This post is part of an ongoing series on the books that I have read as part of my continual professional development (CPD). All of my CPD posts are available at the following link: Continual Professional Development
Most of the problems that stall a technical team look like talking problems. The requirement that was explained three times and still came back wrong. The stand-up where everyone reports and nobody connects. The handover that left out the one detail that mattered. We tend to respond by talking more: clearer briefs, more documentation, another meeting to align. The thing we rarely fix is the other half of every conversation.
Oscar Trimboli’s “How to Listen: Discover the Hidden Key to Better Communication” is a corrective to that habit. Trimboli has spent years researching listening as a discipline in its own right, and his central claim is one that should make any leader pause: most of us are far worse at it than we believe, and almost none of us treat it as a skill worth practising. This sits naturally alongside the lessons I drew from Charles Duhigg’s Supercommunicators; where Duhigg looks at connection across the whole of a conversation, Trimboli zooms in on the part of it that we are usually getting wrong.
This post draws on the ten quotes I found most useful from How to Listen, and what they reveal about leading technical teams well.
A Definition Worth Sitting With
Listening is the willingness to have your mind changed.
If you only take one idea from the book, take this one. It reframes listening from something passive, a thing you do with your ears while you wait to speak, into something active and slightly dangerous: a willingness to come out of the conversation believing something different from what you walked in with.
By that definition, a great deal of what passes for listening in technical teams is not listening at all. Consider the architecture review where the decision was made before the meeting even started, or the 1:1 where the manager has already written the outcome in their head before the other person sits down. People are hearing words and processing them, but nobody is willing to be changed, so nothing actually moves.
For a leader, that willingness is the whole game. If your team learns that talking to you cannot change your mind, they will eventually stop trying; and the moment they stop trying is the moment you lose access to the information you most need.
Why Seniority Raises the Stakes
The more senior you are in your organisation, the more listening matters.
There is a cruel irony in how careers tend to work. The more senior you become, the more your job depends on the quality of information reaching you, and the harder it becomes to get that information undistorted. People edit themselves around authority. They tell you the version they think you want, or the version that is safest to say, rather than the version that is true.
Trimboli’s point is that listening scales in importance with your position. The higher you sit, the more your effectiveness depends on it. A junior developer who listens poorly inconveniences a pairing partner. A CTO who listens poorly makes expensive decisions on the basis of filtered information, and never finds out why the strategy that looked so sound on the whiteboard failed to land in the team.
This is one of the patterns I pay closest attention to in fractional CTO work. When I join an organisation, some of the most valuable signal is in what people have stopped saying to the leaders above them. The cost of poor listening at the top is not a single bad conversation; it is a slow narrowing of what leadership is allowed to know.
The 86 Percent You Are Missing
The first thing the speaker says is 14 percent of what they are thinking. This means that 86 percent of what they think and mean is obscure and opaque to the listener.
Trimboli builds this around a set of figures: that most people write at around 125 words per minute, speak at around 400, and think at around 900. He is careful to note these describe neurotypical speakers and that neurodivergent people will differ. The exact numbers matter less than the gap they point to. We think far faster than we can speak, so the first thing out of someone’s mouth is a heavily compressed summary of a much larger thought.
The practical consequence is uncomfortable: if you act on the first sentence, you are acting on a fraction of the meaning. The developer who says “the deadline is too tight” has compressed a paragraph of concern into six words. The first words are a doorway, not the room.
This reframes the most useful thing a leader can do in a conversation, which is often nothing at all for a beat longer than feels comfortable. The silence after someone’s opening sentence is where the other 86 percent has a chance to arrive. Most of us fill it instead, and then wonder why the same issue keeps resurfacing.
You Are Not As Good At This As You Think
The first listening barrier is self-awareness bias—we think we are better at listening than others perceive us to be. We believe we are a better listener than the speaker does. There is no universal and shared understanding of the characteristics of how to listen effectively.
This is the quote that should give every confident communicator pause. The first obstacle to listening well is the belief that you already do. Almost everyone rates themselves an above-average listener, which is statistically impossible and personally inconvenient.
The reason this bias is so durable is that we judge our own listening from the inside, by our intentions, while everyone else judges it from the outside, by our behaviour. You know you were paying attention; the person speaking only knows whether they felt heard. Those two things come apart far more often than we like to admit.
ℹ️ Note
If you want a quick, humbling experiment, ask three people who report to you how well they think you listen, and make it genuinely safe for them to be honest. The gap between their answers and your self-image is the size of the problem you did not know you had.
Naming this bias is useful precisely because it removes the excuse. Once you accept that your sense of your own listening is unreliable, you start looking for external evidence instead, and that search is where improvement begins.
The Business Case for Listening
When you are more open to improving your listening, conversations and projects take less time because there is less wasted effort re-explaining. The additional people, resources, and quality costs are minimized because your initial conversations are focused and more effective.
Listening can sound like a soft topic, the sort of thing that gets a nod in a values workshop and no place on the delivery plan. Trimboli makes the harder, more commercial argument: poor listening is expensive, and the cost shows up everywhere except the line item that would let you trace it.
Every requirement that has to be re-explained is rework. Every project that drifts because the brief was half-heard is wasted capacity. Every defect that traces back to a misunderstood expectation carries a quality cost that is real even when nobody attributes it to the conversation that caused it. The effort does not disappear; it gets paid later, with interest, in re-explaining and rebuilding.
Across nearly twenty years working with more than fifty organisations, the teams that move fastest are rarely the ones that talk fastest. They are the ones whose first conversations are good enough that they do not need a second and a third. Time spent listening properly at the start is one of the highest-return investments a team can make, and it almost never appears on a budget.
What Goes Unsaid Still Shapes Everything
The unspoken influences the relationship, the issue, and the outcomes.
A short line carrying a large idea. The words spoken in a meeting are not the whole of the meeting. What people choose not to say, cannot find a safe way to say, or do not yet have the language for, shapes the result just as powerfully as what makes it into the minutes.
Technical leaders are trained to work with what is explicit: the ticket, the spec, the stack trace. The unspoken is harder, because by definition it is not in front of you. It is the reservation a senior engineer holds but does not voice because the room has clearly already decided; the reason a team keeps missing estimates that nobody will say out loud; the silence in a retrospective that is itself a message.
Listening for the unspoken is a different activity from listening to words. It means paying attention to hesitation, to what gets carefully avoided, to the question that nearly got asked. This connects directly to psychological safety: the unspoken stays unspoken until people believe it is safe to say it, and creating that safety is squarely the leader’s job.
The Rinse Cycle of the Mind
Speaking is like the rinse cycle for the mind. When you say something to someone else, it crystallizes what you want to say and how you want to say it. It’s unlikely that what you say the first time is what you completely think or meant to say.
I love this image, partly because it explains so much frustrating conversational behaviour. People do not arrive at meaning fully formed; they arrive at it by speaking, often several times over. The first articulation is a draft. The second is a revision. The clearest version frequently comes third, once the earlier attempts have done their work.
This has a direct implication for how leaders run conversations. If you treat the first thing someone says as their settled position, and respond to it as such, you cut off the rinse cycle before it has finished. You end up debating a draft the speaker has already mentally discarded.
The skill here is patience under the urge to respond. When a team member is visibly working something out as they talk, the most useful thing you can do is let the machine run rather than reaching in and stopping it. The clean version is usually a sentence or two away, and it is almost always worth more than the first.
A Strategy for the Wandering Mind
Internal distractions are inevitable. Rather than reacting, create a reset strategy to return your attention to the present. It could be as simple as a leaf, a pen, or the colour of the speaker’s eyes.
One of the things I appreciate about Trimboli is that he does not pretend attention is a matter of willpower. Your mind will wander. You will start drafting your reply, remember an unanswered message, or notice you are hungry. Treating this as a personal failing to be scolded away does not work, because it is simply how attention behaves.
What does work is having a deliberate way back. A small, pre-chosen anchor that returns you to the conversation when you notice you have drifted. The specific anchor matters less than the fact that you have decided on one in advance, so that catching yourself wandering triggers a return rather than a spiral of self-criticism.
For anyone who spends their day context-switching between code, calls, and crises, this is more relevant than it might first appear. Walking into a conversation still mentally inside the previous one is the default condition of technical leadership. A reset strategy is a practical way of arriving in the conversation you are actually in.
From Monologue to Dialogue
It’s your presence and focus that send powerful signals to the speakers to help them tune into their head and their heart—their thoughts and feelings. This moves the conversation from monologue to dialogue because your listening presence is drawing more out of the speaker.
This is the idea that turns listening from something defensive into something generative. We tend to think of listening as receiving: information flows from speaker to listener, and the listener’s job is to capture it accurately. Trimboli’s framing is that your listening actively shapes what the speaker is able to produce in the first place.
The quality of attention you bring changes the quality of what the other person says. A speaker who can feel that they have your genuine focus reaches for better, truer, more considered words. A speaker who senses you are half-present, or waiting for a gap to jump into, gives you the shallow version and moves on. The same person will say something more useful to a better listener.
Having interviewed more than 170 engineers, architects, and technology leaders on The Modern .NET Show, this is the clearest single difference I have noticed between conversations that go somewhere and conversations that do not. The cleverness of the questions matters far less than the quality of the listening between them. The guests who said the most surprising things were responding to the space they were given to do it.
You Are Part of the Story
Remember that you are not an objective observer in their story. Your presence in this discussion will change the speaker’s awareness of the issue and their perspective, whether you choose to say anything or not.
Technical people are fond of the idea of the neutral observer, the engineer who simply assesses the facts without influencing them. Trimboli quietly dismantles that comfort. The moment you are in the room, you are part of what is happening; your presence shapes the conversation whether or not you intend it to.
For a leader, this is heightened by authority. Your job title walks into the meeting with you. The questions you choose to ask signal what you think matters. Your reaction to the first answer teaches people what is safe to say next. You are never a passive recorder of your team’s reality; you are continuously, often unconsciously, shaping it.
The useful response is to own that influence rather than wish it away. If your presence inevitably changes the conversation, the question becomes what kind of change you want it to be. Listening, in this light, is a way of using that influence deliberately, to draw out what is true rather than what is convenient.
Listening as a Practice
What unites these ten ideas is a single shift in how we treat listening: as a skill you practise rather than a trait you are born with, and one that improves with attention like any other.
That should be encouraging news for technical leaders, because it means the gap between leaders whose teams feel heard and leaders whose teams have quietly given up is not a gap in talent. It is a gap in practice. The willingness to have your mind changed, the patience to let the rinse cycle finish, the humility to doubt your own self-assessment, the discipline to reset your wandering attention: none of these require a different personality. They require deciding that listening is part of the work, and then doing it on purpose.
The conversations that matter most in a technical organisation are the ones where the real thing is hardest to say. The risk nobody wants to raise. The doubt about the plan. The concern that the deadline is going to cost more than it saves. Whether those things get said, and whether you hear them when they do, comes down to how you listen. It is a skill. It is learnable. And for anyone leading a team, it may be the most valuable one you can choose to build.
If the ideas in this post resonate with challenges you are navigating in your own team, let’s talk.