1. Appoint a devil’s advocate. Someone whose excellence is demonstrated by the quality of questions they ask. Great questions include: “What are the best reasons not to do this?” “What don’t we know that, if we did know, would change our decision?” “If we had more money or time, what would we do?” “If this were a documentary, what would be the narrative arc?” It’s important that different people play the role of devil’s advocate: if it is always the same person, they’ll get tuned out — and burned out.

2. Find allies. If you have concerns, try asking others privately, “Are you okay with this? Does anything about this bother you? Is there another way to frame this question?” Having allies allows you to work together to be creative and solve the problem.
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3. Listen for what is NOT being said. If the conversation is being framed about money, consider what is not being talked about. If everyone’s talking technology, what have they left out of their equation? Sometimes it’s helpful to bring in an outsider to help with this. They should do nothing but listen. Then, ask for their impressions — not recommendations. They may notice trends that people embroiled in the conversation simply can’t.
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4. Imagine you cannot do what you all want to do. In other words, think about what you would do if you could fire someone, if you could change the timetable, or if you were allowed to cancel the deal. If you could do any of those things — would you still proceed with your plan? What are the hidden orthodoxies nobody is challenging?

5. After a decision is made, declare a cooling off period. Ask everyone to go home and think about the decision on their own as well as discuss it with their family. Come back after a prescribed amount of time and ask the group: does the decision still look great?