We ALL need to work on effective listening. Yes, even you!
Each of us has a default position by which we enter into conversations and listen. I remember hearing research on listening styles asserting that all of us fall into one of four categories developed by researchers Watson, Barker and Weaver in the 1990s. In short, we spend most of our listening time in conversations predominantly as 1) a task-oriented listener, focusing on efficiency, staying on topic, and achieving outcomes; or 2) an analytical listener, seeking to understand the complete message and analyze issues before reaching conclusions; or 3) a relational listener, paying attention to emotions, feelings, and building interpersonal connections in the conversation; or 4) a critical listener, evaluating the messages being conveyed for accuracy, consistency, credibility, and quality.
Additionally, I have spent significant time engaging in professional learning around the knowledge, skills, and competencies needed to effectively demonstrate active listening. The work of Carl Rogers and his colleagues from the 1950s emphasizes the importance of empathy, reflection and understanding when listening.
If we combine these two constructs, I might argue that effective listening is the sum of your listening style and high-quality active listening skills. But I would be wrong.
Listening Effectiveness = Listening Style + Active Listening Skills
For example, I am an analytical-oriented listener, so my default focus is on understanding and examining all aspects of an issue. If I am engaging in active listening skills and behaviors given my preferred style, I am encouraging curiosity and clarification before drawing conclusions or offering solutions. Active listening serves as a corrective balance for my weaknesses as an analytical listener. In short, I am an analytical listener; I may overanalyze. Active listening encourages me to take time to genuinely understand the speaker, not just the problem.
Problem solved right? Not quite. There is one more thing we need to consider. As the individual doing the listening, this type of effective listening needs to happen in two directions, both to the other party and within yourself. Self-awareness serves as the multiplier in enhancing the power of our listening styles and our active listening skills. So our effective listening construct actually looks like the following:
Listening Effectiveness = Self-Awareness (Listening Style + Active Listening Skills)
The complexity of listening well given this construct cannot be overstated. It explains why we ALL need to work on it. Through my experiences in serving as a leader and coach, I have both observed and experienced that the hardest part of this work is the “self-assessment” part of the equation. This newsletter is focused on that. Let’s try to figure out how to do this better.
What is “self-assessment” while listening?
Self-assessment while listening is when we turn our attention briefly toward our own experiences while remaining engaged in someone else's experience. It is a quick check-in with yourself. It works across three dimensions.
Cognitively: ask yourself whether you're tracking both what is being said and what is being implied.
Am I paying attention to their words (explicit and implicit)? Do I understand what they’re saying?
Emotionally: notice the feelings present in the speaker's words alongside your own emotional response as you take their words in.
What emotions are present in what they are saying? What emotions am I experiencing?
Behaviorally: ask yourself if your actions match your active listening intentions of reflecting the speaker's experience back, decentering your own perspective, and communicating genuine understanding, particularly when their view differs sharply from yours.
Am I behaving as if I am interested in their perspective? Am I reflecting their experience in my responses? Am I decentering myself and my experience? Am I communicating a real understanding of their perspective, especially when it is different from my own?
How do I engage in self-assessment while listening when I am supposed to be listening?
This is the perceived paradox right? Self-assessment sounds like a step outside the conversation, a pause to check your own cognitive, emotional, and behavioral state, but the conversation doesn't pause for you. Either the self-monitoring wins and you drift out of the conversation entirely, or the conversation wins, self-assessment gets abandoned the moment it gets hard, and you're back to listening on autopilot. In both cases, you are not listening.
Let’s reframe how we think about what we are trying to do. You might be treating self-assessment and listening as two tasks competing for the same cognitive resource. When coaching others around this skill, I find my clients trying to do self-assessment as a foreground task. They think they need to engage in a continuous second conversation with themselves, resulting in a competition for the same bandwidth as the prioritized conversation with another person.
Instead, shrink these self-assessments down to a small set of pre-built check-in points rather than a running commentary, and anchor them to something physical. For example, consider one or two of the cognitive/emotional/behavioral questions from above and attach them to natural pauses that already occur in conversation (e.g., a breath the speaker takes, a transition between topics, a moment where you'd normally be formulating your response). In that half-second break, ask one question silently: Whose experience am I in right now, theirs or mine? Answer it quickly, using your body to help you gather evidence (e.g., notice your own posture or the tension in your jaw). Then make the adjustment in your body (e.g., relax your jaw, take a sip of water, straighten your back), as a way to intervene and reconnect to your intentions around effective listening. Over time, with repetition, this kind of check-in will not require deliberate effort and will move into procedural knowledge (see our August 2026 newsletter). The self-assessment stops being a second task and becomes part of how you listen.
How do I know I am getting better?
For most of us, the signal that you are getting better at something is that it becomes easier to do (increased procedural knowledge) but the problem is that this feeling is often an unreliable signal in a specific, misleading direction. As the work of doing quick self-assessments in conversations becomes more automatic, it also becomes less conscious.
Self-monitoring efficacy requires you to engage in both external evaluation, leveraging individuals you interact with regularly, and internal quality checks, looking for opportunities where you caught yourself not engaging in effective listening.
First, periodically, ask a trusted colleague or direct report to share their experiences with you. The more specific the question, the better. For example, ask them "In our last few conversations, was there a moment you felt like I wasn't fully with you, or where I moved to advice before I understood the problem?"
Second, track your own behavioral evidence rather than your internal sense of it. Improvement here doesn't look like your self-assessment check-ins are disappearing. Instead, you are consistently finding moments of ineffective listening and most importantly, you are acting on what you find, more often, with less friction.
These types of evaluation are critical because external feedback bypasses your own self-reporting biases (while tracking catches-and-corrections) and brings us back to the goal of this endeavor (to get faster and more honest at using self-assessment when it matters).
So if you want to get better at effective listening, remember:
Listening Effectiveness = Self-Awareness (Listening Style + Active Listening Skills)
As always, this section is about unlocking/disrupting your thinking. As you read, think about the ways in which your current models of leadership are serving (or not serving) you well!
Gate 14
The storm had closed half the airport by six, and by eight the chairs at Gate 14 had become a kind of waiting room for the stranded. Elena sat with her coat still on, half-watching the departures board flick from DELAYED to DELAYED to CANCELLED, when the man beside her said, without preamble, that his father had died on a Tuesday like this one, in a hospital an hour from where he was now sitting, and that he wasn't sure why he was telling her this except that the storm had a similar color to the sky that day.
She turned toward him. He was maybe sixty, hands folded over a boarding pass he wasn't looking at.
She noticed she was noticing — her own spine straightening, a private inventory starting up: am I tracking this, am I present, is my face doing the right thing. The checklist unspooled faster than he was talking, and somewhere inside it she lost the thread of what he'd actually said. He was still speaking — something about a hallway, a vending machine, the smell of it — and she caught herself nodding at a pause that hadn't been a pause, just a breath.
"That sounds really hard," she said, a half-beat late, the words arriving with no weight behind them.
He glanced at her, then away, toward the window where nothing was landing or leaving.
She felt the miss like a dropped stitch. So she did the opposite. She let go of the checking altogether, decided to just be in it, however that worked, and folded her attention outward toward him with nothing held in reserve. For a while this felt like relief. He kept talking. She kept nodding. Somewhere in the unwatched middle distance of her own mind, she started composing what she'd say when he finished, something about grief having no schedule, something she'd read once, ready before he'd stopped.
He hadn't stopped. He was telling her the vending machine had given him the wrong chips he had tried to buy with his credit card, twice, and that he'd stood there trying to order the same chips with his credit card a third time before he understood he was crying.
That detail, the credit card, swiped three times, landed somewhere underneath her prepared sentence. She felt something in her jaw she hadn't noticed was tight. A gate agent's voice cut across the terminal, garbled, half the room turning toward the board.
"Sorry," Elena said. "Say that part again? About the machine."
He looked at her for a second longer than the question required.
Outside, the rain kept coming sideways against the glass, and the board still hadn't changed.
Apply the Learning - A Case Study: The Q3 Board Meeting
Remy Ibarra had chaired eleven board meetings as CEO of Halden Systems, a mid-sized enterprise software company, and she'd learned to read the room before anyone spoke. This one, she could tell within the first ten minutes, was going to be different.
The company had missed its Q3 growth target for the second consecutive quarter. Not by much, four points, but enough that Halden's lead investor, David Feld, had flown in rather than videoconference, and had spent the first half of the meeting mostly silent, which Remy had come to recognize as its own kind of signal.
When he finally spoke, it wasn't about the numbers.
"I want to understand something," he said, closing his laptop. "In the last three board meetings, every time someone's raised a concern about the product roadmap, you've had an answer ready before they finished the sentence. I'm not questioning the answers. I'm asking whether you're actually hearing the concern, or whether you've just gotten very good at responding to it."
The room went quiet in the specific way rooms go quiet when someone has said the thing everyone else had been circling.
Remy felt her attention split immediately. Part of her began an internal audit, was that true, had she done that, was she doing it right now—while another part of her tried to keep pace with what David was still saying, something about the CTO's resignation three months earlier, something about whether the team felt safe raising problems. She caught herself nodding along to words she hadn't fully registered, aware only that a pause had occurred and that a nod seemed to be required.
She asked him to repeat the part about the CTO. He did, visibly noting that she'd needed him to repeat what he said.
It got worse for Remy from there, though not in the way she expected. Having missed him once, Remy swung the other way, she stopped monitoring herself entirely and let herself simply react; defending the roadmap decisions point by point, citing the Q2 customer retention data, the competitive analysis, the hiring plan for engineering. It was, by any normal standard, a strong response. David let her finish.
"That's the answer you'd give in a press interview," he said. "I asked what you're hearing."
Remy sat with that for a moment longer. She noticed two board members exchanged a glance and she pretended not to see. She thought that maybe her pause was making people uncomfortable. She had, in the space of four minutes, first disappeared into her own head checking whether she was listening, and then disappeared entirely the other direction, defending instead of hearing, and both times by any measure that mattered to the person across the table, she had not been listening at all. Remy took a deep long breath.
"Give me a second," she finally said, and meant it as something other than a rhetorical pause. "I think I need to actually answer your question, not the one I assumed you were asking."
David said nothing. He waited.
Case Study Questions
Remy's two responses to David, the internal audit that made her miss his words, and the rehearsed defense that replaced listening with reacting, look like opposite failures. What do they have in common, and why might a leader oscillate between them in the same conversation?
The case ends before Remy answers. Using the self-assessment framework (cognitive, emotional, behavioral check-ins anchored to natural pauses), what should her next move actually look like. Don’t concentrate on what she should say, but what should she do internally in the next ten seconds?
David’s real question wasn't about the roadmap; it was about whether Remy was capable of hearing bad news without immediately managing it. What organizational cost does a leader pay when senior people conclude they're being managed rather than heard?
Remy has presumably navigated eleven board meetings competently before this one. What does that suggest about the reliability of "it felt fine" as a signal of Remy’s (and your own) listening effectiveness and what would a better signal look like for a sitting CEO?
