A friend of mine is the CEO of his own small business. We’re not very close friends, but we know each other well enough to have visited each other’s houses for dinner and drinks a few times.

His business is advertising a role which interests me. I have suitable skills for this role but limited experience, so it’s likely to get better candidates than I – at least on paper. It is reporting to one of his subordinates, and I have no idea how much (if any) input my friend might have into the recruiting process.

I would like to apply for this job but I don’t want to cause problems for my friend, nor to have our friendship unduly influence the recruiting process. I have not yet spoken to my friend about it because doing so would certainly result in the latter outcome.

They work in quite a small office. There is a strong chance that, were I to manage to get to the interview stage anonymously, my friend would see me when I arrived. But I also know he’s out of the office a lot.

How should I proceed? I am happy to consider that “not proceeding” may be the best course of action here, especially given that I may well not get the job.

I am trying to find/change my career trajectory. Its a good cozy job, but I want something that I get excited to work on in the morning. Career change is hard, for a lot of reasons. So I cant just try out a lot of different careers, and need to be more methodical in finding out the ideal fit.

have a general idea of the direction I want to go in. However, I think a lot of my decisions have been made under peer pressure or expectations of other people. I am looking for somebody who can provide me an objective assessment of my strengths and weaknesses, and to move towards a career which relies more on my strengths and innate (unconscious) drivers. There are millions of coaches online.. and it seems everybody these days wants to become a coach. So I am wondering how to find a reliable coach who will get you to where you want to get to?

What do you look for when searching for a career coach and how do you determine whether it’s beneficial?

I’m 6 months into a new job that uses a technology I’ve had no experience in (but am trying really hard to learn). Often I get tasks that I have real difficulty with. I flag this: I say that I’ve never done that before and I’ll have difficulty. I get some help, but the task always takes way longer than estimated and is done pretty badly. This puts me under a huge amount of stress and is embarrassing as my tasks often get rejected at QA.

I’m all for learning but its just too much. I need to master things incrementally, not all at once. Or else do a proper course on the subject.

How can I talk to my boss about this without looking like I’m useless or backing away from challenges?