
Last week, I explained why listening becomes more valuable as AI gets better at transcription. But there's still the practical question: What does 'deep listening' actually look like when I'm on my eighth Zoom call of the day and my brain is fried?
Fair question. Let's get tactical.
The techniques I'm about to share aren't about becoming a better person or achieving some zen state of presence. They're about developing a professional skill that creates measurable career and business value. These are concrete, everyday practices that compound value by building trust, social capital, and deep understanding of clients, partners, and their pain points. Then converting that into "Yes" and wins.
Before technique, you need to understand what you're listening for. Most people think listening is about understanding what someone said. That's table stakes. Effective listening in professional contexts has five distinct objectives:
You're listening for information that contradicts your assumptions. Not defensively—eagerly. Because being wrong and discovering it early is far more valuable than being confidently wrong until failure proves you out.
When you enter a conversation already certain of the answer, you're not listening. You're waiting. The best listeners expect to learn something unexpected in every substantive conversation.
This sounds soft, but it's ruthlessly practical. In their story, they're the protagonist. If you're listening for how to fit yourself into their narrative, you're doing sales. If you're listening to understand their narrative so you can help them succeed in it, you're doing partnership.
The distinction matters. People can sense when you're trying to position yourself versus when you're trying to understand them. One creates transactional relationships. The other creates the kind of partnerships that refer you to their network and keep you employed through economic downturns.
Extra Credit: Listen for contexts and situations in their story that they aren't fully aware of. If you can find a new (or at least newly recognized) way for them to be the hero in some other part of their life, you've multiplied your credibility.
You're listening for leverage points—where small interventions could have disproportionate positive impact. The team process that's creating unnecessary friction. The assumption that's constraining their thinking. The connection they haven't made that you can facilitate.
AI can't do this because it requires understanding not just the current state but the possibility space—what could be different, and what would it take to get there.
The most valuable conversations aren't where you provide answers. They're where your questions help someone discover answers they already had but couldn't access.
A client describes a technical problem for 20 minutes. Most consultants respond with solutions. The best consultants respond with a question that makes the client say "huh, I never thought about it that way" and then solve their own problem. Guess which one gets hired back?
This is the hardest to describe but the most important. You're listening with enough presence that you can hold their full context without immediately collapsing it into familiar patterns. You're thinking alongside them, not ahead of them.
AI thinks instantly. That's its strength and limitation. You can think patiently. That's your advantage.
The practice: Be quiet and give the other person a chance to think and be right.
In technical cultures, we fill silence. Someone pauses, and we jump in with clarifications, solutions, or our own experiences. We think we're being helpful. We're actually being impatient.
Here's what I learned from watching the most effective technical leaders: they can sit with 10-15 seconds of silence without discomfort. They ask a question, and then they wait. Really wait. Not "waiting while mentally composing my next point" but genuine generosity and openness to the speaker and however they respond.
Why this matters: Most people don't say the most important thing first. They say the safe thing, the obvious thing, the thing they've said before. Then, if you give them space, they say what they actually think. That second or third thing is where the real information lives.
The secret story behind this is that we are often expected to perform tasks so rapidly that two things happen: 1) we rarely get a chance to think below surface level, and 2) we are conditioned to be efficient (aka hurry). This hurry creates a constant state of background stress and subtle dehumanization as we simplify what we think and feel to be more palatable and time-sensitive. Every day, pursuing efficiency teaches us that we're not worth the time to think deeply and be fully known. So, by embracing quietude and patience in our listening, we openly present the opportunity for the speaker to be more authentic. The power of freely providing that opportunity cannot be understated. Some will not be interested in it. Those who do, however, will find talking to you to be a unique experience, and a fulfilling one at that, that will give you a clear, differentiating advantage over less effective listeners.
How to practice:
In your next technical discussion—standup, sales call, 1-on-1—try this: After someone finishes talking, count to five in your head before responding. It feels eternal. Do it anyway.
You'll notice two things:
Remember the last time a someone asked you a complex question, and you paused to think before answering? That pause communicated respect and careful consideration. Your silence told them "your question deserves a thoughtful answer." That respect works whether you're speaking to junior or senior colleagues. Either way, you give respect, you get credibility in return. These are the benefits of practical humility.
Do that for everyone. Your peers will feel respected. Your leaders will feel heard. Your clients will feel valued.
The practice: Give your counterpart an experience that makes them feel lighter.
Just like your favorite restaurant, your comfy chair by the fire, or when someone volunteers to do that task that you always dread, lightening refers to that complex feeling of relief, rest, and enjoyment. There are many ways that you can lighten someone's experience with you. Some are environmental and others are inter-personal.
The important part to remember is that lightening is intended to create in others a sense of being wanted that calms the doubt that "you're just selling to me." The result of listening someone is always the same: their experience with you leaves them in a better mood because that is a connection that money can't buy. In this article, we will focus on lightening by giving deep attention because of its unique importance in professional conversations.
Deep attention doesn't mean intense, serious focus. It means relaxed, interested presence. Think about the difference between someone interrogating you and someone genuinely curious about what you're saying. Both are paying attention. Only one creates psychological safety, comfort, and relaxation.
In technical conversations, especially, we conflate "serious attention" with "critical scrutiny" (I'm a horrible offender at this, smh). It's well-intended behavior that ends up doing more damage to rapport than it creates - someone describes their approach, and we're mentally compiling our list of potential problems. They feel it. They become alert, self-conscious, maybe even defensive. The conversation becomes an accusation rather than an exploration.
Here's the shift: listen to understand their reasoning, not to evaluate their conclusion. You can disagree later, if necessary (careful use of the "yes, and" structure could avoid disagreement). But first, genuinely understand why they think what they think.
How this shows up:
You're reviewing someone's design. Instead of: "Why did you choose Claude over ChatGPT as the code writer here?"
Try: "Walk me through how you thought about the root question—I'm curious what led you to use Claude."
The information you get is identical. But the first question puts them on defense, preparing to justify. The second invites them to share their thinking, often revealing considerations you wouldn't have thought to ask about.
Practical tips for lightening:
These are small adjustments. They compound into someone feeling "this person is easy to talk to" versus "this person is judging everything I say."
That kind of connection can't be bought. It can only be given.
This is where listening becomes a genuine skill worth premium compensation. You're listening on multiple levels simultaneously:
What's not being said:
In sprint planning, a team discusses the upcoming features but nobody mentions performance testing. In a marketing meeting, someone proposes a new sales channel but doesn't mention data consistency. In a project kickoff, stakeholders describe deliverables but not success criteria.
These absences are data. They tell you where blindspots exist, what's being avoided, what hasn't been considered.
What they might not be aware of:
A team says they "need better documentation." You hear: they've experienced painful knowledge transfer failures and they're trying to prevent it happening again. But what they might not be aware of is that documentation isn't the answer—their processes are too complex, their domain knowledge is too tacit, and their turnover is too high for documentation to solve it.
You can hear this because you've seen it before. Not their exact situation, but the pattern.
What's beneath the surface—fear or hope:
A tech lead pushes hard for comprehensive test coverage. On the surface: engineering best practice. Beneath: they got burned by production incidents in their last role and they're terrified of it happening again.
A product manager insists on detailed specifications before development. On the surface: clear requirements. Beneath: they don't trust the developers to build what's needed, or they're afraid of being blamed if the product fails.
Understanding the fear or hope beneath the surface doesn't mean you indulge it. But it means you can address the real concern rather than arguing about the proxy concern.
Listening with all 5 senses:
Yes, literally. In person or on video:
The AI captures the words. You capture everything else.
The implications for you, them, and others:
You're listening to a staff member describe their plan of action. AI notes the technical details. You're simultaneously tracking:
You're not just listening to their plan. You're listening to ripple effects across a system of people and dependencies.
The practice: Expend extra energy remembering what was said, and why it mattered.
AI remembers everything perfectly. So why should you remember anything?
Because memory + context = relationship. When you remember not just what someone said but why it mattered to them, you demonstrate that they matter to you.
A colleague mentions they're working on a difficult migration. Three weeks later, you ask how it went. That's basic professional courtesy.
But if you remember they mentioned the migration was difficult because their tech lead was skeptical and they were trying to prove the approach worked—and you ask "how'd the tech lead respond when you showed them the results?"—that's relationship-building.
The difference is minuscule. The impact is massive.
How to practice:
After important conversations, spend two minutes writing three things:
I keep a simple note for each person I work with regularly. Not exhaustive. Just:
Before meeting with them, I review it. After meeting with them, I update it. Takes five minutes. Worth thousands of dollars in relational capital.
The practice: Understand that the same words mean different things in different contexts.
"We need to ship faster" from a CEO means something different than from a developer. "This is good enough" from a perfectionist senior engineer means something different than from someone who always cuts corners.
You're listening not just to what's said but who's saying it, when they're saying it, and what else is happening around them.
A team says they're "on track" in Friday's status meeting. But you know:
"On track" might mean "we're pretending everything is fine because we don't want to look bad" or "we genuinely don't see the problems coming."
AI can't make this judgment because it requires historical context, political awareness, and understanding of individual communication styles. You can.
Lift others up and give everyone an equal chance to speak. One of the things that I found while researching this article was the patterns that many Native American peoples have about listening and sharing in groups. At the outset, I want to be clear that I am not, nor do I identify as, Native American or an expert in the studies of Native American peoples and cultures. For what deeper cultural meaning or implications on Native American identity these techniques may have, I express no opinion or special understanding. Only respect for their inherent value for solving common problems. I am simply a researcher looking for the best sources, and that search led me to these customs and attitudes. Having said that, there is much to learn, and what follows is drawn from my research on Native American practices:
Everyone else is always an "elder"
This isn't about age or seniority. It's about approaching every conversation with the assumption that the other person has wisdom you don't possess. Even—especially—when you're the acknowledged expert.
The junior developer who just joined your team? They're seeing things you've stopped noticing because you're too close. The non-technical stakeholder asking "dumb questions"? They're seeing user needs you've abstracted away. The consultant who doesn't have industry experience? They're using "fresh eyes" to notice patterns and assumptions you've normalized.
Treat everyone as having valuable perspective. Not in a patronizing way, but genuinely. You'll learn more, and they'll feel heard.
Listening circles
In many Native American traditions, conversations happen in circles where:
You're not going to implement literal talking sticks in team meetings, but the principle applies: create space for quieter voices. The best technical insight I hear tend to come from people who barely speak in meetings. There are many, valid reasons why someone might not speak up in meetings. That doesn't mean that missing their contribution is acceptable. Specifically designing meeting formats to explicitly invite each person to share, easily opens the door to new perspectives - that might be what has been missing.
How to adapt this:
In meetings you run:
Not everyone processes or expresses information the same way. This is an area to which I can speak with unique knowledge as someone who has wrestled with depression and ADHD my whole life (for this article, I choose to take an expansive view on what is considered neurodivergent). Effective listening requires adapting to different cognitive styles:
For listening to neurodivergent speakers:
Some people think by talking—they need to verbalize to process. Don't interrupt their processing by trying to solve while they're still formulating.
Some people need preparation time—asking them to "share thoughts" on the spot creates anxiety. Give them questions in advance. Period. (besides, that kind of preparation is looks good)
Some people communicate better in writing—the real-time verbal processing is hard. Follow up meetings with "any additional thoughts via Slack/email" to capture what they couldn't say in the moment.
Some people don't think in easy-to-follow "straight lines"—that's an important part of why they tend to be creative. Asking them to slow down, focus, simplify, or stay on topic is distracting and embarrassing. Apply a double-measure of effort on Technique 1.
Some people may seem like they're always looking for "the cloud in every silver lining"—they're not. Nobody wants to find problems and sound like Eeyore. But certain forms of neurodivergence, like depression and/or anxiety, are given to deep thought and threat recognition.
For neurodivergent listeners (like me):
Technique 1 will take much more effort if you have ADHD because you're naturally wired to anticipate what people are going to say before they finish…sometimes before they start. It's a blessing and a curse. Even so, it's worth putting the effort in to go slow.
If you've ADHD and struggle with limiting the scope of your attention: take notes, doodle, do crochet, whatever. Just do something to direct your attention away from everything all at once. I like hand writing notes. There's a nice tactile quality to it and there's pretty good science that it benefits understanding and retention. Remember, it's not meant to be extensive transcription—AI does that—but write key points and maybe some surprising observations to anchor your attention. Final note: be cautious that your notes don't trick you into daydreaming and drifting off to thinking about whatever is more immediately interesting than what the other person is talking about.
If you're autistic and struggle sensitivity to background noise, difficulties filtering speech from noise, and cognitive overload: focus on intentional breathing and address environmental factors directly. "I'm having trouble understanding you because of competing noise, could we have this meeting in a less active environment?" tone—are you concerned about this approach, or just thinking through implications?" "Can we do this as a walking meeting?" Or, "Can I turn off my camera to reduce distraction?" Moderating your breathing helps to keep you calm and manage the existing inputs so that you can more effectively address reducing the inputs. And if you end up reaching overload, ask for a 5 minute break. Chances are most people will want one anyway. Remember though, avoiding cognitive overload is best done on the front end, so do your best to avoid back-to-back or very long meetings that limit your ability to take breaks.
Effective listening isn't about forcing neurotypical communication patterns on everyone. It's about creating conditions where everyone can communicate and be heard effectively. And if you're not neurodivergent, avoid the temptation to ignore these suggestions because they don't apply to you. These techniques are effective for the most sensitive users, meaning they can probably do some good to help you remain calm and sharp listeners.
To be clear, I’m not a therapist, counselor, or expert in neurodivergence. I'm just speaking from tools that I've found effective for dealing with the unique obstacles that people like me face. If my suggestions don’t work for you, chances are that talking to a professional will reveal techniques that are a better fit for you and your unique situation.
The key takeaway from this part of the article is that neurodivergence isn't a disorder - it's a fundamentally different way that a brain can be "wired." It's like the differences between different body styles of vehicles. They're all designed to get you somewhere, but they all have unique features for the journey. Likewise, neurodivergences all have unique strengths and challenges that are essential for surviving and thriving in uncertain and fast moving situations.
The workplace NEEDS neurodivergent professionals, but it does not yet offer an environment designed to lighten their experience.
Listening and trust-building create a reinforcing cycle:
Trust → Listening → More Trust
When you're trustworthy, people open up to you. They share more, including things they wouldn't say in official channels. The junior developer tells you they're struggling. The product owner shares doubts about a decision they publicly supported. The business unit stakeholder admits they don't actually understand the technical tradeoffs.
This gives you more to listen to—richer, more honest information.
And when you listen well to that information—when you prove you can be trusted with it by not weaponizing it, not dismissing it, actually acting on it—you become more trustworthy.
The result: over time, you become the person people confide in, the person who gets the real story, the person who understands what's actually happening beneath official narratives.
That's the person who finds the best solutions. That's the person clients hire at premium rates. That's the person who adds value far beyond that of the bot.
Here's what I've observed across hundreds people in professional and everyday situations: the ones commanding the highest pay, the most influence, and the greatest reputation aren't necessarily the most technically brilliant. They're the ones who listen well enough to:
These capabilities compound. They make you more effective at technical work because you're solving the right problems. They make your perspective more valuable because you understand what people need. They make you more successful because clients feel understood.
And none of this can be replicated by AI, no matter how good the transcription gets.
We've now covered the first two SCARRLET skills: Trust-building and Listening. These are the foundational relationship skills that make every other capability more effective.
Next week: Emotional Intelligence—when machines handle the work, EQ becomes THE work. As AI takes over technical execution, what's left for humans is navigating the messy, unpredictable, irreducibly human elements: motivation, conflict, fear, ambition, politics, and meaning.
Most technical professionals were taught that emotions are distractions from "real work." In 2035, understanding and navigating emotions is the real work. And the ones who master it will earn multiples of those who don't.
Until then, here's your practice: In your next three conversations, try the five-second silence technique. After someone speaks, count to five before responding. Notice what happens—both in what they say and in how you feel doing it.