It's Halloween again. That means a lot of things for us at work, from costume contests to candy-laden Halloween potlucks to Halloween parties gone bad.

Some of you may end up sitting next to a dude dressed up as "Thing 1" for the day, which I guess is OK as long as Thing 1 gets you the Operations Report on time despite his self-imposed quest to search out the rest of the company to see if anyone dressed up as "Thing 2."

Some of you may end up in a meeting being run by Steve Jobs (or at least a co-worker living out his or her tech icon dream for a day) since dressing up as tech icons is surprisingly fashionable these days. Maybe you'll be lucky and get to interact with a much nicer version of Steve Jobs this time around.

This year for Halloween, though, I'm reflecting on the two scariest presentations I've ever had to give at work. And maybe more importantly, what I did to help me get through the fear. Some of you may have been through similar or relatable situations (or are facing them now). I hope my examples help.

1. "We've got 20 misaligned SVPs and C-Suite leaders in a room. Get them working better together."

This was what I was told by my boss in my first VP level job. I thought I had ascended to the adult table where leaders strategized together. Turns out that some of the bigger adults weren't playing well together. Given my role as an organizational effectiveness specialist, I got the task of straitening them out before things got really scary.

At the time, I was a mere two months into my tenure, and the company was experiencing significant tumult. Rather than facilitate this nasty meeting, I might have preferred getting lost in my neighbor's DIY Haunted House inspired by his teenage son's love of horror movies.

How did I get through my fear of it?

  • I painstakingly talked to each of the 20 meeting participants in advance so I knew where they stood on key issues.
  • I got to know my audience so well that I could predict who would talk and who wouldn't at which points.
  • I asked in advance for key members who were willing to voice certain viewpoints so that those perspectives could be brought up when I wanted them.
  • And then I contingency planned until the cows came home so that there wasn't any possible scenario that could occur that I wasn't prepared for.

The meeting went surprisingly well. No boardroom brawls. We got the big issues out on the table despite some moments of painful silence. And I even got the added benefit of not having to live out the rest of my time at that company working in an executive zombie wasteland.

2. "Three members of this ELT aren't going to like what you have to say in there...but we're here to support you."

It was years ago and my first time ever presenting to an Executive Leadership Team of a company. I had been working hard on a making some significant changes to a program that had been put in place years earlier but needed improvement. I had the sponsorship of key leaders, including the SVP of R&D, for whose people most of my proposed changes would impact most.

Then there were the three ELT leaders who had sponsored the original version of the program I was now changing. They were in the meeting, and there wasn't an opportunity (mostly for political reasons) for me to pre-socialize things in advance with them.

Aside from being my first time in the proverbial "Lion's Den", I felt unprepared to deal with the potential dissent despite being confident about the changes I was leading.

How did I get through my fear of it?

  • I made sure I knew my content inside and out - in particular what was different and why we needed to change those things, even if it wasn't popular with some.
  • I carefully created my talking points to be directed at my three potential dissenters - but in a way that created common ground around program goals so it would feel less to them like "undoing" their version of the program and more like taking an alternative path to get to the outcomes they wanted.
  • I made what felt like a bold move and decided to bring some authentic but strategically placed self-deprecating humor into the presentation to attempt to disarm the leaders (something to the tune of "I hope this goes well today or I might not ever see many of you again in this room.")

To may amazement, I received applause from the ELT when I was done with my presentation, to which I responded by spontaneously saying something ridiculous like, "Thank you, Cleveland" (to a surprising amount of ELT laughter), and I walked out. I received little to no dissent from the three leaders. The meeting couldn't have gone more smoothly.

I hope these two examples help any of you who are in the midst of preparing for scary meetings. In the end, it's all in the preparation.