A friend of mine (let's call him Jim), asked me for advice on an tricky situation where I'm not sure how to handle it either. So maybe one of you can help how to approach it.

Jim actually is working in a young company. The product is still in development so it is important for them to finalize the product as soon as possible. They make team meetings on daily base (he was saying something about scrum but that it is anyway totally diferent... what ever...), but "recently" he got asigned a project (a standalone application) where his progress isn't that easy to track. After he noticed that, his motivation to focus on work got lost over time. He feels uncomfortable with that situation but is lacking of self-discipline to force himself to make his job as long their is enough time left1.

The 2 main problems for Jim, he told me and I was aggreeing are:

  • No given milestones, just a requirement, and when it has to be accomplished.

  • No consequences of missing the deadline.

Also he told me about his previous 2 week deadline which he missed, that when he had the timepressure he felt like beeing very productive and focused.

But his boss rarely gives strict deadlines, and even if he does, his boss handles the deadline more like asking for a favour, than ordering it.

So now to the question he came up with:

Since he really likes working for the company and the working conditions are verry enjoyable, he neither wants to risk loosing his job nor intends to passively damage the company as he actually does.

He wants to bring this up to his boss, and ask him for more modular assignments connected with tighter(at least any) deadlines and asked me how to approach this.

I couldn't help him out, since I wasn't even sure this is something he should bring up, but try to find a way to handle it himself (what he explained is hard for him).

So, should Jim bring this up to his boss? And if so, how he'd best approach it, that it doesn't sound like "Now I want to start doing my job, can you help me boss?" ?

1He told me, the last assignment before this big project he had 2 weeks to finish a assignment but made it within less then 2 days (while just 1 day was left; deadline was missed, but this had no consequences at all)

3 Answers 3


Why not just propose his own deadlines? If there's no pressure to hit them that's even better, but if he can say

Hey boss, you've asked me to do X. I think sensible milestones to achieve it are A, B, C and I think I can deliver them on these dates.

and then he can practice hitting his own deadlines. This also gives him opportunities to practice estimation and communication: the really important thing about missing deadlines is that you identify you're going to miss it as early as possible and communicate that upwards, so that between you you can work out steps to either correct what's going on and hit the deadline or mitigate the impact of missing it.

So worst case he gets to learn all of this in a pressure-free environment, and best case he gets a reputation for being reliable and easy to manage (which bosses like). The issue is if this isn't enough of an external stick to overcome his self-discipline problems, but it seems safer to try and tackle that himself without deliberately risking his own job in the process. And there are better ways to solve self-motivation problems!

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    It's something he'll just have to learn, to be honest. Going to his manager/boss and saying "I'm supposedly an adult, but I've never learnt how to motivate myself to do tasks that I know need to be done in order to complete them on time, so can you micromanage me to the point where you're breaking down larger assignments into individual steps and giving me a strict deadline for each one, please?" isn't going to end favourably for him, I imagine. There's no way to word it that doesn't say that, either, as far as I can see. Commented Apr 21, 2016 at 13:52

So basically he wants deadlines enforced to motivate him to work? In the daily meetings, he could say to his manager, "I'll have such and such module / functionality / whatever done by Friday" (Setting realistic time-frames of course).

Even if the boss isn't too put out by him missing this, the risk of embarrassment of having to admit he didn't do what he said he'd do might motivate him to treat it as a proper deadline.

Also, use a spreadsheet - divide the project into tasks and assign his own deadlines. Never underestimate the psychogical power of having tasks highlighted in Green and not Red on a spreadsheet! ;)


This has nothing to do with his tasks and it's not something he should expect his boss to fix for him.

He has identified a personal weakness, now he needs to strengthen himself in that area. No one can hold his hand to do this or he will just lapse back in to apathy as soon as they let go. There's many many ways he can do it, but mostly boils down to how he manages his time.

One way is just make a short list of mini deadlines for himself

Accomplish XX by Tuesday Accomplish YY by Friday

and hold himself accountable if he doesn't produce. Anything like this takes time to rectify but is easy enough. Find whatever works, Consciously adhere to it and soon enough it becomes second nature, like doing scales on a guitar.

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