As a person, I have been brought up in a family to have very high ambitions and been pushed to constantly strive and to reach a certain level of achievements. Not in an extremely pressurized way but more of a 'leave all your doors open type of way' for example my parents would always say:

"It doesn't matter if you don't know what you want to do when you grow up, as long as you get straight A's you can do whatever you want."

As a teenager I would find it puzzling when I came across some of my peers that seemed to lack any drive or ambitions. I have fortunately known what I wanted to do since I was 16 years old and have been striving towards that career since then. I would meet these kind of people and over and over ask them:

"Come on, you must know what you want to do when you grow up or what you want to study at university?!"

I am very detailed organised in  combination with my ambitions. I find more and more as I go on in life that not everyone is wired like this. Situations where I try and learn to do better:

Situation 1
A friend and I sit in a pub, he tells me that he wants to start running an open mic night at a venue. Before I know it I have spent 30 minutes doing check lists on napkins and structured up the whole venture. You have to know that I used to run my own nightclub events and he has brought this up to ask for help. I leave him with the list and every once a while query him in regards to his open mic night - nothing ever materialises.

Improvement 1
A friend tells me that he is going to raise a quite large number of pounds (£) to cycle to Australia from the UK, in 2 years time. I bit my lip and listen to the story. I do not draw any diagrams or write any check lists on any napkins. However, I break down and gently asks if he has factored in for injuries in his budget - turns out he hadn't.

Situation 2
I will tend to get very frustrated (internally) towards people at work - who doesn't not have my sense of detail focus. I recently had to take over a half-finished project - hunting down 3rd party companies we work with and asking all sorts of detailed questions because the person before me either did not ask them or did not communicate this information to me clearly. I have a feeling that no matter how politely you phrase the email people will still act slightly defensively - especially when you are questioning them in regards to work that has already been done.

Improvement 2
This is very much a work in progress for me still. So far I have found out that:
- Yes you can try and phrase the emails more politely - use lots of positive adjectives where appropriate
- Don't ask all of questions the same email
-  Use as few questions marks (?) as possible in the email
- Try and remove any accusing undertones from the email