The key to a good one-on-one meeting is the understanding that it is the employee’s meeting rather than the manager’s meeting. This is the free-form meeting for all the pressing issues, brilliant ideas and chronic frustrations that do not fit neatly into status reports, email and other less personal and intimate mechanisms.
If you like structured agendas, then the employee should set the agenda… During the meeting, since it’s the employee’s meeting, the manager should do 10% of the talking and 90% of the listening… While it’s not the manager’s job to set the agenda or do the talking, the manager should try to draw the key issues out of the employee. The more introverted the employee, the more important this becomes.
Some questions that I’ve found to be very effective in one-on-ones: If we could improve in any way, how would we do it? What’s the No. 1 problem with our organization? Why? What’s not fun about working here? Who is really kicking ass in the company? Who do you admire? If you were me, what changes would you make? What don’t you like about the product? What’s the biggest opportunity that we’re missing out on? What are we not doing that we should be doing? Are you happy working here?
(1) Note the open-ended questions Ben asks in his one-on-ones.
(2) Cf. Mark Suster’s advice about how to ask great questions.