Get Better at Estimating Your Project Timelines

Gerry Saporito
Jun 28, 2020 · 8 min read
Photo by Isabella Christina on Unsplash

TLDR: Here is a link to the table with the points to consider when planning a project timeline. NOTE: there are 2 extra points not discussed in this article in the table (Architecture Effort and Effort vs Calendar), I’m still learning more about those.

If you read the title, then maybe you’re like me and struggle with making half-decent time estimates for your project timelines. Or maybe you always make perfect predictions and are here to laugh at this article and problem I encounter quite often. Or maybe you make ok time estimates and wanna see how you can improve in making estimates. Regardless, you are reading this right now and you are about to gain a little insight in a few things I learned from my struggles and from my supervisor. But first, let’s talk about my greatest projection failure.

My failed timeline projection

I later scrapped this site and created a plan to fix the front end and parts of the back end. With only 2 days of planning, I was able to recreate most of the website in 2 weeks (because the back-end was mostly functional which saved me 1 week).

This is when I realized how important it was to plan. Without a solid roadmap, the scope of the project is never set. Certain menial tasks will end up taking much longer to do, leaving the important tasks to be hastily done. And above all, you will never feel satisfied (at least in my case) with your work due to the lack of a vision of what your successful project is supposed to be.

For those interested, my current site can be found here.

What to also consider

Photo by NordWood Themes on Unsplash

External Dependencies

With this, plan according to the worst case time. For example, if a contractor says they can get the task done in 3 to 5 days, plan as if it would take 5 days. If they finish sooner than 5 days, then great! If not, you already accounted for it and the project can still move forward.

2. Known Unknowns

Start your project with the known unknowns if possible, and if not then start them as soon as possible. The sooner you start them, then the sooner you can find where the roadblocks are, and if necessary the rest of the project tasks can be shuffled around to accommodate for the known unknowns which are behind schedule and something can still be delivered by the deadline.

3. Unknown Unknowns

When the project timeline has been decided, add some padding as a safety net to your project. According to industry standards, every project should have about 20–30% extra time allocated to it. Saying your project won’t need it is hyper-optimistic, because every projects has its bumps in the road. Regardless, you will be happy you did it!

4. Insufficient Level of Detail

When planning out the project, it is important to provide enough detail to see all the tasks that need to be done. As you go along tasks will be added to the list; it is a given that things always come up. Maybe the project scope changes. Maybe a conflict between 2 processes occur. Plan out enough to uncover as many unknowns as you can, while not getting lost in looking for something that you can’t find.

5. Complexity

When considering the timeline for specific tasks, give each a complexity rating from 1 to 3. Depending on the score:

  • Tasks with a score of 1 should have their time allocation stay the same
  • Tasks with a score of 2 should have their time allocation multiplied by 1.5
  • Tasks with a score of 3 should have their time allocation multiplied by 2

6. Dunning-Kruger-Effect

Dunn-Kruger Graph
Dunn-Kruger Graph
Source: Reddit

At the start of anyone’s career, we are filled with confidence after gaining a little bit of knowledge. We believe we know enough to do tasks with ease, and end up overestimating our abilities. As we gain more experience in a field, there will come a time where we are exposed to so much we didn’t know, leaving us feeling lost and confused. After that point once we know what we don’t know, we begin to catch on and learn until we can accurately gauge our ability and make proper estimates.

The way to combat this lack of knowledge and inexperience is by asking someone who is experienced to join the planning. They can make better guesses at how long it will take someone based on that person’s experience to perform a task. And having another set of eyes doesn’t hurt either.

7. Skillset of the Implementor

When assigning tasks to people, consider their skill set. Try to match skill sets and accommodate for those who aren’t a good match by allocating more time to them.

8. Time-Off

To counter this, create a timeline with a calendar next to you. Let people add when they will be taking vacations and PTO, and add holidays to the calendar. If a project would take about 3 working days but there is a holiday in between, add an extra day to account for it. Your co-workers will also appreciate the extra time so they aren’t scrambling to get the job done.

9. Working Hours

When allocating time, it is safe to assume that a person will work for about 50–70% of their working hours, depending on the person. Architects, PM’s, and other people who are always in meetings will have even less time to focus on their work so be considerate when allocating time.


Nevertheless, these points will help make your life and the others involved much better. And if you still tend to over/underestimate yourself and your team, don’t stress too much! Remember, at the end of the day, estimates are just estimates. There are times it will be wrong, we just have to learn from them and accommodate as best we can.

I would like to thank my supervisor Anatoly Volkhover for his advice and insight in mentoring me on this topic.

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Gerry Saporito

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I don’t know where I’m going but I’m going.

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