Matthew Thompson

The reason Riley has his incredible resume is that he understands leaders don’t need a resume or banners. They need: 1. Honesty without fear of confrontation. 2. Be direct, don’t pull punches, but don’t act in anger. 3. Set the standard, become the standard. 4. Don’t play favorites. 5. Remain confident with a sense of humility. 6. Blame no one. 7.

I think “And what else?” is the best coaching question in the world. It does two things: It extends the period of curiosity, and it tames your advice monster.

(The first) question is “What’s your mind?” The last question is “What was most useful and most valuable?” The other one is “What’s the real challenge here for you?” It’s almost an identity element. It helps people figure out the real challenge rather than be the person who has the ideas. That’s actually a much rarer, more useful skill in most orga

The way I define coaching is behavioral. Can you stay curious a little bit longer? Can you rush to action and advice-giving a little bit more slowly?

Everyone has ideas, but ideas are cheap and easy. Knowing the real problem is rare and precious and strategic. If you’re in an organizational setting, if you want to be seen as different and valuable, be the person who’s going, “What’s the problem? What are we really trying to solve here?”

Actually, what’s really powerful is to give people responsibility for their own freedom. There’s this paradoxical way of showing love.

Curiosity unlocks insight about the situation and yourself. Curiosity helps people feel seen, understood and encouraged. If you lead with curiosity, it’s a more powerful place to lead from most of the time.

One of the most intelligent case studies in design is the Chinese tea cup. They’re made without handles simply because if it’s too hot to touch, it’s too hot to drink.

Humans naturally want to add more. Add a cardboard sleeve, add a warning on the outside of the cup, add a handle. The result of all these things never cools down the actual contents.

You have to bet on yourself and how you're different to make it work," he said.