My biggest win at Uber came around when I stopped trying to convince the decision maker or even his number 2, but instead focused on turning all direct reports of the number 2 and had them lead the meeting I prepared. Yes, it took time, but how else do you turn an oil tanker?
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Another hard lesson at Uber was that in-person 1:1 meetings are critical, even in a globally distributed company
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Good decision makers delegate a lot, because they don’t have the time to go as deep as you can. That does mean part of their decision will be based on “do I trust this person to have done their homework.” And trust comes faster in-person.
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So yes, flying across continents pays off for big decisions. People in sales or business development don’t just travel a lot because they enjoy it and the same holds for your internal “sales pitch”
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Trust also comes from being a known quantity: Send key stakeholders personalized updates. Highlight particularly useful tidbits for them. Think through how they will explain their decision to a third party. Give them talking points, either implicitly or explicitly.
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Especially “meet people before the meeting” and “share material beforehand” works miracles.
Also make sure to pro-actively highlight benefits for key stakeholders — have them champion your proposal
Lots of folks crash and burn in their first attempt in convincing a LargeCo group of something. Could be a promo you want to push for your report or a product proposal you want to pitch.