How to talk about deadlines at work

Why it feels awkward to push back on deadlines, and how to make these conversations more approachable and effective

Image: Imgflip

👋 Hey, it’s Wes. Welcome to my weekly newsletter where I share frameworks for becoming a sharper marketer, founder, and operator, based on my experience as an a16z-backed founder. If you’re interested in sponsoring this newsletter to reach 27,000+ thoughtful operators, fill out this form and I can share more.

In this week’s newsletter, we’ll cover how operators can push back on deadlines—without being perceived as less competent—and how managers can encourage their teams to speak up.

• Part I: For direct reports

  • Speak up at the first sign that you might miss a deadline

  • Scripts of what to say

  • Suffering in silence is not useful

• Part II: For managers

  • Encourage your team to be honest about timing

  • Temporarily “over-correct” to convince your teams it’s safe

Read time: 10 minutes

---

For longer than I’d like to admit, I thought if a task took longer than expected, it must be my fault. I must not be as smart or capable as my manager thinks I am. Therefore, I must hide how long a task really took at all costs.

It never occurred to me that my manager’s time estimate could be wrong. Or that there might be a better approach they could share with me, if only I weren’t so hell-bent on putting up a front about how competent I was.

My managers would probably have admitted that their estimates were exactly that: an estimate. But as a direct report, their estimate felt like an anchor, especially if I agreed to and helped set that deadline. I didn’t feel like I could share new information that contradicted their anchor. This led to anxiety, emotional labor, and flaming out that could have been avoided—if I had the confidence and vocabulary to discuss deadlines effectively.

Given how often we set, agree to, and update timelines every week, we should get better at having conversations about it. These conversations can be friendly and fast, and both parties are on the same team, but make no mistake: they’re a negotiation nonetheless.

This post isn’t about tactics for estimating project timing—there are already many articles on that. I want to talk about why it’s so awkward to push back on deadlines at work, and how to make these conversations lighter and more effective.

Intellectual honesty is key

Let’s be honest: Deadlines are created by people. Managers don’t like mentioning this because we don’t want teams to abuse the flexibility. The fear is if folks realize deadlines are set by mortals, they might say, “LOL these deadlines were made up, so why try to hit them?”

This is where trust and intellectual honesty come in. Do you trust your team to push back when they objectively have a reason to? Or do you think they’ll abuse your openness? It’s worth noting this post is for high performers and overachievers who tend to care too much. Because high performers want to do their best, and often have a hard time asking for help or admitting when there’s too much on their plate, it’s especially important to remind them to speak up if trying to hit a deadline is not worth the upside.

To have more productive conversations about deadlines and timing, we should aim for less opacity and more open information sharing. If a manager doesn’t know what’s on their team member’s plate, they can’t help triage. If a team member doesn’t know why a deadline matters, they can’t manage their effort well or suggest an alternative path. Sharing more openly doesn’t mean you can change a high-level deadline coming from above, but you can discuss the scope and milestones along the way, and make sure people who are actually executing the work are able to share information upwards. This leads to more informed decisions, higher morale, and fewer avoidable surprises.

Part I: For direct reports

Why is it hard to speak up before missing a deadline? If this were purely a knowledge issue, this wouldn’t come up as often as it does. I think it’s because there are logical reasons why you might hesitate to speak up.

1. You’re afraid your manager will think you’re slow.

2. You think you can still make the deadline, i.e. you’re overly optimistic or in denial.

3. You think you’ll miss the deadline, but aren’t sure how to say it without blowback.

Those are legitimate fears. I’m not going to gaslight you and say your manager isn’t judging you. This is why it’s important to have solid reasoning behind why you’re pushing back, and not just to speak up—but to speak up in a way that shows you’re competent, open to questions, and want to do what’s best for the business. We’ll cover how below.

Speak up at the first sign that you might miss a deadline

This is a pet peeve of many managers: A team member agrees to a deadline. The deadline comes and goes. No word from the team member. When the manager asks, the team member reveals why they missed the deadline.

To be clear, the issue isn't about missing a deadline. The problem is not pointing it out before you missed it. If your manager had to ask for you to admit you missed the deadline, it looks like you’re shirking your responsibility, hoping no one will notice, and trying to get away with bad behavior. Worse, if you give excuses about why it’s not your fault, this makes you seem flippant and immature too.

If I said I would send you a draft by Thursday morning, and I send it later in the evening, what’s the big deal?

First, you can’t always tell if your part in the relay race is the bottleneck for someone else’s work, so you may be putting your manager or coworkers in a tough spot without knowing it. Second, your word is a promise. You want to be the type of person who people trust will be straightforward and dependable. Third, any single instance might not matter, but if you come through half the time, and I can’t tell which half, I can’t plan around you. I have to assume you won’t deliver—and this slows down the entire team and diminishes trust in your abilities.

Luckily, this is all avoidable if speak up sooner rather than later. If you’ve agreed to a deadline but think you’ll miss it, here are 4 scripts of what to say:

Give a simple heads-up:

“Hey, X is taking longer than expected. I was going to share with you today, but will send it tomorrow. Let me know if that works, thanks!”

^ This works well for non-urgent or weekly tasks. This might cover 80% of use cases. For what to say for more “serious” deadlines, see below.

Recommend a new timeline:

“Hey, it looks like I likely won’t be able to get Y done by later this week because I’m prioritizing X and it’s taking longer than expected. I recommend we skip Y this week and use the time to work on X, then ship Y next week. How does that sound?”

Share your logic:

“I’m looking ahead to our launch date next month, and am worried we may miss that timeline if we want to execute well on our GTM plan. Instead of using brute force to make it happen, I’m thinking we either cut scope or push the deadline out two weeks because we haven’t announced the launch date publicly yet. I have some ideas around trimming scope on a few things I don’t think will make a huge difference on the outcome. When can you chat about this?”

Mention trade-offs:

“I’m looking at our ship date, and I have a hunch it’ll be tight. We can rally to make it happen, but that would mean putting X and Y on the backburner for a few weeks. Can we discuss?”

One thing to note: You should be prepared for a conversation because deadlines are not items you should push out haphazardly. So don’t be defensive if your manager wants to get more context or vet what you’re saying to make an informed decision.

Suffering in silence is not useful

I used to feel like a martyr when I suffered in silence. Then I realized no one gives you brownie points and I was only making myself miserable. If you find yourself feeling resentful and overwhelmed, take a pause with this internal narrative.

• Does your manager know what you’re working on?

• Do they know what’s involved?

• Do they think a project is simpler than it actually is?

These are context and knowledge gaps you can fill—if you speak up.

Your first reaction might be “They won’t care,” but I’d encourage you to test this hypothesis before you treat it as fact. And when you speak up, don’t just say “I can’t do this.” That’s not helpful and is a self-fulfilling prophecy with your manager not understanding you. Put effort into explaining to “sell” them on why what you’re saying matters. Practice building a business case and sharing your thought process, logic, and rationale.

Notice how the lesson is not, “I’ll delay [this important thing] to meet the arbitrary deadline for [this less important thing] because you originally told me to do the less important thing.” That’s another way to be a martyr: working on less important stuff to stick it to your manager and organization, when deep down you were afraid of initiating a conversation.

There will always be a lot going on. There will always be too much to do. To make things tougher, we usually realize a project is taking longer than anticipated in the middle of it. Because of this, you will regularly have to update your priorities based on how long things actually take. There’s no way around this even if you get better at estimating timing. That’s why it’s worth getting better at communicating and keeping each other in the loop overall.

Takeaways:

• Use deadlines to plan and have intellectual honesty around hitting them.

• But don't blindly bend over making deadlines that we set for ourselves. Always work on what you think will make the biggest impact and explain your reasoning.

• The moment you think a deadline is at risk or you feel you need to push it out, say it explicitly, explain why, suggest a new timeline, and be open to questions.

Part II: For managers

Encourage your team to be honest about timing

One of the most annoying things is when leaders are disconnected from the work, then act like you’re being too slow doing the work.

In my first jobs out of college, I remember managers being impatient with me and wishing I could tell them why X was taking so long. For example, with pulling data, depending on how janky our set up was, I was piecing together data from 3-4 different sources and cross-checking to make sure the numbers rolled up. Often, the numbers didn’t match so I had to investigate and reconcile. My managers thought it should be fast, and I didn’t feel like I could tell them otherwise.

Now as a manager, I make sure my team knows they can be honest with me about how long a task takes and why. I never want folks to suffer in silence. And if I feel there was a mismatch between how long I expected something to take, I default to curiosity. I’m not judging their ability or intelligence.

You might agree already—which is why you need to be explicit and say this out loud to your team. You assume they know, but meanwhile, they might be hesitant to share news with you if they think you won’t be pleased.

When you dig in together, it’s possible you realize your team member’s approach is suboptimal. Here are examples I’ve encountered:

• A junior team member didn’t realize there were Google Chrome extensions to handle tasks they were doing manually.

• An admin was typing testimonials and I taught them how to copy/paste text from screenshots. This was a relatively new macOS functionality that I myself had just learned about.

• A senior team member didn’t trust a new software system so they kept a separate spreadsheet with all the data. The dual systems took twice as long to maintain.

When you discover this, don't shame them or act like they should have known better. When people feel embarrassed, it creates a dark spot in their memory and a visceral reaction of “Next time, let’s not tell the boss.”

Usually, there’s a misalignment of expectations: They thought the task was a bigger scope, more detailed, or higher fidelity than it needed to be. Or it’s a knowledge gap—they didn’t realize a tool was available, so they were doing it in a more cumbersome way.

This is your opportunity to share an insight, like “This is higher fidelity than we need it to be—we can get by with something fairly directional. Instead of gathering info for 7 columns, let’s go with gathering info for the 3 most important ones.”

Or you can share a helpful mental model like, “Whenever you’re doing anything repetitive that feels like a slog, there’s a chance a computer might be able to do it. Do a quick Google search to see if a tool can help, or feel free to ask me to gut check.”

You can have all kinds of conversations that make work more fun and effective, but that can only happen if your team is willing to reveal information that you otherwise don’t have visibility into.

Temporarily “over-correct” to convince your teams it’s safe

Whether we want to admit it, conversations sometimes go like this:

Manager: “I want you to speak up.”

Direct report: “Are you sure?”

Manager: “Yes, I’m not going to judge you or think less of you.”

Direct report: “Okay, I’d like to tell you about X.”

Manager: “Wtf why couldn’t you just make it work??”

Managers, it’s not only about telling team members to speak up and be honest. You need to celebrate the behavior. During this time, it may feel like you’re overreacting or over-correcting because you’re dislodging an existing norm and setting a new norm. Once your team believes you, you can talk more directly or jump straight into tactical mode.

Before: “Okay but… why couldn’t you just work harder/smarter and make it work?”

After: “I’m really glad you spoke up early. This is exactly what we talked about, and I love that you’re raising your hand. Because you spoke up early, there are multiple options of what we can do, which is great. [Then go into feedback, tactics, reminders for next time, etc.]”

After, once you’ve established trust: “Okay makes sense. Yeah it’s not great, but not the end of the world. Did you consider A, B, or C? Next time, let’s build in a bigger buffer. I agree with your next steps, TY.”

Celebrating the behavior you want to see is easy in happy moments. But it’s most important in moments of micro-conflict when you’re trying to change your default culture.

Takeaways:

• You will always have too much work and incoming data points that may change your priorities, so practice speaking up about timelines.

• Managers, you should openly tell your high performers to push back. If you trust them, don’t make them bend over backward for deadlines that don’t make sense given new information.

• Operators, you may think deadlines are set in stone, but they’re not. If you have a good relationship with your manager, you should sync on how you can best raise your hand if you think a timeline doesn’t make sense anymore. Your manager won’t think less of you—they’ll actually respect you for speaking up.

Thanks for being part of this growing community of thoughtful, rigorous builders. If you enjoyed this post, consider taking a moment to:

1. Refer a friend to unlock my favorite book recommendations for free.

2. Sponsor this newsletter to reach 27,000+ tech operators and leaders.

Thanks for being here,
Wes Kao

PS See you next Wednesday at 8am ET.

PPS If you’re loving this and want to binge-read, check out these other posts on organizational dynamics:

Be more assertive with customers

How to present to your CEO

Are your standards too low? In defense of raising the bar