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How to Develop Your Leadership Skills Through Challenges and Crises

Sean: Now what do you think are the things that keep leaders and entrepreneurs from being their best self. What, what is keeping them from being successful? So having the right company culture is something that is elusive. Not a lot of entrepreneurs do this. Not a lot of entrepreneurs invest in this. And a big reason why is because it’s just not measurable in terms of ROI.

That is one big reason, but. I want to know what are the things that keep the leaders, the top people in an organization from being their best self and thus hindering their success.

Jason: I would say that the first thing is self; lack of self-awareness because the problem tends to be is the more successful you are, the less people will tell you the truth and that you will listen to them.

And that a lot of times your blind spots that your not aware of are the things that end up causing you the most problems. And pretty much I’ve found that universal typically historical patterns that stem back from things that we’ve done as a child or learned. Right. And that’s how we play it forward.

So an example of something like that would be. So I’ve had leaders. Similar example happened to quite a few people. It’s the people around them think that they’re not listening, right? They’re not hearing them. And the leaders believe that they are, that they’re getting that feedback and they just can’t fix it.

And they don’t really understand it. And it becomes a huge challenge in order for them to operate as a business. Right? And so they end up having like, they’re having problems because of all this. And so a lot of the times what I found is when I’ve gone back and talked to leader, they’ve grown up in households of larger families and what ends up happening there is an order to get mom’s and dad’s attention.

They’ll have to yell over siblings. They’ll have to get in their way, and they won’t really understand the value of listening. Because when they listen, they don’t get anything. They have to talk over to everyone to be heard, to get what they want. Well, the problem with that is, is, you know, then it helped them, but now it’s sabotaging their success.

So they’re unaware of their pattern and it recreates itself in business, right? The one time makes good salespeople that they don’t necessarily listen as well in a sense that they don’t take no for an answer and they find a way around it. Right. And they can talk them the other person into a deal. Well, the problem now is when you’re leading people, if you don’t listen to them and value them and hear them, they start to reject and avoid you and dislike you.

And that causes a lot of problems. Well, when you give people negative feedback, they tend to not like that in a recoil because it’s a function in your brain about how we see the world. So when you show people a pattern, they’re much more receptive to it because then they know that it’s neither good, nor bad.

It’s something that they’ve done because they learned it from something else that has just happened over time. And so a lot of that is really helping people understand their own beliefs, values, framework for seeing the world and showing them places that it’s really getting in their own way, because.

Like I said before, the other problem is cause of that is the people around them. Like if you’re the CEO of a company who’s sitting down to tell you that you’re making a mistake and why, right. I mean, the only time you may be doing that is a board may be doing that, but that’s in a really conflict driven way.

They’re not usually giving you feedback in a positive way to be helpful. They’re giving you negative thing, right? And the people that you’re managing, aren’t going to most likely, I mean, rarely come to your office and try to give you feedback and do that because they’re worried about like losing their job or like some repercussions in their career.

So there’s not a lot of people that are telling you the truth and sharing with you information and feedback. And that really is the first place where people don’t really do that. I would say the other thing that happens is that people don’t invest in learning management and leadership skills, right?

And these are all learned behaviors and they’re no baby comes out of a womb ends up great leader, right? You learn this and you have to invest and learn these things in order to become better, because these are neither soft skills, right? These are not stuff that you can like, you can learn SEO at some level by watching a computer program.

Now putting it all together. Do you have to do it? But you can learn SEO from it. You can’t learn how to manage other people from watching a video alone, I mean, there’s a lot more into it, but you have to put all these things together. I would say the third thing is really people don’t understand the value of teamwork and that it’s a, it is a company strategy to get people to work together.

And do it in a way that’s effective because all of the conflict and not getting along creates disruption, slows down processes, people miss deadlines right? And all these other things start to happen across like I think its teaching people and learning ourselves. How do you do great teamwork and how do you keep people, you know, collaborating?

And I think that part of it is really the challenge because I look at a business itself and I look at like the human behavior and the people element moves along with the strategy part. And then that equals an extraordinary business, but a lot of people look at, Oh, I’ve got the business itself and the business strategy and how I’m making money is here.

And then the people aspect is down here and that’s not how the equation works. And that’s how a lot of people view it or that’s how they live it out. And the problem comes is that every business. Is about the people and they have to execute it. And most really, almost you could argue every business today is a service-based business.

And so all of these skills and the people aspect are paramount to being successful. And if you don’t take that in consideration, I think that’s where people miss. And that’s the thing. They leave out of business school. They don’t teach enough of and how to do it. And people just don’t invest in it. Some of it cause their ego and some of it is, they don’t know what they don’t know and aren’t willing to learn it.

So I tell everyone like, that’s how you can create and scale businesses way faster, way quicker with way less people and way more competitive. It’s about the team. And how do you get them to work and get the best out of them?

Sean: You mentioned earlier that self-awareness is important. Now I’m wondering what if there’s an entrepreneur who’s self-aware aware of his blind spots or her blind spots.

And you mentioned also the people aren’t just going to be telling you the truth because they’re afraid of their career impact. I’m wondering, is there a way for people to go ahead and do that? Like tell you that these are your blind spots and you have to, you have to work on them, or you’re already aware of your blind spots and people will go ahead and tell you that, Hey, you did it again here and I just wanted you to know, because I know you want to improve.

How does a CEO or a CEO, founder enable or empower his people or her people to do that?

Jason: Well one. I think that you share with people, the importance of understanding, the things that you aren’t great at, and that everyone has things to work on.

And that our job here is to get better. Right. It’s not to be perfect. It’s to get better every day. And. And then you articulate to people the challenges, some, a couple of the challenges that you are having, that you are aware of because you want to keep yourself accountable, right.

And that you like have things you have to work on. And what you want people to do is to tell you when you aren’t living up to those things that you’re working on. And that you will take that feedback. Listen to it, ask questions, not get defensive and start to implement it. And then you, the person has to do that, but you have to enroll people in by sharing and seeing something like that to get people to do that.

And then you have to execute that meaning when they give you the feedback, if you’re defensive, then they’re not going to tell you because then they’re going to be fearful that you’re going to get mad at them. So you have to be willing to take the feedback and implement those types of things. Right. And that’s, that’s an easy way.

Now, like another way I have clients do it to make sure that it’s happening, because you may say that to people. You’re not really sure whether they’re actually going to do it or not. So sometimes you’d be more proactive than that. So I have people, clients of mine do an exercise, which is a relationship checking right.

I call it. And I have them do that with the people that they manage and they can also do it with pictures and you can do it with the person that manages you as well. It really is any, you can do it in any direction, but it’s ask a question, but how would you rate our relationship right now on a scale of one to 10?

One being poor, 10 being extraordinary. Why did you rate that? And then how can I move it closer to a 10? And you can ask any clarifying questions that you want to know, more information. And then when someone gets done with that, you can agree with them. You can disagree with them, but you come with a plan.

To start to move things forward. And then it allows someone to give you feedback that is helpful for you because it will change over time. So I have people ask the question, you know, every month or every two months, because not all the time is someone willing to give you a really high number. There could be a problem going on, but then you learn, you learn it, right.

You understand it. And you’re keeping a dialogue open and you’re understanding the other person’s viewpoint. Which is practicing empathy, which is important because otherwise you may think you’re doing a great job, but you’re on aware that other people don’t think that you are, well that’s the worst place to be, right?

It is not having a calibrated where people’s expectations and view of you differs from where you think it is. And that happens all the time. Right? So you have to have some check and balance in that. And that’s another way that you can do that to keep yourself accountable to other people and to keep them accountable to you.

By also forcing them to be honest and real with you. Right. And that also helps because it keeps it open dialogue, a vulnerability. And having real conversations with people other than hiding it or not talking about it or avoiding it, which never helped or served anyone.

Sean: That is something that I am personally going to practice that kind of NPS or net promoter score for your relationship with other people.

That kind of feedback is important. And sometimes it’s just, it’s just that people don’t know where to start with giving you feedback. And that actually is a really good starting point.

Jason: I mean, I think the challenge is you’re right. When you have people ask each other questions you can do in a group, a lot of the times people will want to open up and share and tell you who they are.

They just don’t know how, and they aren’t giving an avenue and they just can’t come up with the questions out of the blue and bring them up. It seems really weird or odd, or like, how do you do that? So you as a business, have to start institutionalizing some of this and keeping that in and starting to introduce them as part of the way you do business to allow people to share and to tell you the truth and like to do the things that are, is going to help the business overall and all of these things.

Right. Are about creating a better balance sheet and making money and being successful, right? It all goes to the bottom line because all of this stuff, that’s how people work, right. People work harder, but will work longer. They’ll try to do the best possible job because they want to be in a place and work for an organization that believes in these things, because.

Most people don’t have something like this and they haven’t worked in there. So when you create it, right, it’s like a magnet. They don’t want to get away because the fear that they might not find it again, or find something as great as that. So that’s another huge piece of this that works in people’s favor by doing this and will make an impact in their competitiveness, in the marketplace.

No matter what business you’re in, no matter what you’re doing.


Company Culture and The Leader’s Common Road Block To Growth

Sean: I want to rewind a little bit to something you mentioned earlier that is about company culture. You mentioned you want to be part of company cultures that succeed, and they had this successful, successful business, With these companies that you helped build and you were a part of, or even the companies of these thought leaders that you were doing work for.

What did you notice about their company culture that made them win? Or those that made them lose and not succeed.

Jason: I think the difference was, and it’s funny, I was talking to one of my business partner in another business of mine about this today. And I think the differences is that a lot of people were focused on success and ego and money.

And that’s hard to build long-term success because there are people that feel left out and there’s a lot of ups and downs. And what I found in the other businesses, they were looking more fulfillment and a higher purpose. Like we’re serving other people and we’re helping them. We’re on a noble mission.

This is bigger than the company itself or the money that we’re making. And it’s about the people and the relationships that you’re building here. And so success was a piece of it, but it wasn’t the sole mission. And they think that they understood that that was the requirement to get people enrolled in things like that, because you’re not going to get someone to work 60, 70, 80 hours.

And operate at peak performance and give them their all, if you don’t feel like you’re doing something important and you’re making an impact, that’s outside of the dollars being generated. And they think that that was really the secret sauce in what they were able to do, that other people fail to see.

And they actually really believed it overall, where there was a lot of other people that did it because they wanted to be CEO of a company and make a lot of money. And they wanted to ensure themselves that they made a lot of money, but they don’t really care if anyone else did. So they, people saw that.

And I think that ended up having short-term success. And then a lot of those businesses ended up failing. And I think the other part of it was, – Netflix is a great example, is they invested a lot in their people. They understood that creating an atmosphere of re – belonging connection inside of the company and really creating and focusing on the people was the core part of what they had to do.

To sustain the business for a long time. And I felt like a lot of other people give it lip service didn’t really believe in it or didn’t invest in it. And the people were actually not even second, but they were like last. And I think what ended up happening is that you’ll see a lot of businesses didn’t do well because people figured that out.

Right. And then they just job hop and they just left and you have a lot of turnover and there’s environments. And then people really aren’t working their best because they know. That they’re essentially just being used. Right. And no one allows to be a part of all of that. So I think that those were the main, like larger concepts that I saw people do it, and I don’t think it really plays itself out any differently now.

And I don’t really think it matters the scale of your business, whether it’s a five person business or it’s a 50,000 people business. I think all those things stay true today and probably even more so. Especially being in the environment that we’re currently in and what looks like to be what we’re going to be facing probably for the next couple of years.

Sean: What would you say, you know, with these companies that have people who actually believe in a higher purpose and were working towards that purpose. That is exceptional because not a lot of companies would be able to cast the vision like that to the point of their people actually buying into it, believing it.

And so reinforcing that culture, what would you say. Were the things that these companies who had people who actually believe a hundred percent in the vision and mission and purpose, what do, what would you say they did right? In order to do that, because I believe that they must have done something every day or every week, at least for that to happen.

Jason: You know I think , what you saw on Netflix is they created a company culture, but coming up with values that they lived by, meaning that people were accountable in their reviews, like in their compensation right. I think that they did a lot of stuff overall. To create, they invested in learning and development training people before it was really something that people really had done.

Right. I think that they had fun on with it and made that part of the business itself, but they did a lot of stuff like serving the employees, doing a lot of things before people were really doing it. And then coming back to people and saying like, here’s what we’re seeing, here’s what we’re doing. Here’s what we’re changing in the business.

And then I think you’d see. See people, you know, like Steve jobs would, was really about like, you know, they have the teaching and education mark. And I remember one time he said like, we’re enabling teachers to use these computers and artists to create things that they never would be able to do and learn locking the genius in them, by allowing them to use this and really become great and to change the world around us.

But they need the technology to do that because that’s the missing link. So without us, we’re holding people back and it’s our job to be able to help them. You have to find a way and we have to find a way to do it in order to enable them to do that. Right. And, and I think talking to people like that and going around and making phone calls like he used to do.

There’s a lot of stuff in the company. And then I think having really high standards and keeping people to that, and himself, all those things, I think really make a difference. But a lot of it was the focus on the people and creating standards. And values that people actually had to live by. And then I think doing stuff in a lot of the companies that would make people feel like they actually were a part of it and doing it way before other people had started to even think about these things, made people feel like they mattered.

And that what they were doing was creating like an impact. Like, you know, I can’t remember what client of mine there, but they brought in all of their customers and talked about like the impact that those customers were seeing in the front lines because of the products that people were using and mean, people think about that, what they did every day mattered.

Because without them, those things wouldn’t have happened. Right. So, and I think that was another thing that people did as well as to make it real by bringing the customers forward and having them speak and tell meaningful, vulnerable stories about like what was really going on and what was happening.

And I think that’s important for people is to feel like their work matters. And it’s making a real impact and what that impact actually is in the world itself. Otherwise they don’t really know, and it’s hard to go to work every day, if you don’t know what you do matters and how it actually matters.

Sean: Very, very good point.

So maybe one of the, one of the things that these company do is to show the results of the work and explain why your position matters in how it’s contributed to these results. A lot of entrepreneurs who are listening in most of our listeners are entrepreneurs or those who are going to be getting into the entrepreneurship journey.

A lot of them are wondering how do you build that kind of a culture? How can they adopt that kind of culture? Cause you talked about some big things like having values. Crafting, maybe a mission and vision and purpose statement and having the discipline of telling people how you contribute into the, these numbers or these results.

And you matter, because these things matter to us, those are big things, SMEs or small to medium entrepreneurs and startups, and those who want to get into the entrepreneurship game, maybe they’re wondering “but how can I do that? Like core values. How do I. How do I extrapolate that? Where do you find that in yourself?”

Do you have anything to share with our listeners about that?

Jason: Just do some research and look at some companies, right? Like that you model what you want to do. Right. So it requires some research and they think you can look at their values and start to fashion things and ask yourself, okay, well, what are the values I really want by looking at what other values are out there.

And I always say, when something like that, I would pick three to five and start there. You don’t have to get like 10 of them. Right. But you have to start somewhere. And I think that’s important. I think, you know, one of the things I was looking at WD-40, right. And it’s a company that’s a spray can. Right.

Spray it on stuff and they have an amazing employee culture. And one of the things that they do is they have this thing called an employee pledge that every new employee has to sign. And it’s a series of things that they required them to do as part of the company. It’s not legally binding, but they have them find it.

Because it has self, like if you have a challenge or a problem, you can’t stay silent, you have to ask questions and go out and seek the answers. Well, you can look at something like that and have people start to do those types of things and you can model it, probably copy it and use it and leverage it right for yourself.

I think those are things that you can do. I think then when you start to look at your culture itself and you say, well, how do I do this? End of the day, you have to think about the best team you’ve ever been on personally or professionally. And like, what did that feel like? What did that look like? What were you able to accomplish and how do you view the future on that.

And it’s all rooted in trust. And I found that the key thing then is understanding is you have to build people who trust each other at an extremely high level and are willing to take leaps of faith and risk together as a group and have everyone buy into that. And so that requires you to build super high levels of trust.

And from research I’ve done, what ends up happening is that most people look at trust is something that trust takes a long time to occur over time, or it’s just some experiences that end up creating that. And that to me is very much a viewpoint of being out of your own control rather than actually being able to replicate over time.

So one of the things that I’ve done is just have people share in a group and ask them a question and have everyone start to answer it, right? If it’s a small, you know, whether it’s 10 people or a hundred, you can form small groups and have people start asking and sharing about themselves. Right? Sharing questions, such as, tell me about the most important lesson you’ve learned in the last year.

If you had to thank one person for helping you become the person you are today, who is that person and what did they do? Like, what was your biggest setback in the last five years? And how did you overcome it? Right. I mean, there’s a lot of other questions, but when you start sharing and opening up and other people start hearing it, they start realizing that you are the human being in vulnerable and just like them and they like you more, they understand you better and they start to trust you.

And so those that’s an important part of building the framework in a company. Right. And another thing to do is just like, have people appreciate each other. Right. When I was looking at the data, one of the things that I saw about people who love their work and are extremely passionate,  and engaged, it was about people that feel like they’re growing, making an impact, feel like they’re supported and appreciated.

And that are building great relationships with people, colleagues in their companies. So the other thing to do, which is super simple is do things like peer recognition, right? Have other peers recognize other peers, something super simple, right? And you can do this many ways. You can do this on a team level by just having every person once a month go around and say, what person on this team helped me? What did they do? What impact did it make? Right. And you thank someone, and another thing you can do is if you have a larger team of people is I’ve had people sit down and email or text someone and do the same thing outside the team.

And imagine getting an email or a text from someone. That works with you closely thanking you for helping them and telling you what they did and the impact it made for them. You’re going to feel like you matter. People care about you and the work you’re doing is significant. And I think it’s a lot of those little things that when you create it right, make a major difference.

And all the things I am talking about are super cheap to do right. Or to zero. So it’s not about the money, right? Because I have friends right now that are working in Silicon Valley that you know, literally they’re getting paid. Like the company does everything for them. They grocery shop for them. They give them like they can get lunch dinner, they have drinks at the office they can have, they pay for their dry cleaning.

Like literally they have the only expenses are their car or the place that they’re living in. And both the people I know are doing this are unhappy. Right. They’re not excited about it because they don’t love the company and the people that are working with.

So you can pay people a lot. You can give them all these perks, but that’s not what drives people. Its doing great work. It’s feeling appreciated and it’s having relationships. And if you understand that you then can orchestrate and build a business that actually matters.

Sean: For those of you listening in. And you’re an entrepreneur, or you want to be an entrepreneur and you think this is going to be a problem for you or a roadblock.

That is some really good advice. It is not the money. It’s not perks, not pay, it is the recognition and the fulfillment and these things are not expensive. And you can do that. Whether you have the budget for it or not, but these things are super important for having a great company culture.

Jason: And the other thing about it is it doesn’t matter where people live in the world, these things that are pretty universal.

I work with people in every con and everything else. It’s not about –  Culture, sure you have to change some things and shape things a little bit differently, but a lot of these are universal. It’s not like it’s any different. And end of the day, no matter where someone is, they want to feel like they matter.

And they want to feel like people care about them and have their back. And when you do those things for people, the other thing I’ve found to the data shows is that a company has to pay people anywhere between 15 to 20% more to lure someone who’s really happy working in their company before they would leave.

And that’s a lot more money, right? So that’s pretty unusual that people are going to be throwing out. That and that’s for someone to think about leaving, right. But an unhappy employee is not getting this it’s way less, because at that point, the only thing they’re rationalizing as well, I’m not happy. So why wouldn’t I want to make more money and that’s a pretty reasonable thought.

So then the money starts to matter no matter what it is, because you’re not happy and you’re not feeling like what you do is making any difference. So then you have a lot of high turnover and you’re going to lose people which is going to cost her business. A significant amount because every, anytime a person leaves the data shows on the low side, it costs you 40% to replace that person.

But it’s anywhere between 40 to 300% of that person’s salary to replace them depending on the complexity of the job and other things. But that’s a lot of money, right? It’s not like if someone leaves it’s freed for you, but there is a lot of costs. Every time you lose an employee. And so it’s something that you need to think about in managing your own business.


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