Irrational Exuberance!

Presenting to executives.

August 6, 2018. Filed under management

Yahoo! BOSS was partially powered by on an internal Yahoo! search technology named Vespa. We'd run into a bunch of challenges, and I'd decided to convince my team we should migrate to SOLR. My manager asked me to put together a presentation for our next team meeting. The meeting came, I started to present, and within two slides things fell apart.

"No, no, this isn't the way to put this together. This is like an academic presentation. You have to start from conclusion first," my manager lamented sadly as he abruptly terminated my presentation. Pausing to brush my deck's fragments from his boots, he offered some final wisdom, "And don't use curved lines in your diagrams. Those never make sense."

It took me a few years to glean a lesson from that experience, but it comes to mind frequently now when I work with folks who are just starting to present to executives. Giving a presentation to senior leadership is a bit of a dark art: it takes a while to master, and most folks who do it well can't quite articulate how they do it. Worse yet, many folks who are excellent rely on advantages that resist replication: charisma, quick wit, deep subject matter expertise, or years of experience.

That said, few people watching me bomb my Yahoo! presentation would have bet I'd ever figure this one out, so you should know it is a learnable skill. Along the way I've picked up some tips which I hope will help you prepare for your next presentation:

  • Communication is company specific. Every company has different communication styles and patterns. Successful presenters probably can't tell you what they do to succeed, but if you watch them and take notes, you'll identify some consistent patterns. Each time you watch folks present to leadership, study their approach.
  • Start with the conclusion. Particularly in written communication, folks skim until they get bored, and then stop reading. Accommodate this behavior by starting with what's important, don't build towards it gradually.
  • Frame why the topic matters. Typically you'll be presenting on an area that you're intimately familiar with, and it's probably very obvious to you why the work matters. This will be much less obvious to folks who don't think about the area as often. Start by explaining why your work matters to the company.
  • Everyone loves a narrative. Another aspect of framing the topic is providing a narrative of where things are, how you got here, and where you're going now. This should be a sentence or two along the lines of, "Last year we had trouble closing several important customers due to concerns about our scalability. We identified our databases as our constraints to scaling, and since then our focus has been moving to a new sharding model that enables horizontal scaling, which is going well, and we expect to finish in Q3."
  • Prepare for detours. Many forums will allow you to lead your presentation according to plan, but that is an unreliable prediction when presenting to senior leadership. Instead, you need to be prepared to lead the entire presentation yourself, while being equally ready for the discussion to derail towards a thread of unexpected questions.
  • Answer directly. Senior leaders tend to be indirectly responsible for wide areas, and frequently pierce into areas to debug problems. Their experience "debug piercing" tunes their radar for evasive answers, and you don't want to be a blip on that screen. Instead of hiding problems, use them as an opportunity to explain your plans to address them.
  • Deep in the data. You should be deep enough in your data that you can use it to answer unexpected questions. This means spending time exploring the data, and the most common way to do that is to run a thorough goal setting exercise.
  • Derive actions from principles. One of your aims is to provide a mental model of how you view the topic, allowing folks to get familiar with how you make decisions. Showing you are "in the data" is part of this, and the other aspect is defining the guiding principles you're using to approach decisions.
  • Discuss the details. Some executives test presenters by diving into the details, trying to uncover an area the presenter is uncomfortable speaking on. You should be familiar with the details, e.g. project statuses, but I think it's usually best to reframe the discussion when you get too far into the details. Try to pop up to either the data or the principles, which tend to be more useful conversations.
  • Prepare a lot; practice a little. If you're presenting to your entire company, practicing your presentation is time well spent. Leadership presentations tend to quickly detour, so practice isn't quite as useful. Practice until you're comfortable, but prefer to prepare instead; getting deeper into the data, details and principles. As a corollary, if you're knowledgeable in the area you're responsible for, and have spent time getting comfortable with the format, over time you'll find that you won't need to prepare much for these specifically. Rather, whether you're able to present effectively without much preparation will become a signal for whether you're keeping up with your span of responsibility.
  • Make a clear ask. If you don't go into a meeting with leadership with a clear goal, your meeting will either go nowhere or go poorly. Start the meeting by explicitly framing your goal!

That's a lot to remember, so I've synthesized these ideas into a loose template. There absolutely is not a single right way to present to senior leaders, but hopefully the template is a useful starting point.

My general approach to presenting to senior leaders is:

  1. Tie topic to business value. One or two sentences to answer, "Why should anyone care?"
  2. Establish historical narrative. Two to four sentences to help folks understand how things are going, how we got here, and what the next planned step is.
  3. Explicit ask. What are you looking for from the audience? One or two sentences.
  4. Data-driven diagnosis. Along the lines of a strategy's diagnosis phase, explain the current constraints and context, primarily through data. Try to provide enough raw data to allow folks to follow your analysis. If you only provide analysis, then you're asking folks to take you on trust, which can come across as evasive. This should be a few paragraphs, up to a page.
  5. Decision making principles. Explain the principles you're applying against the diagnosis, articulating the mental model you are using to make decisions.
  6. What's next and when it'll be done. Apply your principles to the diagnosis to generate the next steps. It should be clear to folks reading along how your actions derive from your principles and the data. If it's not, then either rework your principles or your actions!
  7. Return to explicit ask. The final step is to return to your explicit ask and ensure you get the information or guidance you need.

I've had a lot of luck with this format in general, and think you'll find it pretty useful as a starting point. That said, the first rule remains true: communication is company specific. If things don't quite work for this format in your company, then watch how other folks present. Given a few examples, you'll be able to reverse engineer the discussions that go well into a workable template.