The Nonprofit Website Insider

Issue 29: 🎯👕 Estimate work the T-shirt way

Practical strategies to estimate website work, plus why your 'quick fixes' are never actually quick (and what to do about it)

Hi website champions,

As we settle into the new year, you might be mapping out your website goals for the coming months. Start by estimating the work. By far the most common mistake when it comes to pretty much any project is being too ambitious about what you practically can take on. (Raise your hand if you've ever said 'Oh, that'll be quick' and found yourself still working on it three days later 🙋‍♀️)

Estimating work can be tricky, but it’s an essential skill—especially for all of us managing a nonprofit website with limited resources. Plus, successfully completing even a small project can energize you for everything else that needs to be done. Whether you're planning code updates, content revisions, or other improvements, having a clear process helps set realistic expectations and keeps projects running smoothly.

When combined with smart prioritization (as I mentioned in my tip about "The Prioritization Dance"), you'll have a data-driven approach to deciding what comes next. Stay tuned (or sign up for this eNews, if you aren’t already) for a specific process and template for defining what should be included in your project.

Here's how to estimate work more effectively, whether you're flying solo or working with a team:

1. Start with the One-Hour Rule

Even seemingly simple tasks—like updating a page or tweaking a graphic—take longer than you think. By the time you figure out precisely what needs to change, make the edits, proof them, get approval, and switch your focus to the next thing, you're looking at least half an hour. Add in any unexpected hiccups, and you're easily at 1-2 hours. Using this one-hour minimum as a rule of thumb helps prevent the common trap of underestimating multiple small tasks.

2. Use T-shirt sizes instead of exact hours

Precise time estimates can be tough for anyone to determine, especially if there are unknowns. Instead, use T-shirt sizes to estimate task scope. You can tailor how many hours each of these sizes equates to — but as a starting point, for a small project, you might use:

  • XS (Extra Small): Quick fixes, about 1-2 hours

  • S (Small): Half-day tasks, about 4 hours

  • M (Medium): Tasks spanning 1-2 days

  • L (Large): Week-long projects

  • XL (Extra Large): Projects of 2+ weeks (consider breaking these down into smaller chunks)

This method not only simplifies estimation but also works well with team members who might be reluctant to commit to specific timeframes.

3. Define a project by looking at priorities, then ballpark hours

Look at your available resources and set reasonable project boundaries. For example, if your writer can commit 8 hours per week for a month, then they (in theory) can do 24 hours of work total. Estimate each task at the high side of its T-shirt size range: like an XS is 1.75 hours, and a M is 1.75 days, or 14 hours.

Arrange tasks by priority until you've filled your time budget. Most importantly, run this plan by your team members—they know best what they can realistically accomplish.

4. Adjust as you go

Estimation is a skill, and you’ll get better over time. Track how long things take, so you can use it to estimate future tasks. One of the big advantages of having an estimate in advance is that it makes it clear whether your expectations are reasonable, so you can adjust for the future!

Armed with these estimation strategies, you're ready to tackle every project realistically—no more trying to squeeze XL goals into XS timelines.

Cheers to that,

Laura

Dive Deeper

Why a lot of developers don’t like estimating | Hybrid Hacker

Creating detailed estimates is both hard and time-consuming… so much so that some tech experts argue against doing it at all. But when should you estimate, and when should you skip it? This article offers a balanced perspective on project estimation from both engineering and management viewpoints—particularly valuable when you’re talking to the people who do your website development. 

Story Points, Fibonacci, and other ways to estimate complexity | Avion

Are you looking for ways to estimate more granularly than T-shirt sizes without putting actual hours and days on tasks? There’s other well established ways to think about this issue, and yes, they do include the Fibonacci sequence and poker. (I promise this isn't just an elaborate excuse to play cards at work.)