in before that day. (Due to break scheduling, I might not work at all the day before the semester starts). I also take a look around at what’s happening on campus. If we’re heading into Fall, I know that it’ll be steadily busy the week before classes, but church quiet for three weeks before that. Heading into winter it’s a mad rush with final exams and preparing for Winter courses.

          Fall project deadline is two weeks before the start of school. I know I’ll get requests for assistance after that deadline, but most faculty will have contacted me. I also have some wiggle room.

          Winter project deadline is a month before the start of school. I have less wiggle room, plus work is consistently busy.

  12. Biglaw Stormtrooper*

    What do you do when you have urgent deadlines to meet but you also have indications that the people on your team are not always doing what they need to do? For example, in the legal context, when there is a filing a bunch of urgent last-minute tasks can come up, and they are all important. I’ve run into issues where I assign work to people, things slip through the cracks because of the sheer amount of work there is to do, and then people get annoyed because I then start looking over their shoulders because I worry that things aren’t getting done.

    (In an ideal world, there would be more people on hand when things get crazy enough that this becomes an issue, but sometimes that just isn’t an option.)

    1. FiveWheels*

      Welcome to my world! Is all law like this? Somewhere I imagine a law office in which everyone is calm and happy most of the time, papers are filed and letters drafted days or weeks in advance, and everyone bills filthy amounts of moolah every month despite never having to work past 5.

      Hmm.

      Nah, I’d get bored.

    2. Cat*

      I absolutely look over people’s shoulders in that situation. Well, I make a point of not literally hovering except in extreme situations, but regular check-ins about the various tasks to make sure they’re getting juggled appropriately, I do and I don’t see any way of avoiding. Because you’re right – things do fall through the cracks when they’re that crazy. Some people will just get annoyed at that period, which is a problem and I tend to avoid using them for those projects but, in general, I’ve found people respond well when it’s clear that you’re trying to keep everyone on track, including more senior people, and not just watching them in particular.

    3. neverjaunty*

      Short-term, firm internal deadlines. “The Motion to Strike Dumb Facts has to go out for service Friday at noon, therefore I need your draft no later than Thursday at 9 so I can review it.” Then you have a built-in check in: if you don’t get the draft by Thursday at 9, you have every reason to ask where the hell it is.

      Long-term, it’s not sustainable to run a legal practice on triage. Things ARE going to slip through the cracks when they are asked to do fifteen equally important things and there’s only enough time to do six of them. And if it just isn’t an option to have enough people to do the work, it’s not fair of you to punish your employees for the firm’s staffing decisions. That’s a no-win situation and it’s just going to demotivate people and have them move on – which then adds to your staffing issues.

      1. Cat*

        This is completely true for things you control. But there’s a limit to the deadlines you can give clients, especially large bureaucratic clients with their own internal pressures and processes, and sometimes that means it’s an all-out crazy push with things coming in from various corners through the last minute through no fault of your own. And throwing more bodies at it isn’t necessarily going to mitigate the nuttiness you have to keep track of.

        Of course, being transparent about when that is happening with your staff so it’s clear you’re not dumping stuff on them at the last minute unnecessarily (and also being clear that you’re trying to stand up for their needs with the clients too) also limits the negative reaction.

        1. neverjaunty*

          Sure, but if the issue is that there are too many balls and not enough jugglers, then balls are going to get dropped, period, and all you can do is triage to make sure they’re balls that can get safely picked up later. It’s not fair to the employees to say “we know there’s too much work for you to possibly get done, but you better do it anyway”.

          1. Biglaw Stormtrooper*

            Oh, I completely agree. I think a lot of it is what Cat mentioned above, that everything goes to hell when the client is slow. We can set a calendar with a cushion built in, we can remind them, but at the end of the day some of it is fundamentally out of the lawyers’ control and sometimes asking for a deadline extension isn’t a viable plan.

            Also, unfortunately, I am not in charge of staffing. The best I can do is raise the issue when it comes up, as early as I spot it (which I have) and do my best to triage.

            1. Cat*

              Yeah and we’re actually, if anything, over staffed. There comes a point when it doesn’t matter because you can’t split a task among any more people and expect fewer balls to be dropped. So I think to a certain extent, it’s the nature of the biz and the important thing is making sure people understand that and that you treat them respectfully when it’s crunch time.

      2. Anonsie*

        Long-term, it’s not sustainable to run a legal practice on triage. Things ARE going to slip through the cracks when they are asked to do fifteen equally important things and there’s only enough time to do six of them. And if it just isn’t an option to have enough people to do the work, it’s not fair of you to punish your employees for the firm’s staffing decisions. That’s a no-win situation and it’s just going to demotivate people and have them move on – which then adds to your staffing issues.

        Thiiiiis.

        This was a huge problem in a previous job of mine. It’s one thing to acknowledge that this is a quagmire for the staff and try to keep a close eye to collaboratively make sure the right things are being taken care of, but it’s entirely another to be scrutinizing a team punitively because they are facing an impossible/extremely challenging and not ideal situation. Nothing is going to demotivate and lower productivity like busting your hump continuously against an endless stream of challenges only to receive constant disappointment and increasingly tense micromanagement from your superiors.

  13. Lily in NYC*

    I have the opposite problem – I am not a manager so I have zero power to get people to stick to deadlines. And because we are quasi-governmental, it’s so easy for people to put the blame on others – everyone blames an outside budget agency. Which is total BS – I can see their trackers, which clearly show that the item I need is sitting ignored on someone’s desk. Since I have no power to get these people to actually do their jobs, I had to create an internal motto – “If they don’t care, I don’t care”. It’s so cynical, but it saves me from lying awake at 4am in the morning fretting about it.

    1. Lily Rowan*

      In my work, “managing without authority” is a really critical skill — especially if you’re going to be in trouble if you don’t get the stuff from the other people.

      1. Lily in NYC*

        It’s not like that here! It’s extremely hierarchical and a “know your place” kind of office. I would get in more trouble for trying to “manage without authority” than for being late on a deadline (it’s a quasi-governmental office which probably explains a lot). Taking initiative is frowned upon. Hence my new motto.

        1. TG*

          That’s such a frustrating situation for someone who cares about work getting done. I feel your pain and have had to modify my expectations for some people/offices like you have

  14. neverjaunty*

    OP, I see a lot of things in your post that aren’t the actual problem (making sure deadlines are met) but are a lot of side issues that are fueling your anxiety: you’re a millenial supervising older workers, this is your first serious management position, people have gotten fired for screwing up, etc. Please try and set those aside; the important thing is that you have actual authority and tools to make sure deadlines are handled. The other stuff is a distraction that will make you needlessly anxious.

    As others have said, it is REALLY demoralizing to have a boss who, in essence, is saying “I need you to reassure me that everything is OK because I’m anxious.” Boss-hand-holding should NOT be a part of anyone’s job description.

    1. AnotherHRPro*

      I agree, but it is ok for a boss to express if they are concerned about a project and why. Instead of just continuously asking where everyone is on the project, I would let them know that I am concerned about XYZ (maybe the tight turnaround time) and that you would like to get more frequent updates. Giving context is always helpful.

    2. katamia*

      As others have said, it is REALLY demoralizing to have a boss who, in essence, is saying “I need you to reassure me that everything is OK because I’m anxious.”

      This. I grew up with a relative who did this, and now I have basically no patience for it in the workplace. It’s okay to occasionally ask for updates (as long as it’s understood that people might be working and not checking their email constantly, and therefore the update might not come right away) and give concrete feedback and explanations when necessary, but, OP, you need to let your workers work instead of trying to get them to manage your emotions.

      1. TootsNYC*

        Interesting!

        I actually suggested that–partly because I think that flat-out openly acknowledging it defuses it.

        And also because I envisioned it happening ONCE. Not over and over.

  15. Lady Kelvin*

    If I were in your shoes I would have this basic conversation when starting the project: “So I need to have the final project to the client on X day at Y time, therefore I want your part of the work in its final form to me on X day Y time, but I’d like a rough draft or your working plan and outline by X day/Y time.” That way you know that 1, people are thinking about how much time they are going to need to complete the task, and 2, you have plenty of time to catch problems or mistakes before the final final deadline. Then as you become comfortable with how your team works and they become comfortable with how you manage, you can change the timing of them as necessary.

  16. INTP*

    If the OP is new to the workforce, they might not yet be aware of workplace norms on deadlines versus school norms.

    When you’re in school, teachers and professors like to say that responsibility is starting things as early as possible to finish it all well before the deadline. If you manage your time to just meet all your deadlines, you’re being lazy. God forbid you have a last-minute computer issue and email your paper at 12:03 AM instead of 11:59 – that is the absolute pinnacle of being an irresponsible procrastinating horrible student.

    At work, though, people who work on multiple projects juggling multiple deadlines are expected to do as much work as possible without missing deadlines, not finish everything early – turning in everything early means you’re probably doing a lot less work than you actually have time for and you aren’t helping the team out on last-minute tasks. It’s totally normal to schedule so that you are wrapping things up right before the deadline. It’s just much different from school because the total volume of work you can complete (with acceptable quality and timeliness) is generally the priority. Generally the internal deadlines are set with some wiggle room so that if someone finishes their part 3 minutes late or revisions are necessary, it still gets to the client on time.

    The key here is to, within reason, give your team deadlines that you would be comfortable with getting the work right at that deadline. No one will be upset to find out that you padded the deadline a bit, but you will drive them nuts with constant checkins or expecting things early. It’s reasonable to ask for occasional updates on larger scale projects so that you can make sure that they’re on track to be finished and the employee understands the task, but constantly asking for updates before the project even reasonably needs to be started to meet the deadline give a clear vibe of “I don’t trust you to finish this and I want you to do it before the deadline I gave you” and will alienate your employees.

    1. Allison*

      In college you did have one deadline, usually, but in high school we usually had draft deadlines so the teachers could give us feedback and guidance, so it wouldn’t be totally foreign to ask the same of your employees if you really felt it was necessary.

      1. Ad Astra*

        Yeah, the only people who actually turned things in more than a few hours early were athletes and other students who missed a lot of class for some pre-scheduled reason. If teachers wanted us to make changes based on their feedback, they’d throw in another internal deadline. More often, though, they wanted us to apply that feedback to future papers because they didn’t have time to look at every paper twice. After all, both students and teachers are juggling multiple projects with multiple deadlines — just like the real world.

    2. Callie*

      When I first started my grad student-turned-adjunct gig, I wanted to be lenient about deadlines. I’d have some very conscientious students FREAK OUT if they had to turn in an assignment 5 minutes late because Life Happened, and I wanted to eliminate that stress. So last term I simply said, “I’m not enforcing a late penalty. Get it done and don’t panic if you’re five minutes late.” Then I had the whole class turning a pile of work in the VERY LAST DAY of term and I simply didn’t have time to grade it.

      So, this term I’m being a hardass. My rule is:

      1. Submit your work on time. If you don’t, there is a 30% late penalty, whether it’s 4 minutes or 4 days late.
      2. Work turned in over one week late is an automatic zero.
      3. If you turn in your work on time but you get a low grade, you have one opportunity to revise and resubmit that assignment for full credit if you revise according to my suggestions. But if you turn in your work late, you get what you get and you don’t get a revision attempt.

      It’s amazing how many students are suddenly finding time to get their work in on time, and I don’t have a pile of work waiting to be graded at the end of term.

      I tried giving leeway and they ran all over me and took advantage.

      1. LQ*

        I always liked the “everybody gets one” kind of angle of thing that means, yes, if you screw up once or you had Life Happen once you get a bye. But you get one shot at it. It also means you can be flexible without being a push over.
        (I had a hospitalization that kept me from taking a big test and turning in a paper on time. The test I couldn’t do anything about because there was zero leniencey for being the hospital. The paper, I had one pass for that class, I used it then, I turned it in a week late and was fine. I’m totally pro a little leeway, but your first try seems like too much.)

        1. JaneB*

          I use a ‘drop the lowest mark’ model for courses with multiple assignments or assignments with multiple bits, like weekly lab reports – everyone gets to have one bad day/sick pet/hangover, and I don’t have to deal with nearly as many excuses/lengthy emails/special cases…

  17. Xarcady*

    OP, is your project the only project these people are working on? If it is, then ignore this. If it isn’t, this might offer some perspective.

    When people have multiple projects, they are dealing with multiple deadlines. They tend to work on the project with the earliest deadline. If they have a long deadline, and someone asks if they can take on another, smaller project with an earlier deadline, they’ll say “yes,” because they do have the time. That means that the larger project, with the farther away deadline, doesn’t get worked on right away, while the employee works on the smaller project with the closer deadline.

    You can’t stop people from doing this. But you can do things to reassure yourself that your project is getting worked on.

    Set up deadlines that give you enough time to review things and get corrections made.

    Set interim deadlines. A summary of the statistics involved, a draft report, the final report. All with some wiggle room.

    Check-ins. Depending on the length of the project, these could be daily, weekly or monthly. It’s a time when the employee can tell you what’s going on, or, if nothing is happening, why that is so. They are waiting for someone to get back to them with the info they need, your project has been put on hold for 2 weeks while they work on another project, that sort of thing. They can ask for help if there’s a blockage along the way–they can’t get the info they need from an outside source, or an office in your own company isn’t being cooperative. You can pass on info that other people have discovered, “If you ask Tara for that instead of Tim, you’ll get what you need a lot faster.”

    You are new to managing this team. They don’t know how much communication you want or expect. It’s possible that their last manager knew them all very well, and trusted them to just get the job done. So they aren’t used to updating their manager frequently. If you would like more frequent communication from them, you have to make that expectation clear, and make it easy for them to do.

    1. OP*

      Thanks–this helps a lot. Interim deadlines, check-ins, clear expectations. Also–knowing people’s areas of expertise or subspecialities to expedite information-seeking. (And thanks for everyone who contributed to the thread, it definitely helps!)

  18. Carrie in Scotland*

    As well as what everyone else has said above, just because the person before you was fired for a few missed deadlines, doesn’t mean you know the whole story (or maybe you do). There is no way that you/your team will never mess up. The trick is what you do about it if/when that sort of thing happens. You also may need to push back on deadlines occasionally as well.

    Also on deadlines: if someone gives me something to do, I’ll do it. If I’m having problems I will come to you. If not, then I’m doing just fine and don’t need constantly asked about the progress of the task.

  19. micromanagedrat*

    Please, please, please, don’t have secret deadlines. Set the deadline WHEN YOU NEED THE STUFF. I have a colleague who would tell me a deadline for something, and then pepper me with questions about how it was going, was it done yet, do I need any help, in the weeks and days leading up to it. This was really part of the larger issue of her severe anxiety about all kinds of things. Unfortunately, her system of secret deadlines in her head that I was not meeting made her perceive me as flaky and not getting stuff done, even though I never missed a deadline and always do what I said I’d do. Her anxiety and conviction that I was flaky and unreliable just made her more anxious and more micromanaging. If people are meeting deadlines, you really need to step back and let them work.

  20. TootsNYC*

    I think, esp. w/ a new team, etc., that you can say, to each one of them individually:

    “I’m getting nervous, since you’re so invisible from where I am–would you give me a short update and reassurance?”

    1. neverjaunty*

      This sets my teeth on edge, and it’s not even my manager. “Would you give me a short update and reassurance” – well, I don’t know how much of an update you want, and I’m not your therapist. A manager doing a brief check in to make sure something is on track, setting internal deadlines for stages of a project, or letting a new team know that they prefer to do regular check ins to make sure the larger project is on track? Makes sense, if it’s not taken to the extreme of micromanagement and hovering. But it really is not OK to make competent professionals drop everything to soothe the boss’s worry that they might screw up.

  21. amapolita*

    OP, I’m not sure if you’re answering questions, but as I have worked as a PM before:

    Are you actually managing these people in the sense that they report to you, you do their performance evaluations, etc.? Or are you managing a project that they work on, but they have different bosses?

    I get the impression it’s the former, in which case there is a lot of good advice upthread for how to avoid making employees nervous in order to reassure yourself, not over-requesting updates, etc.

    But if it’s the latter, I can tell you from experience that you need to tread cautiously. PMs who assume that they manage people, not just projects, can rub people the wrong way quickly. I’ve seen this dynamic elsewhere, and it will influence how people respond to you. I know how tough it can be to be responsible to the end client for the successful delivery of a project and yet not have any control over the people who work on it, but you will cement better relationships with them if you treat them like colleagues with whom you are working *together* on the project, rather than direct reports.

    (And if I have misread the situation, please ignore me!)

    1. OP*

      Thanks. The latter. And that is very useful to know; there’s a lot of people, different main supervisors, and I do a bunch of projects.

  22. Marty Gentillon*

    I find myself inherently skeptical of deadlines. Far too often they are set by people distant from the work who have little idea as to the capacity of the team. When this is done, they will often be missed. Worse, consequences attached to missing a single deadline will prevent effective communication, and cause unneeded heroics (leading to eventual burnout and unneeded turn over). Fundamentally, a team (or individual) only has so much capacity. No amount of nagging, screaming, or complaining will change this. You can sometimes reallocate resources to help, but this is often of limited use (people will require training, take time to adjust to new workflows, etc.). The real world doesn’t care about your schedule.

    If you are in this situation, there is little that you can do. You should ask the team about how confident they are that they can easily meet the deadline. If they aren’t extremely confident, you should prepare people for the inevitable. Have a conversation with your boss about what will happen if the deadline is missed. Have a plan for what to do next.

    There are three things you can do to avoid this situation: plan for the unexpected, and estimate better, communicate better. When planning, it is important to add a buffer of slack time to the project. This means that if one deadline is missed by a day or two, it is ok, because you were planning for it. With large groups, never forget that there will be time lost coordinating.

    When estimating, it is important that you try to estimate how much unknown work there is. Remember, estimates are ranges (it will take between one and three days), and people can be trained to gauge their confidence better (so they can give 90% confidence estimates). Use Monte Carlo simulation of the project for planning of deadlines.

    While the project is running, you should learn about surprises when they happen, not near the deadline. When something happens that may impact a deadline, people should be comfortable telling you. If they aren’t, by the time you learn about it, it will be impossible to fix (even if you had spare resources you could have allocated).

    Some good books:
    How to Measure Anything http://www.amazon.com/gp/product/1118539273/
    While you can’t actually measure anything, you can come surprisingly close. This book will explain how.

  23. auntie_cipation*

    I used to be an always-running-just-a-bit-late kind of person, but in the last decade or so I’ve changed my life around dramatically and now tend to be early or ahead-of-the-curve for most things. One side effect is that I’ve gotten rather judgy about people who are always running late. I recognize that it’s just me being judgy, but I also see some logic to it, and I thought it might be useful to present the perspective of that side, ie why a supervisor might tend to get all hovery about a project deadline as it approaches and the person hasn’t turned their work in yet:

    What I see around me an awful lot are people who leave something to the last minute, to the point where they have no room to deal with any unexpected obstacles or interruptions. If they leave it to the last day and that last day goes fine, that’s great. The problem is that we all know that life regularly provides obstacles and interruptions. What I found is that when I made the decision to stop being sideswiped by those obstacles, I naturally started doing things sufficiently early that I could deal with most obstacles and still meet the deadline. I do get frustrated with people who are in constant crisis because they didn’t allow for obstacles, especially since those obstacles are really not all that unforeseeable — it’s just that everyone likes to pretend “it won’t happen to me, at least not now.” So they leave their work to the last day and then get sick. Or they run their car with bad tires, because “nothing bad has happened yet” or because “we’re just too busy/broke to get good tires” (even though they have plenty of money for less practical things). Then they call their friends to help them tow their car when the tires go bad 100 miles from home, or they call their work to say they can’t make their deadlines because they can’t make it in because the tires are flat on the car.

    So for me someone I’m depending on who waits until the last minute IS going to make me nervous, until we’ve built up enough history that I know whether they’re progressing appropriately, in which case turning in a completed project just before the deadline is nothing to worry about, but if they are actually leaving the whole thing to the last possible moment and then crossing their fingers that no obstacles appear, I will be very uncomfortable about that.

  24. TG*

    The trick is to build into your deadlines the time you will need to reasonably manage your anxiety about this. It took me some time to figure out that my secret deadlines weren’t fair and if I needed to set an earlier deadline (but not too early) to give myself a small cushion, that was okay.

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