BE 07 | Leading By Listening


Communication is a two-way street. However, most of us mistake communication as only the talking process and tend to forget one of its critical aspects which is listening. Jaime Jay, the Founder and Managing Director of Bottleneck Virtual Assistants, shares that we can learn so much more by listening. He says people don’t realize how bad it is when we wouldn’t let people finish their thoughts. Oftentimes, many business leaders with very dominant personalities don’t want to hear and listen. It’s either their way or the highway. In reality, a leader can learn much in listening to the feedback from the upper management down to the security guard. They can then lead with better understanding and kindness.

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Leading By Listening with Jaime Jay

Sometimes we feel alone when we fall, but also we feel alone when we arrive. How do we connect really? Through this Beyond Ego mission, we are united in knowing that where ego ends, life begins. We’re going to take ego into the culture of our workspace and our offices because I have a very unique guest. His name is Jaime Jay. He’s the Managing Director and Founder of Bottleneck Virtual Assistants, an organization that offers professional growth opportunities for ambitious leaders like you, OnBeyonders. He’s a bit like me. He’s been podcasting a little bit over a couple of years, so I have a few years to catch up.

Jaime loves podcasting. He was super excited and super engaging when I was on his podcast. He’s enthralled by it. I know it’s fun to have great dialogues with people. Conversation and communication are what makes this world a better place. I haven’t had a TV in over twenty years with dialogue and communication. Conversations have been my tool for survival in this digital world. Jaime loves to share his passion with leaders around the globe on his podcast called Culture Eats Strategy. I was a guest on his show. I couldn’t wipe the smile off my face because we dove deep into conversations about ego and vulnerability and all the great topics that come to life on this show. Jaime, I am so pleased to welcome you to Beyond Ego. Answer this question, Jaime, I go beyond in my life every day by?

I go beyond every day by listening and also continuing to try and better myself through empowering others. Listening is a big part of that I missed out on a lot.

Jaime, most of us miss out on it. I love the awareness and the consciousness that you’re saying, “At this point in my life, at this point in my career, I’m going to listen more.” Active listening is such a valuable tool. I write articles on it all the time. There are three chapters in listening in my new book, The Kind Communicator. Jaime, was there something that was a tipping point in you to say, “I’m speaking over others or I’m not paying attention. I’m not listening?” What was the tipping point for you to say, “2019 is my year for listening?”

Yes, there was a tipping point. We have a lot of meetings here honestly. People want to know how I can help them so they ask me questions. I tend to go on and on. In the beginning, I didn’t realize it. I kept catching myself. They would start to say something and I’d say, “Okay, so.” I wouldn’t let them finish their thoughts. My word is listen and I have an acronym attached to it. It’s, “Listen Intently and Soulfully To Engage Notably.” I want to practice that. It means the world to me because I can learn so much more if I’m not talking but if I’m listening.

Jaime, I can sense a lot of the people that I coach their bosses right to you directly. The world is not listening. Not everyone has the vulnerability or the cojones to stand up and say, “I’m not good at this.” I commend you on your journey. Let me know how it goes.

Thank you. Your words completely resonated with me. Life begins where your ego ends, that’s huge.

Apparently, you were listening to what I said in the beginning. Jaime, that’s the tagline of Beyond Ego. It’s the tagline that I use in all of my books because when we talk about compassionate leadership, when we talk about kind communication, when we talk about the ego, it’s a separation from the head and the heart space. When we talk over people, we’re going from the headspace and not the heart space. It travels into what you do with Culture Eats Strategy as well as with your virtual assistant company. It gets down to that vulnerability of owning our weaknesses. You’ve met hundreds of leaders in your path. As an entrepreneur yourself, you’re the CEO of a virtual assistant company, you’ve done so much. In a nutshell, what has been your most transformative experience in business so far?

You can learn so much more if you’re not talking but listening. Click To Tweet

There are two sides to my business. I’m a big systems and processes freak. I’m a geek. A little side note here, kudos to you for no TV for several years. That’s amazing. It’s unbelievable.

It’s a funny thing because for a while, Jaime, when I was living in my apartment back in Hoboken, I had a TV. I had the remote and everything. When I paid for cable back then, I had the TV and I wasn’t using it. People would come over and they would put the TV on. I would go up to the TV and press the button. They were like, “What are you doing? You have a remote.” I was like, “I never get batteries for it because I never use it.” After a few of those laughing episodes, I was like, “I’m getting rid of this sucker.” That’s a transformative experience for me. What was your transformative experience in business?

My transformative was looking at my company from a vanity point of view instead of a sanity point of view, meaning I look at revenue as opposed to profit. I was like, “We’re doing so much revenue.” For me, it was a big deal. We were turning it on but the profit still wasn’t there. I said there were two parts to it because that’s an internal part for my business. The external parts of my business were keeping up a strong front. I don’t want to cheapen it by saying it upfront. I don’t know maybe you can help me.

It’s ego. You said vanity. I immediately said ego. We’re on the Beyond Ego pass. It’s okay to say it. Say it healthily, Jaime. I was filled with ego.

I wanted people to know too that I’ve had something that I still believe deep in my heart that I could do to help them. I believe that. At the same time, I knew in the back of my head that I didn’t have a sound business. That was my big transformation and understanding that it’s okay to let people know and be active about being authentic and telling people the truth. What I found is when I finally overcame that and realize that, so many people loved the story. They embraced it. I was completely thrown off and surprised by that.

When we share our most authentic, naked selves that we do get the “me too” effect. I’m using that from my marketing perspective. It’s not the actual #MeToo. What I mean by that is that people want to say, “I feel that too.” That’s why most of the aspirin campaigns and all the things that you see on TV for pain relievers, they show people hurled over in pain because people are like, “I get that. I have PMS and I have cramps. I’m going to get that.” It’s that “me too” factor. It’s like saying, “I messed up too.” Jaime, that’s beautiful that you shared that because that’s the whole purpose of this Beyond Ego movement. It’s being able to talk about ego healthily at the table on conversations with some of the coolest leaders like yourself. There are so many people out there who are running businesses, who are executives, who are entrepreneurs and they’re messing up. They’re failing. They’re afraid to fail. You know what they say, “Fail hard, fail fast.” They’re not getting that information. Jaime, how did you get back up from that fall? How did you get from one point to another after sharing your transformative story and authenticity with people? How did you get back on track with your business?

It was a process. It’s still a process. It’s ongoing. It’s ever-changing much in the same way that our workflows and processes that we document, we realize that those are living, breathing documents. There are always going to be changes. We’re going to learn more. We’re going to switch up and try to find another word other than tentative. It is so overused. We’ll continue to adjust and find ways to improve the process. The more we learn, the better we are. What are the challenges? If I can go back was that I hadn’t been touting when I first started, I didn’t have a lot of clients. I didn’t have a lot of experience. I was trying to fake it until I make it type of mentality. This has been my own experience, this is what I believe.

In my opinion, people that start out with this mentality, it’s a reason why they do that because they’re looking for maybe bigger deals or to make more money in the beginning. If I went back, I would be more honest, I don’t have experience with that. Maybe I didn’t win a couple of the bigger accounts. Maybe I started off with smaller businesses or smaller deals. Those smaller deals would have put me so much further ahead because of being authentic, being real, being honest in learning what I needed to do and getting the experience to graduate to the next level. By going back in time and realizing that the way that I chose to fake it until I make it type mentality was hurt me because it took that learning curve and it stretched it out. It was so much longer than if I were to hit it head on, straight up, honest, authentic. I will not be able to do this for you. I’m highly experienced. Will you trust me on this?

BE 07 | Leading By Listening
Leading By Listening: Be active about being authentic and telling people the truth.


That’s interesting because a lot of people are at that place. I know that a lot of us will say yes to things, “Yes, I can do it.” We end up not liking the business relationships. We don’t like the situation we’re in and we fail at it. That’s okay. What you did was you made the pivot, the change and transformation. You took the chance to say, “This isn’t a process for me.” Jaime, I also commend you for saying processes are ever evolving. I had a marketing agency for a couple of years. I still am a marketer as a business coach, so people get the value of my business coaching. I’m a sweet ass marketer behind the scenes. I also worked with digital agencies who had processes or didn’t have processes and the processes kept failing. The agency was working on the process instead of the work. It’s an ever-evolving workflow for all of us. You’re the CEO of a virtual assistant company. What are you not good at that you have learned to delegate?

It was one of the realizations about my own self that I had to come to terms with. There are two: follow-up and details. These are two critical aspects of doing business, of being professional, of making sure that you’re able to follow up certain things and pay attention to the details at the same time. My head is in the clouds a lot. I’m always thinking of creative ways to improve the company, “What can we do? Here’s your insurance for the staff.” There’s all this stuff, upper levels that my clients could care less about. My clients need to know that I’m paying attention to the details, that I’m servicing their needs. If they need me to talk with them and then make sure I follow up with them and I dropped the ball there, that’s terrible. What I did is I went out and I found Rena. She is amazing. She complements my weaknesses because those are probably her two best strengths. She even put into my calendar, “Don’t forget to take a break. Get something to eat.”

It sounds like we all need a Rena. Send her over.

She is amazing. Ever since we’ve implemented the details, the follow-ups, all of that stuff because Rena was on top of it until it has blossomed.

Most people don’t have the art of follow-up because they’re not aware. They’re not conscious of it. They’re going onto the next thing. That’s okay but it’s really not okay. I’m glad that you came to terms with that. I find that if we miss details, then we’re having a lack of integrity or lack of respect for the person or the project. That’s a direct reflection on how you show up in the world for work. Understanding that you’re not that person and you have somebody else to help you with that, that’s huge. If you’re finding that you’re probably one of those two or both, take Jaime’s advice because we’re not meant to do it all. If you think you can do it all, then you are officially Superman. I definitely want your autograph. We all have mentors. I love Robin Sharma. My ultimate guru is Wayne Dyer. One of your favorite guys to talk about is Peter Drucker. He’s huge. I’m giving you a bit of a chance to talk about your love for Peter, your admiration for his business mindset and what inspires you about what he does. Go ahead, tell us a little bit about what Peter Drucker has inspired you to do or do differently in your business.

He was at the forefront of understanding what culture meant. He worked for the big auto manufacturer, wrote out this big plan for them. They basically said, “No, we don’t want you anymore. We want to let you go because that’s not how we work here.” His story is amazing, the growth and how ahead of the curve he was. What I love about his process in his book, Culture Eats Strategy for Breakfast, is that strategy is obviously very important in any business. However, if you don’t have a positive culture within a team environment or even the clients that you take on, if they don’t buy into a similar belief system that you, me, whoever it is, believes it. If they don’t buy into that system, it’s can be very hard for you to execute any type of strategy. That’s probably the biggest thing that I took from him.

I am enamored with everything that he talked about because I took a huge interest in culture. From the experiences in my own team, culture to me is a belief system that everybody can buy into. With that, you can identify certain areas for each staff member what their roles and responsibilities are. It’s like a basketball court. Get them inside that basketball court and let them run. Let them be free, let them be creative, let them do their deal so that they feel like they’re part of the team. Their voice is important to other people in the team and to the leadership that’s within that company. The second the ball goes outside of that boundary, then we need to reel it back in. We need to blow the whistle, stop the play, let them know what happened, how we feel about it and continue on. Let them be creative again. All of this is culture. This is what I’ve taken from Peter Drucker. I love that whole aspect of it

It’s taken it from the story of people not believing in him and saying, “This is a no go.” All of a sudden, he becomes this mastermind for getting it right and creating a strategy. There’s a line in my new book, The Kind Communicator, where it says, “A lot of companies think that culture is taking your team out to go for beers or to get a ping pong table for the office.” You give people a bunch of beers, they smile for a few hours, then they come back to the same BS and tethered conversations, broken communication, everyone’s crying at their desks, that’s not culture. In the book, I encourage people to hire my services as their culture strategist because I believe that coaching can be so widely used at small to midsize businesses and corporations. It helps us go beyond ego. Jaime, how do you think Peter Drucker went beyond ego?

Leadership is not about giving speeches or being liked. Leadership is defined by results, not attributes. Click To Tweet

I can’t think of a better way to explain it, how he went beyond ego. It’s a great descriptor of what he was. He was a very good listener. He was very attentive. He took many different perspectives in presenting his plans, his projections or his recommendations, whatever that was. He listened a lot. If you overcome and go beyond your own ego, it ties back into listening again. He was an amazing listener. He learned so much from the feedback they would get from a security guard, the office administrative assistant, middle management, lower management, upper management. He listened to everybody else’s perspectives.

That’s how he was able to come up with such unbelievable information to provide to the leaders of these organizations. The problem with the leaders in these organizations at this one particular example that I’m referring to with the auto manufacturer, they didn’t want to hear that. They didn’t want to change. A lot of business leaders with big Type D personalities, very dominant personalities don’t want to hear that, it’s their way or the highway. We all need to, as leaders ourselves, shift our mindset into a space where we can lead with kindness. Leading with kindness is not leading from a position of weakness but leading from a position of caring and being considerate in hearing, understanding and listening to people.

It comes down to listening and being able to change, being flexible like Wayne Dyer says, “The storms and the Maui trees and those palm trees, they sway. They never break. They always sway.” It’s not just for the leaders, it’s also for the employees too. A lot of employees don’t want to change. You get a change in anything, change of rule or something and some employees get an attitude. They roll their eyes, they slam desks, they fold their arms. This message goes for you too. One of my favorite Peter Drucker quotes is, “Leadership is not about giving speeches or being liked. Leadership is defined by results, not attributes.” That tailors this message on these podcasts, Beyond Ego and Culture Eats Strategy, to know that it’s not about you, it’s not about how you’re liked, it’s about what results you can bring in. Jaime, you’re telling us if you want to be great, if you want to lead without ego then you have to listen. Take the messages of Peter Drucker and put them into action in your work and in your play and become the person that you wish to be. Let’s have a little fun because this is too much fun. Jaime, if you had intro music to your board meetings, what song would play?

The first thing that comes to mind is Mama Said Knock You Out.

Jaime, if you had an autobiography, what would it be called?

Leading with Kindness.

With all this Peter Drucker talk and culture talk and eating for breakfast, what are you curious about in life right now?

I’m curious to see where things go. We implemented a lot of new ideas and concepts. I’m excited to live this journey. I am so excited about not necessarily the destination. I’m a big believer in understanding and getting the direction. I can’t tell you with 100% understanding of where we are as far as clarity is concerned. I don’t know that. I do know the direction. I’m in love with it.

BE 07 | Leading By Listening
Leading By Listening: Leading with kindness is not leading from a position of weakness but from a position of caring, being considerate, listening, and understanding people.


There’s a line in my book that says, “I believe about the infinite horizon being the best view of life.” You said it best. Most of us who are leading, we’re in a boat and we have to know where we’re going next. We have to see it. We have to be able to see that next destination. My belief is that the infinite horizon, getting in that boat and knowing that you can’t see what it is, but knowing that it’s there, that is what makes us more connected as human beings, as business people, as leaders, fans and listeners and better people all around. You’re teaching us a lot about listening and Drucker. It’s been such a breath of fresh air to know that there was someone else out there that’s corny, that loves ’90s music, loves culture, who is also open and vulnerable enough to talk about things that we suck at, we’re getting better at and we are doing things about. Jaime, you’re a rock star.

I asked you to ponder the thoughts that Jaime shared to welcome a greater you, to welcome greater culture in your work and also in your life. If you’re looking to make that happen and need a business coach or consultant to hire for your office teams who need a rebrand on their culture, you can visit my website, Follow me on LinkedIn for tips on the life fulfilled. Don’t forget to join our Beyond Ego Facebook group because that’s where Jaime’s podcast is going to be live, shared and lots of other details too. I love you, Jaime. Let’s go beyond.

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About Jaime Jay

BE 07 | Leading By ListeningJaime knew he had to incorporate more of himself and by redefining this category through conversations, he began this epic journey. He wants to embrace each person’s differences rather than delivering strategies that make people think we are better than others. Due to his insatiable appetite for uncovering cultural concepts that instills confidence within his own staff, Jaime reaches out to creative business leaders that want to share their stories.

Jaime shares his own experiences and chimes in on the conversation with leaders from around the globe to address how Culture Eats Strategy every time. Do not be surprised to listen to a few episodes without guests. As Jaime learns more from his own experiences and those of his accomplished guests, he is focused on delivering real-life experiences to help you create a culture you can be proud of. Build a business that puts the people first. Not the strategies. Jaime is also the managing director and founder of Bottleneck Virtual Assistants, LLC. The organization offers professional growth opportunities for ambitious leaders by creating an efficient and systematic approach to identify, hire and cultivate team members who focus on specific roles and responsibilities.

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