The Big Question: How Should We Set Deadlines?

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Hal Weitzman: Deadlines have the power to motivate and give us and give us focus, but they can also produce stress and sleepless nights, not to mention brinkmanship and immobilization. So are deadlines really the best way for managers to get the most out of their employees? And are there better ways of using them that can capture some of the positives, with less of the stress?

Welcome to The Big Question, the monthly video series from Capital Ideas at Chicago Booth. I’m Hal Weitzman, and with me to discuss the issue is an expert panel.

Devin Pope is an associate professor of behavioral science and the Robert King Steel Faculty Fellow at Chicago Booth. He studies a variety of topics at the intersection of economics and psychology including the dynamics of racial bias, used-car auctions, and college admissions.

Ayelet Fishbach is the Jeffrey Breakenridge Keller Professor of Behavioral Science and Marketing at Chicago Booth. She’s an expert in social psychology, with specific emphasis on motivation and decision-making. Her research has won her several international awards, while her teaching earned her the Provost’s Teaching Award from the University of Chicago in 2006.

And Oleg Urminsky is an associate professor of marketing and the Charles M. Harper Faculty Fellow at Chicago Booth. His research focuses on goals and motivations, intertemporal decision-making, consumer beliefs, and inference.

Panel, welcome to The Big Question.

Ayelet Fishbach, let me start with you. Basic question. How do deadlines work? What’s the psychological process that goes on when we set a deadline, when we see a deadline?

Ayelet Fishbach: Well, probably you set deadlines for one of two reasons: either that you want to motivate someone, including yourself, or that you want to facilitate coordination. If you have different people that need to work together somehow, then you need to set deadlines so that they can better arrange their schedule.

In terms of motivation, what deadlines do is basically like goal setting. They remind us that we need to give some priority to something because there is a certain time by which that has to be completed.

Hal Weitzman: OK. Oleg Urminsky, what’s really going on when we see a deadline? How does it affect us?

Oleg Urminsky: So I think there’s also an informational component to deadlines. So deadlines are a way that we kind of keep track of our progress. If we’ve missed a deadline or if a deadline’s coming up, it’s a way for us to kind of know if we’re ahead of the game or falling behind.

And I think . . . you were talking about social coordination. I think it can also be a way that we communicate information to each other. So by providing deadlines for each other, we also convey expectations or prior experiences of how long things might take.

Hal Weitzman: Devin?

Devin Pope: Yeah, so one thing that’s interesting about deadlines as well, on top of these things, is that sometimes people will self-impose them on themselves, which seems a little bit crazy if there’s no coordination needed or you’re not necessarily trying to motivate yourself in a forceful way. But it could be that you realize that your future self is going to struggle with something, and so just having a simple deadline is going to help.

Hal Weitzman: OK, so just go back for a second. Your future self. What does that mean in real world English?

Devin Pope: Yeah, yeah. So as academics we like to talk about mini selves that we all have. We have our current self who is making decisions right now for our self, but our current self could also make a decision for our future self, which is our self a week from now or a month from now.

And so I might want my future self to lose some weight, and so I’ll make a decision now. I’ll commit myself in the future to a deadline in order to do so.

Hal Weitzman: The idea being that there’s a separation between me and my future self?

Devin Pope: Yeah, there’s a lot of work that suggests that we have very different feelings about what we want our future self to do now than our future self is going to have about what they actually want to do once we get to that point in time. So I want my tomorrow self to eat healthy, but once tomorrow comes, that self’s not going to want to do that anymore. So I can commit my future self now.

Hal Weitzman: I see. So is that why it’s easy to set deadlines? Because it’s not me that’s going to keep them, it’s somebody else? Is that how it works?

Devin Pope: Right. So deadlines are easy to set in the moment. If we set future deadlines unwisely, it can turn into kind of a trap we’ve set for ourselves in the future.

Hal Weitzman: And, I mean, why do we so often miss deadlines, whether self-imposed or whether imposed by other people? Deadlines are something that often, you know, we’re hopelessly overambitious in our ability to get work done by this particular date.

Why is that, Ayelet Fishbach?

Ayelet Fishbach: Yeah. So part of the reason that we miss deadlines is what we refer to as the planning fallacy, which is the idea that we underestimate how many other things we want to accomplish in the future. So you know I open my calendar two month from now and it looks pretty empty and I don’t take into account the fact that everything that I needed to do today I might also need to do in two months. So all these daily tasks, all these things that come up that we didn’t anticipate, they still happen, and we don’t quite give them enough room in our planned calendars. And we know that.

Another maybe even more interesting reason why we miss deadlines is that we, to begin with, set some challenging deadlines on ourselves. We were trying to motivate ourselves. You suggested that we want to be healthy. OK. We want to be more successful, and so we set these somewhat unrealistic deadlines that, obviously, many times we are going to not be able to meet. They were in advance set such that it’s really hard to meet them.

Hal Weitzman: We talked about that, Devin Pope, before on The Big Question about marathon runners. How they’re very aggressive in terms of the time they’re going to get, and then as the marathon creeps closer, they suddenly become much more realistic and maybe even slightly below their ability.

But that suggests that deadlines really, or goals perhaps, and we’ll talk about the difference between the two, have the ability to fire us up, to get us motivated.

Devin Pope: Yeah. So I would add the one reason why sometimes I think we fail to achieve our deadlines is oftentimes the deadlines, especially those that we impose on ourselves, don’t really have a lot of bite. We say, all right I’m going to do this by next week, or I’m going to lose 10 pounds by next month or 5 pounds by next month. But what’s going to happen if I don’t? It’s kind of cheap talk is what some people would call it.

And so some of the more effective deadlines are those deadlines that are also somehow coupled to an actual consequence. And couple that . . . so an employer that imposes a deadline needs to make sure that the employee understands that it’s not just an expectation or a hope, ot’s something that if it doesn’t get done, then there could be a consequence as well.

Hal Weitzman: We’re talking about linking pay to hitting certain deadlines?

Devin Pope: Absolutely.

Hal Weitzman: OK. It seems like that would be fraught with dangers in itself, and the quality of the work might not be the best. But Oleg Urminsky, what’s your view on why deadlines are so easy to miss?

Oleg Urminsky: So I think there’s two sides to it. One is all the issues that we talked about and just by the time you get to a deadline, you’re operating in a different world than the world you were in when you set that deadline.

But I think that you can also look at it on the flip side, which is that there’s kind of a dark side to deadlines, potentially, which is deadlines exert this kind of motivational force. We feel bad about missing deadlines. And so then we might make choices that we wouldn’t have made, and we might be in a position to kind of know better. We’ve talked about this before, right, that me now may be better able to judge than the me who had set the deadline before, right?

So as much as having an immediate upcoming deadline may help me to focus on that, if circumstances have changed and I should be working on something else, it may actually be a distraction and I may be overinvesting in the most immediate deadline instead of allocating optimally.

Hal Weitzman: Resources, yeah, efficiently across other deadlines.

And Ayelet Fishbach, what you said about in two months’ time, my calendar looks free and, presumably, in two years’ time it looks completely free. It looks great. So let’s set a deadline for then. Does that suggest that there’s a danger in moving it further out when those details of daily life that slow you down aren’t there, and it’d actually be better setting a deadline for the end of this week or the end of next week?

Ayelet Fishbach: Well, I personally try not to commit to anything that is more than a year away because I know that I am going to fall prey to that, like, to the planning fallacy. You should not do that because the calendar will look empty.

But I think that you might be exaggerating how bad it is that we don’t meet our deadlines. Deadlines are there to motivate us, and we can reevaluate how important they are. You suggested that deadlines should have some external force in a way. There’s some penalty for not meeting the deadline. Well, unless the deadline was just there to get me going, and it doesn’t really matter if I finish it next week or next month, then don’t impose penalties on the deadline. Just use them in a very flexible way to get people to put things on their mental calendar. I am going to do this by some time that is not very far away.

Hal Weitzman:I guess that problem is that the planning fallacy can just . . . things can be postponed forever.

Ayelet Fishbach: Yes, and I believe that you don’t want to set a deadline too far. First, because if it’s very far away, then really I should do nothing about it right now, and that’s probably the risk with externalities, with putting some real cost of not meeting deadlines that if people are strategic, what they might do is just set the deadlines so far so that I don’t really need to do anything about it right now. So something that might take me a week will end up taking two months because I set the deadline then.

One thing that we know about deadlines is that before they loom large, you do nothing about that, OK. It’s there. I don’t need to work right now. You kind of want to set the deadlines close enough so that they motivate yourself or your employees, not so far that you don’t care about it at the moment.

Hal Weitzman: Right, I wonder about that. That you suggest this idea, Devin Pope, about having a consequence. Is that motivating in good way? Or is that the right kind of motivation that you want in a typical work environment?

Devin Pope: Yeah, so this relates to whether deadlines serve as a penalty or maybe more of a goal, and I think you can frame it in different ways. You could think of a deadline as being, ah, I want to achieve my deadline, and I get this reward. I’ve achieved it. Or a deadline can be: you’re just worried about avoiding the loss of not meeting the deadline.

And there’s a lot of research that suggests that losses can be very motivating, and in some cases more so than gains. But it’s going to depend on the situation, and in a manager-employee situation, it’s going to depend very much on the type of feeling you want to give your employees when they hit that deadline, I think.

Hal Weitzman: OK, we’ll come back to motivation. Because you talked about goals, deadlines versus goals, talk to us a bit about how those two things are different, Ayelet Fishbach?

Ayelet Fishbach: Goals are more general than deadlines. Well, deadlines mainly have the time component. OK, goals can also be in terms of quantity. OK, how much I want to achieve. Also goals can be really general, like, I want this project to be successful. I want to be a successful employee. Whereas deadlines are very specific. And we know that specific goals have their advantages, OK. It’s more concrete. It’s easy to aspire toward a specific goal.

Hal Weitzman: OK. They could be complementary in that sense? I mean a goal could be a big picture ambition and a deadline could be a specific way of getting there?

Ayelet Fishbach: Yes, and one thing that you might want to consider with this regard is that in most work contexts, it’s impossible not to have deadlines. You have to have some schedule, so maybe the conversation should be more how to do that well than whether to have deadlines. Because if I work on something, my coworkers need to know when do I plan to finish it.

Hal Weitzman: That’s true. Well, it’s an excellent point, and we’ll come to that, but I just want to talk about the difference between the goals. Because actually you said, maybe we shouldn’t think of a deadline as you do a 100 percent of the work and that’s it. You can achieve 90 percent of the work and it still fulfilled a purpose, even though apparently you failed to meet the deadline, there’s still some value in it, right, which I think is a compelling argument, Oleg Urminsky?

Oleg Urminsky: So I was going to add to this point about goal-based deadlines versus other kinds of deadlines. I think it can be helpful to think of deadlines being used for two different purposes. One is to manage processes where there are concrete external deadlines, right? So we’re working as a team and we have a deadline for a project, and so we may set internal deadlines. And for those it may be very beneficial to have costs associated with missing the deadline because better to have a small internal cost early on and realize we’re behind and take that seriously than to have the big externally imposed cost at the end, and those can be very different than deadlines we set for ourselves, right, either within an individual or within an organization to just motivate better performance or greater effort.

Hal Weitzman: Well let’s come to this question about: How do you do it? I mean, as you said, Ayelet Fisbach, it’s impossible to live without deadlines in a work, in a typical office environment. What does research tell us is the best way to use deadlines? Are we setting too many deadlines? How should we think about it?

Ayelet Fishbach: We are probably setting many deadlines. Too many? Well, if we want to meet them all, then maybe too many, but if we just try to do our best and having, erring on having too many is better than having too few.

I would say that for deadlines to be effective, they need to be challenging. We probably err on making them too challenging, but both too challenging and too easy are not good. And also they need to be at least somewhat self-imposed, so to the extent that you involve the person in setting the deadline, that works better, at least my research shows that.

Hal Weitzman: Tell us about what you found then.

Ayelet Fishbach: So what we find when we study deadlines is that if you let people set their own deadlines and they expect something to be harder, they actually set a sooner deadline. We basically, in one study, used our students as supposedly employees and had them take a task to do at home, which we said was either difficult or easy. As a matter of fact, it was exactly the same task. We also asked them, “How soon will you return it for us?” And we find that they return it, they say that they will return it more quickly when they expect the task to be difficult because they said that they are going to return it more quickly, they actually return it more quickly, although later than they said.

OK, so they are missing their deadlines, however, they are doing it sooner than those that expected an easy task, and set the deadline to be later.

Hal Weitzman: Translated to an office environment, does that mean that managers should set artificially aggressive deadlines, which they know their employees are going to miss?

Ayelet Fishbach: You should involve the employees in setting the deadline. OK, you should encourage them to set that aggressive deadline. Yes, yes, it’s OK that it’s aggressive, but then you should not punish them too harshly for setting the aggressive deadline because you should understand that they were trying to motivate themselves to do that.

Hal Weitzman: OK. Oleg Urminsky, advice for managers how to set better deadlines.

Oleg Urminsky: I think one useful way to think about is in terms of the context you’re operating in, right. So in some situations, the work that’s being done is repetitive and quantifiable, and in those settings I think trying to set deadlines that are fairly realistic and lots of deadlines leading up to whatever the big outcome is, kind of drawing on past data can be really valuable.

And then in other settings where you need your workers to be flexible and adapting to situations, and the workers may know more than the manager about the scope of the work and how the trade-off should be made, when is it good to spend more time or when should they hurry up, there, I think, you have to draw a lot more on treating the deadlines as something that you’re going to help the workers to set in exactly these kinds of motivating ways that give them the flexibility they need, but you still retain the motivational benefit of the deadline.

Hal Weitzman: Devin Pope, in an office environment, we often face multiple deadlines, not all of which are easy to compare—different clients need different things or different departments need different things to be done by different dates, and we don’t really know how serious those deadlines are or how to compare them. I mean, how do we behave when we’re faced with multiple deadlines?

Devin Pope: It’s a tough spot to be in when you have multiple deadlines all coming down on the same day. I think we do very poorly in situations like that is the easy answer.

I have some research where Ian Fillmore, a PhD student here at Chicago, and I have looked at situations where students have AP tests, which are these high-school tests, these big important high-school tests that occur over a two-week period. We have situations where those two tests occur very close to each other, on the same day or a couple of days apart, and other situations where they occur 10 days apart or so and it’s very clear that they perform much more poorly when those tests are close together, even though they had the whole year to prepare for those tests, having those deadlines right at the same time makes it hard.

People need that time right before the deadline to finish up because they’re probably going to be delaying some of their studying until right before the deadline.

Hal Weitzman: And it sounds very obvious that you would spread out your deadlines, but I wonder how many of us put a deadline on a Friday or on the 31st of the month or the day before we’re about to go on vacation, we’ve got to finish these five projects. It’s actually kind of a very common situation that we don’t stagger our deadlines, whether self-imposed or not, right?

Devin Pope: That’s right. Yeah, we could easily, through our own fault or through the fault of someone else, just end up with a lot of deadlines at the same time and that can be very unfortunate.

Hal Weitzman: OK. Ayelet, any advice on juggling multiple deadlines?

Ayelet Fishbach: Well, I have a somewhat more optimistic view, I think. Like I think that we are always doing multiple things at the same time, so it’s like whoever only has one deadline, I don’t know, maybe these high-school students, but that’s not the life of most people in a work environment.

Devin Pope: The really big things that are all having, all coming together on the same day is going to be bad.

Ayelet Fishbach: Yes, I agree. OK, so yeah, that’s a fair point. But just our daily life are full with many deadlines, and it’s good to prioritize and organize things in a way that makes sense, but I wouldn’t think it’s necessarily a problem that you need to finish several things in the same day or in the same week. That keeps us busy and productive.

Hal Weitzman: But how would you think about, Oleg, how would you think about this question of the deadlines that you have that come from different people, whether yourself, other people, they’re very, very hard to compare those things and how important priorities are, and some deadlines don’t mean anything and some are very, very consequential?

Oleg Urminsky: Yeah, so I think one of the things deadlines do is they impose a focus, right, so the deadline that is . . . either screams the loudest, right, or that is the first is going to attract a lot of our attention, and then the risk is in your example the test happening right after that, right, gets insufficient attention.

And so one way to think about this is to try to plan before the deadline comes is to think about deadlines as sets of deadlines rather than allowing yourself to fall into this trap of just thinking about the most immediate deadline.

One example, a simple heuristic thing is, I think, deadlines that happen at the beginning of the month attract a lot more of these problems than deadlines at the end of the month, right. So a deadline at the end of March, I’m thinking about it all of March. A deadline that’s April 1, that’s that thing I need to do in April, and so goes into the April category.

Exactly, and so we try to simplify these complex decision environments in various ways, and they often lead us to forget or neglect important things. And so recognizing that mistake that we make and getting in the habit of checking your calendar a week ahead or a month ahead can be useful for returning to the back of your memory what are the other deadlines that you should be trading off against.

Hal Weitzman: I wonder then if the problem is that your department constantly sets a deadline on the first, should you think in sort of quarters or blocks of six months or whatever?

Oleg Urminsky: Yeah, yeah, I think . . . but it’s both, right? Part of it is there are some times that deadlines might, you might be more likely to spontaneously remember them, but any deadline is going to, at least at some degree, blind you a bit to the deadlines that come after it. It takes effort to go against our natural tendency to focus on the most salient thing and return those to our memory and keep them in our memory.

Hal Weitzman: OK, well, we went out onto the streets of Chicago to ask people what questions they had about deadlines. Here’s what they said.

Speaker 1: What is the best type of deadline to set for yourself? Like do you set it periodically, week-to-week basis, or do you set it long term? Saying like this is due, for example, first semester of the week or something like that?

Hal Weitzman: Ayelet Fishbach, what do you say to that?

Ayelet Fishbach: Well, it’s probably a good idea to try to break the goal into subgoals and in this context, try to think about small deadlines for the big deadline that is coming so that you’re on top of things and you make sure that you are making progress. You don’t get to, like, a day before the giant deadline and start to think about how am I going to do it now?

Hal Weitzman: Is that a way to overcome the planning fallacy?

Ayelet Fishbach: Yes, one way in which that could help is that you introduce things to your calendar earlier, so I kind of know what my schedule is going to be this week, which means that if I can impose this deadline then part of the big deadline, something this week, I can better plan for that than something that is found in the future and is hard to plan.

Oleg Urminsky: And after I miss that first deadline, then I know that I’m behind. That provides additional motivation to catch up.

Hal Weitzman: Right! OK, well, let’s go back to the streets of Chicago for another view on deadlines.

Speaker 2: I’d like to know what the real driving motivation of deadlines is, whether it makes people more tense and that they lose time worrying about the deadline or whether it actually helps people because they’ve got a finish line to work toward?

Hal Weitzman: Oleg Urminsky, what about stress because we talked about how deadlines stress people out and that can’t be positive?

Oleg Urminsky: So it can be positive and negative, right. Too much stress is a bad thing, and some people react very badly to too much stress and shut down and need to escape from it and do less than they would have otherwise. But I think for most of us, moderate levels of stress are actually motivating, where we feel like there’s something . . . it’s a cue to us that there’s something important to work on. And the combination of a little bit of stress and having a concrete deadline or a finish line, in his terms, to work toward is, I think, a really important part of what motivates us and why deadlines can be effective.

Hal Weitzman: OK, Devin Pope, is stress a useful thing for motivating us?

Devin Pope: Yeah, I agree, I’m a big fan of, at least in my own personal life, if I don’t have some stress attached to the deadline, the deadline’s not going to be very effective for me. I can make up deadlines any day I want but unless I feel attached to that and feel some obligation to achieve it, it’s not going to work. So I don’t think you can have stress-less deadlines that are very functional.

Ayelet Fishbach: Yeah, I agree. You have to worry about not meeting your deadline and then there has to be the relief or the enjoyment from, I did it, not only, I achieved the goal, but, I actually did it on time. That feels good.

Hal Weitzman: OK, well, on that note, we have hit our deadline, and our time is up. My thanks to our panel: Devin Pope, Ayelet Fishbach, and Oleg Urminsky.

For more research, analysis, and commentary, visit us online at chicagobooth.edu/capideas and join us again next time for another The Big Question.

Goodbye.

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