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Let’s continue exploring overworking:  Over the last several weeks, I’ve talked bout the habit of overworking, talked about email, the action of overwhelming,  and wastefully lamenting being busy.

This week I want to discuss how poor estimating can result in overworking.

We make five common mistakes when estimating how long something will take. Today, I’ll give you ten questions to ask that will fix them.

Humans are notoriously terrible at estimating how long work will take to complete.

REALLY AWFUL AT IT.  We’re wrong all the time. 

Don’t believe me? Well. Did you ever make a really ambitious weekend to-do list and then accomplish less than half of it because you ran out of time?  Or did you procrastinate starting something you thought would take forever, only to surprise yourself and finish it quickly? You are not alone in this.

Poor estimates greatly contribute to overworking because we make commitments and then have trouble keeping them because we underestimated the work.  

Five mistakes people make when estimating.

  1. Avoiding: We avoid making commitments. “I’m not sure; let me get back to you.”  
  2. Speeding: We rush to give an estimate without thinking it through.  “Sure, I’ll do that today.” 
  3. Pleasing:  We want to please other people, so we estimate based on what they want to hear. “You need it by the end of the day tomorrow? I can do that.”
  4. Overwhelming:  We let overwhelm cause us to assume that every new request is “hard” no matter what it is.  Every ask is estimated as “too much.”
  5. Guessing:  We create estimates with bad or incomplete information.  

These five mistakes create chaos in our lives and make it much more difficult to keep our commitments. So, to avoid those mistakes, here are ten questions to ask yourself that will help you create spot-on estimates.

For every estimate you create, I want you to ask yourself ten questions. It might seem like a lot, but it’s not as hard as it sounds.

I’ll show you how these questions help you by using an example: “How long will it take you to travel to New York City?”

  1. What is the requestor expecting?  You need to know if you are being asked how long it takes in general, if you are being asked when you will get there, or whether you can get there by 5 pm on May 1st to attend a scheduled event. Those are different questions. So find out what the requestor is expecting before you give an estimate.
  2. What are you estimating?  You need to decide where the estimate starts and stops.  Is it just the time in the car?  Or the time to get ready, pack, shower, fill the gas tank, stop for snacks, find parking, and walk to your destination? Make sure you know the whole scope.
  3. What do you already know?  Look at what you know already.  You live N miles from New York.  Rush hour is a thing.  Parking takes a while to find.
  4. Where are you starting?  If you are starting from the middle of Connecticut, you will have a different estimate than traveling from L.A.
  5. What tools do you have or need?  You might need a car, a train, money, taxis, a specific parking garage, a specific budget, and the ability to walk at a certain pace.
  6. What else is going on?   Rush hour traffic.  Needing to get the kids ready and in the car.  A currently empty gas tank.  Four other commitments on May 1st.
  7. Are you dependent on others?  Is the whole family going or just you?  Can the kids walk as fast as you?  Do you need to pick up a friend?
  8. How does this compare to work you have experience with already?  Have you ever made the trip before?  How long did it take then?
  9. What is different about this time?  Are some roads closed?  Is there construction on your route you need to consider?
  10. Do you still need more information?  If you still need more information, then keep asking questions, or add time to your estimate to discuss and answer them.  i.e. Do you have the address you are going to, and is there available parking there?

Do you see how asking these ten key questions will enable you to make an excellent estimate?  They will also enable you to make very good decisions about what to say yes to and what to say no to.  

Don’t fall into the trap of thinking that answering these ten questions will take too long. That will result in the mistakes of avoiding, speeding or guessing. ‘

In my experience, most of the time, you can answer all ten of them in 5 minutes or less.


At least, that’s my estimate.

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