Deep Listening: An Unfair Advantage

By Esteban Reyes, Founding Partner at Las Olas VC (a.k.a. LOVC)

Deep listening skills are critical for founders and investors, and I believe deep listeners have an unfair advantage. Deep listeners will likely pick up on non-obvious insights that non-deep listeners will miss because their minds are so busy. It’s even more basic: when you listen you’re learning. When you talk you’re broadcasting information and exerting energy. Investors and founders need to do both, and I’ve found that great deep listeners are great at both. Conversely, bad listeners are bad at both, generally speaking.

Since listening happens inside of each individual’s mind it’s really hard to define its meaning with absolute purity. Many people believe they’re listening (when they aren’t), or argue they are “special” and can multi-task. And I actually think that’s the core problem — we don’t have a common understanding for what listening is about.

What isn’t listening (in the context of startups)?

• Investor talking over founder is (obviously!) not listening.
• Founder interrupting a team member half sentence to say something that’s “more important”.
• Doing something else while a team member presents isn’t listening (i.e. emails, checking phone, Slack, etc).
• Investor assuming already knows what founder will say next, or viceversa.
• Analyzing or judging founder while (s)he presents to investors.
• Listening solely to know what to say next and “win the argument”.
• Dismissing an argument because one disagrees.

Deep listening requires self-regulation and mental stamina. I’ve observed that the best founders and investors are great listeners. They’re self-aware, emotionally intelligent, and consciously opt-in on listening first. They know how to cope with (internal and external) distractions, and turn-off any desire to control the conversation. They intervene to ask clarifying questions and confirm their understanding of what’s being said. They are genuinely interested in what others have to say, and are masters at putting themselves in the speaker’s shoes.

In my own experience, deep listening helps me better understand the founders I work with. Often times founders are so deep into their subject you have to listen to nonverbal queues to get the full picture. It’s remarkable how much more I learn, which in turn enables us to better work together.

My objective isn’t to criticize, or claim the “truth”, but rather to keep myself accountable whenever I’m not listening. Hopefully, other founders and investors find this useful too.

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by +405,714 people.

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