Why listening will make you a better communicator

Dec 15, 2022

Text: Brian OliverSmith Photo: 

A busy CEO was in the early stages of the largest round of financing her company had ever done.  She was flying into a regional airport a few states away to meet with a Super Angel, who was very interested in making a sizable investment in the company to lead the round. 

The CEO had already looked up where he was located and saw that his ranch was about 30 minutes from the small airport and timed her travel appropriately to make it there with plenty of time. Well, as luck in financing rounds would have it, the route to his ranch was closer to 45-50 minutes away.

No worries, in college, her friends called her Maria Andretti, so she knew with some hard driving she would be there in fine time. 

However, she soon realized after pulling from the rental lot that this region had no mobile data, zippo, nada, so mobile directions might be hard. Ugh. 

She started out towards his ranch based on the info she had saved and was flying down a country road when she started to doubt herself and direction.

Her coach always told her that going faster and harder in the wrong direction always gets you nowhere faster. Up ahead she saw a young preteen walking his bike along the road, so she slowed down and stopped opposite of him and rolled down her window.

“Excuse me, young man, is this the correct direction to the Flying J ranch?”  Just then her text messaging chimed, and she looked down at it as the young man started to answer.

“Yes maam, it is, but, the ….”

“Great” she said, and zipped off, having confidently confirmed she is going the right way.

About 2 miles down the road, she completely missed the small detour sign, as she was texting with her assistant, but, luckily,y she saw the orange barriers ahead and slammed on her brakes such that she ended up about 20 years away from dropping down 8 feet into the muddy creek bed.  What she completely missed as she zipped away from the young lad was the second part of his sentence, “Yes maam, it is, but the bridge over Muddy Creek is out so be sure to grab the detour in about 2 miles.”  She wasn’t actively listening.

Active listening is a communication skill that is insanely powerful and essential in growing a company and building relationships.  It is often defined by what we don’t do as much as what we do in conversations with others.  This CEO wasn’t actively listening so let’s pull it apart a bit to help you understand what this skill is and how to practice it.

  • Active listening demands focus.  You cannot be distracted.  This CEO was distracted as she asked the boy about her direction.  She was texting her assistant and only hearing or listening for what she wanted, not what is.  If you are in a conversation with someone but busy with other tasks (checking your phone, looking at stock scores, looking at the employees laughing across the office, etc) you are NOT actively listening.  Oh, you might hear parts, but you will miss the emotion, intention, verbal cues, or parts that are incredibly important.  There is no multitasking in listening.  You are either actively listening or you aren’t.  This takes eye contact and if over the phone means you are not flipping through last weeks schedule while talking.  I have 3 teen daughters, they know when I ask, “did you hear me” that if they say, “yes”, while cruising tik tok then I stop until they look up and say, “yes, dad, I got it”.  Otherwise, their butt may be freezing outside the football game because I’m not picking them up and they needed to secure a ride.


  • Active listening demands that you stop predicting, wishing, or presuming what the other person is going to say. This is a hard one for us CEO’s, as we know it all already so we just need people to confirm our brilliance of thought or plans and do it quickly.  Nope, we don’t. In fact, one of the biggest challenges is our hiring amazingly talented people who believe in our vision and not actively listening to them enough.  When you ask a question patiently let others answer and answer fully and try to wipe your mind of what you think they will say, and just listen.  Actively listen.  This is especially important in team meetings.  Give your opinions and thoughts last.  Let others shine.  You hired them and work hard to pay them, so listen.


  • Active listening demands clarity.  This is especially hard in early-stage companies because so many plans are as firm as strawberry jello.  “Yes, we’re going to go to that trade show and probably have a corner booth...if that investor check I’m expecting shows up this week.” This can be hard on the team because your questions lack clarity because nothing is clear for you yet.  However, your team needs clarity in questions or questions on plan A and our back up Plan B so they can answer in context. Practice clarity in your questions and you will get greater clarity in your team’s answers.


  • Active listening demands openness and control on your part.  People are going to surprise you but the key to active listening is to be open and not show excessive surprise or shock at comments.  Reactions like, “what are you thinking”, or “are you not aware of what is going on in our financial world” or “that will never work” are terms that kill future open conversations for active listening.  Young children demand active listening at bedtime when they really open up and share what’s on their little minds. It is precious.  However, it only takes one wrong comment or teasing, and they will shut down for a long time.  Well, employees are the same and they need patience and respect.  The future conversations are worth it.


I could do another page or two, and, in fact, I may do a part 2 of this article because it’s so very important.  But let’s just wrap it up that if you want to keep from driving your company right into Muddy Creek at 60 mph then you need to rapidly move from sometime listening or sometime hearing to actively listening.  The rewards are many and your relationships will be less muddy.




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