How to Break "Over Promise & Under Deliver" Cycle

Aleksandra Doknić, May 16, 2024

Over promise and under deliver cycle

Here’s the equation that covers the basics of the “over promise and under deliver” cycle.

Time=money, right?

Consequently, less time=less money, and more time=more money.

Traditionally, we've thought that more time equals more money, but the mantra of the 21st century is "work smarter, not harder." So, in today's terms, less time can mean more money.

And in 2024 it’s also true that poor time tracking=poor money tracking.

It's no secret that better time tracking equals more revenue, and most people agree on the high impact of proper time management on work productivity. Numerous stats prove it.

On the other hand, for you, a freelancer, it’s important to note that manual time tracking can become a side hustle itself. Just think of setting timers, coming up with task descriptions, and adding hours to timesheets. Plus, the extra time it takes to regain focus.

But how does all this fit into the “over promise and under deliver” cycle?

Well, when you don’t know where your time goes, and how you should use it, you’ll promise a client anything, just to impress them. However, making promises you're not fully committed to can damage your reputation and lead to long-term harmful consequences.

So, how can you break free from this cycle? Here's everything you need to know.

Making a mistake by over promising and under delivering

What does the “over promise and under deliver” cycle look like?

Simply put, it usually starts with a guesstimate of how much time a project will take and running with it.

When reality hits in the middle or end of the project, you start realizing that there is no chance of delivering on time, so you end up being late and sending a poorly executed result.

Here’s an example.

Let’s say that there’s a talented freelance graphic designer named Jake.

A client approaches him, asking him to design their new logo.

With all the work Jake already has, he promises to deliver the logo in three weeks. He approximately counts how much time it will take him to get to know the client’s industry, and the additional work he’ll have to put in after the client’s feedback mid-project. To Jake and the client, it sounds like a decent offer.

But Jake made a mistake because he wasn’t tracking his time.

Tracking time for multiple projects

He wanted to get the logo done and delivered in less than a month. But trying to fit in a new project with the existing workload can’t go as planned if you don’t track time properly.

The result? Jake exceeded the deadline and delivered a pixel fiasco. There was zero aesthetic harmony, no visual hierarchy, just a bunch of mismatched elements sorted in all the wrong ways.

Despite Jake's good intentions, he fell into the trap of over promising and under delivering.

The client was understandably dissatisfied and held Jake accountable for breaking his promise.

This incident affected Jake's reputation, portraying him as unpredictable, unreliable, and untrustworthy. Ouch.

Why do people end up over promising and under delivering?

People who tend to over promise and under deliver are commonly considered lazy, irresponsible, even self-absorbed, and incompetent.

In reality, that couldn’t be farther from the truth.

People who tend to over promise and under deliver are just bad at planning and time management. They get distracted by more urgent tasks, and let unpredictable circumstances dictate their daily routine, making it difficult to stick to their commitments. They are bad at estimating and don’t know where their time goes, working more time than promised and being burnt out.

So, rather than assigning blame, let’s recognize that many people face similar challenges with balancing their workload and allocating their time effectively.

Over promising and under delivering vs. under promising and over delivering

Is under promising and over delivering better than over promising and under delivering?

I mean, it might be.

You talk to a client, say you can’t deliver what they expected, they somehow agree to hire you and you end up delivering more than promised and quicker. So, you get the project delivered a few weeks before the deadline or you’ll include some extra features you haven’t discussed with a client.

It’s not a bad idea. I’m sure you’d rather be a person who finishes before the deadline than one who delivers late.

But under promising and over delivering can backfire.

Just because you delivered before the agreed upon due date and added an extra “sparkle”, a surprise to the project to wow a client, doesn’t guarantee client satisfaction. They might be impressed by your delivery time but not so much with the extra features you’ve added. As they say, sometimes the best surprise is no surprise.

So, I guess this is long way of saying:

  • You are a professional.
  • You need to make realistic estimates of how long a project will take.
  • You don’t need to impress but to progress.

Now that you understand the dangers of both under promising and over delivering and over promising and under delivering, let's explore how you can break free from the “over promise and under deliver” cycle in just 3 quick steps.

#1 Don’t make a promise right away

When you hear a potential client talk about the project, you can get quite excited. And it’s understandable一a new project can sound appealing and challenging and your hopes and wishes for the project can be at their highest.

But to avoid over promising and under delivering, pause before you speak.

Pause before you speak

Take time to assess the situation.

Count to ten and breathe.

Tell a client that you need time to go through project details and that you’ll send a summary email, with a contract, or a project proposal that outlines the deadline and details of the deal.

There’s no need to give a potential client an answer and commit right away. Let them know that you’ll estimate project delivery time after carefully planning out and visualizing all the steps between start and finish. That’s how professionals do it.

A quick note: if you are a yay-saying freelancer, this is your reminder to stop saying “yes” when your schedule is already full.

Similarly, if you have a lot of pending work, negotiate. If the client can wait for you when you have space in your schedule一great; if not, you might need to pass on this business opportunity.

And remember : you can say “no” in a diplomatic and assertive way without sounding conceited. 🙂 Saying “no” to the projects that don't align with your current workload or priorities means you are setting boundaries and managing your workload effectively.

#2 Plan the project down to the smallest tasks

This step is simple: make a list of project tasks that need to be completed. Include all the steps required to ensure the project's top-tier output.

And when planning a project, please understand there's a difference between a project list and a to-do list. They serve different purposes and are used in distinct contexts.

  • A project list is formal and official; it's something you can share with a client, as it includes a project structure with all the tasks, phases, deadlines, milestones, and requirements (like client feedback). It's there to help you run the project smoothly from start to finish, assisting you in achieving project goals.
  • A to-do list is a personal list that doesn't necessarily contain deadlines or milestones. It can contain your tasks, not related to just one project. To-do lists always have a shorter time frame, and are not necessarily tied to a project you decided to complete.
Making a project list

The only question left to answer is how to create realistic project and to-do lists if you don't know how much time each task requires.

And sure一you can rely on previous projects for estimation, but every project is different. Plus, your skills and efficiency develop as you gain experience. So, for example, for a project that took you 12 hours to complete six months ago, you might need 5 hours to complete today.

Perhaps it's time you start measuring time in a consistent and continuous way that's not disruptive and won't mess with your focus.

You can do it with Memtime. 🙂

Memtime works in the background (there’s no START and STOP button) so you’ll forget you're time tracking. But all your time spent working will be captured down to the minute, even if you switch between programs and tabs a lot, allowing you to make informed decisions about project planning and time management.

At the end of each day, you can revisit your captured activities and decide which count as billable and which don’t. The billable hours can be recorded as your time entries and exported to a project software. Even if you don’t use project software, you can create custom projects in Memtime to organize your work better. This feature doesn’t cost extra and it gives you an overview of client projects and how you manage your time.

All you need to do is start your free trial and download Memtime.

#3 Add extra time to your estimation

Not all projects are exciting and challenging, and it’s okay to admit that you sometimes lose motivation mid-project.

  • Some days, you don’t feel inspired.
  • Some days, you procrastinate more than others.
  • Sometimes, unforeseen situations happen, disrupting your productivity and efficiency.

And all that’s understandable; it happens to the best of us.

Knowing you can feel unmotivated, I suggest you leave an extra 10% to 15% buffer in your estimation for circumstances out of your control.

Leaving an extra 10% buffer to estimation

While we’re on topic of motivation, here’s a well-known fact: just before project completion, it takes you extra time to deliver the final 10%. Meaning, the last 10% of a project is the most difficult to complete.

Why is that?

Because that’s when the perfectionist in you takes the wheel, making you doubt and question everything you’ve done. Insecurities creep in, making it difficult to finalize the project with confidence.

To avoid feeling like a failure just before you submit the project to a client, remember the saying: it’s the darkest before dawn. So, don’t feed the thoughts saying you should start all over; that’s probably not true. Get a snack, watch your favorite series or a movie, do a spontaneous dance party, and then go back to the project. By stepping away from the project, you’ll gain clarity and perspective.

Deliver on time and budget

When it comes to project delivery and promises, the rule of thumb is: deliver on time and on budget. No need to rush, no need to surprise.

Delivering on time and on budget will demonstrate your professionalism, value and reliability. And meet the deadlines, quality standards, specifications and requirements that you agreed on with a client.

It may not sound simple, but it is when you manage time properly. So, let Memtime be Robin to your Batman when it comes to time tracking. You won’t be disappointed.

Meet the author:

Aleksandra Doknić - post author

Aleksandra Doknić

Aleksandra Doknić is a copywriter and content writer with six years of experience in B2B SaaS and e-commerce marketing. She's a startup enthusiast specializing in topics ranging from technology and gaming to business and finance.

Outside of work, Aleksandra can be found walking barefoot in nature, baking muffins, or jotting down poems.