When Under Promising Sucks — For Everyone
By: Alex Peyser
Tags: Leadership, Management And Leadership, Project Management, Organizational Culture, Management

Everyone knows the adage “under promise and over deliver.” Generally, it’s a good rule of thumb. Nearly everyone has been in the opposite situation once or twice and knows its perils: over promising and under delivering leads to disappointment, frustration, and almost certainly will not lead to a promotion or a renewed contract. It’s a one-way ticket to eroding trust. But what I want to talk about today is the opposite foible: when a person or organization swings so far in the other direction (can we describe this direction with a sentence? What is the opposite pitfall here? I see the damage, but my mind didn’t immediately put together the opposite problem) that it can paralyze a project and undermine trust in a more sinister, drawn-out way, since it doesn’t always lead to the immediate reckoning in the way that a clearly missed deadline can prompt remedial action.

How is this a thing?

Who does this? you’re probably wondering. Human instinct almost certainly skews toward the over-promise-under-deliver. Most of us have self-preservation and self-promotion instincts that push us to agree to aggressive timelines and spin missed deadlines in the most optically pleasing way. So who would actively undersell themselves and what does it look like when it happens?

I find this most often happens in organizations where there is great uncertainty. Not just for the group under promising, but across the board. Often the group under promising feels like they are being asked to commit to deadlines when they are highly dependent on things that may be out of their control. They almost certainly have also been burned before (Why? Because of their lack of control?). That means that this is probably a group that has already a reputation for missing deadlines and blocking other parts of the organization, and someone — likely with some authority in the group — has told her underlings to CYA. Leaders, on the other hand, have to trust their managers to accurately gauge and tell them the truth about what they can deliver and by when. When you’re doing something that has never been done before, no one knows how long anything will take. So there is a temptation to cut the struggling manager some slack.

What does this behavior actually look like? In extreme cases (which I have experienced and you likely have to), a group manager can flatly refuse to provide hard deadlines at all for his deliverables. This can come dressed as “it’s our top priority; you’ll get [deliverable] as soon as we have it.” Or “we’re behind schedule but we think we can catch up.” Or, worst of all (which I have experienced): “things are just too uncertain to estimate a timeline right now.” When pressed, a manager might finally cave and give a very large span of time in which they could deliver — an entire month, maybe, or even a quarter. Let me tell you right now, don’t fall for this!

The impacts

Let’s pretend for a second that the root cause of this wasn’t just poor management; let’s say this group was actually being stalled by a super complex problem and dependencies outside their control. Under promising is still a critical issue in this situation.

First, it reduces the likelihood that the rest of the org can step in and help the situation. The project leader has the responsibility to ferret out bottlenecks and if necessary, provide them with extra resources to unblock them. If you hide the ability to measure progress in ambiguity, the leader doesn’t have the opportunity to fully understand when you are falling behind. Of course, keeping any inevitable delays to yourself feels safer in the near term; it buys you time to figure stuff out. But in my experience, you rarely do figure it out in time. For the leader, it can feel like a death by a thousand cuts — what could possibly be taking this long? For the manager, it can feel like you’re protecting your team from heat. No one — and I mean no one, likes to be called out as the bottleneck on a major project. Not committing to hard deadlines can feel like you’re providing air cover for your team in the middle of a difficult project. But remember, people can’t help what they don’t know about. It’s incumbent upon a manager to suck it up, raise the flag, and make sure everyone who can possibly help knows about the problems you’re facing. Do you need more people? More expertise? The first step to getting help is admitting you have a problem.

A second, also serious, impact of under promising is often underappreciated by managers, but it’s very simple: even if don’t provide a delivery date, someone else will do it for you. This can happen explicitly or implicitly. But it will happen. This is because if you are on the critical path of a project, the project as a whole has a timeline. The leader of the project has communicated to her bosses and to an overall delivery date, and that has some assumptions in it about your specific delivery. The less precise you were in your timeline, the greater the risk of there being a serious disconnect between your team and leadership’s expectations. Did you promise your deliverable by “November?” I bet you that you have your team shooting for the end of November and the project leadership has baked early November into their overall timelines. Of course they did; it makes the overall timeline look more attractive to their bosses. The knock-on effects of this disconnect are obvious. If you mean end of November, say end of November.

What can you do

So what can you do if you find yourself tempted to fuzz a deadline? What if you’re a leader who has a seemingly recalcitrant team that’s refusing to provide hard deadlines? Here is what I recommend.

Try to think big picture

If you’re the team member or manager stuck with the tough task, try to remember the bigger team you are a part of. You may be thinking of who’s blocking you and what you can do to speed them up, and that is important. But also remember that you are part of a bigger project, with a bigger deliverable and a bigger deadline. Someone will be relying on your work to come through. Someone will be making more concrete assumptions about your output, even if they seemingly accept your nebulous targets, so best try to control your narrative. Protect your team by asking for help. This is different than shielding them from pressure. Of course, if an unrealistic deadline has been given to you, it’s incumbent on you to push back — with data. So make sure you have it.

Leadership must acknowledge the uncertainty

It’s also incumbent on project leadership to foster a culture where deadlines can get pushed. Yes, this sucks. But it is better to have many smaller deadlines that get missed along the way than to have many fuzzy deadlines that unbeknownst to you may or may not be getting missed on the way to a single major deadline. You can course-correct along the way, calibrate expectations with leadership, and push for more resources if you know where the weak points are in the chain. There is nothing worse than having to fudge your away around the sentiment: “we are two months late…and I don’t really know why.” In an uncertain world, deadlines will get missed. Everyone can understand that, as long as they understand why, and they can understand what steps you took to mitigate the situation.

Just give an estimate!

What do you do if you really, really don’t know how long something will take? See the point above. Just give it your best guess. I beg you. Trust me, everyone will understand. Think of it this way: what do you think a leader would rather have — a deliverable that’s four weeks late, or a planning cycle that has “?” next to it? 9 times out of 10, it’s better for the project as a whole to give an (educated but perhaps) inaccurate estimate than no estimate at all. This isn’t true for all organizational functions — sometimes it is better to have no product than a bad product, for example. But not in planning,not here. Remember, you’re not shielding your team. Also, this gives you a chance to hone your estimation skills. Maybe you are a month off on estimating how long something will take. Next time you are two weeks off. You can only improve as a manager if you consciously think about stewarding the resources you have in a responsible way. Know why deadlines are slipping,what is it in particular that is taking longer than you expected? Be as precise as you can.

And if you really, really can’t provide a date for delivery, give a range. As I mentioned earlier, it’s important to make that range as tight as you can so you don’t end up with misaligned expectations, but sometimes you really just don’t know. Figure out how to measure progress here, and make sure you’re improving over time.

One final thought. Don’t just cave and tell a project leader the date they want to hear, either. If you are tempted to under promise, it’s possible you felt pressured into over promising in the past and got burned. The only remedy against this is having data to back up your estimates. And if you have that in the first place, you won’t have to under promise, either.