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)