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Ask Better Questions

Updated: Oct 6, 2021

As a product leader, focus on asking better questions to let stakeholders add their expertise

A friend shared a delightful story with me recently that reminded me to one, make sure I ask better questions and two, give my product stakeholders: clients, prospects, development, operations, service, sales, marketing, and finance, with 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's an older house with charm and lots of updates, but it's close to the road and had an old, 5-foot-high retaining wall in the front. The wall was cracked and nearly falling. The owner called in a landscape firm and asked what it would cost to rebuild the wall. The landscaper gave him a $25,000 estimate. That was too much money to ever recoup in a sale. The next landscape firm said $30k. The third said $27,000. With this, the property owner threw up his hands and said, "I hate this wall. I wish it weren't there!" To which the landscaper replied, "Okay. For $5,000 I'll get rid of the wall, regrade the lawn and take down that ugly tree out front." That would be perfect! The property owner asked the landscaper why he hadn't offered this simple solution earlier. His response, "You asked me for a bid on rebuilding the wall. I figured you wanted a wall."

So, the moral of this story - 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 had the benefit of the experts' suggestions and gotten to a solution sooner. But because he thought he knew the answer to the problem, he discouraged input from knowledgeable people who could contribute to a much better solution.

“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 don't take 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. I often ask how they know this. The answer, "Well it's always the same. Sales wants 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 get snorts, eye-rolls, and nervous laughs. Please don't be that person.

2. Ask Open-ended Questions. Start by setting the stage for the conversation you want to have. Then ask an open-ended question. "What so you think is the most important value of this product/feature?" "What do you wish we could achieve with this product?" After you ask people for their input, be quiet. Let them think. Let them talk. 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 prompt a conversation.

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.

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