SPEAKER

Alexis Rask - Executive Coach & Partner @ Sweat Equity Ventures

Named 40 under 40 by Silicon Valley Business Journal, Alexis is an experienced business operator turned Executive Coach to Silicon Valley's top founders and VCs. Prior to founding her coaching firm, Future Consulting, Alexis founded the Marketing Solutions team at LinkedIn in 2006.

"When I say a powerful question, I'm saying 'What's the really right question, for this right moment, that is going to TRULY unlock someone's thinking, in a way that gets at new information.'"

- Alexis Rask

She opened offices, hired out the sales and customer success teams, and developed the go-to-market plans. She has also served as COO/CRO at Shopkick which sold for $250million in 2014. She is also a faculty member of UC Berkeley's Executive Coaching Institute.

Check out our friends and sponsor, Jellyfish!

Jellyfish helps you align engineering work with business priorities and enables you to make better strategic decisions.

Learn more at Jellyfish.co/elc

Show Notes

• What’s the most powerful question you’ve ever been asked? (4:40)
• Failure-modes of open-ended questions & how to use powerful questions to get to “the heart of the matter” (11:54)
• The impact of a more powerful question (18:55)
• Emotional intelligence & how to get the best from people (25:40)
• Why “WHY” is the perfect follow up question (31:24)
• How to use powerful questions in your 1 on 1’s (38:49)
• How to get over the fear of silence… (41:40)
• Identify opportunities to ask more powerful questions with the “mental review” (48:18)
• Takeaways (54:19)

Transcript

Patrick Gallagher: Alexis, Thank you so much for joining us here on the show.

Alexis Rask: Well, Patrick and Jerry, thank you so much for having me! It's always fun to talk and I'm excited to see what comes up today.

Patrick Gallagher: I know we're here to talk about powerful questions and we're going to be going through this a little bit differently than how our show is normally structured.

In anticipation of the conversation, I've been reflecting on, you know, the popular Tony Robbins quote of "The quality of your life is determined by the quality of questions you ask."

And before we kicked off, Jerry and I were talking about how we feel like, in reflecting on this conversation, that there are a lot of really powerful questions missing from our life.

At least for me, I feel like I struggle with coming up with what questions should I be asking? And even in hard situations, my default is to avoid conflict. So if there's an opportunity to ask a hard question or a powerful question, I tend to avoid that.

And I know one of your specialties first as a C-suite operator. And now as an executive coach is to help founders and CEOs ask questions that people aren't expecting or want to avoid. But these are the most important ones that they need to address.

All of that in consideration, really excited for this conversation. And to open it up to you, Alexis, what's the best way to bring everyone into this topic? What's the best way for us to kick off?

Alexis Rask: Alright, well first of all I realize that we're recording a podcast I should not be keeping notes on the interesting things you're saying that I want to come back to... typed. So I have to switch over to paper. But you know I'm going to come back to what powerful questions are missing from your life. So let's bookmark that for later...

What's the most powerful question you've ever been asked?

But as we kick ourselves off today, you guys are the expert interviewers. But if you'll let me, I'm going to flip it a little bit and I'm going to ask you each to tell me if you have a moment or a story where someone asked you a powerful question that transformed your life, transformed your career, had a big impact on your thinking, made you take a different decision.

Just want to hear about one moment where a question was a big, significant thing in the life of Jerry. In the life of Patrick. So I'll turn it back over to you.

Patrick Gallagher: I think one... was doing some yoga this morning and what it reminded me of is about two years ago I attended a meditation retreat at Spirit Rock in the Marin Headlands. And it's the first time I'd ever done any, anything like that. So towards the afternoon, the two leaders a man named Vinnie Ferraro and Wes Nisker, Vinnie Ferraro's very like nineties, punk, and Wes is an old radio broadcaster who was also a little bit in the nihilistic Buddhism like, "Oh, we're all in this rock, just flying through the universe. So like none of this matters anyway, but you know, here's how we, human beings deal with suffering..." So incredible people, but we were doing, a visualization meditation.

And one of the things that they were prompting was, you know, we're all dealing with or carrying different things. And it's not about what you're holding, but rather it's about how you're holding it.

And at the time of this retreat, it had been a few weeks, but my parents had recently let me know that they were going to be getting a divorce and I hadn't really had the time to process that emotionally for like what that meant for me. I more so was the responsible son trying to support my parents through that emotional time for them.

And so thinking about, " What am I holding and more, so how am I holding?" was a really releasing moment for me because it was the first time I had got to actually sit there and realize that I was sort of holding on to these things as like this really fragile and tightly gripped and tightly wound thing. And I realized that that was my experience through a lot of things in life was that I was just really now fragile and tightly wound with everything. Not just related with what was going on with my parents. And so for me, those questions it felt like a big release in that moment to recognize that.

And so that was, what I think about. It has been a really powerful question that I think helped me out significantly.

Alexis Rask: Well, how amazing at THAT moment and one that you could ask every day in every situation on any emotion or set of circumstances. So a pervasive, powerful question. even better.

Okay. You're starting us off strong! That's a high bar for a powerful question before we've even defined it.

Jerry, tell us about your moment.

Jerry Li: Reflecting the years I spent in the past, hoping that some of those powerful questions will pop up. But it didn't. Actually I found one of the most powerful question I asked myself is through Tim Ferriss show where he listed a few questions . He asked himself, from time to time. And yield a lot of really insightful moments.

So for me, one of those is "What if it is easy?"

Alexis Rask: What if it is easy?

Jerry Li: Yes. What if it is easy? That can be applied to a lot of things. Building company. Running a team or make a difficult decision. So, it just drives me to think that actually a lot of things we perceive as difficult. Is that not because it HAS to be difficult. Is it because that our assumptions or we see things, through our own lens, so there's filters. What if we can identify those filters and remove them if possible?

And the lack of those powerful questions when I try to think hard on it, means you know, we should do more of this. Leveraging powerful question is a missed opportunity. But we just don't get enough of those.

Alexis Rask: We don't, we do not get enough. Which is what we're going to talk about as well as why is it the role of the leader to pay attention to this and to leverage this as an important tool, not only of management, but of true leadership.

But I'm going to say thank you in advance to both of you, because in my coaching, there's going to be a lot of CEOs asked over the coming months... " How are you holding this?"

And "What if it were easy?"

Because those are two phenomenal and extensible and reusable in many are all moments, powerful questions. So the two of you have already overachieved.

I'll tell you my story. Mine is less applicable in any moment as those two are, but here's the first time I can remember being truly blown over by a question...

I had just flown from New York to California and was sitting in the LinkedIn office in Palo Alto. It was the old PayPal office that had become the LinkedIn office.

I had been reticent to come out for this trip because I had a great job at this company Google. People knew what that company was and all things were sort of good.

I meet these awesome people and they convinced me to fly out. And I'm sitting here with Reid Hoffman. First shot out of, you know, the gate. He goes, " What's someone going to say about you in your eulogy?"

Patrick Gallagher: First question?

Alexis Rask: First question! Maybe he said something like, "How was your trip? Thank you so much for coming out." like some pleasantries.

They were hiring me to build out how to monetize LinkedIn in 2006 in a day where it had no revenue. It just knew it was probably going to do something with advertisers and probably was going to do something with recruiters. And I was who they were talking to to take a look at the former.

And so, you know, I'm expecting... "Which agencies do you know? Which clients do you have? How much have you sold? Like all the practical nuts and bolts. And here's this obviously brilliant person just going, "I want to know what makes you tick. I want to know what drives you." That's what was within the question.

And so I had to really stop and sit and think and pause and let there be a few moments of silence. And construct my answer and it came to me very clearly. And it's the question itself, but it's my answer to the question that I've taken with me... that was in 2006. And so over the last 15 years, I often revisit what I gave as my own answer. To be able to understand, am I still tracking to that? Am I not? Do I want to revisit this in any way?

So in that way, even though the question was not one that you're going to ask yourself or your team every day, all the time. Just tracking the answer and how it, how fixed it remains or how it might shift and progress over time was the first time I realized the genius of the power of the right question at the right time.

And so here we are defining, what do I mean when I say a powerful question? When I say a powerful question, I'm saying "what's the really, really, really " best" is the wrong word, but what's the really right question for this right moment, that is going to truly unlock someone's thinking in a way that gets at new information.

Right. The right question for the right time, that unlocks thinking to truly get at new information. That's what we can sort of hold. And I use in my coaching practice as the definition of a powerful question.

Failure-modes of open-ended questions & how to use powerful questions to "get to the heart of the matter"

I guess, for everyone listening to the podcast, we should probably take a second to go what are the other types of questions?

Patrick Gallagher: First off from your response, I was just sitting with the power of that moment. And then the impact that, that has had on shaping the next 15 years of your career and really your life's mission and focus and purpose. And then just how powerful that is. So first off, just wanted to sit with that but yes, please! What are the other types of questions to differentiate from powerful questions?

Alexis Rask: Okay. So we went really deep right away. Now we're going to zoom back up and go practical and then we'll, we'll go back down.

Okay. So there there's lots of types of questions, but there are many types of questions that have a fixed answer, a fixed question, or a closed question. Yes. No. Black. White. Did you like the soup? Yes. Are you going to take that new job that's being offered to you? No. So these are the least revealing of new information.

The opposite of closed is open. where you don't give the opportunity for a yes, no black, white, red, green kind of answer.

So you say, "What do you think of that new job that you're being offered?"

Or "How did you feel about that new soup that you tried?"

And so the question asker inherently is leaving some room to tease out some thing more nuanced. That said, there are a lot of managers and a lot of leaders who become aware of these two and then default to one of two error modes.

So with a more open question, a very common tactic, especially in the workplace, is to ask the question and then proceed to answer it for the person.

"So, what do you think of that new job? Isn't that hiring manager really great? I worked with her before. She's super awesome."

Or "what did you think of the soup? It took me 12 hours to make, and I got the most beautiful stuff from the farmer's market. Couldn't you tell?"

Patrick Gallagher: The leading question. Oh my gosh.

Alexis Rask: Totally leading me right. Answering it for me, leading me, telling me what you think, bringing yourself in. So what's the person going to say? "Yeah, you're right. Yeah, you're right. That hiring manager is awesome... yeah, you're right. That those farmer's market ingredients were great."

So that's pitfall number one is that we think we're asking a question to let the other person ponder something for themselves and/or reveal something important to us. But in fact, we've robbed everybody of the opportunity for either of those two things to take place.

But the even. Sneakier pitfall is... You get really good at asking those more curious, open questions without ever getting to the heart of the matter. And this happens a lot when you see people go, "okay, well, I'm asking, Hey, what did you think of that meeting?"

"Hey, what's your feedback for me?"

" What do you think of how the slides turned out? How did it go in the board presentation?"

These are all open-ended questions. These are all gonna bring new information to me. They're not the same as getting to the heart of the matter. When the person's asking, "What did you think of that meeting?"

" Oh yeah, I thought it was, I thought it was pretty good..."

Did we get anything new there? Not really. So the "powerful question" gets to the heart of the matter. The powerful question goes, "Hey, listen, I know you have historically not liked attending this meeting. Can you tell me today why that really is? And what did you notice today that worked well? And what did you notice today that it didn't work well?"

" Oh, yeah. You know, I haven't like coming to these conversations cause I feel like the same people talk all the time and I'm more introverted. And so it doesn't give me a lot of space. So what was good about it is, you know, I got to hear new information, but what didn't work as I have a really different opinion and I didn't get to bring it up."

Right. And then the leader can follow up with another powerful question... "What would it take to make you feel comfortable bringing up your opinion? What kind of conditions could we better create here?"

Oh, you know, if you asked me first, it would make me feel less uncomfortable because then it's not like I'm disagreeing with Sally, but I can just kind of tell you right off the gate. And I would feel more comfortable if I'm the one who brings the opinion first."

Well, okay. Now, as a leader, you have an entirely different way to engage this member of the team in a meeting in such a way where their voice is going to be heard, they feel part of the community and instead of dreading something, hopefully it at least becomes neutral if not a positive force in their life.

And so you two, like I said to come back to, have set the bar really high because those are powerful questions that cause the individual being asked to ponder an entirely different way of thinking. And if answered to a listening party, unlock probably, you know, an entirely new direction.

So we love the curiosity. We love the open-endedness, but we're paying attention to what really matters. What is the heart of the issue here?

So this is not to say that closed ended questions are bad, or you should never receive a yes or no answer. Those things are perfectly acceptable. But, in the role of leadership where we're responsible for getting the best out of people. When we're responsible for figuring out how to optimize things over time. When we're responsible for sometimes changing the perspective of others or asking others to change our perspective. That's where this comes in as a really significant tool.

The last thing I'll tell you is I didn't realize how significant this was even being asked that question 15 years ago, and sitting with it in all these ways that have informed my own career trajectory, and otherwise. I really realized it when I was running a couple of workshops for the ELC and seeing all the engineering leaders who probably had teams of somewhere between 10 and a couple hundred, just based on who was attending. And they were doing a back and forth with each other in a sort of workshop style. And people kept circling around.. "Well, what do you think about that? What do you think about that?"

And like, you could tell that they had had some training on this and then, you know... unfairly, I could listen and kind of hear the heart of the matter and ask a new question. You could see like, "Whoa!" The eyes went wide and then they started becoming more brave to ask each other the really meaningful questions.

So people started asking things of each other, like I remember, "What's holding you back?"

Or "How do you think you're landing with your team? Like, how do you think your presence is propagating that pattern with your team?"

And so then they started taking this over and really deepening. So it's, it's a practice to work on over time.

The impact of a more powerful question

Patrick Gallagher: Speaking of practice ... My reaction just from the few questions we've talked through so far is what I feel right now is almost floored or taken aback at...

Like I'm getting more information. But it's also, it feels more rich and it feels more meaningful. And it also feels more valuable.

But it also, like I'm trying to acknowledge that this is not where I live every day. And I'm like, I don't know where to begin get there..

To rewind a little bit. I feel like I'm probably not the only one who's like, "Oh my gosh, like this feels like there's a lot of impact."

Do you have a story or an example you could share of the impact you've seen when somebody changes their level of questions to be able to pull better information and get to the heart of the matter? Where do you even begin ask more powerful questions?

Alexis Rask: Well, I'm going to answer both of your questions in one.

There is a visual metaphor that I give to the founders that I work with as a coach. Which is the question you can think of as the medicine ball. And whatever, you know, in non COVID times, if you're ever able to work out with a partner... You're passing the medicine ball back and forth, and whoever is grabbing the medicine ball, their body kind of comes down with it cause it's heavy. And then whoever is passing it over kind of lifts up cause they're lightening their load.

So you think of this as... when you ask the question, you're shifting the weight, the heaviness to the other person so that they can sit. And think. Maybe they need some time to sort of process all the way through and respond. And the level of depth is what's harder as the person being asked the question.

Right? It's easier. Did you like that person? "Yes."

Why did you like that person? "Oh, you know, there was a bunch of things and dah, dah, dah..." and so what has taken me one word to answer now? It takes me a hundred words to answer. It's more effortful for me.

So I want to give everybody the tool of the visual metaphor of it's heavy to hold that medicine ball for that last second to come up with the powerful question. But once you release it out, now, the other person can sit with that knowledge and try to parse it through and try to construct a response. And so your only job is to really hold the space. And you still have to be paying close enough attention cause that medicine ball might come back at you!

So you can't just dump it and be like, "okay, now it's all this, this other person's job to think and worry about... I have to be ready that when you know this weight shifts back to me, I've paid really good attention."

So active listening is the very closely related cousin of the powerful question.

I've given that metaphor to countless folks over time. And I've seen it work in a lot of areas and I'm going to tick through a bunch of them for you, cause I think these things might be relevant to who listens to this podcast.

So first of all, I've seen the role of powerful questions work in a negotiation. People can be very uncomfortable in negotiations. And one of the most uncomfortable things is advocating for what you want and asking for what you want. And so the powerful question can actually alleviate some of that stress and some of that natural human resistance by shifting the medicine ball to the other party.

And so I've seen folks in negotiations use their powerful question to say things like... " What do you see is sort of good versus great in this role? And what's the impact of a person who does a good job versus a great job? And what type of value is that going to create for this organization? And what's that worth?"

And when they've gotten the answers to some of those powerful questions that has made it clearer that, you know, "of course their new job offer should come in in such and such a range." Or "Of course, on their promotion path there should be a significant step up."

So anybody in the engineering leadership community who's going through any types of negotiations. The use of questions versus statements can actually help make that an easier thing to approach. So that's one practical example.

The second is perspective shift, which is exactly Jerry, what you just described. Your perspective was that "This thing is going to be hard..."

And your perspective shift was "What if it was easy? What if I looked at it as easy?"

And so a lot of times leaders will have goals. That feel insurmountable... maybe to them, but certainly to their teams... and they're getting a lot of pushback about that and grumbling and, "Oh, I need more resources for this!" And Oh, you know, "what, if the CAC on this goes crazy..." and blah, blah, blah, blah, blah.

And the leader can go, " Okay, I hear everybody. Can I please have three creative solutions for how we're going to get there anyway? Can I please understand what one limit or roadblock or constraint I could remove for you that would make this feel much more doable? Can I please understand the mindset that you're in when you're approaching this and what if we introduced a different mindset? What type of new ideas would we come up with?"

All of these are powerful questions to essentially move the perspective from fear and scarcity and stress towards... in control, powerful, problem solving, creative. So the use of powerful questions can really help leaders make not only perspective shifts in themselves, but in their teams.

And then, a lot of leaders come and say, "I want to get the best from people!"

So the final practical example I'll give to you... Jerry you've told me, that's a very common sort of aspiration for why people even join the community. "I want to know how to get the best out of the people I can lead."

Well, you know, one of the most powerful questions a leader could ask... " How do I get the best out of you?

The blueprint is sitting right there! And maybe the person knows it and they'll give you an answer right away. And then you have the blueprint. Thank goodness. What a gift. And maybe they don't know it. And maybe they need to give both of you the blueprint right there.

But "Hey Jerry, what motivates you? How am I going to get the best out of you over the next 12 months?"

" Oh...?" Well, at least one person is leaving that conversation with new information. Me! Maybe two of us. Maybe three, four, five, six of us! If I happen to have asked it in a room with other people that was a safe space to do it.

So these are, you know, I'm trying to give practical examples of the things that the audience will be really facing, but there's really no scenario in which asking these great questions at the heart of the matter, that reveal new thinking or information don't help in some way.

Emotional intelligence & how to get the best from people

Jerry Li: The last question you mentioned "How do I get the best out of you?" That should be the number one question, when we hire someone or work with someone... There's no reason we don't ask that question. So it's easy to ask and it brings out a lot of information that could help us to have much smoother collaboration and more respect, more

I can imagine people can immediately apply right after this conversation to the next person they're going to start working with. Or even their existing team members during one-on-one start with this question.

Patrick Gallagher: I'll add it to our agenda for our one-on-one Jerry.

Alexis Rask: Yeah. I mean, you have someone right here who needs to share that answer.

Jerry Li: Yep!

Patrick Gallagher: Well, I'm also just thinking of like the intent behind the question implies that the asker wants to find the answer to that. So as the person receiving the question, in addition to, you know, providing the information increasing the context, but it also, I think, feels really good that somebody wants to get the best out of you.

So the intent feels really powerful as well.

Jerry Li: And I want to go back to the " What if this is easy question, because a lot of managers, we try to figure out, "Oh, this is a new person, let me dig into to her or his background and see how I can bring the best out of her or him? We try to do that on our own. It's pretty easy! Just ask the question. They will give you the answer.

Alexis Rask: Yeah. The two of you, even in your back and forth dialogue there just brought up two extra points I want to focus and the benefits of this.

So first of all... It is NEVER too late to start... as you said, Jerry, this is not just about new hires for you now. This is about current team. This is about current partners. This is about current collaborators. New deeper, better understanding is something we're always after when we're in relationship with others, which is what working together is. And you know, whether that's reporting line or at the peer level. Better understanding is always a good thing and can always be used tomorrow, and today in ways it wasn't used yesterday.

And, Patrick, you brought up something that I was going to say at the very end. But it's probably worth saying now...

We're talking so far about sort of the intellectual level of "someone thinking in a new way that they hadn't before" or "someone understanding in a new way they hadn't before..." To drive business outcomes, et cetera. Which is all very much in the IQ space, right? We're in the sort of like rational intellectual part of our brain.

There's a huge emotional implication of being asked questions. And listened to. Which is "Somebody cares about me. Someone's paying attention to me. Someone sees me and hears me and witnesses my answer."

And, you know, EQ gets sort of the short shrift. If you think about business school curriculum. Like there's no EQ classes, right? It's like how to do finance and how to do marketing. And when you see, you know, CS, it's like how to write code and how to build in which particular language.

But really leading people is making them feel seen and heard and understood and recognized and accountable and responsible. And so questions have that additional benefit as well. And the more powerful the question is, the more you know the person who asked it had to really care. And really pay attention.

So there's all these amazing benefits to it.

Why "WHY" is the perfect follow up question

But really quickly... to go back Jerry, to your new question that's going into the, you know, lexicon day-to-day... " How do I get the best out of you?"

What's the logical additional question you could ask, that might reveal something else in the equation with this person, very related?

After you asked this person, "Hey, how do I get the best out of you?"

Okay. They give you their answer. If you want to deepen it one tiny bit further to make sure you REALLY get what makes them tick and what doesn't make them tick... What would you ask them next?

Jerry Li: Maybe why? Why this better? Maybe it ties to a deeper value or deeper principle, some deeper belief? So that now you're operating on a deeper level, which gives you freedom to try other things.

Alexis Rask: That is the most powerful question of all... Why?

One word works all the time. "Hey, you know, how did you feel about this?"- Why?

"Hey, how am I going to get the best out of you?" -Why?

There's also the, "Tell me more about that." Which is essentially "Why?" in more words.

But that's exactly right. Cause we're deepening and deepening and deepening the understanding of this person. And now as a leader, you know, their values, you hear some stories and anecdotes that shaped their thinking. And you really get it! And they're going to answer the negative side too... most people will.

And if they don't, you can ask that too... "Well, how do I get the worst out of you?" Right. Most people in answering, how do you get the best out of me are going to tell you, "Well, I hate being micromanaged!" Right? And so we know that micromanaging is going to get the worst out of them.

And "Why?"

"Oh, because I have this experience and I just could never get any of my own decisions made. And then the company ended up going under and if they had taken my decisions, we actually would've made it." Right? "And so I have these deep battle scars around this."

Like that might be the person's answer. So "why" is the perfect follow-on.

Patrick Gallagher: Far more information came out of the "why" than the first part of the question. The first part of question was, was useful. But it almost feels like I have a deeper understanding of YOU having asked why.

Alexis Rask: Yeah! And then, you know, right, if that's the person who's had this experience of their opinions, not being taken in the company, going under... Well, they have fear right? With early stage stuff, "Cause what if it goes under...?"

They might have unfortunate confirmation bias that their opinions are always right... because had they been listened to in this case, maybe a different outcome when would have happened. And so that's the thing to watch out for. So there's all this good stuff.

Which is why I'm saying active listening is so important as well. Because you have to really zone in on the answer to hear all the good stuff. And there's a lot that can come in a really short period of time.

So just from again, like a practical tools perspective, I highly encourage everybody to have a notebook.

It's so much less distracting to jot a couple of notes with pen and paper when someone is revealing detailed, important information like this. Than it is on your computer. First of all, things stick in your brain differently when you write them physically versus type them. So your recall of the answer is, probably scientifically bound to be a little bit better. Even though there's a digital record of it in one case.

But the emotional intelligence part is "I might feel snubbed... if I see someone typing notes when I answered this really important question that you just asked me..." Because they could be Slacking. They could be checking email, they could be doing something else. And I don't realize that this is so important to them that they're trying to capture it in Evernote so that they can remember it and come back to it.

So, even in this world of Zoom all day and Slack for everything... I still would say, great leaders need a piece of paper and a pen somewhere to jot a couple important things about their team. So that people feel really acknowledged and not accidentally looked past.

Jerry Li: I want to go back to the the why question? I can think of a few examples where it can be applied...

In an earlier interview of our podcast with Will Larson, he actually mentioned a very good example of asking why.

In certain companies where the leveling is quite flat. People may tie their identity or seniority to other things that they want to give meaning to. For example, be part of a certain group, getting invited to a meeting or being on a committee of some sort.

So if we don't ask about the "Why" question... the behavior is driven by the fact that people need to know, or have a sense of identity THAT way for, basically revealing what drive that behavior. And then gives you insight to go back and I'll fix that in the right way. Versus, try to fix things on the surface. So, uh, that's one example.

The other example is that the "Why" question not only applies to the individual, understanding better about a person. But it can also apply to undestanding a, challenge or problem, or a product incident, for example... "Why this happened?"

"And because x, y, and z..."

"And why that happened?"

So, there are very good examples if you ask a few "whys" you can quickly get out to the root cause of problem. But if you don't ask that's wasted opportunity.

Alexis Rask: Yeah. and we're talking about this whole... other than Patrick starting us off with something that he sat with in a meditation and mindfulness practice, which was inherently a question prompted by an expert, but facilitated within yourself... the powerful questions tool works perfectly within yourself. You know, if you ask yourself five times why then you get to the heart of, of your own issue. Right?

So you know, why is it problematic that there's not shared leveling? "Oh! Because I care about recognition. Because I care about benchmarking myself against others."

Why?

"Well, because I don't know if I'm doing a good job otherwise and because that's the system I come from in all my schooling and all of my work life up until this point..."

Well, why does that still matter?

" Well, because I don't know who I am without that..."

Okay. Well, who are you? If you have no external barometer?

Right! You just went from like, how do we make the meetings better? And the organization better to like, who are you and what makes you tick as a human being in 30 seconds I think?

Maybe a manager's not going to ask you all of those questions and maybe are not going to have that dialogue fully, you know, in a dual person construct. But maybe that person's going to go home and sit with, "Why do I need such an extrinsic barometer? Why don't I know that my work is good whether I am recognized or not?"

Or maybe the leader who set up that structure is going to go home and go, "Why don't I trust people to give them more responsibility and more authority? Why do I keep things, you know, so flat? Because I want to have control in everything? Cause I'm afraid to let go? Cause I believe I'm better at doing everything, you know, than anyone else?"

Okay. Well, how long is that going to be scalable for? Not very long.

There's always, you know, a lot of detail if you can take the time to be curious and really probe.

Jerry Li: And this is also a timely topic because for a lot of companies, we are in performance review season. So this is a perfect time to start practicing asking powerful questions.

How to use powerful questions in your 1 on 1's

I'd like to explore maybe one more typical use case of powerful questions in the realm of management in one-on-ones with their managers there direct reports...

The one thing that came to my mind is... oftentimes people come in to the one-on-one meeting bringing a concern or a request without asking the powerful question. Then the result of conversation tends to stay on the surface.

You fulfill a request or you talk about a concern. But you never get a chance to get a deeper level. So, by asking powerful questions, you can get to the core of it.

Alexis Rask: I think that's exactly right. And there's a great one don't know the one-on-one that you're mentally envisioning here but, as sort of a universally applicable question, like "Why..." What do you think is behind that? Or what's behind that? That's a seven word version and a three-word version of a pretty extensable question that any person sitting in a one-on-one hearing about a complaint or a concern or a friction from somebody within their team could use to immediately deepen things.

" What's going on here?"

" Well, I just told you what's going on here. You know, this project is going off the rails."

"Yeah. But what's behind that?"

"Oh, engineering and product are not on the same page. Each think that they should be in charge of sort of writing the spec. And so it's going back and forth waiting for that tension to break..."

"Well, what's behind that?"

"Oh, so-and-so and so-and-so don't respect one another..."

"Okay. Well, what do you think we could do to change the dynamic here?"

...okay, "my manager", can you please help me navigate, you know, how to broker a peace conversation between these two parties? Just by way of example, but " What's behind that?" Or " What do you think is behind this?" Is a really good way to immediately drop it into something more substantive.

Jerry Li: And We should to have a collection of those questions.

Alexis Rask: Well let's do it! If you want to create an ELC repository of powerful questions that the community can share with one another, why not? I can either go in and start us off, or I can go drop some in when I see things not coming. But the community is going to do a better job of this than me.

And we don't need all the context in the preamble of why and anyone revealing sensitive information, we just needed a cool, awesome repository of powerful questions that people can go to when they're stuck.

Jerry Li: Yeah, it'd be really exciting to have it.

Patrick Gallagher: That is fantastic. If you're listening to this right now, please send us your best question. We would love to hear it and collect it. Maybe collect it might be the wrong word, but we'd love to hear it. And we'd love to empower the community with those questions.

So please share them our way!

Alexis Rask: That's the power of what you guys have built is collectively everybody can get better and work together on some of these things.

Jerry Li: Yeah, we don't have to go figure things out on our own because, those are the things that people have been dealing with all the time.

How to get over the fear of silence...

It looks like asking powerful questions takes a lot of intentionality... And once you know them, you can actually build up the list of questions you can repeatedly use for different scenarios.

So assume people get through that step. They have the, the powerful question to ask. But from past conversation with other engineering leaders in the community... one thing that holds back people asking those questions is the fact that sometimes it feels very uncomfortable asking those hard questions. Because it takes time for the other person to think about it.

So there will be potentially a long silence... during a conversation. And that's not comfortable. So, how do you, advise people to get over that?

Alexis Rask: Just get over it. What's so wrong with silence? What's so terrible about that? That's my powerful question back to those people. What is so terrible about silence?

Jerry Li: In the past, how do you see what helps people to... they know they don't feel comfortable. They don't have good reason to answer your "Why" question. But what are the things you help them to do to sort of have a real feel... and then now they know how it feels. They know it works, then that's a start.

And from there they can build out more exposure potentially like getting used to it. Anything you can share there?

Alexis Rask: Yes, a ton of practical or not a ton, but several practical tips here.

So the first is...

Just like any muscle memory, you know, repetition is what build up endurance and strength over time. So, even starting with what I was calling earlier, more of the curious, more of the open questions, and going after the fact and reviewing your meetings mentally and going, "Wait a second... I think I missed the depth. What's the additional question I should have asked, at what point in that meeting, to take this to a different level of understanding?"

Not because we want anyone to beat themselves up about it, but it just can be easier that after the meeting, you sit quietly, you mentally review things as many of us do anyway and go, "okay, what do I wish I asked? And at what point?"

And write it down for yourself. And then start logging it. So you have a log list of some powerful questions that you necessarily didn't apply real time.

And so then the next time you have some meetings coming up, whether that's a team meeting or a one-on-one, or some high stakes conversation... prepare ahead of time:

"What are three really meaty, powerful questions that I want to introduce into this discussion?"

And so you're relieving yourself of the pressure there of having to react all in real time. You're setting your intention that I go, "Well, listen, you know, I know that I have a new hire starting this week. And so I'm going to ask them:

"What are your hopes and dreams and aspirations for yourself in the big picture and how do you see this company as helping make that a reality?"

I can prepare for that. I can know that I want to ask that person that very meaningful, powerful question without sitting in the room. So, going back in hindsight and finding the flags for yourself and preparing in foresight with some things that do feel more comfortable are two of the practical tips.

And then the very hardest part might be asking the question, in the room, that you've prepared for... and then zipping it. But practically speaking, you can give yourself a tool to use such as... Taking a sip of water or jotting a couple notes.

So if I say to you, "Hey Jerry, listen, you know, I've noticed that we've had some friction in the last couple of meetings of ours and you don't seem to like what I'm recommending here. Can you tell me why?"

And then I sit and drink some water...

At least you have something to do. And it's your, and you know, you've, you've decided in advance... "I'm gonna ask this hard question and then I'm going to drink my water!"

Doesn't mean it's not going to be awkward. That there's a silence. Doesn't mean we all of a sudden all became comfortable with silence. But you've bought a little bit of time and you've given yourself something and you're trying to give the other person their space to think it all out and start talking.

Jerry Li: I think you made a really good point of the benefit of giving other people the space while taking break for yourself. Because the other person, they don't feel the level of comfort to take time to think about the real answer. ... , instead, let me just flesh out a really quick answer..." defeats purpose of the question.

So maybe it's important also to intentionally, give a space for example, in your case, you mentioned drinking water. But make it really clear... Don't try to answer my question right away. Feel free to take time.

Alexis Rask: Take your time! Take your time. "Hey, I have this, I have this BIG question to ask you... Why is this so important to you? And take your time. Take a second."

I say this all the time in coaching. "Hey, take your time. Don't give me the first answer that pops in your head. Can you sit with this for a second? Can I let you sit and jot some notes on a piece of paper for a minute? And then once you're ready, then go ahead and answer my question?"

So, okay... the coaching construct is a different one, so I, you know, it's natural that I'm going to say, "I want you jotting this out."

But you can steal from this. "Hey, take your time. This is a big question, take your time."

You know, what other secret, powerful, wonderful tool we all have at our disposal... Besides water?

Jerry Li: What is it?

Alexis Rask: It's another key sustaining life function...

Patrick Gallagher: Breathing?

Alexis Rask: Breathing! Yes. If you go like this... Here's my question for you... "blah, blah, blah, blah, blah." What just happened?

Patrick Gallagher: I feel like I just relaxed three notches down the dial.

Alexis Rask: Okay, but do you know, I didn't tell you to breathe... I just breathed and then you emulated me. So I also relaxed three notches down the dial. I sat back and relaxed, and you EMULATED me and YOU relaxed three notches down the dial!

So just by breathing, I'm calmer as the listener who asked the question and you're calmer as the person who was asked the question. And oxygen, lets your brain think.

That's why we think poorly when we're in fight or flight. Cause all the blood rushes out of our brain and goes to our extremities. So our actions and our physicality is good, but our thinking is less good.

And when we breathe and we have lots of oxygen in our brains are thinking!

So, take a sip of water and take a breath. These are life sustaining habits and actions anyway. And they are fuel for good thinking, good dialogue and holding space for the answer.

Identify opportunities to ask more more powerful questions with the "mental review"

Patrick Gallagher: In thinking through the, practices you just shared, like I'm looking back at my own experience where applying those have had a really big impact. And the moment of awareness for me was...

At a previous organization, I used to work for, we host different events. And I remember being at one of the events, talking with a number of different people, helping introduce different folks and helping people connect and gel and have more meaningful conversations. I was having a soda water, I think I was drinking LaCroix. And at the end of the evening, I think I had eight LaCroix's in this two hour networking event.

And nobody in their right mind should ever drink eight LaCroixs in a two-hour sitting...

Applying the mental review and looking back. That was something I found really impactful because the "Why" question was Patrick, "why are you drinking eight laCroixs in a, in an evening?!"

"Well, I think it's because I'm nervous..."

"Why do you feel nervous?"

"Because I'm dealing with professionals that feel like they're way above like where I should be in my career. And I feel insecure."

Well, then it's like, well, "Why do you feel insecure?"

" Well it's because I'm wrapping up my identity with whether or not I look smart in front of these other people..."

And it became this really profound thing. In then assessing I was able to prepare questions from a different place instead of like asking questions to impress people. It was more so can you take a deep breath, not drink sips of eight LaCroix's but rather, you know, take a breath and actually listen to people.

The mental review was so impactful for me in that moment of awareness.

Alexis Rask: So great. And I, you know, I don't want to put words in your mouth but... what is continuing to show up that way due to you in the long run?

Right? If your goal is to be feeling as a peer to these people, but you show up to the evening and you drink the LaCroix's and you kind of don't operate that way.

What'll happen in the long run, if that's your pattern over and over again?

Patrick Gallagher: Well, the thing I jump to is then a lifetime of shallow, unfulfilled conversations because all I'm trying to do in that moment is to impress somebody. Rather than actually actively listened to them and get to know them or come from a place of curiosity to try to deepen my understanding of who they are.

So it impacts my relationships and their relationship and how they ultimately essentially feel about me.

Alexis Rask: And what's the impact on how others perceive you, if you keep going that way?

Patrick Gallagher: I probably wouldn't want to talk to me if that was the situation.

Alexis Rask: Yeah! And you, it's a self fulfilling prophecy because then, you know, the shallow questions come across as more junior, less confident, less of whatever was in your mind as sort of, you know, what these other people were. So your best way to be how you were wishing to be was to go ahead and go be like that.

Patrick Gallagher: Yeah...

Alexis Rask: RIght? Yeah.. Well, thank you for sharing. That's such an amazing example and you have such a gift of self reflection. I can hear it. That the tool that you know, I was sharing in answers to Jerry's question... you're very much skilled at bringing back to your own situations in your own professional and personal endeavors..

Patrick Gallagher: Well, these types of conversations, Alexis, like being in conversation with you... personally, it's my happy place like to be in this level of self inquiry and for somebody who's as masterful as you are at being able to spot these things and to coach and to share and to help people along their own path ask these types of questions.

Like this is entirely my happy place. I wish we could talk like this forever.

Alexis Rask: Same same here. But you know what? I actually, I there's one thing I really want to say as we come towards the end...

We talked a lot about this and I focus a lot on like the humanity of the experience and "bravery" and "courage" and "holding space." And I use all these words that historically, you know, can sound like "nice to haves" when you lead people and run companies and manage and might even sound like fluffy and "woo-woo" to some...

And THAT'S the one thing I want to draw a huge asterisk on here is...

This is to help you run better companies and build better businesses. Employees quit bosses more than they quit companies. So this helps with retention. And so we can't say that recruiting is, the hardest thing in Silicon Valley that we're all after. And then go, "Oh, but it doesn't matter how we treat the people on our teams. And it doesn't matter if we know how to motivate them..."

Right? This is going to help you hire the best people. It's going to help you get the best out of the best people. Which is going to help you build the best product. Which is gonna help you capture the most revenue. Which is going to help you move from Series A to B, to C, to D to IPO.

This whole idea that this is just sort of a... a footnote to what it really takes to lead and what it really takes to drive the financial and commercial and sort of external benchmarks of success... is a fallacy.

Leaders need to be great at this JUST like they need to be great at writing code and reviewing code, and fundraising, asking for money from first customers, and attracting talent and all these other things. Because it's through the powerful questions that you can find the right path and bring others along with you on that journey.

So... this absolutely has hard bottom line practical benefits of doing well AND has all these interpersonal emotional social benefits.

Jerry Li: And can be very easy to, to do it.

Alexis Rask: Yes. And it's so easy! That's the thing that I always give people as their final exercise, right? As they're starting to build these habits and muscles.

So we're reviewing back or planning forward, we're using the tools of breathing and water and then the final is... You're keeping it short...

"Why? What's behind that? What could happen differently? What would success look like? what, if there were no roadblocks?"

These are one, three, five, seven word questions. These are not 19 word questions with, you know, two periods and a question mark mixed in. So keeping it short and simple. Jerry, you gave us for the metaphor for the whole thing.

"What if it's easy?"

All you gotta do is show up and be curious...

"What if it's easy?"