Often the discussion continues well into the evening as we decant to one of the local pubs for dinner & beer, sometimes chatting away until closing time (probably quite regularly actually, but I'm normally long gone).
It was at one of these nights at the pub two months ago (sorry!), that we ended up chatting about storytelling as a teaching tool, and a colleague asked an excellent question, that at the time I didn't have a ready answer for, but I've been slowly pondering, and decided to focus on over an upcoming trip.
As I start to write the first draft of this post I've just settled in for cruise on my first international trip in over six months, popping over to Singapore for the Melbourne Cup weekend, and whilst I'd intended this to be a holiday, I'm so terrible at actually having a holiday that I've ended up booking two sessions of storytelling time, where I present the history of Google's production networks (for those of you reading this who are current of former engineering Googlers, similar to Traffic 101). It's with this perspective of planning, and having run those sessions that I'm going to try and answer the question that I was asked.
Or at least, I'm going to split up the question I was asked and answer each part.
"What makes storytelling good"
On its own this is hard to answer, there are aspects that can help, such as good presentation skills (ideally keeping to spoken word, but simple graphs, diagrams & possibly photos can help), but a good story can be told in a dry technical monotone and still be a good story. That said, as with the rest of these items charisma helps.
"What makes storytelling interesting"
In short, a hook or connection to the audience, for a lot of my infrastructure related outage stories I have enough context with the audience to be able to tie the impact back in a way that resonates with a person. For larger disparate groups shared languages & context help ensure that I'm not just explaining to one person.
In these recent sessions one was with a group of people who work in our Singapore data centre, in that session I focused primarily on the history & evolution of our data centre fabrics, giving them context to understand why some of the (at face level) stranger design decisions have been made that way.
The second session was primarily people involved in the deployment side of our backbone networks, and so I focused more on the backbones, again linking with knowledge the group already had.
"What makes storytelling entertaining"
Entertaining storytelling is a matter of style, skills and charisma, and while many people can prepare (possibly with help) an entertaining talk, the ability to tell an entertaining story off the cuff is more of a skill, luckily for me, one I seem to do ok with. Two things that can work well are dropping in surprises, and where relevant some level of self-deprecation, however both need to be done very carefully.
Surprises can work very well when telling a story chronologically "I assumed X because Y, <five minutes of waffling>, so it turned out I hadn't proved Y like I thought, so it wasn't X, it was Z", they can help the audience to understand why a problem wasn't solved so easily, and explaining "traps for young players" as Dave Jones (of the EEVblog) likes to say can themselves be really helpful learning elements. Dropping surprises that weren't surprises to the story's protagonist generally only works if it's as a punchline of a joke, and even then it often doesn't.
Self-deprecation is an element that I've often used in the past, however more recently I've called others out on using it, and have been trying to reduce it myself, depending on the audience you might appear as a bumbling success or stupid, when the reality may be that nobody understood the situation properly, even if someone should have. In the ops review style of storytelling, it can also lead to a less experienced audience feeling much less confident in general than they should, which itself can harm productivity and careers.
If the audience already had relevant experience (presenting a classic SRE issue to other SREs for example, a network issue to network engineers, etc.) then audience interaction can work very well for engagement. "So the latency graph for database queries was going up and to the right, what would you look at?" This is also similar to one of the ways to run a "wheel of misfortune" outage simulation.
"What makes storytelling useful & informative at the same time"
In the same way as interest, to make storytelling useful & informative for the audience involves consideration for the audience, as a presenter if you know the audience, at least in broad strokes this helps. As I mentioned above, when I presented my talk to a group of datacenter-focused people I focused on the DC elements, connecting history to the current incarnations; when I presented to a group of more general networking folk a few days later, I focused more on the backbones and other elements they'd encountered.
Don't assume that a story will stick wholesale, just leaving a few keywords, or even just a vague memory with a few key words they can go digging for can make all the difference in the world. Repetition works too, sharing many interesting stories that share the same moral (for an example, one of the ops review classics is demonstrations about how lack of exponential backoff can make recovery from outages hard), hearing this over dozens of different stories over weeks (or months, or years...) it eventually seeps in as something to not even question having been demonstrated as such an obvious foundation of good systems.
When I'm speaking to an internal audience I'm happy if they simply remember that I (or my team) exist and might be worth reaching out to in future if they have questions.
Lastly, storytelling is a skill you need to practice, whether a keynote presentation in front of a few thousand people, or just telling tall takes to some mates at the pub practice helps, and eventually many of the elements I've mentioned above become almost automatic. As can probably be seen from this post I could do with some more practice on the written side.
1: As I write these words I'm aboard a Qantas A380 (QF1) flying towards Singapore, the book I'm currently reading, of all things about mechanical precision ("Exactly: How Precision Engineers Created the Modern World" or as it has been retitled for paperback "The Perfectionists"), has a chapter themed around QF32, the Qantas A380 that notoriously had to return to Singapore after an uncontained engine failure. Both the ATSB report on the incident and the captain Richard de Crespigny's book QF32 are worth reading. I remember I burned though QF32 one (very early) morning when I was stuck in GlobalSwitch Sydney waiting for approval to repatch a fibre, one of the few times I've actually dealt with the physical side of Google's production networks, and to date the only time the fact I live just a block from that facility has been used at all sensibly.
2: To date, I don't think I've ever actually had a holiday that wasn't organised by family, or attached to some conference, event or work travel I'm attending. This trip is probably the closest I've ever managed (roughly equal to my burnout trip to Hawaii in 2014), and even then I've ruined it by turning two of the three weekdays into work. I'm much better at taking breaks that simply involve not leaving home or popping back to stay with family in Melbourne.