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How To Accurately Estimate Your Tasks and Projects

This article was based on episode 137 of The Modern Manager podcast. To hear this episode, and many more like it, you can subscribe to The Modern Manager Podcast on iTunes, Google Play, Spotify, iHeart Radio, Amazon, and Stitcher. Get 15% off coaching with Jessica Katz when you become a member at

Question: How long will it take you to make a peanut butter and jelly sandwich? If you’ve made dozens (if not hundreds) of these throughout your life like I have, you’ll probably estimate fairly accurately. This is because the task is straightforward and you’ve had plenty of experience to draw upon. Unfortunately, much of our work these days is less like making a peanut butter and jelly sandwich and more like preparing a Thanksgiving feast for your entire family who won’t commit to a meal time or communicate their latest dietary restrictions.

If you primarily engage in knowledge work, whether running a team, writing blog posts, or making sales, chances are your time estimates for tasks will be wildly off. As Jessica Katz explains, there’s a painful gap between what people think they can accomplish and what actually gets done. In Jessica’s work providing Agile coaching and change management to organizations, she’s seen how much friction poor estimations cause. Jessica shares advice on how to hone our guessing abilities in order to create reasonable plans that can actually guide us effectively..


If you’re bad at time management estimates, you’re not alone. It’s something we all struggle with because of how we’re wired as human beings. One reason is the planning fallacy; we don't take into account all the things that need to be done. We assume we have a complete picture of the work and therefore estimate only those activities without recognizing how much we’ll learn along the way. A second reason is our optimism bias; we generally assume things are going to work out wonderfully. We don’t take into account problems and issues that will arise, causing delays or additional work to be done. Combined, these two cognitive functions lead us to severely underestimate the time any given task or project will take.


The good news is that estimating task time is a skill anyone can develop.To help improve your projection accuracy, Jessica recommends the following approaches.

1. Break tasks down to their smallest reasonable action.

The smaller the task, the more accurate your estimate will be. Break down larger tasks to the smallest action that still has value. For example, the smallest task for a customer service worker may be to just understand the customer’s problem. The smallest task for a sales rep may be to make one outreach phone call.

2. Estimate the amount of time each task will take.

Now that you have a series of smaller tasks, estimate the time for each. To get a picture of the full scope of work, add up these times. For fun, you can compare this compiled estimate with your original projection of the full task to see how off you were.

3. Build empirical data by tracking actual time against projections.

To become even more accurate and efficient, keep track of your times in a simple spreadsheet. Make note of how long an action takes and compare it to your initial guess. Given that most tasks will vary given different circumstances, Jessica suggests tracking a task multiple times to get a range of actuals which can be used to find an average.

4. Block out actual time.

Decide based on your data how much time is reasonable to spend on a task. Then, block off time on your calendar to accomplish that work and do best to hold yourself to that time allotment.


Now that you have all of the data and time estimates, you’re probably itching to get a plan in place. However, Jessica urges organizations to treat their plans loosely. As she puts it, “A plan is just a lie that we're all agreeing to for the time being.” She sees too many organizations get “Plan Focused” instead of “Outcome Focused.” Instead of focusing on the dates, focus on what you’re trying to achieve and adjust the plan as you go along. Jessica offers additional guidelines for your team as you go about forming a plan:

  1. Allow For Experimentation. Don’t put pressure on your team to come up with a new idea and deliver it perfectly. Give them room to test their ideas and learn along the way in order to improve their plan.

  2. Adjust For Context Changes. Life happens. Global pandemics happen. As the team leader, look for the balance of viability (does this continue to make good business sense?), desirability (will our customers want this?), and feasibility (is this actually possible to deliver) in order to determine if you should change directions. If your context changes, your team can pause and decide if a new plan is needed.

  3. Review Your Plan Frequently. Jessica swears by having team review meetings every 2- 4 weeks to reexamine your plan and what’s been accomplished. Frequent meetings will also increase a sense of responsibility.


Our awful estimation abilities are one contributor to high stress levels at work. Having unreasonable or uncertain expectations is a recipe for frustration. Managers can help their teams take the guesswork out of their time management habits. Track your activities, build empirical data, and determine the average amount of time a task should take. Build a plan from this information, but keep your plans flexible. By using these methods in collaboration with your team, you lead your employees to create sustainable, methodical work practices that yield great results.





Get 15% off coaching with Jessica Katz when you become a member of the Modern Manager community at Purchase individual episode guides at to help you implement the learnings and continue to enhance your rockstar manager skills.

This article was based on episode 137 of The Modern Manager podcast. To hear this episode, and many more like it, you can subscribe to The Modern Manager Podcast on iTunes, Google Play, Spotify, iHeart Radio, Amazon, and Stitcher. Never miss a worksheet, episode or article: subscribe to Mamie’s newsletter.




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