Imagine you and I are cofounders. We’re talking about the direction of the company. We have different ideas. I am making fair criticisms of your idea and you are doing the same to mine. But my idea is inside my head, so it feels like you’re criticising me, not it. The conversation escalates. It doesn’t end productively. I’m sure you’ve had conversations like this.
Ideas are deeply personal. Brutal honesty is good in theory, but not when it risks hurting people’s feelings. Some founders believe everyone should “man up” and take it. I disagree. Re-orienting these conversations away from people’s egos is so easy that you’d be a fool to risk damaging morale over them.
First, get the ideas out of people’s heads and onto something physical. Draw it on a whiteboard. Use a business model canvas. Spread blank cards on the table. Now you can point at an idea and say it’s stupid instead of pointing at a person and saying they’re stupid.
Now literally get on the same side of the table. When you’re sitting across from each other, you’re having an argument. When you’re shoulder-to-shoulder, you’re collaborating. This sounds goofy, but it works. Putting your ideas on a wall is great because it forces you to stand side-by-side.
If you’re still having a frustrating conversation, break the ideas into smaller pieces. It’s easier to evaluate pieces of the idea than the whole thing. If I say your idea to shift the company to enterprise sales is stupid, then it sounds like I’m saying you’re stupid. If I say that I’m not sure we have the expertise to drive a heavy sales process, we’re now having a useful discussion.
Finally, instead of trying to decide whether it a good idea (evaluation), ask what would have to be true for it to work really well (dependencies). In above example we would ask what had to be true for it to really work. Well, we would need significantly stronger sales skills, so we’d need to either make a key hire or train ourselves up. And we’d need a pipeline of enterprise leads who took us seriously. And we’d need much more reliable uptime than we currently have. And so on.
We’ve taken the idea, de-personalised it by getting it out of your head and onto paper, broken it up into sub-components we can talk about, and then looked for dependencies rather than trying to evaluate it.
Sometimes the reasons are personal rather than rational. You might end up realising that for this to be a big success, you’d need to be spending most of your time doing sales.
“Do you like doing sales?”
“Me neither. Would you really want to run a business like this?”
In the abstract, it’s your idea and you’re excited about it. Once you can get the egos out of the way and discuss it, it’s easy to see where it falls apart.
The point isn’t to coddle people. It’s to structure the conversation which makes it easy to be brutally honest without any of the consequences or difficulties of brutality.
 The “what would have to be true” question is from Lafley/Martin’s book on strategy called Playing to Win, which, in combination with Rumelt’s Good Strategy Bad Strategy, is probably all you need to read on the subject.