Want to make your job, life, and small business better?

Learn the the incredible super power that almost no one teaches you, mostly because it looks boring and involves spreadsheets: Project Estimation

Mhhmm…Convince me.

You probably want to, and know it would be great to, have more time back in your life. I bet you would be less stressed knowing you had enough time to do your best work, knowing that you can honor your commitments. You’d probably find your creativity sparked by figuring out how to fit your ideas into real world constraints. How are you going to make that happen? Many people would turn to their fortune tellers, crystal balls, or hold their finger up into the wind, thinking to themselves that these are just as likely to provide insight as anything else. However...there is another way… a way you can make happen routinely and on demand. This powerful magic is called project estimation and I’m going to show you how to harness it! (And I promise you that despite the dull coat of paint on the name this an amazing skill worth building.)

The super powers you shall have

Project estimation, sadly named, and hitched to a number driven, spreadsheet filled “awhh man do I have to do this" wagon, when done right imbues you with these extraordinary oracular powers:

1. An easy to do, structured, standardized process for exploring ideas and translating them into practical projects, while also acting as a thought partner that identifies not just the top level work you need to do, but the often overlooked secondary work you need to perform as foundation or support to the main effort.
2. A framework that allows you to easily compare things you’ve completed successfully to ideas and plans for things you haven’t even started
3. A shortcut for quickly eyeballing a problem and getting a ballpark sense of effort and complexity
4. A magnifying glass that highlights where automation, process improvement, and efficiency gains will actually make your job easier, your projects more profitable, and your quality of life better.
5. A magical recipe for creating proposals written by AI that aren’t garbage and full of risk & inaccuracy.
6. A little helpful assistant that remembers all your good ideas, the hard knocks lessons you’ve learned, and reminds you to always eat your vegetables. (In a project sense… =)

Ok late night informercial guy, how does project estimation give me these things?

The magic happens in two places, and this is actually one of the reasons that a lot of software/online sites that offer “estimation calculators” and features fail, and another reason why most people never realize the real power and value of estimation.

Making your next idea or project more successful

The first major spell is that project estimation helps you organize and think through a project in a way that helps you prioritize your efforts, provides timeboxes for you to design solutions to fit into, and helps you remember and include all the little details that are important to a quality result. Pretty much 99% of the conversation around project estimation focuses on these benefits. They’re great, but they’re only part of what you COULD be achieving.

The other thing that is often overlooked here, is that if you are engaged in selling your work to others, and hey this is an article on LinkedIn so I’m guessing chances are high, is that these project estimates let you have much more informed discussions with your prospective clients about why you think certain work is complex or time consuming, the assumptions you are making that they might not be, and allow for faster scope/feature trading with those same clients.

For small businesses and freelancers these estimates offer another big benefit. With a well crafted prompt and a “pro” ChatGPT/ClaudeAI account or what not you can quickly turn these estimates into a useful draft of a proposal. Try something along the lines of “take this spreadsheet which is a project estimate for a project with column A having the name of the task and column B having a description of the task, and column c having the estimated time for the task and draft a project proposal for a client based off of it. Each task in the proposal should be designed to fit into the available time for that task in the spreadsheet. Each task should have a description of how it's important to the project, and where appropriate where it provides value to the client.” You’ll need to do some editing of both this prompt and the resulting document, but WOW will you suddenly have a lot of good stuff to work with.

Making all your future ideas and projects more successful

This second aracana and impressive power comes from revisiting your project estimate after each project completes, and then from browsing through them before you estimate your next project. This is because at the end of each project you’ll plug in your best understanding of your “actual” effort against each estimated effort. This helps you see very quickly what the connection is between your current ability to estimate work, and the actual effort required to succeed. This information is invaluable for you to improve your approach, uncover hidden work, and makes all of your future estimates more accurate as you gain wisdom and feedback.

During this process you’ll identify incorrect assumptions you had while estimating, risk factors or “gotchas” that you can flag for investigation in future projects, and start to develop data-driven baselines for different activities. (It turns out it always takes me about 3 hours to write these articles for example…) The other thing you will do is to “tag” each estimate with the kind of project it turned out to be. This will vary from wedding planners to website designers, but you’ll start to figure out what your different categories of projects are, and which ones are the simple, regular, and complex ones.

These reviews will also highlight parts of your process that are time consuming, but maybe you could make them more automated, more efficient, or create templates or checklists to make go faster. You’ll also see the areas where your estimates vs actuals are wildly off, these highlight areas where your understanding of the work before the project wasn’t clear. That can be for a variety of reasons, but you should highlight and note these so when they come back in a future project you’re prepared. Finally, you’ll also see tasks you thought you would do in the estimate, but you didn’t actually need to do, or you got them done in the course of other work within the project.

All these learnings should be plowed back into your project estimation starter-template. This allows you to capture things like “average design review meeting with client takes 30m prep, 30m meeting, 30 minute followup with client” and to add in things like “this activity has a lot of risk & uncertainty in it” and even bigger approach stuff like “we should always hire a freelancer to do X activity, average cost is $100/hr.”

Then the next time you are planning a project you do these things:

1. You quickly and easily use your tags to find near neighbor / “look alike” projects from your library of estimates and you can use that as either a cut & paste or starting point estimate for work, letting you easily ballpark the project size & complexity.
2. You copy paste that estimate into your current (and thus best) copy of the project estimation starter-template so that you can update any baselines, assumptions, or evolutions of your process to this estimate. (Especially useful as your project-estimate library ages, and for those occasional project types that pop up once in a while.)

There will be a sudden drop in the effort and time it takes you to make these estimates, and that will be matched by an increase in confidence in your ability to do the work, and the quality of the product that will come out. And all that just from a little filing and cleanup. Wow!

Getting started

A quick google for “project estimation” will quickly send you into a briar patch of thorns and wrong turns. This is because project estimation is often presented as a fancy calculator where you just plug some stuff in and you get a number back, and you are done. To get started just break out your trusty spreadsheet! For most people and most businesses there is way more value in owning and operating your own spreadsheet template than from using any of the software tools for estimating. (At least for the first year or two.)

Create a list of all the things you want to do. After you get it all in there, organize this list based on order of operations, what do you need to do first, to make the second thing easier / more successful?

1. Go through each item in the list and think to yourself: What Q/A, editing, review will I want for this item, if any? Add those elements to your list, coordinating with others can eat up some time.
2. Then go through the list one more time and think to yourself “will I need to present any of this work or create documentation for any of this work for myself or others? If so, add those things to the list too, the documentation of stuff is often a hidden time sync in projects.
3. Finally, go back through the list and think about any other people you’ll need to coordinate with, sub-contract to, or liaison with. Add tasks for this to the list too, and note any “hard costs” associated with them as well. (Bob the catering/baker services guy charges $500/project, for example)

Ok, you’ve got an awesome project plan sketched out here, let’s add in some of your expertise:

1. Beside each task assess how critical it is the project to succeed "Vital" "Necessary, but flexible" "nice to have"
2. Beside each task add in your best guess as to what the “likely time it will take” is as your “low” time/effort guess. Then think about a moderately bad scenario/harder/complex version of that task and put in your guess as a “high” time/effort guess. (For example: Washing your car could take 15 minutes at the automated car wash place that you usually go to, but if you really wanted it nice you might do it by hand, and it might take you 75 minutes.)

Next steps:

1. Go for a walk or do something else for 30 minutes. Then come back and read through your estimate, ohh wow suddenly stuff pops out at you to add, adjust, refine. Yay!
2. Generate some proposal language for your project using an AI tool, or ask it to summarize the project for you if you want to shoot the estimate over to someone in an email.
3. If you use a task management system, marry up your estimated tasks to that system. (Warning this can be a whole topic/area of discussion, but generally try and make it easier for yourself to do future analysis of actual effort vs estimated effort)
4. Pop your estimate into your folder/category organization system so you can easily compare it to peer projects, and find it later for use as a fast copy/paste start for future estimates.

Whew! All done! Glory and super powers await! Trust me, this all gets pretty easy and routine after 3-4 estimates. Way easier than learning French, but still I know it is a lot, persevere and you shall be rewarded. (And a small plug for my own professional coaching practice here, if you want some hands-on coaching and moral support, reach out!)

A starter template for yah

I recommend tailoring this template to your exact business needs, but hopefully it helps get you started and lowers the intimidation factor of “making your own estimation engine in a spreadsheet.” But hey, feel free to use it however you like, please just keep me credited in it somehow and maybe send some business my way.

Get your copy of this estimation template here: https://docs.google.com/spreadsheets/d/1kIbxl99kODtSSUMVagTSoBWeT0W6sIiQJs3N-vEisAo/edit?usp=sharing

Next Level Powers

While we’ve covered a lot, there are a number of areas we haven’t had time to explore. I help teach these other areas in my one on one coaching practice, and perhaps might pen blog posts on the following subjects in the future. However here are some of the kinds of things you should be thinking about after you master the basics of estimation.

• The magic of converting project estimates into achievable, risk managed project schedules.
• Using “similar to” and “like for like” previous estimates to get quick estimates
• Schedule based estimates, time boxing your work and when it’s effective
• Estimating projects with multiple, related phases
• Managing project risk and its relationship to high & low cost estimates of work

Should I get fancy and what about X kind of estimating?

TL;DR: No.

The various mathematical approaches to estimating have been thoroughly investigated by researchers, and the fancier methods are of vital importance in some industries such as construction. However, there is a whole world of approaches to the project estimation process, most of which you can safely save for later in your project estimation journey. For example try googling “three point estimation” or reading about Program Evaluation and Review Technique (PERT) , a fancy method developed by the US Navy in the 1950s. These are all well and good, and do offer some statistical and psychological advantages, but like all things there is a direct relationship between the “accuracy” benefit of these advanced techniques and the “effort required” to create these estimates by you, the person in the room.

The reality is that all of these fancier techniques still rely on the domain experience of the estimator, and of the comfort and practice of the estimator in creating estimates. They all also expect you to use a feedback loop. So the long and short of it is that you’ll get most of the benefit of this practice by starting simple and then keeping it simple as long as you can. If you find yourself estimating extremely costly or important things, consider investing some time into this fun world of statistics. Also, most of these fancier techniques have online templates & calculators for them, if you are ready for your blackbelt in estimation, or somehow you make this your full time job. =) And I will say that the math on the three-point estimating technique is very compelling.

References:

Love these folk’s coverage of project management stuff, even if it is a little dry. The PERT graphic is from them: https://project-management.info/three-point-estimating-pert/