One thing that’s come up in discussions with a handful of folks recently has been about presentations & talks with folks in various awkward/difficult situations. And I’m not going to pretend that I’m any good at any of this, so I hope this doesn’t come off like, “I’m awesome at this s**t, learn from me:” – more, “I’ve had some experience with this s**t, and I’ve at least shaved the most awful edges off, here’s how:”

Practice.

I know, right? Seems crazy. But over the last 3.5 years, I’ve now given probably hundreds of presentations – many are just little weekly updates, some were talks about the company’s philosophy, some were attempts at motivation – they’ve run the gamut. And I think consistently, everyone underestimates how much preparation goes into these things.

For the most part, preparing for a significant (and new) 30 minute talk in front of a team takes me about 8 hours. I’ll make a Keynote presentation as a way of “thinking it out”. Usually this comes with at least a little bit of structure – how to reinforce a point I want to drive home. What kind of visual “language” will help reinforce it, and be memorable. The slides start off all text, and over the course of development, I’ll try to replace as much text with images as possible – in part because text sucks for presentations, in part because the presence of text encourages you to just read your slides, and in part because the images just look better & are stickier.

But the whole time, every iteration (of which there are usually dozens), I’ll “walk through” the presentation, and try to think about what I’d say. I don’t generate a “script” – I think part of trying to be engaging is reacting to things, and being spontaneous. But it’s spontaneity within a structure which is provided by the slides, so you don’t forget the things you’re trying to get across.

So (hopefully) the end result feels “off the cuff”, because a lot of the actual content is improvised on the spot. But the main points are not. The overall flow is not. This goes for presentations to large groups, and it also applies just as much to difficult conversations with individuals, though those don’t usually involve a Keynote presentation.

One thing to note – I think the bulk of the “work” building presentations is figuring out the correct order for content. Getting the ideas in the right order can have a huge impact on how it’s all ingested by the viewer, and having a flow to your presentation that makes sense takes a lot of iteration and practice.

If you’re going to have a difficult conversation with someone in a work environment, HAVE NOTES. Practice. If you need to, practice WITH SOMEONE ELSE (if they’re in the position where you can talk to them about the issue you’re having with whoever). These conversations are always insanely difficult, and it’s very difficult to get your points across in a clear, coherent, and memorable way if you do it all off the cuff. The other person’s reaction and emotions will pull you WAY off your “plan” – but having a plan means you have something to come back to. Practicing with someone else means you can anticipate some of the things that won’t go to plan and have another plan.

Anyway – the point of this is that for me, the way I got through these things – presentations, difficult conversations, etc. – is practice. Is planning. Is preparation. Is iteration. A 30 minute presentation may feel like it doesn’t require much forethought, but if you’re talking to a team of fifty people, consider what that costs to the company in time and money, and then invest the time preparing accordingly to make it worth their while.