ASK HR: Is there a good or bad way to resign from a job?

Q. I have a friendly relationship with my boss but not close enough to tell him that I am job hunting. When I finally present my resignation letter, I know that he will ask why I didn’t tell him beforehand. How do I prepare for this conversation?

Bosses might be surprised by the timing and reasons of a team member’s resignation, but rarely the possibility of it, unless they are deluded, since there will always be a proportion of employees who may not achieve their desired career trajectory by way of a prolonged stay with one organisation.

Few organisations could claim to hold exclusive custody of all their employees’ career aspirations, one way or the other, external career moves are bound to take place.
You seem certain about how your boss would react if you were to resign. What informs the apparent trepidation at the thought of having to explain your resignation?

Early timing of letting your job hunting efforts out of the bag would usually be driven by the nature of the relationship between you and your boss, otherwise you are expected to announce your resignation in accordance with the terms of your employment contract. How long have you been in your current role? Have you spoken to your boss about your career aspirations and how you are experiencing your job? Are you chasing your career aspirations through job hunting or running away from undesirable experiences?
Unless the relationship with your boss is sour and you are certain that the kind of opportunities you seek are unavailable at your current workplace, nothing should stop you from sharing your view about your current job with him, perhaps during a performance review session.

The chances of your boss helping to orchestrate circumstances to suit your career aspirations are better stoked when your career needs find expression in your conversations.
If your boss is aware that the kind of career experiences you seek are currently unavailable in your organisation, your resignation would not be surprising, especially if it is not abrupt and if it is informed by you having found a more desirable career opportunity.

It is best to be candid in your conversation when you eventually speak with your boss concerning your resignation, chances are that he will understand and respect you for it, discomfort notwithstanding.