One of the most powerful lessons I’ve learned is to ask the next question. So often early in my career I’ve thought to myself, “here’s the answer” only have someone more senior or experienced than me burst my bubble with the next logical question. To which I had no answer. Silence. Awkward.

It can seem like the answer was hard enough to get that you should be “done” at that point. When the person asking realizes you don't know the answer to the next question, to them you've not done a complete job. You're not done. When you can plan for it before someone calls you on it, you can stay ahead.

The most effective way to get good at this is to simply ask yourself "what will they ask next?" You won't get it right the first time, or maybe the first bunch of times. And if you try and keep track of what you thought someone was going to ask you can course correct. It will be heavily dependent on the person (what do they care about, what is their natural disposition) so this is a person-by-person exercise.

“How much money do you need to raise to start your company?” Someone will inevitably ask “What will you do with that that money once you raise it?” “How long will it take for you to spend it?” “When will you start seeing the benefit?"

"How many people do you need to hire?" You should expect to also answer “How long will it take you to get those three people on board and productive?” “Do you already have people on deck?” “What’s the impact of not hiring them?"

"How long will it take to complete this product?" You should anticipate “Who is ready to use the product once it’s finished?” "What if you only had half that time?" “How are you going to deploy it?” “Who is giving you feedback along the way?"

Each question illuminates that difference between the short term goal and the long term objective. What are you trying to accomplish? Or maybe what should you be trying to accomplish? Are you asking the next question of yourself so that you can stay one step ahead?

Often there are more than one “next questions” from various vantage points. Sales. Operations. Development. Consider the different points of view that might be important in the next question.

Always there are different styles of people who will ask questions depending on their natural style. An action oriented person may ask active questions like "What will you do next?" A people oriented person may ask something different like "What will the team feel about this decision?" Knowing the audience will help you know the next question that is likely to come (and will help you see the world from their point of view).

So start asking yourself "what's the next question?" Target your boss, you likely have many interactions with him/her that you can test your hypothesis on what will be the next question. Adjust and continue.