The Startup
Published in

The Startup

What my therapist taught me about listening and asking questions

I love therapy. The idea of sitting on a couch for an hour and just downloading all my thoughts to a third party is so, dare I say, therapeutic. I wish I had more time for therapy because I would go weekly. I believe we all need to talk to someone from time to time who is there to simply listen and be a support mechanism for the stress of our daily routines.

On the TV show Billions, the hedge fund that Bobby Axelrod owns has an in house therapist who regularly meets with the staff. Personally I would ditch all the high priced snacks and free lunches in my office to be able to book a room and invite the house therapist to download my week. Imagine being able to walk out of a string of interviews for a role that you’re hiring and then have your final meeting of the day be with the house therapist. What if you were just having an awful day? You could finish your Uber Eats delivered lunch and talk it out by 1pm.

Therapist are amazing listeners. They are trained to hear your thoughts and guide you to solutions. They don’t make suggestions that are without the assistance of leading you to the answer first. Therapists spend time hearing your thoughts and dissecting the issue from multiple angles allowing you to think about the solutions. Their job isn’t to give you answers or to tell you what you should do. They help you deal with issues or challenges in your life that you otherwise need assistance with. Therapists help redirect emotions, give you perspective to manage the stress associated and provide clarity for you by asking questions.

Everything a therapist does for a patient, a good leader can do for an employee.

Good leaders, just like good therapists spend time listening to the problem statement. Good leaders, just like good therapists dissect the problem from multiple angles providing clarity for the solution ahead. Good leaders, just like good therapists are listeners first and problem solvers second. Good leaders, just like good therapists provide an environment for comfort for open and honest dialogue. Good leaders, just like good therapists ask questions to assist with the problem solving.

As a leader, we are born problem solvers. We think that because we have the title of “Manager” it is our job to solve problems. Often times leaders think they are working at full function when they solve problems all day. At the end of the day I’ve often heard leaders say they had a great day because they solved a lot of problems. Leaders want to naturally help their team and going right into problem solving mode gives them that fuel to check a box and say they are helping. I can argue that good leaders never actually solve a problem, they shephard the employee who has the problem into the right direction to solve it for themselves.

Have you ever had a leader who was quick to solve your problems? How did this make you feel as an employee? Did you continue to take your problems to them or did solve on your own without their assistance or input? Did you feel beaten down at times because they jumped to solutions first without listening?

I had an amazing leader early in my career who is still a mentor of mine today. If we would have tested the trait of “problem solving” then this leader would have been off the charts. There was never a problem that this leader couldn’t solve. No matter what the issue, by the time I was done stating the problem, this leader was already telling me what I should do. At first, I found this to be an amazing talent and trait and I remember being impressed with their solutions. Over time, it became difficult. I often just wanted to talk through the issue or give this leader my perspective on how I think we should solve. There were times where I had the solution and wanted to cover them off before I did anything with the problem but by the time I could go into, “here is what I plan to do,” they were already telling me what to do next. To be frank, it was exhausting.

This leader had excellent listening skills. They were able to hear me out but they were too focused on solutions first instead of working through the challenges with me. Listening is a skill that takes effort. As a leader, to listen, all you have to do is close your mouth, open your ears, put away the laptop, the iPhone, and focus all your attention on the employee. It is the first skill they teach us as kids as early as preschool. Good listeners are not born they are made. Good listeners are focused on being there for their employees and they focus attention first on the person in front of them to assist with the challenges at hand.

I learned over time that in order to present a problem to this leader I had to start the conversation off like this, “I have an issue, I’m going to explain it, before I finish, let me tell you my proposed solution so we can talk through it.” This leader would often laugh as they understood their off the charts problem solving skills but they would listen and work through the issue with me then accordingly. What made this leader so good was that they were willing to listen and talk through the challenge when asked. Often times we need to be reminded that we’re there to help guide to solutions instead of problem solve.

Imagine the first time you visited a therapist and it went like this:

You: “Thanks for seeing me, I recently had a death in the family and I’ve been incredibly emotional in dealing with it.”

Therapist: “Well you should just stop crying then.”

That therapist would be out of business in a matter of weeks. The reviews online would be so awful that they couldn’t escape it. You would run out of the room immediately.

As leaders we must consider our ability to listen and diagnose problems. The therapist above would begin to diagnose by asking questions such as, “tell me about this loved one” or “how long ago did this happen” and. “what did this person mean to you?”

Let’s consider the workplace now:

Employee: “I’m having an issue hitting my goals, I think I need some help.”

Leader: “Ok you just need to work harder.”

If that therapist would go out of business in a matter of weeks then why are leaders like this still in place? Consider recent problem statements you’ve heard from your team. What method did you use to help solve them? Did you ask questions and dissect through listening or did you go right into problem solving?

In a fast paced moving business line it’s hard to stop and listen and ask questions. We believe we’re put into leadership roles to solve problems but often we slow down the business long term by being straight solution problem solvers. When you stop and listen and work through the issue with the employee you build competent solutions oriented employees who think about the solutions before coming to you in the future. If the entire org is built on the ability for you or your leaders to be the only problem solvers then you build a house of cards that will topple due to poor listening skills and incompetent problem solvers.

The next time an employee comes to you with an issue, consider asking a few questions that can help guide them to the solution. The questions can be as simple as; “tell me more about that” or “let’s talk through this, how would you like to solve this” or “what are some alternative solutions that we could implement” and “what support would you need from me in order to solve this?” You’ll find that by listening and asking questions your employee will ultimately solve the issue themselves and you will never have said anything along the lines of, “do this.”

The beauty of this is you don’t even need a degree, an office, or a long couch for someone to sit on in order to start executing this immediately.

by Scott Bond



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Scott Bond

Scott Bond


Scott Bond has 14+ years of experience leading sales & customer service teams for media and tech companies. Learn more at