3. Identify a shared goal

After you’ve gotten permission, articulate the other person’s point of view. What is the idea, opinion, or proposal that you’re disagreeing with? Stating that clearly, possibly even better than your counterpart did, lays a strong foundation for the discussion.

“You want your counterpart to ...

After this risk assessment, you may decide it’s best to hold off on voicing your opinion. Maybe you haven’t finished thinking the problem through, the whole discussion was a surprise to you, or you want to get a clearer sense of what the group thinks.

If you think other people are going to...

When you move on to expressing your concerns, watch your language carefully to avoid any “judgment words” such as “short-sighted,” “foolish,” or “hasty” that might set off your counterpart; one of his tips is to cut out all adjectives, since “the...

Emphasize that you’re offering your opinion, not gospel truth. “It may be a well-informed, well-researched opinion, but it’s still an opinion, [so] talk tentatively and slightly understate your confidence.”

Say, “This is just my opinion, but I don’t see how we will make that de...

Ultimately, the person in power is probably going to make the final decision, so acknowledge that.

You might say, “I know you’ll make the call here. This is up to you.” That will not only show that...

This step may sound overly deferential, but it’s a smart way to give the powerful person “psychological safety” and control.

• You can say something like, “I know we seem to be moving toward a first-quarter commitment here.

I have reasons to think that won’t work. I’d like ...

Most people tend to overplay the risks involved in speaking up. “Our natural bias is to start by imagining all the things that will go wrong.” Your counterpart might be surprised and a little upset at first.

But chances are you’re not going to get fired or make a lifelong enemy. First, con...