directly, but if your boss is sold on the idea, he may simply dismiss your perspective and order you to proceed. Here’s how you might use information gathering to challenge the plan: Boss: So we’ll go with Todd’s marketing strategy. I need you to tell your team about it and map out the plan to execute it with Amar (the sales manager). You: Got it. Can I ask you a question? Boss: Sure. You: What’s the length of time we’re planning on using this strategy?