I was talking with a client today who’s been frustrated for a long time because of their team missing deadlines. This is a software startup founder who has seen their product release dates push out now for months.

Every founder I know is passionate about their product, app, service, and can’t build their product without help.

But it feels helpless when you’re relying on others for your business — especially when it’s a public-facing thing like an app or technology.

Your stress levels go up.

Your frustrations with your team go up.

And you’ve probably started questioning whether you’ve got the right team.

Let’s take a moment to back that mental assumption train up.

We have to slow down to speed up.

Let’s get to some root causes and how we can begin fixing the problems so we don’t repeat them.

Common Reasons Deadlines are Missed & How to Start Fixing Them

Employee burnout & bandwidth
Unclear expectations
Changing goal posts for what “done” looks like
Lack of urgency or buy-in

Employee burnout & bandwidth

I think we’ve all experienced burnout at some point in our career.

Everyone in every startup that I’ve encountered is facing some kind of burnout or bandwidth issue.

And there’s tons of messages culturally and systemically that tell us:

we’re only worth what we create / do / produce
there’s someone else waiting to replace me if I can’t do the job
asking for help is a sign of weakness
your boss will question your ability to do your job if you say no

So burnout and bandwidth issues can feel inevitable and incurable.

We’re irritable, stressed, get sick more often, and maybe more importantly, we procrastinate or drag our feet on things that we don’t like doing or are hard.

As a founder, you make this worse by assuming you know how much bandwidth someone has and where they spend their time. [Truth is: we all do this, no matter our title or role.]

I love this image (below) I saw on social about what someone’s actual day looks like, versus what we see, and what we assume. I hope this challenges you to be aware of times that you make these assumptions. We can only start to change those thoughts and behaviors when we know they’re happening.

Think your team might be burnt out? Learn how to beat burnout yourself and for the people you lead.

Unclear expectations

Time and again, I see that leaders and especially founders haven’t done enough to set expectations.

“I told them”

That statement is a trap. We can’t tell people things one time and expect true understanding.

We all process information differently — you’ve probably been exposed to “learning styles” language in business. When we’re moving fast — like you are in your high growth startup — most of your assignments, projects, ideas come in the form of meetings.

So if you give an assignment or deadline in a meeting and only say it that one time, what can go wrong?

What if:

your employee got a text from a family member
they space out for a second because they’ve been in back to back meetings all day
they spill something
someone comes to their door
their kid needs something
they were on vacation
and on and on…

In a split second, that crucial expectation you set wasn’t heard or understood. Because life happens.

Get real with yourself about your expectations. Have you set expectations clearly? Reset them. And do it again. It may feel hard at first, but it does get easier.

Document your expectations. Review it with your team members, and bring those expectations back up when challenges happen.

Changing goal posts for what “done” looks like

When you’re really honest with yourself, you’ll admit you do this, too.

As founders, we get so excited by our ideas, products, customers, that we are always thinking about them. This causes us to have those middle of the night aha moments where you want to change something.

The worst that I see founders do is assume that the changes they’re asking for are “small” and so they shouldn’t impact the deadline.

The trouble is: you’re not the one doing the work.

You can’t be as entrenched in the build because it’s your responsibility to lead. Therefore, it’s impossible for you to accurately judge what’s small, or how long something might take.

Talk to your team first. Explain your idea, why it matters, where you think it falls on the priority, and why you think it’s “small.” Give them the opportunity to push back.

Try something like this: “So I have this idea, and I want to hear whether you think we can do this while still meeting our deadline. Please be honest — we’re in this together.”

THEN: actively listen to what your team is saying. And be willing to make the hard decision to change priorities and deal with the impact.

Lack of urgency or buy-in

You wouldn’t be reading this if you didn’t have urgency about these issues. The trouble is that your team might not feel that sense of urgency. This can come from a number of things:

Not understanding why the deadline matters
Feeling you’ll “just change your mind anyway” (see goal posts above!)
Disagreement with the deadline, the project, the approach, or purpose (hello unclear expectations!)
Being enabled by you (or another leader) when deadlines are changed

Let’s focus on #4.

I’ve seen so many tech companies create a culture of missing deadlines simply by allowing the deadlines to shift and change. This immediately erodes the validity of the deadline in the first place.

Here’s a great place we can borrow some lessons from theatre.

You’ve heard “The Show Must Go On” right? But what that really means might surprise you.

First, the deadlines don’t change. People have bought tickets. The theatre is booked. Artists are under contract.

With this as the baseline premise, we start with better planning. We always know that problems come up. So you build in contingency time to your deadlines. You also look critically at what specifically has to happen by when. All of this planning is referred to as backwards planning. You take your due date (aka the first performance) and plan your production schedule and resources back from that.

Despite the best planning, things still happen.
[Every director and designer has trouble with moving goal posts, not having clear expectations, perfectionism, etc.]

Unless something catastrophic happens, the performance dates do not change.

So what is the crew left to do?

We re-evaluate our vision and see if it can be accomplished another way.

We make hard cuts to work that can’t be finished on time.

We rethink how something could get done that will meet the need we have. Usually this is a redesign or new materials.

We bring in additional resources — especially staff. And we reallocate resources from something else to the most priority things.

We hit the deadline.

Returning to your team, if you were to take similar actions that theatre artists do, could you keep your deadline?

Get back to Meeting Deadlines

Each team and person is different. To create lasting culture change so your team and company thrive, you’ll have to take the time to investigate the specific reasons your team is missing deadlines. If you try to apply a solution without addressing the root cause, you might get some success, but in the end, you’ll still keep missing those deadlines.