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Guides / Present to executives

Have you presented to company executives about a key engineering initiative, walking into the room excited and leaving defeated? Maybe you only made it to your second slide before unrelated questions derailed the discussion. Maybe you worked through your entire presentation only to have folks say, "Great job," and leave without any useful debate. Afterward, you're not quite sure what happened, but you know it didn't go well.

Early in your career, you probably won't interact with company executives frequently. Sure, if it's a small enough company, you might, but it isn't the norm. As you get further into your career, though, increasingly, your impact will be constrained by your ability to influence executives effectively. While staying aligned with authority is a prerequisite to influencing executives, there are also some new communication skills for you to develop.

Why this is hard

Everyone has worked with a terrible executive at some point in their career, but most executives aren't awful. Almost all executives are outstanding at something; it's just that often that something isn't the topic you're communicating about with them. When you combine that lack of familiarity with your domain with limited time for the topic at hand, communication is a challenge.

Those are garden-variety communication challenges, though, and communicating with executives can be unexpectedly difficult for a less apparent reason: the executive has become accustomed to consuming reality preprocessed in a particular way.

Any given executive is almost always uncannily good at one way of consuming information. They feel most comfortable consuming data in that particular way, and the communication systems surrounding them are optimized to communicate with them in that one way. I think of this as preprocessing reality, and preprocessing information the wrong way for a given executive will frequently create miscommunication that neither participant can quite explain.

For example, some executives have an extraordinary talent for pattern matching. Their first instinct in any presentation is to ask a series of detailed, seemingly random questions until they can pattern match against their previous experience. If you try to give a structured, academic presentation to that executive, they will be bored, and you will waste most of your time presenting information they won't consume. Other executives will disregard anything you say that you don't connect to a specific piece of data or dataset. You'll be presenting with confidence, knowing that your data is in the appendix, and they'll be increasingly discrediting your proposal as unsupported.

In most other scenarios, miscommunication creates latency rather than errors. Still, when you're communicating with executives, you'll often not get a second chance to discuss a given topic before the relevant decision is made. Invest ahead of the discussion to avoid lamentations afterward.

How to communicate effectively

The foundation of communicating effectively with executives is to get a clear understanding of why you're communicating with them in the first place. You might be used to communicating with folks to change their mind or inform them about your project, but that's probably not the case here. When you're communicating with an executive, it's almost always one of three things: planning, reporting on status, or resolving misalignment.

Although these are distinct activities, your goal is always to extract as much perspective from the executive as possible. If you go into the meeting to change their mind, you'll probably come across as inflexible. Go into the meeting to understand how you can align with their priorities. You'll come across as strategic and probably leave with enough information to adapt your existing plan to work within the executive's newly articulated focuses or constraints.

The best way to extract their perspective is by writing a structured document. Writing forces you to think comprehensively about your beliefs and data. The structure ensures you focus the reader on what's important. Barbara Minto, whose The Pyramid Principle is the most influential work on effective business communication, is also a big fan of structure:

Controlling the sequence in which you present your ideas is the single most important act necessary to clear writing. The clearest sequence is always to give the summarizing idea before you give the individual ideas being summarized. I cannot emphasize this point too much.

There are many structures that can work, but I'd particularly recommend every document's opening paragraph follow the SCQA format:

  • Situation: what is the relevant context? Example: We've been falling behind our competition in shipping product features for two years. Last year, we doubled our engineering team but shipped fewer features than the year before.
  • Complication: why is the current situation problematic? Example: We plan to double our engineering team again this year, but based on last year's experience, we think that will decrease velocity further while significantly increasing our organizational budget.
  • Question: what is the core question to address? Example: Should we keep moving forward with our plan to double engineering this year?
  • Answer: what is your best answer to the posed question? Example: We should stop hiring for the next six months and focus on gelling our existing team. Based on progress at that point, we should refresh our hiring plan for the remainder of the year.

In many discussions, a well-structured opening paragraph is enough to spark an important conversation. Although in those cases, you might not discuss the rest of your document, the process of writing the document is still an important step in refining your thinking.

Relatively few folks employ a formal structure for the entirety of their document, but there is at least one popular format that some folks find valuable: Minto's Pyramid Principle from the aforementioned book. Start by brainstorming your proposal into a series of arguments that support your answer. Once you've written them all down, group them into related arguments. Shape those groups into three top-level arguments, with up to three sub-arguments supporting each of those top-level arguments. Recursively apply this approach, ensuring each argument summarizes its at-most-three sub-arguments. Order the arguments within each group by descending importance. At that point, you're done.

Although I personally found SCQA immediately useful, I'll admit that when I first tried to follow the Pyramid Principle, it gave me the same emotional response as staring at Brutalist architecture. It's grown on me with practice, but I'd still recommend most folks start by adopting SCQA as a core practice and only adopt the entirety of the Pyramid Principle if you get feedback that your presentations are hard to follow.

After you've written your structured document, gather feedback on it from your peers and stakeholders. Aligning with stakeholders before your presentation, sometimes called nemawashi, is extremely effective at reducing surprises. Some of your peers should have experience presenting to the executives and will have useful feedback on improvements.

For the presentation itself, set a clear agenda, but don't focus on rote conformance. A great meeting with executive leadership is defined by engaged discussion, not addressing every topic on the agenda. Some will consider this a controversial position, preferring to measure every meeting by its action items, but this ignores the often more valuable relationship establishment and development aspects of these meetings.

Mistakes to avoid

Even if you do a great job preparing for your executive presentation, these things sometimes go wrong. There's nothing you can do that will avoid every bad path, but you can avoid most of the anti-patterns that routinely sink these meetings.

Never fight feedback. It's very common for an executive to have a critical piece of feedback but to not quite have the right framing to communicate it within the moment. You want them to deliver the feedback anyway, not hold it back and probably forget to give it later. If you show up as resistant to feedback, then they'll start swallowing their comments, and you'll get relatively little out of the meeting. Focus on gathering feedback; don't worry about whether you agree with it until you have more time afterward. If there's a decision that needs to be made that you disagree with, then you should inject one or two pieces of relevant data that might change their mind, but afterward, let it go. You'll be more effective by reflecting on the feedback and changing their mind later than continuing to push back within the meeting.

Don't evade responsibility or problems. Many folks try to hide issues from their leadership, and this always goes poorly. Successful folks look at informing executives as absolution: once it's on the table, you can move towards solving it rather than hiding it. This is particularly true if an executive sniffs out a problem during a meeting. Lean into the feedback, don't evade it. You will create more credibility by agreeing with their perspective and following up with more data later. You will harm your credibility by arguing with them about it.

Don't present a question without an answer. A frequent piece of advice given to new leaders is to "never bring your manager a problem without a solution." That's not generally great advice, but if you present a problem to an executive without a proposed answer, then in the back of their mind, they're wondering if they need to hire a more senior leader to supplement or replace you. You can't create alignment in the room unless you have a proposal for folks to align behind.

Avoid academic-style presentations. The way you're taught to present about topics in school is more-or-less the entirely wrong approach for presenting to executives. The Minto Pyramid Principle will steer you in the right direction if you follow its scripture.

Don't fixate on your preferred outcome. It's very common for folks to get so caught up on the outcome that they want that they spend their energy resisting the clear, unavoidable signs that it isn't going to happen that way. It's very easy to get frustrated about the "wrong" decision getting made, but it's helpful to keep in mind that there is a great deal of context that you're missing. There is no such thing as a permanent decision: almost every decision will be reconsidered multiple times over the next two years.

Presenting to executives can be intimidating, and this might be more advice than helpful. If you want to boil it all down to one concise tip: send an early draft to an executive attending the meeting and ask them what to change. If you listen to and apply that feedback, you'll figure out the other pieces as you go.

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