Co-Founder at Level Up | Board Director

Honolulu, HI
Joined May 2009
Early in my career, I used my OOO message to stand out to senior executives, here are the 3 things I included (it works):
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How do you find time to make a difference when you already have a demanding job and family? It's incredibly hard. But Amir Satvat does it.
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He shared his 6 honest lessons on how he makes time for what matters. No magical productivity hacks. He makes deliberate choices about his time. Puts in extraordinary effort. Pushes himself outside his comfort zone. And above all, is driven by a mission bigger than himself.
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You will learn something from his approach. Read and bookmark his guest newsletter article. levelupwithethanevans.substa…
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When I was a manager, the most useful career conversations I had with direct reports started with curiosity (not evaluation). I wanted to know:
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1/ What work gives you energy? 2/ What do you want to be known for? 3/ What opportunity do you want before you feel ready (stretch project)? 4/ What part of my management is slowing you down?
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The answers will give you insight about their motivations and goals. Not all direct reports operate the same way nor need the same help. Some need practice. Some need access. Some need a different path. It's your job as a leader to help your team uncover their strengths.
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Early in my career, one of the top reasons I earned fast promotions was that I built trust and credibility with my managers. This resulted in getting bigger and more complex problems to own:
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Instead of asking yourself: "How can I appear more senior?" Ask: "What would reduce the risk of my manager trusting me with more?"
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This mental reframe will change how you operate. Stop trying to "look" ready for the next level. Start building the trust that makes giving you more responsibility an easy decision.
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When @EthanEvansVP (fmr Amazon VP) and I communicate, we use a simple 3-part structure to get to decisions faster: 1/ Recommendation / Answer. 2/ Evidence. 3/ Implication.
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Remember BLUF (bottom line up front). Your audience can always ask for more context. Or you can end with "Happy to share more context if needed."
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The goal is not to share everything you know. It is to communicate what key stakeholders need to know to help make a good decision.
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Jeff Bezos on why compromise and stubbornness are terrible ways to resolve disagreements, and what to do instead: 1/ Compromise is low energy (easy) but does not necessarily lead to truth (e.g. I say the ceiling is 11 ft, you say it's 12 ft, we agree to call it 11.5 ft). 2/ Another bad (and common) resolution mechanism is who's more stubborn. Two executives disagree, have a war of attrition, and whichever one gets exhausted first capitulates to the other. You do not arrive at truth and it is demoralizing. 3/ A solution is escalation. Escalate to your boss and say "We cannot agree on this, we like each other, we are respectful of each other, but we strongly disagree, and we need you to make a decision so we can move forward."
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I like this because it separates disagreement from dysfunction. A misconception I've seen from strong operators is that escalating to the boss signals weakness or failure. It does not. Knowing when and how to escalate quickly is a leadership skill. It prevents organizational paralysis, protects relationships, and keeps decisions moving.
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Remember, the goal is not to win every disagreement. It is to arrive at the best decision possible and keep the organization moving at high velocity. Bar raising leaders optimize for the best outcome, not for being the person who was right.
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The most expensive hiring mistakes I made came from urgency. My org was growing quickly, the team overloaded, pressure to deliver was intense, and an open seat felt like a problem that needed to be solved ASAP.
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What I learned from those mistakes was to define non-negotiables upfront and make it clear to stakeholders that we would not bend to the pressure (get commitment).
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Pressure can (will) make "good enough" look like the smart timely move. You must fight that urge. A clear bar helped me remember that we needed to hire for both now and six months later.
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