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Deep Listening - Impact beyond words - Oscar Trimboli

Nov 11, 2022

Oscar Trimboli: The sophisticated and paradoxical power of deciding if and when to listen. G'day, It's Oscar, and today we have a question from a Deep Listening Ambassador in Japan.

Shaney: Hi Oscar. This is Shaney from Tsukuba Ibaraki, Japan, and my question is about listening as a leader.

Do you have any suggestions about how to continue to listen deeply as a leader when you tend to receive comments, suggestions, and ideas from so many people all day every day.

It can be quite surprising for people who are new to leadership positions to realize just how much time leaders spend listening to people and how tiring it can be when the fourth or the eighth person in a day asks you if you have a minute and then launches into a rant or a criticism or a suggestion of how to improve something.

Listening is so very important to leadership, but it can also be really, really hard to listen to comments and suggestions all day long, especially because you feel a personal obligation to fix the problems that people bring to you.


Oscar Trimboli: Thanks, Shaney. This is a wonderful paradoxical and universal question independent of organization, culture, location, or country.

My favorite kind of question, if you like Shaney, have a question about listening in the workplace, email

This question, it's a question about choice and timing.

It could be about when to listen and when NOT to listen.

It's also a question about attention and your listening batteries.

When it comes to your listening batteries throughout the day, you need to check and notice what's your battery level right now is a green, yellow, red.

You need to check what color your listening battery is before you start listening.

Something I learned from James Clear in episode 67, advice is often context dependent.

Shaney, I'm going to avoid giving you advice here as James points out questions can help you navigate beyond the context.

Let's listen to how James explained it.


James Clear: And one of the women that as a reader of mine and I talked to as I was working on the book, she lost a lot of weight, and she had this really great question that she carried around with her.

Questions are often more useful than advice in the sense that advice is very context dependent.

It's like, "Oh, it works in this situation, but what if you find yourself in a different situation now it doesn't apply as much."

And the question that she carried around with her was what would a healthy person do?

And so she could go from context to context and sort of have that question to reinforce the identity.

That's actually in many ways, more useful than having a good workout program or a good diet plan because that you can only do once. But no matter where you're at, you can ask what would a healthy person do?


Oscar Trimboli: Shaney, I'll share with you four types of questions, four categories of questions for groups of questions that have helped my other clients.

It's important to understand that the question you are asked is very, very common and it's amplified when you're in a leadership role.

The categories of the four questions are what, when, how, and who.

Let's start with WHAT.

  • What would make this a good conversation?
  • What would make this a great conversation?
  • What would make this an effective conversation?
  • What do you want from this conversation?

In the book, how to listen, we cover off the use of this question throughout the book, creating a listening compass for you and the other participants.

It's a great way to hack the conversation to make it much shorter for you and for them.

The reason we want to ask a WHAT question right up front is you want to understand the context for them and for you, because shortly I'm going to invite you to make a choice about when you should think about answering this question, Shaney.

So let's move to WHEN

  • Here's a group of questions to think about.
  • When is the best time to discuss this with you?
  • When is the best time for us to discuss it?

And finally, although I'd love to discuss it right now and listen to you, I don't think I can effectively listen to what you want to achieve in this conversation. Can we discuss this at another time?

Professor Cal Newport is very particular about the value he places on his time. And rather than dealing with each individual and their specific question, request feedback experiment, he encourages each of his students or peers to attend a regular weekly meeting. In that meeting, everybody can bring their request or their question along.

He does this for three very specific reasons.

1. he has a defined time and more importantly, a defined process for dealing with these random rants, as you call them, Shaney, or the feedback or any of the other issues he's dealing with. He's placing them in space, time, and context where he can arrive with his listening batteries fully charged.

2. he creates the environment where others can participate. Others can listen to the range of questions that Professor Newport is asked, as well as listening to the way he thinks about answering these questions.

3. he thinks about his time being multiplied in a group context with many of the participants either self-solving when hearing others' answers, resolving their question with other participants, helping them in doing so. Newport is building a culture of mutual support. He's making himself independent of the process, and ultimately Newport explains how he would approach thinking about the issue rather than his recommendation to the other person or group about how to solve the issue.

Shaney, one of the things I invite you to think about is if you feel like you need to fix, give them a simple framework to think it through rather than giving them an answer.

In adopting this approach, Newport creates a sustainable listening process ensuring his listening batteries are fully charged before arriving at this regular meeting, whether it's face to face or virtual.

Shaney, back in episode 61, when I discussed this issue with Professor Stefan Van der Stigchel from Utrecht University, he's written multiple books on the importance of attention.

He reflected on his more direct approach when students or peers approached him with a question.


Stefan Van der Stigchel: People come into my room when I'm on my work quite often to ask me questions or to talk about a certain experiment.

And of course, when you're in your working environment, they're things are not always positive, right?

What I've tried to learn is that communicate to, if people enter my room to say, this is not the right moment. I cannot listen to you. My mind is not open, my working memory is full, I'm worrying about something.

And I've started to realize that people actually appreciate that if you say it in the past, there are too many occasions in which I was claiming to be listening and they ask me questions and I just noticed my mind is somewhere else.

My mind wandering about the meeting before, and then I simply have to admit that I have no idea what they're talking about. And that's quite embarrassing and it's frustrating what I've learned from my peers that there are people who can acknowledge that they can acknowledge if somebody walks into the room, ask them a scientific question, please, not now.

It's good to have a culture and in a work environment when you can admit that although I might be looking at you right now, I am honestly not listening. And this is not due to you.

You're very interesting and you're probably a very interesting question. But what's happening to me right now is that my mind is wandering, and I'm not ready to receive your information.

Again, my environment, people have to learn that's a possibility and that they can come back at a later time, but it's not something personal.

Previously what happened to me is that I was sort of almost afraid to tell the other person because I was afraid that they were going to take it personally, right? That you are not interesting to me. And I try to make sure that it's not about them, but it's simply that the current situation is for some reason not appropriate.


Oscar Trimboli: Shaney, when thinking about the WHEN of listening, the most generous thing, the most sustainable outcome for you, and the person asking the question, the rant, the person wanting to bounce something off you.

The most generous thing I think you can do is NOT listen.

When you're listening, batteries are drained when they're moving from yellow to red or from red to black.

It doesn't help them, you or the organization you lead by listening, transactionally, listening superficially, bouncing between level one and maybe level two, listening for symptoms rather than moving between level two, three and four and listening for systemic implications.

Listening is a skill, it's a practice, it's a process and ultimately a way to impact systemic change in a sustainable way for the organization you'd lead.

As I mentioned earlier on, Shaney, the question you pose is a universal leadership issue. It's a common question my clients ask me.

This is an interview with Katie Burke, who is the leader of people and culture at HubSpot, an organization where she's responsible for 6,000 employees globally.

In this interview with Shane Metcalf, Chief People Officer for 15Five an employee engagement software company from June 21, it was called Reviving the Art of Listening with HubSpot's Katie Burke.

Listen carefully as Katie describes how she manages her energy to make a bigger impact with her listening.

Notice how she conserves her listening batteries and shares the difficult and draining parts of listening with other leaders and members of her team.


Katie Burke: In my own journey on this front, I think a few things that have really worked for me, I got some really tough feedback my first few years as CPO that I was distracted and I was, and it was because I was trying to be everywhere at once and be all things to all people.

And so the biggest tack for listening that I know is I say NO to almost everything, including I don't get a ton of energy from doing one-on-one coffee chats with people.

I've just learned over the years. I feel like I'm saying the same thing over and over again. And also just I got emotionally worn down. It was just tiring. And so I don't do our new hire welcome as a group anymore because it just felt a little tiring. And then I don't do a ton of coffee chats both internally and externally.

And the reason I don't do that is not because I don't enjoy doing that occasionally, it was because it was starting to really interfere with my ability to listen and be a great leader for my team.

Great listening actually starts with being intentional around what you say no to. So you can be present for the people in your org and be the best leader possible when you're there.


Shane Metcalf: It's so interesting around our own energy management, our own state is going to dictate are we able to listen?

Especially HR is often the punching bag in an organization because HR people, we are the recipient of so much feedback, positive and negative, humans get flooded with emotion.

When we're in a fight or flight state, there's a physiological change that happens in our ears and we actually stop listening.

What I'm hearing from you is you needed to set boundaries and create the experience for you to do work that energizes you so that you could actually listen.


Katie Burke: I personally think there should be much more discussion for CHROs, for HR business partners, for anyone who bears the emotional breadth of an organization, of talking about how I think people talk a lot about self-care and break and rest.

Those are all great, but don't get to the core fix. And I think what I had to learn is I have to actually just be really disciplined around my schedule because it creates space for me to do the things that I know make me a better listener. And for me, that's getting outside once a day, getting my run in the morning. I'm a much better person, leader, manager, you name it. If I get outside and get a workout in.

And then the other thing is just being intentional around what gives you energy and being honest about that. I grew up very much a people pleaser.

It was a really hard habit for me to break, and I don't think people love that. It's my habit. I've had to get really comfortable with the fact that it is the only thing that allows me to keep listening, to HubSpotters and being a good leader for my team.


Shane Metcalf: It's a worthwhile process for all of us to check in.

Am I actually in a state where I can listen?

Because I've gone through this, I've gone through periods where I'm like, I don't want to hear any more feedback.

I'm sick of it.

People just complain.

We're never going to make people happy.

I'm in the pretty negative state and then I have no receptivity to actually listen to what my people are saying and anything they say will probably be viewed through that lens of I don't want to hear it.


Katie Burke: Agreed. I've also just had to say no.

There are times when I think taking a meeting does you want to listen to someone. If you're not, there is actually a bad use of both of your time.

And so one of the things I've said to some people is. Hey, I'm actually not in a great spot to really have the conversation I think we need to have, and so I need to wait until tomorrow.

I need to wait until I'm in a better spot or I think someone on my team is better suited to have this conversation given that they can really understand and empathize where you are because I think when people are in an acute state, they need someone to listen to them a 100%.

I need to be honest if you're not there.

The other thing is just that's where I come back to you're not going to make everyone happy.

I used to hold myself to a really high bar. I wanted to think that everyone who, if we had a tough meeting to listen to people that everyone would leave saying like, "Wow, our people operations team is great."

What I've started doing is now leaving those meetings where the goal is just to make people feel heard, not to make them feel better, just to make them feel heard.

That takes some of the pressure off because the other thing is I'm a bias for action person. I tend to lean into how do we solve things? It takes the pressure off to solve it because my only job there is to be present to what they're feeling.


Oscar Trimboli: Shaney, the most impactful, sustainable, and generous listening could be when you choose NOT to listen in that moment, reacting and trying to fight the urge to fix, kind of showing up like the shrewd listening villa from our listening quiz, becoming conscious that your ego wants to fix, solve, and answer.

It's great in the moment, but it doesn't drive systemic change.

Create a phrase that works for you.

The four A's at this point, ask, acknowledge, assess, and agree.

  1. Ask what would make this a good conversation or outcome?
  2. Acknowledge their point and issue or even question, or problem
  3. Assess when is the most effective time for a sustainable, impactful discussion?
  4. Agree, when or who to meet with to progress it.

Shaney, we've covered the what and when.

I just want to quickly talk to you about how and who.

These additional categories of questions are really useful when the conversation happens.

First, let's talk about HOW.

  1. How would you like to discuss it?
  2. How will we allocate our time exploring the past and the future?
  3. How long have you been thinking about this?
  4. How will we know if we've made progress?

Let's move on to the WHO

  1. Who else noticed this issue originally?
  2. Who else does it impact? and
  3. Who needs to be involved in discussing or resolving it?

Shaney, to make this very practical, very pragmatic, and actionable for you.

My go-to question for the random rant, the curious question, or the feisty feedback,

What would make this a good conversation for you?

They will either tell you they want to have a rant with no outcome, or they may request you to be their thinking partner, or more likely than not, they'll try and put the problem-solving monkey back on your back.

At this point, Shaney, notice the pattern in their questions three or more of the same kinds of questions.

You're probably dealing with a systemic issue, and I speculate you probably can't solve it alone, or at least in the pair that are discussing the problem.

Define an allocated time on a regular basis for you to triage all of these kinds of discussions into one context where your listening batteries are fully charged.

As Katie mentioned, sometimes people just want you to hear them out rather than fix, especially when you don't have the listening batteries available to listen and fix in the moment.

Finally, every conversation doesn't and can't be a process of deep listening.

You can't always deeply listen.

You need to be flexible and adjust accordingly in the situation.

Sometimes just being present and allowing them to be heard will be enough.

This makes your listening light and easy and it doesn't drain your listening batteries.

A quick reminder, your role as a listener is not to comprehend everything the speaker says.

It's your role to help the speaker better understand what and how they're thinking about an issue and ultimately help them to understand what they mean and where they want to progress.

Shaney, thanks for the brilliant question.

G'day. It's Oscar.

This podcast episode is an experiment in a few parts and one of the things that's happened in between the time Shaney sent me the question, I recorded the responses that I sent it back to her in draft format to ask her for a few reflections.

I gave her four questions to ponder. Shaney listened to what I sent her and shared it with her team, and I've asked her to reflect on four questions. Also, in between that time I have been completely flat on my back with a virus for seven days, so my voice is probably sounding a little different.

What you'll hear next is Shaney reflecting back on the questions I posed to her.

Let me know what was most helpful in what I've explored.



I don't need to fix, solve, or answer anything when I'm listening to people.

I just need to make sure that people are heard.

When I played it for my team, they really reacted positively to the concept of a listening battery and also to the idea that not every conversation can or should be a process of deep listening.


Oscar Trimboli:

  • Which one of these will you experiment with?
  • Which one will be easy for you to implement? and
  • What will be sustainable in the context in which you leave?


Shaney: I will definitely be trying to remember not to go into conversations with the intent to solve anything. This will be very hard for me as I have a lifetime habit of doing just that.

I think that this is very important and as a leader, I really need to try to help the people that I'm talking to find ways to solve their own problems instead of trying to solve them for them.

People take more ownership of decisions and outcomes when they come to their own conclusions, so I'd like to learn more about how I can suppress my urge to fix things.

I need to do a better job of listening to ensure that my colleagues are heard and that they're supported in finding solutions that work for themselves in their own context rather than just me giving advice to them that may or may not work because I may or may not have fully accounted for the context that they're working in.

In my team, we talked about how saying no can be quite difficult in our context as one of our goals is to be approachable and available to the students, parents, and staff members at our school.

We talked about how we can conserve our batteries by acknowledging the person and their query and actively deciding whether or not this is the best time to have the conversation.

We think that can work well with students and parents, but we're still not sure how to say no in a compassionate way that doesn't make our colleagues feel like they're being ignored or rebuffed when they approach us to talk about something that may be, for example, personal or professional.

The when is difficult for us.

It's pretty difficult for some of my colleagues to have control over when their conversations happen with their colleagues. They can set appointments for students and parents, but conversations with colleagues happen all the time.

Two of the colleagues that were in the meeting with me have an office that is in a rather public area, so people walk by and talk to them all the time, and that can be really tiring and they can often get involved in conversations about both professional topics and personal topics, and they mentioned that it can be tiring to switch back and forth between the professional and the personal conversations.

We decided as a team that we might experiment with having a set time in our meetings where our colleagues can bring up the professional issues that have come up through the week.

This could be one way to say, not now kindly, at least when the issue is professional, by acknowledging the issue and saying, let's talk about it at the next meeting.

What would be easy to implement?

It would be relatively easy to implement the idea of having a pre-conversation with the person we're speaking with to determine what would make the conversation a success.

It could even happen during or after the conversation, or it could be something that we try to remember to ask ourselves as we enter into various conversations throughout the day,

And finally, what would be sustainable in the context that we lead?

In my context, it's sustainable for me to become more conscious of how my ego is reacting to whatever is being said and to remember to have an awareness of both the state of my listening batteries and that I can choose not to listen deeply at that moment if that is the more considerate and humane response because my batteries are particularly low at that moment.

Oscar, I can't believe you made an entire podcast for me and my question.

I loved every second of it. I sincerely feel that all of it was useful and productive.

You really listened to my question.

You heard it and you understood the heart behind the words.


Oscar Trimboli: If you like Shaney, have a question about listening in the workplace or you'd like me to pose a few questions or reflections or framework rather than just answering your question,

And if you don't have a question yet, you learn something from the question Shaney posed today and possibly hers or her team's reflection, email me

Let me know what was useful in this episode, the format, the interaction, the questions rather than the answers, and what possibly is transferable and useful into your workplace.

I'm Oscar Trimboli and along with the Deep Listening Ambassadors, we're on a quest to create a 100 million Deep Listeners in the workplace and you've given us the greatest gift of all.

You've listened to us.

Thanks for listening.

Shaney : Hi Oscar, it's taken a while, but over the past couple of days, I've been able to catch myself in conversations and work on directing my listening

The first step -- self-awareness is so hard, but so crucial as you can't take any other steps until you're actually aware that you're in a situation where you need to test out your new conscious listening paradigm.

In at least three conversations over the past two days, I've been able to get to that level of self-awareness that allows me to pause and remind myself not to try to solve any problems for anyone else, and instead try to ask myself what would make this conversation a success.

This is revolutionary, the whole flavor of conversations changes.

I'm able to relax and actually listen to the person if I don't have to feel the pressure of solving anything.

Conversations are also shorter because people feel heard more quickly and are okay with moving on, so I'm ever so grateful to you and your podcast for opening up my eyes to this whole new world.