Jon Dwoskin is an executive advisor, business coach, and speaker who shifts peoples mindsets, recharge and begin thinking, acting and implementing like the CEOs of their own companies — regardless of their titles.

Starting his career at a young age of 23, Jon created one of the first internet marketing companies in America where he provided online marketing services to giants like Blue Cross Blue Shield and Weight Watchers.

He then went on to create great success at several large organizations holding titles such VP, as Managing Director, COO, and VP. Throughout his 20 years in C-Suite roles, Jon has discovered the common habits that helps leader grow big businesses. 

Join us today to learn what those habits are, and how you can better integrate them into your life so you can build a thriving corporate culture and grow your business BIG.

There were LOADS of great takeaways from this call. Here are some of our favorites:

4:11 – How to effectively plan your day

6:11 – The trick to making work FUN!

7:27 – Using inspiration to be a good leader

8:58 – Building a bridge to future leadership

10:05 – The pros of mentoring programs

12:35 – The importance of understanding your people

13:24 – Developing a clear mission & vision

14:45 – Creating a specific & measurable plan

17:12 – The inside scoop on time management

18:54 – Setting the standard for interruption

22:39 – Defining the ‘tick’ in your people


Derek: (00:13)
We’re going to need to thank you for your analysis. 

Jon Dwoskin: (00:20)
Are you editing this part out? You know, it is weird because when I clicked in it, I knew it was luminary, but then when I linked into the zoom, I linked into, we scrimmage. So now that I look at it, okay, 

Derek: (00:35)
right. That’s moving forward. Yeah. So that’s clear. We’re just getting going with this. So 

Jon Dwoskin: (00:41)
Hey, it doesn’t, it doesn’t matter to me at all. I, so I think it’s great. 

Derek: (00:45)
Okay. Yeah. Thank you. Thank you. Okay. Um, cameras. [inaudible] okay. Okay. Yeah. Okay. Okay. Alright, we’re recording. We’re just gonna go cause that’s not working. So let’s just dive in. Awesome. So welcome. Jon Dwoskin expert business coach leader. Oh, hang on. One sec. Take this is not aimed properly. Okay. You got to stop now. Yep. Yeah. Yeah. So it was an honor to have John [inaudible], a good friend of mine as well as tops on the asker week podcast here. Looking forward to talk with you about how you helped leaders help companies, help people be at their best, the expert coaching and advice and guidance you have. We provide John and we’re going to talk more about just your work and how you help others in the process of learning, developing and, and everything else that you do. So welcome to our show express that we connect with you. 

Jon Dwoskin: (02:13)
Yeah, thanks fellows. I appreciate you having me on, on today. So, uh, so thanks. I’m whatever you guys want to talk about. Let’s go. 

Derek: (02:20)
Absolutely. So this is a big transition since we have a tendency just to talk if we start on your show about learning and education and training some inside stuff, right? That I think taking a step further, how did you get into your line of work? Just tell us about the process that you went through and discovering, find your gift and around helping people develop. 

Jon Dwoskin: (02:39)
So what I do in quick summary, I’ve wanted to do, I’m 47 I’ve wanted to do since I was 18. Um, my dad gave me a set of tape sets by Brian Tracy called the psychology of success at 18. Told me I would learn more from those people than I would college. Uh, he said, if I got less than a C in college, you wouldn’t pay for it and pull me out of college. But I became obsessed with listening to those types of people. And I read every book I could listen to every tape I could from that day to this morning. I mean, I’ve been obsessed with it and knew that I wanted to start a business, um, growing companies, uh, writing books, keynoting speaking, speaking, training, et cetera. Um, so that’s how I started. Uh, that’s where the kind of the, the seed was planted. Um, long story short, after college, I started an internet company, uh, in my parents’ basement. Uh, I was, I ran the sales, I grew the sales team. I was responsible for the business planning of the company. We sold that company two years later to a Silicon Valley company, and then we’re partners in that company. Then I got into commercial real estate or started selling in apartment buildings. I always wanted to do that. My grandfather was in real estate, um, did that for six years, then I ran my office for six years. And then it was time. And just, that’s a long story short. Wanted to start my own business. 

Derek: (04:01)
Absolutely. I love that so. The a bit of a cool thing about it. You’ve had a diverse background experiences that have gotten where you are, but coming back to where you started here is just your own personal development that you focus on every day. Tell us about just your routines for how you incorporate education. Learning into your day. You literally start your day, first thing with listening or reading materials or what’s the, what’s the process you go through to prime yourself for that? 

Jon Dwoskin: (04:26)
So my routine is I wake up and I meditate. Um, and then I do, I go to, I believe in Western medicine, but I also go to a Buddhist monk, uh, MD who’s a medical intuitive and he’s, uh, was raised in a monastery from the age of four and Beijing and his family healed emperors for hundreds of years cause he’s pretty cool. And so he has these 10 energy moves that, um, that I do. They’re actually on YouTube. So I meditate. I do those, the YouTube, you know what, I don’t know the, the exact link, but I’ll email it to you in the show notes. Yeah. I mean it’s great. His, it’s his 10 energy movements and, and they’re amazing. And so, um, I do that and then I will sometimes journal and just kind of breathe after I’m done meditating and then I’ll work out and then it’s the summer. So my kids are in school yet, but once they’re in school, I’m done with everything by seven and, and with, um, with like my kids and my wife, we’re trying to just get breakfast and the kids out the door before I leave for work. Todd

Derek: (05:34)
Yeah. We have, we have a similar morning routine in many ways between intention setting and exercise and focus. 

Todd (05:42)
I was just scribbling my intentions in the car on the way to the studio here. 

Jon Dwoskin: (05:46)
Yeah. Yeah. I do the same. I do the same and the, my day one journal, which is a, a, it’s just a journal I use for my phone 

Derek: (05:56)
Um, one of the things that, you know, I talk good about, uh, three weeks ago was the idea of how do you make work fun, right? So the idea and in my mind marriage, it’s happening in the world between work and play and they intersection of time, you know, the personal and versus work and how that’s all coming together. How have you been able to infuse fun and play into your work in a way that makes it, you know, something that doesn’t even feel like, I think that’s, yeah. 

Then also a little, a little addition to that is you’ve worked with a ton of people and companies and leaders. What have you seen the, you know, your clients do for their team that gets them excited and invigorated, inspired to actually work? Yeah. And it actually really makes it enjoyable and engaging. 

Jon Dwoskin: (06:41)
Yeah. So I’ll answer the first question first. Um, you know, for me, I, I’ve always done what I love and so work has never really felt like work. I’m a believer to follow, you know? No. What if you tried to determine, do your best to determine what you’re good at? I think I figured it out at an early age for myself and, and do what you love. You know, that. And so for me, my ultimate goal was always I had my own business when I was younger. Uh, I got into the corporate world. I always wanted to get back to having my own business. So I, I, I say this to people a lot. Um, I started a business so I could be myself. I started a business being myself. And so I don’t need to play the corporate game. I don’t need to. 

Jon Dwoskin: (07:23)
Yeah. I mean, for those who are listening, you know, you, there’s just corporate politics you kind of have to adhere to. Um, and so I think to, to have fun at work, you really just gotta be able to have your voice and do something that you love. And if you don’t love what you do, find what you love. And some people will say, well, I need the money. I need the security. I need this. But that’s, that’s true. But you also can continue to stay on a path. You can also continue to stay on a path to find what you really love and, and, and you, and you deserve that for yourself. You know? I mean, so, but, but that kind of leads into other what you said. What do I see other people do? Uh, to inspire people. You know, a good leader is somebody who can inspire and doesn’t necessarily have to use a lot of words, but, but has a really strong understanding of vision and people buy into, um, the vision of the leader. And that leader also holds the vision for the individual people within the company and conspire, um, individual, um, uh, conversations with people to, to inspire them to tap into their own drivers so they can really, you know, tap into their unique ability. So if you have a leader that can get somebody to tap into their unique ability and sees the best in them and brings the best in them, then that’s, that’s a great leader.

Derek: (08:49)
So that’s a we can definitely. Gonna not have a theater show. I think that’d be a really fun topic. But just kind of along the same lines, most of that question, um, you know, many of our clients are corporate clients, right? I think that people in corporate America are yearning for that, that leadership, that, that purpose, um, that, that fun at work, that the, the aspects that we as entrepreneurs and business owners get to experience through that journey, I think keep going corporate and some level are seeking to how do, how do we create that culture from your standpoint, um, around, you know, within the constructs of corporate today, within the politics, within the structures that are in place within the way that we’ve been doing business. How do we build that bridge too? What’s possible in the future or the future of leadership and infusing that purpose in that, in that context. Yeah. 

Jon Dwoskin: (09:38)
You know, it’s interesting. Um, there are many studies, um, Huffington post has written about it. Harvard business review, Forbes inc. There are many studies that are pointing to that. Um, by the year 2030, 80 to 85% of the jobs that exist in 2030 do not exist today. And that 75% of the workforce in the year 2025 will be millennials. And those are, those are, um, those are insane stats. I believed them to be true. And the reason they’re, um, they need to be really looked upon and, and um, and somebody and companies and corporations need to zoom in is because the company culture is gonna change so dramatically for sure over the next five years and absolutely over the next 10 years. And so the millennial generation is forcing us to think differently about work and more consciously. And so the leaders need to follow suit. 

Jon Dwoskin: (10:42)
And so what’s one thing that I see in companies is the millennials, the newer people who are coming into the companies in their twenties and early thirties, there’s mentor programs being set up and there needs to be a 2030, 40 year gap between those mentors. Because in today’s world, the 20 year olds can teach the 60, the 50, 60, 40, 50, 60 plus year olds. Just as much as you know this, they can teach the 20 year olds. And so one of the ways to kind of connect with that is for people to, to, to have some type of mentor program like that because the, the older generations need to understand what the millennials are really bringing because I think they get a bad rap sometimes that they, you know, they don’t work hard or they only want to work 40 hours or this and the other, but they have a lot to teach us. We just need to tap into it. 

Derek: (11:32)
Yeah, I mean I completely agree. Obviously we have a fairly young team at scrimmage and you know, we recognize that shift that’s taking place in, I’m candidly a fairly young leader, right? So I think that on the same lines, the reverse mentorship concept is something that I’ve talked with a number of executives about. I think that’s, I think you’re spot on if that’s that. I think the interesting implications of that are how does that change how companies are structured, right? If you look at the way that decisions were made 20 years ago in business and how things are coming now, where everyone has a greater voice, there’s many ways for people to communicate, for people to reach executives. It’s a really fine balance between offering the opportunity for people to share and present their ideas and bring the best ideas forward while shepherding them in such a way that provides the structure and support and discipline that allows great companies, great teams and great organizations that thrive. 

Derek: (12:32)
Right? And I think we’re in this and I think you’ll see it out, you know, in all different facets of life, right? When it’s, whether it’s in sports for kids, whether it’s in companies, whether it’s in politics world wide. Right now we’re seeing this shift and communication mores in terms of leadership structures. Um, and I think that’s all part of it, right? I think that, I think it’s this generational piece, uh, combined with technology that’s allowing this to take place and to really transitional time. Right? I think, I think that’s why leaders such as yourself and coaches such as yourselves and people that can move between different organizations and, and share what’s working and also the risks are so important. Right? Yeah. 

Jon Dwoskin: (13:14)
You know, I think, um, I think Derek, one of the things that’s so important is now more than ever and moving forward as leaders, we really need to understand our people more than ever before. Um, it’s, this sounds so simple, but the, the leadership of walking and talking and connecting with your people on a daily basis is critical. Right now we see people who are working remotely. Um, there’s flex time, there’s things of that nature, but that’s still no excuse to not connect to your people. Whether it’s FaceTime, zoom, texting, emailing, calling. I mean we have so many more lines of communication, but really understanding your people, what makes them tick, what’s their driver, what’s their unique ability, what should they bring to the table? And I also think that this is really important to the company. It needs to be very clear on their vision, their mission, um, their, um, where they want to be in the next 12 months, two years, three years. 

Jon Dwoskin: (14:14)
But also they need to, um, they need to infuse that and have all of the leaders in the organization and all the people in the organization on their own business plan that’s in alignment with the company business plan, but also push personal business plans. And people want the work life balance today. And it’s amazing to me how many people don’t have a business plan, a life plan and none of this sketched out. And so to me it’s really important and the more a company can infuse that type of guidance to their teams, then they will, then they will, they will feel the loyalty to that company and appreciate it. And then you continually train and provide the resources and the tools, not just for the bottom line, for the person’s soul. That is the thread of your business. 

Derek: (15:03)
I completely agree. And you tap on so many different themes there. Um, and the word that just comes back to, you know, to kind of summarize that in some way is culture for me. How do you define, how do you see the best companies creating that amalgamation of ideas that you’re talking about and getting them to work effectively? 

Jon Dwoskin: (15:24)
Well, one, I see that there is a, um, a high level of trust in, in the culture and, and, and I think under trust needs to be accountability and authority. And what I mean by that is not authority in a, in that kind of a a negative way, but everybody needs to know what their plan is. And I see a lot of companies that don’t have specific and measurable plans as a company and specific and measurable, uh, business plans for all the people within the company. And so everything becomes very, everything becomes very vague and everybody can finger points and nothing is around specific, specific and measurables. Nothing is around deadlines. Nobody know who, Oh, nobody knows who owns a project. People go to meetings. This is something that I see all the time. That’s very frustrating for people. They go to meetings they shouldn’t be at and they go to meetings with no agendas and they go to meetings, um, that the leaders don’t know how to end the meeting with actionable items. 

Jon Dwoskin: (16:27)
You know, these are things that need to be very tight in an organization. So some people say, well, I don’t want that type of, you know, that, that, um, rigidness, because I want the culture to be, you know, kinda, you know, laid back. Well, you can have a laid back, relaxed culture, but you still have to have a plan specifics measureables owners and deadlines. This is a business. And so I think there needs to be that. And so when people come and say, Hey, can I work from home or this and the other, then it’s kind of easier, right? There’s certain professions where you have to kind of be at the office, but there’s many that you don’t have to be at the office. And if you know what your, what you, what you need to do and how, for yourself and the team and the clients, then it shouldn’t be a problem if well organized. 

Derek: (17:15)
Yeah, no, I, yeah, 

Can I jump in? So John, on that note, in terms of some of the things you see there that the basics that people and companies are missing sentence structure for meetings, they don’t have a business plan you’ve seen and what you, what you coach people through. Can you comment on something that’s really like a timeless principle? Maybe it’s writing your intentions at the beginning of the day, picking your top key accomplishments you want to make and then something gets more tangible, maybe more modern, like an actual tool or a program that you recommend people use in order manage meetings or organize their day. 

Jon Dwoskin: (17:52)
Sure. So I’m a big fan of one calendar, one to do list. Um, outside of that, I think it’s a mistake for, you know, I do a time management seminar. A lot of companies where, you know, a lot of people are using sticky notes, multiple calendars, multiple to do lists. And, um, so just in quick summary, I think that’s, that’s really important. Understanding what your top three, um, specific and measurable activities that you need to do that day that are, um, the leading activities that will grow the business. And um, having an agenda for every single meeting and emailing out that agenda prior to a meeting. So, and, and having deadlines for people. Hey, if you want to have something on the, on the agenda, send it by this date, the agenda, we’ll go out for the meeting on this date. Um, and, and cut your meetings in half, however long your meetings are. Cut them in half. 

Derek: (18:47)
Yeah, I mean, the key, the key message there is just time, right? Timing. Is this something that’s precious for everyone? It’s the currency, right? That has the same amount of, and something about how you can control and multiply that time. Is this the gift, right? The best from the average, so to speak. 

Sometimes it is something as simple as making an agenda and it does not have to be in my turn. It doesn’t have to be detailed at all. Just bullet points. Here’s the three things we’re going to talk about. You had had four people that say, I have nothing to do with those three things I should be doing instead. So you could save three hours. Absolutely. One agenda list. Yeah, go ahead John. 

Jon Dwoskin: (19:33)
No, no, no. I was just going to, I’ll just quickly say, I was going to say also I think companies need to be conscious of not interrupting their people and so there need to be standards around that. I think people like to focus and um, so you want that balance of approachability and accessibility, but it’s not just free range interrupt people because study after study after study shows that, you know, you interrupt people, it takes somebody 20 to 45 minutes to just get back into the zone to do what they need to do. So there needs to be some good, some standards, um, around that. 

Derek: (20:06)
Yeah, I mean I think that’s a fascinating perspective too because I can personally struggle with this, right? The idea of like micromanagement of their time, right? Like, so literally, how can you be that efficient? And then the way that your flow cycles work and stuff, it allows you to get into getting maximum productivity and it’s like there’s kind of two schools of thought. There’s the manage every minute and then there’s the creativity that it happens when you allow yourself to really drop in and be present in an activity for a period of time. Correct. That intersection of that, you know those two pieces, especially within the corporate structure, it’s really hard to accomplish. Right. I think that I would love your thoughts. Have you seen a certain leader or leaders do that well? Right. Bring that, those two ways of managing your time together from the optimum performance. 

Jon Dwoskin: (20:51)
So say that again. 

Derek: (20:54)
so, so you know, planning the one state, when I’m looking at your calendar, yes, I’m studying your calendar. Right? And you’ve got every minute kind of managed for maximum productivity, right? That’s the one side of it. The other side is your, your inspirational, your flow cycles happen at longer periods of typically 90 minutes or more. Right? It’s when you’re the most inspired in terms of creating stuff. Right? And so you’ve got these two different views that you’ve got the ROI of the minute. Very good. Got the ROI of the inspiration. Right. So how do we bring those things together in a meaningful way so that people can, you can get the best of their time. Right? Yeah. 

Jon Dwoskin: (21:33)
When you say the ROI of inspiration, are you talking about, um, a leader to their people or just as an individual? 

Derek: (21:39)
It can be both. Okay. Yeah. 

And how can I jump in real quick? So I maybe see that as a tangible example is I’ve seen some leaders who are honored for your, your quick, yeah. Derek is quick to answer things like you’re, you shoot off a two word reply. Yeah. Instantly. Very often some people will say, sorry, I get six hours. I’m not even looking at my tone or even, right, right. Like how do you choose which one is best and has the most immediate ROI, hopefully, and positive longterm impact. 

Jon Dwoskin: (22:11)
I think, um, I think you, one of the things that works is you need to kind of bake that into your day. And as a, as a leader, you need to know, you know, when, um, when your flow States are, and so, you know, I can give some examples where like, I see certain clients who might know that they’re spending their mornings walking and talking to all of their people because that’s kind of their flow state where they can really just kind of, you know, be in this, be in the zone and like listen to something and give the response and give people the leadership they need to have a really productive day, whether it’s a word or two, a couple minutes, whatever that may be. So I think as a leader, we need to know our flow state. So we need to know kind of when we need to, when we need to be connecting to our people and when we need to step back. So they don’t feel like they’re micromanaged.

Derek: (23:03)
Yeah. Along the same lines though, so back to corporate, right? Or within organizations, how do we create the space as leaders for everybody, individuals, how do we create the matching, so to speak? Right? Do you have ideas on that? 

Jon Dwoskin: (23:20)
Yes. So we need to understand in a, in a corporate setting, if you’re leading people, you need to understand that, um, you need to understand what makes each individual person tick. And so what I see companies do, what I did when I was leading companies is you, you need to know what each person, how each person gets inspired, what their driver is and that time of the day that they need the inspiration. And then as a leader, you kind of then have to work yourself around your people because your people are your clients. I mean, those are, those are your clients. So I need to know that, you know, Joe gets inspired when he, he needs kind of to be revved up in the morning, uh, for a minute. And he and such and such needs attacks. I mean, even in my coaching business, I mean this morning I’m texting, you know, CEOs, VPs of sales salespeople, you know, just a reminder simply to just, you know, do the fundamental things cause they need that little jolt of something. 

Jon Dwoskin: (24:22)
Some people need it mid day, some people need it at the end of the day. The key is you need to, um, you need to connect with each person that you lead a minimum of once per day minimum. And so you got to know what they’re, and then you fit. You gotta know what their time is and then you fill it in, uh, the rest of the day with what you need to do. On top of that, on top of that, just one more thing. On top of that, you also, on a daily basis, we talked about kind of routines in the morning. It’s really important to take some executive time to, whether it’s in the office or get away from the office and in your business plan, you need to have all your people and you need to have a, a weekly business plan for all of your people. I need to know how I’m gonna move this person forward every single week. Because if I do, then what I’m talking to them, connecting with them, how I’m communicating with them is going to be different every single week. 

Derek: (25:16)
Yeah. Yeah. I love this topic, man. I think, I mean, I think time and time, 

Derek: (25:21)
eh, I wouldn’t have used the word manager. It was more than that. It’s time control, it’s time guided direction, right? It’s like I can actually visualize it. It’s like guiding of a river in some ways, right? And everyone’s part of that. Right. And so I think that that’s when you think about the future of work, this interconnected work anywhere, work anytime, work within the flow of your cycles, individual people tying their best skills, uh, all these, their higher purpose. Like that’s, I think where we’re getting to that. And I think a lot we talk about this is that, you know, we’ve, we’ve, we’ve, we worked and we went to school within the constructs of an eight hour day, a 40 hour work week, you know, a nine months of the year type of job. And the reality is that that’s just not the world that we live in anymore in the sense that you can, you in theory are connected and could do your best work anywhere, anytime in a way that’s meaningful for you. And so I think it’s up to us as leaders and companies to start to foster the environments where we can save CV accountability metrics within that environment. So I think it’s really exciting from that standpoint. I think you’re on the front lines with what you’re doing with the leaders that you work with and the companies that you support. So 

Jon Dwoskin: (26:33)
well, I appreciate it that, you know, and I think, you know, people come to work to do a great job and so it’s our responsibility as leaders to make sure that they do that. And I just want to comment on this to, cause I think it’s important as a leader, you gotta be connectable, which means it doesn’t necessarily mean you know, you just, you know, it’s interesting, there’s so many different types of leaders that, you know, there’s some leaders that you know, you feel very close to and that are warm but, but don’t smile. And then there’s some that smile and you just feel connected to them cause they’re just jovial and just really in the zone. Then there’s ones that you know, that smile too much, you know, so, you know, you just, you just have to, as a leader, be yourself and be of service. 

Jon Dwoskin: (27:19)
I just want to chat about that for a minute because if you believe, um, I’ve always been a leader where I have felt I am of service to the people that I serve. Um, I feel that way with my clients as well. I’ve always felt that way. And so, and if you don’t feel that way, and if you feel as a leader, you’re a leg up on someone, then it’s never, it’s never gonna work. And so to the, to the leaders of the leaders, if you have the wrong leaders in place, your company will crumble. Maybe not tomorrow, maybe not next week, but you have to have the right leaders in place to inspire your people. Otherwise, um, things go backwards quickly. 

Derek: (27:58)
Well said Jon, I just want to again, thank you for your time this morning and everything that you’ve shared with this audience. I’m working how you serve the leaders that you serve. 

Jon Dwoskin: (28:11)
And yeah, thanks so much. So my website is Jon Jon Dwoskin, D as in David, w O S K. I N. Jon Uh, my company name is Jon Dwoskin experience. Grow your business big, very big. And as my tagline, I have a bunch of podcasts. You were just a great guest, uh, two weeks ago on mine, which I am very grateful and appreciative. You had great wisdom to share on my think business podcast. Um, my website has everything about me, uh, that you would need. And then I always give everybody my direct cell two, four, eight, five, three, five, seven, seven, nine, six, and anybody can call me directly. I’m a big believer in, um, full access. 

Derek: (28:53)
Awesome. John, thanks so much again, and we’ll see you very soon. 

Jon Dwoskin: (28:58)
All right. Thanks guys. 

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