Jason P. Yoong

Early in my career, I used my OOO message to stand out to senior executives, here are the 3 things I included (it works):

Brian Chesky (CEO of Airbnb) believes pure people managers will not survive the age of AI. I agree. The next era of great leaders will be builder-managers who can manage through the work. Why? 1/ Context matters. If you do not deeply understand the customer, product, and context, you cannot effectively lead builders. 2/ Judgement matters (tied to above). Teams need leaders who can inspect the work, challenge assumptions, and make calculated tradeoffs quickly. This judgement stems from being deep into the context (otherwise, you are too slow). 3/ Top builders will not want to work for removed managers (aka sitting in their high castle). The best way to manage your team is not by being their work therapist. It's by managing your team through the work. (Brian cited Jony Ive and Frank Lloyd Wright as bar raising design leaders who manage their teams this way)

Strong operators make tradeoffs visible. They do not simply ask: “What should I do?” They explore: “What can I stop, delay, delegate, or reduce to make this happen?” Prioritization is not just choosing what to do. It is also making clear what you will NOT do.

You cannot silently accept every "priority". It is unsustainable. And rarely are all projects equally important.

Early in your career, when everything given to you is labeled "high priority" you must manage up confidently by outlining tradeoffs and your recommendation. Here's a few responses you can use:

Reliability beats talent more than people realize. Say what you will do, do it, and repeat. That will compound and set you apart in the long-term. Important for early career folks to understand.

The phrase is from Ethan Evans and it also applies to questions. Ask sharp, concise questions. Even senior leaders make the mistake of starting their question with "Let me share some context..." (20 seconds later they are still rambling and no one knows the question). Don't do that. Start with your question and say happy to add context if needed.

When communicating with executives, follow this rule: "Be bright, be quick, be gone." Here's what it means: 1/ Be bright — lead with your headline recommendation then back it up with the key insight or data point. 2/ Be quick — be clear, concise, and confident. Do not ramble. Do not over explain. Give space for a two-way conversation. You want a back and forth volley (not a one-way TED Talk). 3/ Be gone — if you got what you needed, end early. Give time back. Do not cram a new topic with 7 minutes left.

Use it both ways. Collect examples of good judgement. And bad judgement. Then study the patterns. And mold them into something that is uniquely you.

Charlie Munger said it well: “I sought good judgment mostly by collecting instances of bad judgment, then pondering ways to avoid such outcomes.”

Judgement is hard to teach. It must be developed through first-hand experiences and mistakes.

6/ Partnered with my manager to let me shadow high-stakes meetings (I played role of note-taker)

5/ Came prepared with my POV and a question in every setting I was around them (e.g. All-Hands, org meetings)

4/ Volunteered every time they needed help (e.g. stretch projects, extra work, messy problems)

3/ Studied their inputs (asked what they read and I followed up when I had an interesting POV to share)

2/ Observed their patterns (how they communicated, what they spotlighted in All-Hands, questions they asked) — note, all where different

Early in your career, one of the fastest ways to grow is to find what "great" looks like. Then closely observe and shadow that person. Here's how I did it:

1/ Identified bar raising execs (people I respected, admired, and learned something from in every interaction)