One thing just occurred to me: the most successful estimation exercise I've gone through so far actually involved me pair-estimating a project with my manager.

One thing just occurred to me: the most successful estimation exercise I've gone through so far actually involved me pair-estimating a project with my manager. I think this is generalizable: If you aren't sure how to do an estimate, the steps are: 0) Stand up straight and chamber your courage in order to be honest responding to the person who just asked you for an estimate. 1) Say: "I don't know how to produce estimates. I'm going to get a more senior engineer to pair with me on breaking down a project and producing an estimate for you." 2) Email your team lead about who would be a good person to sit down with you and go through the process of estimating the task. Tell her that you are going to do #3 Say you are looking to both answers the question you were asked and to talk you through the thought process so that you can learn to be good at producing useful estimates. Book like 30 minutes in the senior engineer's calendar. 3) Write your own draft where you first take the definition-of-done and make sure it is clear, then you turn the task into bullet points of what you can think of are the subcomponents of it. Don't produce times yet. 4) When you have the meeting with the senior engineer, be clear that you want to learn the thought process. If they say "I just go with my gut and multiply by 3" then say something about how their years of experience with estimates allows their intuition to be highly trained, but you need a more rigorous process to follow until your gut is similarly well-trained. (tip: read Thinking Fast and Slow) Ask if they can use their experience to help you think through your breakdown, spot missing subtasks, and put numbers on things. I've not actually tried steps #1 and #2, but I have done steps #3 then #4 together and they worked well. ======= If you think you'll get pushback on the idea of taking some time to go away and do the estimate, imagine yourself calling up an auto mechanic and saying "Hey, my 2010 Peugeot Ion is making a noise like a coffee grinder when I accelerate. Can you give me a quote for how much that costs to fix?" Then imagine refusing to let them take a look at it before they give you a quote.