“What kind of pick-me-up can I get you today?”

Imagine if that were the question you heard when placing your coffee order instead of the usual, “How can I help you?”

The question won’t change your standard order, but it could change what you say. For example, if you pause to think about what kind of pick-me-up is needed, you might be more inclined to reveal more information, like you’ve been traveling a lot, haven’t caught up on sleep and need a jolt of coffee before giving a presentation at work.

It’s a small deviation from your usual script and highlights something I’ve learned after 20 years of asking questions and interviewing athletes as a sports broadcaster: A great question leads people to reveal more than they expected 98% of the time. (And if I hadn’t interviewed Marshawn Lynch and Bill Belichick, I would have bumped that up to 100%.)

More revealing answers allow you to get to real issues earlier in the conversation without overstepping or shortcutting the relationship-building process. Identifying the real issues allows you to showcase your value and expertise — and more revealing answers enrich the interaction.

Let’s go back to the barista and the coffee order. The real issue isn’t that you’re thirsty and coffee is the only thing to quench your thirst; it’s exhaustion and the stress of a presentation at work. An attentive barista could then suggest buying a bottle of water and a snack to take for later in the day, so you have one less thing to think about. The upsell helps the barista demonstrate her value to the store, while enriching the interaction with you, the customer, who then feels heard and supported.

As someone who asks questions for a living, I understand the power and importance of great questions. I also know those are rarely “off the cuff.” Great questions start with me being strategic and thoughtful about the person I’m interviewing, and knowing what I want to accomplish in the interaction. That means the first question that comes to mind isn’t usually the one I ask, unless I’ve run it through a series of filters and determined it really is the best question.


Here’s the process I use in revising questions from good to great, using a topic I’ve asked about previously during Mariners spring training: traveling and life on the road.

Identify the objective. “What do I want to get out of the question?” I don’t just want an answer. I want an answer that connects the athlete to the audience or provides greater insight. In this case, I want to understand what it’s like to play 81 road games and travel for half the season.

Initial question: “What is it like being on the road during the season?” 

Easy swap. Is there a one-word swap that gets to the heart of the objective? In this case, I chose “frustration” because most people talking about business or work travel don’t talk about the joys of spending hours on planes and weeks in hotel rooms.

First revision: “What frustration do you feel being on the road for half the season?”

Make it relatable. What can you personally relate to in this scenario? Frequent travelers can list a number of frustrations, including travel delays, no legroom on planes, overbooked hotels and forgetting to pack something. We’ve all been there, even major league players.


Second revision: “Do you get frustrated with traveling and packing?”

Add just enough context. This is not a long preamble or setup to the question. It is making sure the question doesn’t come out of left field and that all parties are on the same page. If there’s any confusion, I won’t get the answer I’m looking for because no one wants to look stupid when answering a question — especially on live TV.

Final question: “When packing for a road trip, what’s the item you’re most likely to forget to pack?”

When you compare the different variations of the question you can tell the final version is more focused. The frustration showed on the players’ faces when they started talking about the belts, shoes and power cords they forget to pack. I asked that question to more than 30 players and not a single one gave a one-word answer, which showcases my value as a broadcaster in being able deepen the audience’s knowledge and connection with a player.

This process works for every type of question in any industry. You could say the first thing that comes to mind, but for better answers and ways to show your value and expertise, start by asking better questions.