Wrapping A Taste of M365 Chicago – Until Next Time

Wrapping A Taste of M365 Chicago – Until Next Time

Friday, June 4th, was the second M365 Chicago conference. The M365 Conferences are run by myself and a handful of Chicago area Microsoft pros (Craig Jahnke, Heather Ackmann, Michael Blumenthal, and Ralph Rivas), put on through my OTSN, LLC podcast network.

Some stats on the conference:

  • 600+ Registrants
  • 385 Posts & Replies
  • 304 Attendees
  • 79 Speakers
  • 75 Sessions
  • 70 hours of content (some of it recorded)
  • 33 documented lessons learned (15 sub-bullets)
  • 20 volunteer moderators (some doubled as speakers, some did both at once)
  • 11 Keynotes (headlined by the prodigious Naomi Moneypenny)
  • 10 Sponsors
  • 9.5 hours live-streamed on YouTube (in 480p, whoops)
  • 5 Organizers
  • 1 Charity Partner (still working on the balance sheets to know how much we raised)

After kicking off the first conference in the HEIGHT of the pandemic, November 2020, I was not surprised to see that virtual conference saturation had brought down some of these numbers. That said, down about 30 speakers, I was still VERY pleased with the end results of this conference.

While I plan to push out a much more “official” lessons learned post, a few things that I want to post separately, on my blog, as they were very personal.

Work with people who complement your skills, even if you don’t always get along

The organizing committee had our moments of zen and our moments of absolutely wanting to strangle eachother. Or maybe that was just me?

When we attacked things methodically, we were smooth.

When we communicated expectations, things gelled really well.

When we were distracted, it was worse than herding cicadas (I know, I’d normally say cats, but since Brood X is in the middle of mating season, it seemed appropriate).

But in the end, this group worked really hard together to ensure this conference was as smooth as a volunteer conference can be.

Oh, mistakes were made, for sure. Not everyone is going to be happy. And that’s ok. But I honestly am very happy with this team and as we grow, and likely even grow apart in the coming years, I’m very happy to have worked with this crew for a second time.

Just because you CAN doesn’t mean you SHOULD. Or should you?

I did not speak at our November conference, and I was disappointed at the time. I spoke Friday. Twice. I was SO STRESSED ABOUT IT.

I’m a “last minute” speaker. It’s not great, but I tend to do well under the pressure. I was had a good friend running a conference walk over to me, 2 hours prior to my session, seeing me working on my slides, ask if he should be worried (for me? about me? with me? hard to say). Don’t get me wrong, when it’s NEW content I … 9 times out of 10 … put lots of prep time into it.

This week was different. I was running the conference. I had a LOT on my mind. I should NOT have submitted. Twice. Or at all, really.

Joy Apple and I have built a solid rapport and have nailed the 60 minute “flat architecture for M365” session down. So while I was worried about going into it, yeah, we really did have it down.

Craig Jahnke invited me to join him on his “Viva & Workplace Analytics” session. I had never done it before. I really hadn’t done much research on it before. And frankly, if you saw the presentation, this admission is not likely a surprise. However, Craig and I spend WAY TOO MUCH TIME together on our podcast, so we know how to work together. Sure, the session was great, but going into it? Man I did not prepare like I wanted to or should have. I know I could have done better, and I’m sure I will by the time we take this session to NACS.

In short, it all worked out, but next time I run a conference? Just be happy running it, don’t present, too. In the infamous words of Red Forman …

It’s ok – I’ll own it – thanks Red


Don’t speak at your own conferences & find people to work with that complement your skills.

As we’ve posted a few times we documented 33 lessons learned with 15 sub-bullets during our conference – just a running list so maybe there are some duplicates. We’ll figure that out next week when we meet to wrap things up. So, keep an eye out for more.

In the meantime. Thank you all. The speakers, the sponsors, the moderators, the community partners … the organizers. I enjoy this community very much and it brings me back time and time again.

Until next time, see you on the web!

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