O3 with non-communicative directs

First off, thank you so much for everything you guys do.  I am a new manager and Manager Tools have been amazing in helping me!

Anyway, we are on week 5 of the Trinity roll out, and things have been going great with my 9 directs.  That is, things are going great except for one.  This particular staff has always had real struggles when it comes to communication (Very quite, almost never talks in meetings, often frustrating other sales people with his lack of communication, ect.) and our time spent in the one-on-ones are no different.  The first week with him went great, had a lot to talk about and he opened up quite a bit.  Since then, he comes into my office and says that he doesn't have anything to say and just kind of sits there, wanting me to direct the time.  The first few weeks, I reminded him that this is his time to lead the converstation, but he just said that nothing was new and he didn't have anything to talk about.  I spent the rest of the time leading the conversation.  It is not that he wouldn't talk when I ask him a question, it is just that I have to lead the conversation.  (So, tell me about your sales numbers, ect.)

Now that we are a five weeks into it, I can't help but feel that I am doing things wrong.  Should I be pushing this staff more, asking him to spend time preparing for our one-on-ones so he knows what he wants to talk about or should I just keep reminding him that this is his time and if he doesn't want to use it, I have plenty of thing to talk about? Perhaps, just give it more time and hope he comes around? Despite that first good meeting the last four have been pretty frustrating.  Any guidance?

Don't push... pull

Some directs don't like to talk about themselves, or their work.  There are a variety of reasons, but they're not really important (because it's all about behaviour).  With these directs, you may have to lead the conversation more.  Ask open-ended questions to get the ball rolling, and then focus very carefully on the answers they give, to find hooks in which you can ask more questions.  That is actually the key to keeping a conversation rolling -- to ask questions.  I found the MT cast "How to be effective in everyday conversation" to be a *fantastic* eye-opener in that regard.

The key to keeping this a one-on-one, rather than just another place for you to badger them about their status, is to ask questions about things that are likely to be of interest to *them*, not things that will be of interest to *you*.  Yes, you could ask them where they're up to on project X, but unless project X is really getting them excited every day, it'll probably be more of a drag.  Keep an eye out for things at work that capture their attention, and ask about that.  If you don't have anything there, ask about their weekend or something else that's "publically personal" (I don't recall who gave me that phrase, but it's brilliant).

I haven't tried asking my directs to prepare specifically for their one-on-ones.  I lead by example and always have notes about what I want to talk about (in O3s or *any* meeting I'm involved with), and I think that has rubbed off on some of them -- they come prepared with their notebooks.  Other people just turn up and it's more of a "shoot the breeze" session.  I feel that if someone talking about their pet cats for 15 minutes a week is going to make them more effective, I can stand to listen to their cat stories.

Finally, don't be afraid to wrap up a one-on-one early.  Trying to stretch the thing out to 30 minutes just amplifies any awkwardness, and makes people more fearful of next week.  Instead, get a feel for when conversation is flagging, and then wrap up.  I've managed to get a feel for who might have something to say but isn't keen to speak up, versus who will speak up when they have something (but often doesn't have anything they want to talk about).  For the former, I'll never end the meeting early without asking "was there anything else you wanted to talk about?".  Once we're done, regardless of how much longer we've got in our half hour, I'll just wrap up with, "Thanks for the great chat, we'll catch up again next week!" with a smile and a positive tone of voice.  This isn't a natural posture for me, by the way -- I'm not a "smiler" or a "positive tone of voice" person.  It's worth doing what's effective, though, even though it isn't what comes naturally.