Over the years, I’ve facilitated dozens of strategic planning retreats. Sometimes the executive director, CEO, or board president – somebody with a title and the power that comes with it – will pull me aside and ask a thoughtful question:

“How much should I talk?” 

Here’s a variation: “Maybe I should just listen and not speak too much. What do you think?” 

A good day to listen

My first thought: If the boss is self-aware enough to ask that question, it’s going to be a productive day.

“Tell my why,” I respond, trying not to smile too obviously. Their answers sound something like this:

• I don’t want to dominate or direct the conversation.
• In this situation, everyone should be equally empowered to speak and participate.
• I’d like to know what others are thinking.
• You’re the facilitator. I don’t have to run the meeting!

“I appreciate your instinct,” I’ll respond, adding, “Your perspective is important, too. People want to know what you think. But yes – before you speak, it’s a good idea to listen.”

Which brings me to the theme of this post. Listening – I mean listening deeply, with your full attention – is an underappreciated and underused leadership skill.

You can be curious…

I recently attended an interview with the podcaster Erica Heilman, who is clearly one of world’s great listeners. (If you don’t know her work, please check it out.) She said many things that stuck with me, but especially this:

“You can be curious. You can be judgmental. But you can’t be both at the same time.”

Listening without judgment – without rolling your eyes, drifting off, or preparing a rebuttal – requires considerable discipline.

It also means putting aside your ego, turning off your mental chatter, and trying on the other person’s point of view … at least for a few minutes. 

Listening requires empathy, which is another underappreciated leadership skill.

Trying this in real life

I serve as the board president of our local synagogue in Montpelier, Vermont. In the wake of recent events in the Middle East, I pledged to have 50 one-on-one conversations with my fellow Jews about Israel and Palestine. 

This is a fraught, emotionally challenging topic – one that has bedeviled the Jewish community for decades. My goal is to better understand what people are thinking and how they’re feeling. I also want to demonstrate, through deep listening, that our community is open to everyone and we welcome a diversity of perspectives.

As I told the congregation, we will only get better at having these conversations by actually having these conversations. 

My approach: ask questions, listen with intention, take notes, and ask more questions. If requested, I am happy to share my opinions, too. 

What I’ve learned so far

Having completed 45 (!) interviews/conversations over the last month or so, a few observations:

Turning off the judgment is difficult. In the interest of being curious – rather than judgmental – I am learning to simply sit with my reactions, even when my impulse is to challenge the speaker. 

Not surprisingly, if you smile, nod, and ask more questions, people feel safer speaking their truth … even if it’s not your truth. 

Listening means following the flow of the conversation. I start with a list of questions – which grows longer as I do these interviews – but I don’t have time to ask them all. When giving the speaker my full attention, it’s much easier to discern the next question.

Empathy takes energy. Being fully present – and absorbing other people’s emotions and ideas – can be tiring. Oddly, it’s also energizing. Deep human connection begins with deep listening.

Engage others in the process. One of my favorite questions: “If you were conducting these interviews, what questions would you ask?” This often generates new lines of inquiry I hadn’t considered.

Not everyone cares what I think – and that’s OK. At the end of each interview, I often ask, “Do you have any questions for me?” Perhaps half the participants have responded, “Nah, we’re good.”

I don’t take this personally. It could simply mean “I don’t have time right now,” or “That’s all the emotional energy I can offer to this subject.”

Interestingly, one person emailed me two days later to say, “When do I get to ask you questions?” My response: “Let’s not do this via email. When can you meet?”

Listening is leadership 

In today’s world – where so much communication has been channeled into social media – listening to others one-on-one is a lost art. 

If scarcity increases value, then the value of showing up, asking questions, listening to the answers, and suspending judgment is even more important because we do it less and less.

Whatever your leadership role, you can increase your impact by taking the time to really listen to those around you.