A coaching session is time intentionally set aside to do coaching with someone. Asking probing questions, the coach helps the "coachee" to work through problems. These coaching sessions work best if you can find a quiet place to meet, away from distractions.
Where a coaching session is not possible, I recommend taking advantage of an available coaching opportunity. For example, during a 1-on-1 status meeting with someone, you may find an opening in the conversation to ask a few open-ended questions about a relevant issue, bringing you to an impromptu coaching session. A coaching opportunity can present itself anywhere; look for them.
You may also hear me talk about a concept I refer to as "coaching buttons". This is a variation on a different concept ("conversation buttons") for how to impart information to someone when you don't have a long time to spend with them (like, during an elevator rid.) The "conversation button" is something that sticks with your listener. Like the button on a shirt or coat, a "coaching button" doesn't do the whole job, but over time as you use more "coaching buttons" the whole picture comes together. They key is to make those "buttons" easily understood and memorable, able to stand on their own, but part of a larger story.
I've adapted this into "coaching buttons", or coaching of the moment where I take an available opportunity to do a brief coaching conversation with someone. For example, a manager might find him/herself early for a meeting, only one staff member is there, giving the manager a short time for a "coaching button". Never waste an opportunity for coaching, however brief. The "coaching button" might only cover one question without an opportunity for follow-up questions to delve deeper - but if you can find frequent opportunities for several "buttons", I find it can be helpful.
For example, I use "coaching buttons" when I meet with the fraternity that I advise. I show up a little early for each House meeting, and use the extra time to do brief coaching with the guys. Usually, they come to the meeting room in ones and twos, making it easy to have quiet conversations.
Closely related to "coaching buttons" is the concept of conversation "gifts". Just before Christmas, Roger Schwartz published "Giving and Receiving Gifts in Conversation" in his Fundamental Change newsletter. Jim Bruce (my mentor from ITLP) included this with permission in last week's Tuesday Readings email, but let me provide a summary. I think this is tied very closely to "coaching buttons":