Manage your Deadlines so they can’t Manage you
You’ve read my article about Deadlines and Estimates, and you’re saying “well that’s all well and good if you’re a manager, but my boss keeps giving me shit to do and asking for an estimate”.
What a great question! Well, kind of a question. A statement that implies a question.
I’m going to let you know what I advise people to do. But, fair warning, it’s not the most typical advice. There’s nothing about working harder, better, more focussed or with better prioritisation. Instead, it’s about how to manage the negative impact of deadlines to make you feel safer and happier. The good news is, both of those things will make you perform better as well.
The Overall Plan
We’ve already discussed how deadlines and estimates are bad, but sometimes you don’t control them. Our plan is simple, try to remove the deadline, then try to reduce the harm of the deadline and finally, if all else fails, learn to accept the deadline.
Step 1 - Try to remove the deadline
You’ve got a deadline. That sucks. Let’s get rid of it!
We should make sure this deadline is not a result of miscommunication. Who gave you the deadline (sometimes it was yourself)? What is the deadline? Message them to confirm that your understanding is that <thing> needs to happen by <time>. If that was a miscommunication, then we’re done!
If there’s no miscommunication, then what is the damage done by missing the deadline? Ask the person who gave it to you. “Hey, to help with my prioritisation, what happens if we’re late on this?”. If nothing bad happens if you miss it, is it really a deadline?
After this, sometimes the deadline still remains. Onwards! To step 2.
Step 2 - Reduce the harm of the deadline
We went through a few tools from a more managerial point of view in Deadlines and Estimates. But these tools can also be used in the reverse.
Avoid giving estimates or agreeing to timelines with certainty. Provide probabilities.
How long will this take?
I’m 50/50 by the end of the week, but 90% sure we can get it done in 3.
You can’t guarantee 100% uptime, and you can’t 100% guarantee delivering work. Make that clear.
And then update your probabilities as you go. If you have a slow week, things get longer. If you have a super productive week and find out a lot more about the project, things probably get shorter and more confident. Always give the best, most accurate estimate you can. That means timeframe and probabilities using the most up to date information you have. Don’t feel bad for changing what you originally said - you know more now.
If someone gives you a deadline, tell them your estimate of probability up front.
I need this ready in a month
Ok, I’ll try my best, but it’s a big ask. I’m only about 20% confident we’ll manage that.
If someone insists that this is a 100%, no fail deadline, then we talk about scope.
This absolutely has to be delivered by EOY or the regulators are going to sue the crap out of us
Yeah, that does sound important. What’s the precise thing the regulators require? I want to make sure we’re hitting the deadline by avoiding building anything unnecessary.
All of these should work on a reasonable manager, but not all managers are reasonable. So then we are left with 1 option.
Step 3 - Accept the deadline
Once we’re in this stage, you’re in the realm of silly companies and bad managers. The deadline is created to make you feel bad about yourself. To create fear and negative self-image to push you into doing something. The deadline is just some words or a line in a spreadsheet. The feelings they generate though: those can hurt. Sometimes they don’t, and sometimes it feels silly to feel so stressed about something you feel should be simple. But deadlines are designed to trigger negative emotions in you, it’s not your fault for feeling them.
If we can seperate the deadline from our feelings about the deadline, the situation becomes much more manageable. This is a challenging skill, but like any skill, it gets easier with practice. Here are some prompts to get you started. Some might work for you, some definitely won’t. Maybe you’ll invent your own. I’d love to hear about them!
Write down the deadline. Stare at it. Think about the individual drops of ink on the page, or the pixels that make up the characters on the screen. How does the room you’re in smell? What’s the quality of the light? What do the shape of the letters remind you of?
Think about the 3 most important things in your life. How would missing the deadline affect those?
What would happen if you missed the deadline? Then what? Then what? Then what?
Explain to your manager that you’ll give it your best shot, but you can’t promise anything.
Ask someone to just listen to you and not try to solve your problem, then tell them how you feel about this deadline.
Write down how you feel about the deadline
Print off a 100,000 copies of Deadlines and Estimates and fill your managers car with them (maybe don’t do this one)
Do something that makes you happy outside of work, and remind yourself you can still do this whether you hit the deadline or not
Wrapping it up
Hopefully this helps you feel better about deadlines you have, and so be more effective (because happy people do a better job).
If it doesn’t, feel free to let me know or maybe ask follow up questions in the comments below or directly. I’d love to help more if this doesn’t work for you.
