What follows are the steps I used to get a weekly meeting with my boss.
A little background. I had no regularly scheduled meetings with my boss. When something I wanted to talk about popped into my head, I would do a "walk-in," standing up immediately and walking into his office unscheduled and unannounced. (Please, don’t even say it.) I’d do that a couple times a day, and about once a day he would do a "walk-in" with me in my cube.
Here’s what I did.
Week one, I sent a Friday morning e-mail to my boss requesting a "catch up" meeting for the following Friday. (E-mail text: "Hi [boss], Are you available next Friday morning for a 30-minute meeting to catch up? I’d like to give you the latest on what we have going on. I’ll send you a meeting invite. Thank you, [me]") Immediately after sending the e-mail, I sent him an Outlook 30-minute meeting invite for the next Friday. He accepted.
Week two, I stopped doing walk-ins. (This was the hard part. I didn’t, not once or even kinda-sorta, walk into his office. Didn’t stick my head in. Didn’t stop him in the hall. It was uncomfortable.) Instead, when something I wanted to talk with him about popped into my head, I put it on a list. For our scheduled Friday morning meeting, I picked three items off the list and wrote them on a notepad. (I was careful to pick three I could cover in ten minutes.) When we did our 30-minute meeting, I quickly covered those three items, then said, "That’s all I got. You have anything?" He said he didn’t. I said thanks, stood up, and walked out. We were done in fifteen minutes.
Week three, I continued my no-walk-ins behavior. (I also continued being uncomfortable.) I sent the boss a Friday e-mail asking for another catch-up for the Friday following (E-mail text: "Hi [boss], Would you be available for another catch-up meeting next Friday? I’ll send an invite. Thank you, [me]"), and then sent an Outlook invite. He accepted. I continued keeping my list of stuff I wanted to talk about.
Week four, I continued no-walk-ins and the list. For our scheduled Friday morning meeting, I behaved just as I did Friday of week two, but this time, after he said he didn't have anything, I pitched a weekly regularly-scheduled catch-up meeting. (The pitch went something like this: "What would you think about doing this every week? I’ve just been thinking that having me walking into your office all the time can’t be good, and that this might be a way to help free up your time. Give us a bucket we can put stuff we need to talk about. What I’m thinking is something like 30 minutes every Friday morning, or whenever works for you. First fifteen minutes I talk about what I got, second fifteen minutes you cover whatever you got for me. Does that sound like something that would work?") He made a face... but agreed to give it a try. I said thank you, told him I’d send an invite, asked if there was anything else, stood up and walked out. Again, we were done in well under 30 minutes. I sent the invite as soon as I got back to my desk, and he accepted.
We’ve been doing our weekly Friday morning catch-ups for about two years now. I’m still careful to avoid walk-ins and to stay within my fifteen minutes when we meet. He doesn’t make faces anymore.
It’s not quite a one-on-one, but it seems to be working for us.
Hope that helps somebody somewhere down the line.
Best,
Paul Schweer

Re: Getting An O3 With My Boss
[quote="PaulSchweer"]It’s not quite a one-on-one, but it seems to be working for us.[/quote]
Here's the clincher: It's effective for you. That's big.
[quote="PaulSchweer"]We’ve been doing our weekly Friday morning catch-ups for about two years now.[/quote]
Have you ever done a hotwash at one of these O3-esque meetings to gauge how effective your boss sees these meetings to be. I could easily see one of your three items being "These Meetings: What Works Well, What to Take a Look at."
Have you ever used these meetings as a platform to ask your boss what you could take off his plate?
Well done! Welcome to the Forums, and thank you for sharing your experience.
BJ
Re: Getting An O3 With My Boss
Hi BJ,
[quote]Have you ever done a hotwash at one of these...?[/quote]
No.
[quote]Have you ever used these meetings as a platform to ask your boss what you could take off his plate?[/quote]
No, I haven't. I'm actually about eighteen months into a personal improvement initiative consisting of shutting up about his stuff and focusing on mine.
Best,
Paul Schweer
7-1-1-5
Grumpy
Getting An O3 With My Boss
Paul--
That was one of the best posts I've ever seen on these forums.
Très Effective!
--Rich
Re: Getting An O3 With My Boss
[quote="PaulSchweer"]I'm actually about eighteen months into a personal improvement initiative consisting of shutting up about his stuff and focusing on mine.[/quote]
Can you tell us more about that?
Re: Getting An O3 With My Boss
[quote]Can you tell us more about that?[/quote]
Two goals: 1) get better at shutting up (The more I do it, the less I regret it.); 2) improve ability to recognize and get value from an executive heads-up (versus a request for comment, or even random ramblings).
Background: my boss sometimes tells me things about his stuff; I realized I was way too often responding with my opinion about said things; I resolved to hold my opinion about his stuff until asked.
Expected benefits: boss’s decreased dread of talking with me; boss’s increased willingness to tell me things about his stuff; more energy to focus on my stuff.
Unexpected benefit: there’s a lot of really good info to be had in even the blandest-looking executive FYI (stuff I miss if waiting for my chance to comment).
Interesting side note: so far I’ve heard many FYI’s, but only one direct request for comment.
Best,
Paul Schweer