Trudy Jacobson Chats About Leadership And Entrepreneurialism

Trudy Jacobson Chats About Leadership And Entrepreneurialism

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Entrepreneurs are highly motivated and ambitious people who later become proficient in leadership, especially female entrepreneurs. A common path entrepreneurs go through is to be highly successful at whatever position they end up in, even early on in life well before adulthood. When they land their first job, laser-like focus on success often drives them above their peers.

From there, these motivated individuals recognize that working for someone else has its limitations and they will most likely never make it “to the big leagues.” These entrepreneurs then come to the conclusion that in order for them to reach their full potential, they must go out on their own. That often means starting a business and ultimately hiring and building a team to help your business grow.

But leading others towards organizational success is no easy feat. And very few people on the planet know this more than Trudy Jacobson. Trudy built her trucking empire from owning just a handful of trucks to thousands. You can imagine how many hundreds of people need to be involved in being a part of a business that size.

Trudy’s incredible success didn’t happen by accident. It took hard work, dedication and most importantly, effective leadership. In this edition of our Trudy Jacobson Chats interview, Trudy tells us all about leadership and how it can be the difference between females being thriving entrepreneurs and mediocre ones.


JTP: How important is communication between a leader and a subordinate?

Trudy: Very. I say that’s where women really shine. You really need to look someone in the eye and listen. That’s where empathy comes in. You really need to understand where that person’s coming from. Whether it’s a customer, potential customer, employee… you really need to focus not on what they’re going to say next but what they are saying.

You need to be articulate, you need to not belabor an issue. So, communication is extremely important.

JTP: Interpersonal skills are also important to leadership. It’s similar to communication but goes a little deeper. What’s your philosophy about interpersonal skills?

Trudy: My philosophy is that one should try to meet whomever they’re speaking with on their level. Put yourself in their place, again that empathy comes in but more than that. Your warmth… if you exude warmth you will encourage the person with whom you’re talking to, to respond in that same vein. Unless of course it’s a situational issue that’s not so happy. But I think the warmth, along with taking their conversation seriously.

JTP: Empathy is the ability to understand what a person is going through and how it’s affecting that person. Would you agree with that?

Trudy: I agree completely. In the 80’s, maybe still now, the ‘boss who doesn’t care’ what his or her employees are going through, they just keep focused on what their goals are for the business, the profits. If you don’t really put yourself in another person’s place, whether it’s an employee or customer; if you slant that with a positive eye, say ‘I understand what her job needs to be’ and ‘I want to understand them’.


TP: You had great vision as an entrepreneur. How important is vision for female entrepreneurs?

Trudy: It’s very important. That’s part of dreaming, that’s part of being creative. If you’re an entrepreneur and say you want to start a bakery, you have to think about it. ‘Do I want to do a dozen donuts?’ And ‘I want to make that into other bakery items.’ You really need to have vision.

It’s fun to start one [a business] but if you don’t know where you’re going, you won’t get there. If you have a dream, then dream and dream and be creative. But you also have to be practical, so vision is extremely important.

JTP: How much value does having some charisma have?

Trudy: Back in the 90’s, 2000’s, before there was so much email, texts… you had to rely on face to face meetings. I’ve known a lot of sales people and if I don’t click with them or if they don’t have a certain amount of charisma, then I’m not going to connect or relate to that person.

I believe charisma is developed. I know a lot of women who have wonderful charisma and I don’t think you’re born with that, I think you practice it. You need to become sharp, you need to not overdo it. So many women want to be on the level of how men communicate with other people. But I think that women are naturally inclined to have that personality trait, that charm and they know how to be charismatic on a daily basis.

JTP: Perseverance is another important element to entrepreneurialism. Have you ever thought about quitting on a project, or something similar?

Trudy: I thought about giving up on several projects on leadership and organizations and our business. But at a certain point you realize that if you do give up, you’re going to let a lot of people down. And so that becomes a part of the equation.

So for every time you want to close it down, give up… do something else. You know that there’s going to be something positive to help the situation.

End of Interview

Trudy went on to talk about how it sometimes may be a business decision to give up on a project. But that’s a separate topic altogether and one that we will cover on a different edition of Trudy Jacobson Chats.

But for now, hold onto these leadership gems Trudy offers. They are part of the reason for her incredible success in business and life in general.

Follow Trudy on Instagram for the latest and greatest!

Did you read the first edition of Trudy Jacobson Chats? It’s a must read!


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