Leading with Powerful Questions Series: Part 2 - Start a Listening Tour
….and many, many more example questions!
Last week, I kicked off a new 3-part series — this time focused on Leadership and Influence in this Cook’s Coaching Corner.
In Part 1 of this series, I introduced the Power of Leading with Questions:
Why the best leaders lead with questions, not answers.
How great questions create great teams who trust each other, solve problems together, and create innovative solutions.
A framework for shifting from player to coach.
I shared how early in my career, I assumed that being a great leader meant having all the answers. I took pride in solving problems quickly, offering solutions, and moving fast. But over time, I realized something profoundly important when it comes to leadership and influence…
The best leaders don’t give the best answers; they ask the best questions.
I was schooled on this by some of the best in the business including Scott Cook, Bill Campbell, Reid Hofmann, and several others. As a lifelong student of the “Best Ofs” in things I’m interested in, I made a conscious effort to start asking more questions, talking/telling less, and listening way more.
I experimented with my first Leadership Listening Tour around 2010. I’d heard about it but thought it was just another one of those management fads. For this effort, I decided to design my own.
In my previous roles, I would have walked in with a directive roadmap and an impressive five-point plan in an attempt to gain immediate credibility and respect. This time, I spent a few weeks creating a comprehensive set of question prompts (this was long before ChatGPT!). My plan was to ask the same set of questions to critical company leaders. Their answers were designed to give me the data I needed to deliver a CFO roadmap based on what they needed and wanted, not just what I believed was required. These were my customers and my team’s customers after all. What better way to simply ask my customers critical questions such as:
“What does winning or success look and feel like?”
“What does losing or failure look and feel like?”
and many other questions such as:
“What’s the biggest challenge keeping you up at night?”
“What’s one thing finance could do better to help your team succeed?”
“If we could only solve one problem this quarter, what should it be?”
“What’s the biggest blocker to your team’s success right now?”
“How can my team unblock you and help you go faster?”
“Is my team doing something you wished they would stop doing?”
Those questions did a few influential things:
The questions began to build trust by showing I wasn’t just there to impose my own agenda. I knew trust only came from establishing a consistent relationship over time. I genuinely wanted to understand the business, their impact on the business, and my team’s impact on them.
The questions helped me quickly identify patterns and recurring issues that weren’t obvious from the financials alone.
Within weeks, I had a much clearer sense of who our customers were, their priorities, and the steps required to improve the relationships between teams. I wasn’t just trying to be the CFO. I was establishing the seeds of executive partnership in an effort to help prioritize and solve some of the company’s biggest challenges.
This is the power of great leadership questions. This is the power of a leadership listening tour. Over the years, I’ve run over a dozen leadership listening tours with an effort to refine and improve each version.
In this part 2 post, I’ll break down exactly which questions to ask, when to ask them, and how to use them to drive influence and impact.
The Three Types of Leadership Questions
Not all questions are created equal. The ones you want are the ones that open doors while avoiding the ones that shut down conversations. Great questions create focus and clarity. Bad questions? Well, those create confusion and arguments.
I touched on great questions in Part 1 of this series:
Specific and Intentional
Non-Judgemental
Future-Oriented
Help People To Think Differently
Provide Focus and Clarity
Simplify Decision-Making and Prioritization
Let’s put these into Three Categories of Powerful Leadership Questions (through all my years of trial, error, and course correcting). The three categories are:
Relationship Questions – Building trust and strengthening relationships. Creating a “Customer-Owner” partnership where they are the Customer and you are the Owner.
Prioritization Questions – These drive better decision-making with your new partner. These questions help to separate urgent from important and help drive priority actions. My Three-part Series on Decision-Making from last year is great for further reading on this area.
Strategic Questions – Aligning teams and creating focus.
1. Relationship Questions: Build Trust First
Before you can lead effectively, you have to build trust. The fastest way to do that is by asking the right relationship questions. These questions focus on the person and their team as your customer— their success, in turn, drives joint team and overall company success. Your questions here are designed around partnership, never around being a police person.
Great Relationship Questions to Ask:
“Tell me your story on how you arrived here?” Or if you are feeling comfortable….
“Who or What influenced you the most as a kid, a teenager, and now as an adult?”
“What’s the biggest challenge you’re facing right now?”
“Who was the best CFO (*replace with your role*) you ever worked with? Why?”
“Have you ever had a great coach or teacher”?….then “Please tell me more?”
“Who was the worst? ….p.s… Don’t forget the Why? In both those questions.
“How do you like to receive information and data?”
“What is your decision-making style?”
“What’s one thing my team or I can do to make your job easier?”
“If you could change one thing about how we work together, what would it be?”
Looking back on my past notes, here’s one of the questions I asked during my annual listening tours with dozens of Mozilla leaders:
“What’s one thing we could do to make finance more helpful to you?”
The answers didn’t surprise me. Some wanted clearer forecasting, others wanted faster spending approvals, and one executive simply wanted a monthly email summarizing financials in plain English. None of these were huge lifts but asking the question (and acting on the responses) immediately built credibility and a sense of partnership.
2. Prioritization Questions: Making Better Decisions and Separating Urgent from Important
In every organization, there’s more work to do than time to do it. That’s why great leaders use questions to focus on what matters most.
Great Prioritization Questions to Ask:
“If we could only accomplish one thing this quarter, what should it be?”
“What’s the one bottleneck slowing us down the most?”
“What’s the biggest risk we’re not paying enough attention to?”
“What’s something we’re spending too much time on that doesn’t actually drive impact?”
“What system or process do you hate the most?”
“Who should actually be making this decision?”
Example of How This Works in the Real World
At one startup I worked with, the executive team was drowning in competing priorities. Everything felt urgent. So, during a leadership offsite, I asked a “Go Around the Table Quickly” Question:
“If you could only choose one priority for the next 3 months for the company, what would it be?”
I remember clearly when we did this exercise at Mozilla, shortly after Google launched the first version of their Chrome browser. After some debate about what our one company priority should be, the answer became clear: “Are We Fast Yet?”
This one mantra was the rallying cry for our various engineering teams and module owners to optimize, re-design, and win the better browser war.
The lesson: Asking the right question, the right way, created a clear focus on priority and rallied the company behind a critical effort.
3. Strategic Questions: Align Teams and Create Focus
Once you’ve built trust and set priorities, the next step is aligning your team around the bigger picture. Strategic questions help ensure that day-to-day execution is connected to long-term vision.
Great Strategic Questions to Ask:
“How does this decision align with our long-term vision?”
“Was it a good decision with a bad outcome or a bad decision with a good outcome?
“What assumptions are we making that could be wrong?”
“What does winning actually look like?”
“What is our big blind spot?”
“Does anyone have a big elephant in the room we aren’t talking about?”
“How will we course correct this decision?”
Example: How This Works in the Real World
At Intuit, where I started my Silicon Valley career, the leadership team had a simple but powerful strategic question we used repeatedly:
“What are our customers most frustrated by?”
Anytime a team proposed a new product feature, marketing campaign, or investment, they had to answer that question. If they couldn’t, the initiative was dead in the water. It had better be “Faster and Easier”!
This single question created incredible strategic focus. It ensured that no matter what part of the company you worked in, you knew exactly what mattered most:
“How do we create more ‘Wow’ and ‘Aha’ moments for our customers?”
CALL TO ACTION: SCHEDULE YOUR OWN LISTENING TOUR
One of the best ways to implement these leadership questions is through a Leadership Listening Tour as I described at the beginning of his post.
The PlayBook is as follows:
How to Run a Leadership Listening Tour:
Schedule 1:1 meetings with key company or department leaders (executives, directors, board members).
Design your own mix of relationship, prioritization, and strategic questions.
Only ask the questions. Then, listen and take notes.
Summarize what you heard from each participant before the meeting is over.
Pattern match and categorize all answers across all respondents.
Design your follow-through priority actions.
Coach Your Departments To Do Their Own Listening Tours
After a few rounds of successful executive leadership listening tours I personally conducted, I decided to send the teams that reported to me (Finance, IT, Security, Facilities, and People Ops) to do their own listening tours and quickly realized this exercise carried with it additional team benefits:
Teaching the team members how to better establish a partnering-type relationship by starting simple, scripted conversations.
Gathering data on the “Current State” from each department.
Teaching the team how to think and plan “Future State” by gathering “Listening Tour Data” and then how to put their data into their own department's "Strategy - Structure - Execution" framework as they categorized, prioritized, and created their own department's future roadmap based on what they learned.
When doing a “Department Listening Tour”, I like adding additional powerful questions that inspire the Ownership Culture I’ve posted about previously and that I believe should be the ultimate goal of most leaders, teams, and companies.
“Ownership Questions” Example
I have my team members ask and also answer for themselves and their own teams:
“Who are we as a team?”
“Who is our customer?”
“What is the product we deliver?”
“Why is our product needed?”
“What do they do with our product the minute they receive it?”
“How well are we delivering these customer needs today (5-star rating)?”
“Have we received ad hoc feedback recently on our deliverables?”
“What’s the one feature we can add next month to improve our product?”
Other Listening Tour Questions I’ve Historically Asked:
“What’s the biggest blocker to your team’s success right now?”
“If we could fix one thing this quarter, what would it be?”
“How can my team unblock you and help you go faster?”
“Is my team doing something you wished they would stop doing?”
These questions and many others help quickly identify pain points and prioritize urgent issues while building trust with the executive team. Consistently, the feedback from team members post-tour comes in the form of:
“The ‘data’ I got back was eye-opening.”
“I feel much more connected to what other departments and leaders need from my team.”
And to think the only requirement is to structure great questions, ask them, and then listen….and when I say listen, I mean REALLY LISTEN and write down the answers (a.k.a. - document everything!).
Explicitly, this means you aren’t allowed to be defensive or to respond to the negativity or issues being surfaced. Your role on a listening tour is to be a notetaker and reporter only. You must resist the urge to respond.
Your only response should be in the form of:
“Thanks for sharing that. We will take all this great data to heart and come back to you with solutions.”
Summarizing what you heard at the end of all the questions/answers to show them you really listened and captured their ideas correctly.
Finally, I’ll wrap up Part 2 of this series with a compilation of even more questions in the form of categories of Customer-Stakeholder, Problem-Issue-Solution, and Timing Questions. You get the idea. Feel free to roll your own categories and questions in terms of Powerful Leadership Questions. Always remember to design the questions for either the answers you need or to get the person answering to understand what you may otherwise already know.
CUSTOMER - STAKEHOLDER QUESTIONS
“How is our customer impacted?”
“How can our customer benefit?”
“Who are the key stakeholders involved?”
“Who else should be consulted?”
“What’s the largest risk to our customer or stakeholder?”
PROBLEM - ISSUE - SOLUTION QUESTIONS
“Have we identified the Root Cause of this issue?”
“What assumptions are we using?”
“Is there data to support our assumptions?”
“What alternatives have been discussed?”
“Is there a next immediate step to at least pause the problem?”
“Are there risks we haven’t thought about?”
“Is there an easy way or alternative way to gather more data?”
TIMING QUESTIONS
“Can somebody summarize everything we know right now about the issue?”
“What do we not know yet?”
“When are we likely to know?”
“Can we set a deadline for taking action?”
“What solutions have already been attempted and when?”
“What should we try next?”
“What do we expect with our potential solution?”
“When will we know if our assumptions are right or wrong?”
“Can we create some course-correcting solutions once we get our next set of data on the actions we took?”
I just copy/pasted the above into ChatGPT to create an image (below) as an experiment. It turned out pretty well. It looks like it added a few more questions. You may want to print it out and post it near your monitor or keep it in your own “Best Of” files.
Note: If you are reading this and wondering how best to get started or want to go much deeper on Powerful Questions and/or all things Listening Tour, please schedule some time with me here on www.benchboard.com. I spend multiple sessions with clients going much deeper than I could ever cover in this 3-part series, and it’s as good a place as any to start a coaching partnership.
Bookmark this Series!
Up Next Week: Part 3 - Leading With Why
In case you missed it… Part 1: Introduction to Leading With Powerful Questions
