Understanding others viewpoints is key to making progress on projects and initiatives. It is better to ask tough questions and try to understand the other side than keep pushing forward without changing strategy. I often listen to two people having a conversation and totally miss the point of their discussion because neither side is attempting to dig in and ask specific questions. One example that came up was due to friction in a process, a team member vented that a policy for making changes became too onerous but this came across in a way that sounded like removing the entire process. Unfortunately due to not asking questions the discussion became about why is it important we have process. Without asking questions there was no discussion on how the process could be improved and whether it is bringing value in this instance?
Questions benefit me in my day to day life and work life in a variety of ways. I can show interest in a variety of people and their circumstances. I can dig deeper into ideas and concepts and listen to people and learn about things I never knew about. I can accomplish more of the right tasks when I ask questions. I can paraphrase what the person has said to verify that we're both in agreement. I use this a lot with my wife since English is not her first language. Shallow agreement is the worst when two people are miscommunicating but think everything is fine. I almost missed the bus to the airport because I didn't ask what my wife meant by if I had my 'ticket'. A bus ticket not the parking ticket for my car. This could have been avoided if I paraphrased or asked the right question.
Two books I recommend for asking better questions are "Leading with Questions: How Leaders Find the Right Solutions by Knowing What to Ask" by Michael J. Marquardt and "Never Split the Difference" by Chris Voss. Both provide excellent information on question asking from different perspectives one from leadership the other from negotiation.
When working with my teams in software design sessions clarifying the problem is the hardest exercise. When we get near the finish line I have to ask "How is this working in a way that solves the problem for our customer?" If the answer is not clear I put it on myself and say, "I'm sorry, I'm failing to understand could you explain this in a different way?"
Ask people questions and keep digging for answers and asking what else?