I've always prided myself on my ability to ask good questions.
Whether I'm out for drinks or talking with a client, I love conversation that goes above and beyond mundane small talk.
What makes a question "good" in the first place?
If you ask me, the best questions are thought-provoking in a way that's uncomfortable. These types of questions aren't tough for the sake of being tough, they're difficult because their answers are unrehearsed.
They require more effort than simply asking, "How're you?" or "What's your favorite restaurant?" Instead, they get at something much deeper, an untapped thought or feeling that isn't used to having the spotlight.
Like most, this skill takes time and plenty of practice to crack. A great place to start is to keep things simple by asking, "Why?" more often. Not only is it short and sweet, it shifts attention to the other person.
Unfortunately, once this happens, most people use passive listening while they wait for their turn to talk. They miss so much great insight that can lead to better questions and deeper connections.
Instead, try to listen with the intent to understand. Not only will you become more "interesting" to others, you'll also benefit from their personal experience. It's a win-win for everyone.