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Ask Better Questions

Updated: Aug 30, 2023

As a product leader, focus on including a broader group of people and asking better questions to let stakeholders add their expertise

Asking better questions is an essential skill. Asking open-ended questions can bring out real needs that often get missed in traditional interview scripts. Asking all your stakeholders, including clients, prospects, development, operations, service, sales, marketing, and finance, better questions can give you amazing insight and opportunities to deliver products and solutions that people love.

A friend shared a delightful story with me recently that demonstrates how important it is to ask better questions and to give stakeholders opportunities to add their expertise and value to the solution.

Here's the story... A property manager decided to sell one of his real estate income properties. It was an older farmhouse with charm and lots of updates, but it was close to the road and had an old stone 5-foot-high retaining wall in the front. The wall was cracked and ready to fall. It was a big project and impacted the curb appeal of the property.

The owner called in a landscape firm and asked what it would cost to rebuild the wall. The landscaper gave him an estimate for $35,000 which involved weeks of work and permits for closing the local street to get access to the wall. The owner felt that was too much money to ever recoup in a sale. Another landscaping firm said $40k. The third said $37,000. Standing there with the last landscaper, the property owner threw up his hands and said, "I hate this wall. I wish it weren't there!"

The landscaper looked at him and replied, "Okay. For $10,000 I'll get rid of the wall, regrade and seed the lawn, and take down that big ugly tree out front. It will take two days and I can do it next week without closing the street."

"That would be perfect!" the property owner said. Then he asked the landscaper, "Why didn't you offer this simple, better, and cheaper solution before?"

The landscaper responded, "You asked me for a bid on rebuilding the wall. I figured you wanted a wall."

So, the moral of this story is to ask better questions and let your stakeholders share their expertise. If the property owner had asked a better question like, "How can I cost-effectively improve the curb appeal of this property?" he would have benefited from expert suggestions and gotten to a solution sooner. But because he jumped ahead to solving the problem, he unintentionally discouraged input from knowledgeable people who could contribute to a much better solution. Soon the property looked much better and sold quickly.

“Make sure your product stakeholders - clients, prospects, development, operations, service, sales, marketing, and finance, have opportunities to add their expertise and value to the solution.”

Sometimes Product Managers/Product Owners feel the time crunch of meeting Agile ceremony deadlines and roadmap deliveries so intently that they jump ahead to a solution without taking advantage of all the creativity and expertise available from their stakeholders and forget to ask for their input. Make sure to ask - and when you do, ask better questions.

4 Steps to Asking Better Questions

1. Don't Assume You Know Everything. I've met with product leaders who tell me they know what each of their stakeholders want. The product team typically will point to client service requests or sales inputs represented on the roadmap. I often ask how they know this is the right list. The answer is, "Well it's always the same. Sales want competitive features, service wants faster onboarding, and so on. I don't have time to sit with them on every feature." Sometimes when I ask if the groups outside of development, design, and ops have provided input on the solution or the user stories, I'm told that they don't have time to talk to them all. Please don't be that product person.

2. Ask Open-ended Questions. Start by setting the stage for the conversation you want to have. Then ask an open-ended question. "Please talk to me about your role and how you use products like ours? What do you wish we included with this product?" After you ask people for their input, be quiet. Let them think. Let them talk. Feedback is a gift. Don't answer the question for them. Don’t stop with one question. Keep the conversation going. Don't pester people just to ask questions but be prepared to ask questions to continue the conversation.

"Feedback is a gift."

3. Listen with Care. Many of us multitask and as a result, we don't truly listen and open the channel to hear what people are offering us. Listen. When you listen, you learn what you really should be asking. Respect the input you are getting. Care about it and the person gifting this to you. Be genuinely interested in the perspective of the person sharing their knowledge with you. You will learn so much. And your questions will get that much better.

4. Collect the Input. Better questions yield better input. Take careful notes and capture the story and context they are sharing with you. Bring your stakeholders' stories back to the team. Share the feedback and incorporate it into your user stories. It will be a valuable use of your time.

It's common for us to overlook the value of truly listening to others. When we fail to listen, we miss the valuable insights that others can provide. By actively listening, we can discover the right questions to ask and gain a greater appreciation for the opinions and knowledge being shared with us. It's important to respect and care about the input we receive, as well as the person providing it. When we take a sincere interest in the perspective of others, we can learn so much and improve the quality of our solutions.

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