Defensive estimations and time management

This post is part of my mentoring conversation series which includes relatively short posts on topics that have come from a mentoring session. Often, these conversations produce insights which could benefit a wider audience.
Any identifying information is removed and I always inform participants before posting anything we talked about.

In today’s mentoring session we’re dealing with a manager who doesn’t trust task estimations and asks to reduce them, resulting in stress and overtime. Add to that a feeling that you’re not keeping up with the tasks you’ve committed to completing… This is, of course, not the healthiest environment, but unfortunately, still quite common.

Photo by Tima Miroshnichenko from Pexels

Defensive task estimations

So, under the assumption that this organization chooses to give task time estimations (not obvious) and under the assumptions that everyone is terrible at it (including you) and your manager is undercutting the estimates you give, here’s what you can do:

  1. Break the project into tiny tasks. Tiny tiny tiny. Smaller than that. Each task should have a clear definition of done.
  2. Give each tiny task an estimation. No tasks should take less than 2 hours, no task should take more than 2 days, 3 if you must.
  3. Sum all of that up and add 20% buffer.
  4. Add on-call duty, time off, holidays etc.
  5. Add another buffer for customer bugs and unplanned interruptions and delays.

(Some of this is just good task definition and management, but the level of detail and having to explicitly state things like holidays which should be obvious is the defensive part)

At this point this type of manager will say “that’s too much”. Now you can ask: “OK, then what do you want to cut from the project?”. If you’d given an estimate for the project as a whole, or week-long tasks, it would be easy to say “cut the time in half” or “this task shouldn’t take a whole week”, but with such a detailed plan it would be tough to say “this task should only be 6 hours instead of 8”, and since they want “this” done they won’t really be able to cut individual tasks. So they’re going to try to cut time from your 20% buffer. That’s annoying, but there’s not much you can do about it. Next time don’t include a buffer, just add 20% to each task. Your manager has shown their judgement can’t be trusted.

They may try to cut the bugs and unplanned interruptions and delays as well, just make sure you tell them that if you don’t plan for those they will happen anyway and you’ll have to prioritize them as they occur. That’s fine (and actually, the way it should be).

Make sure your plan is recorded and it’s very clear what the manager changed.

As you work, be sure to keep your manager updated on how things are going relative to the plan and exactly what’s causing delays. This is a good practice in general to keep your manager in the loop, but it’s even more important in a low trust situation like this.

You may still fail to deliver “on time”, but you’ve laid down the groundwork to show that you did your absolute best. Hopefully, you’ll be able to show your manager that the buffer was necessary and where the delays happened and move one step closer to convincing them that you can’t just cut time estimations and have the work magically be done.

This might be a good place to stop and say that if this relationship does not improve and there is no immediate reason to stay in such a work situation, you can also consider switching to a different manager or workplace where there is more trust and less need for defensiveness.

Time management

I’m guessing that under such a stressful environment a lot of mental bandwidth is being wasted on your mind buzzing with “not enough” – not getting enough done, not working fast enough, not good enough. Just that part is going to ruin any chance of productivity. This could be the case even if your work environment is fine, but you’re suffering from some form of imposter syndrome.

So, first of all – it’s possible that all of that “not enough” feeling is in your head. If you can get some real feedback on your performance – get it. You might be doing just fine. If you get positive feedback and everyone’s happy with you – try to let it go. You’re enough.

If you can’t get quality feedback at all, are told you need to improve, or can’t accept that you are enough, there are still things you can do to improve your experiences.

I recommend documenting everything you do for a week or two. You can do it every hour, or if you can manage every 15-20 minutes – that’s great. Document what you’ve done in the past period of time, but also how you felt. Were you in flow? Did you feel productive? Were you interrupted? Couldn’t concentrate? I admit, this is not an easy task, but it’s for a short time, so I believe it’s worth the effort.

Now that you have a log of what you did and how you felt, you can identify common themes, which tasks and work environments work for you and which don’t, which hours of the day you feel more productive etc.

If you’re more productive in the morning, but are used to starting at 11AM – try adjusting your work hours. If you have trouble concentrating in the office – try to find a quiet corner or work more from home. If there are tasks you hate doing – try to get them out of the way quickly so they don’t sit in the back of your mind ruining everything else. Figure out a strategy that works for you, get support from your manager or colleagues if you can get it.

I think even a small improvement in your subjective feeling at work can create a virtuous cycle which will improve your overall wellbeing and productivity.

I hope that was helpful!