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Podcast 107: Passion, Work Ethic & SaaS Sales Skills With Katy Tynan
By Kelly Driscoll | July 22, 2019

This week’s Make It Happen Monday podcast guest is Katy Tynan of Liteskip Consulting Group

Katy and John have known each other for a very long time. Katy has tons of experience in Technology consulting, helping teams understand how to make humans and technology work better together. With this, Katy has extensive experience in career development and developing talent strategy. If you want to improve your game as a start-up, Katy is the person you need to see. Having worked together and kept in touch over the years, John and Katy talk about developing your SaaS sales skills, leadership in sales and the balance of working hard – but still learning and improving.

You’ll Learn:

  • Routines around personal learning
  • Owning your sales skills and personal development
  • Building a strong work ethic
  • Creating a healthy culture and retaining top talent

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Introducing Katy

Career Development

Owning Your Personal Development

Work Ethic

Leadership and vision

Introducing Katy

John Barrows: I always say I’m really excited to have about having people on my podcast, but this one’s especially a fun for me because my good friend Katy Tynan who saw me grew up in business and cut my teeth at a very young age is here to join us. We’re going to talk about career development, sales skills and this is going to be a fun one.

Katy Tynan: It’s so great to be here. And yeah, we had some really good times together. Some of which are shareable and some of which will remain where they are! So I spent 10 years in tech and a big part of that was working with John at Thrive and collaborating with him on sales, which was awesome. I did a whole lot of different types of consulting. And what I started to realize after 10 years in consulting is, a lot of people think the problem is technology.

That’s the problem. And it’s almost never the technology. The technology does what you tell it to do. Most of the time it’s the people and the process and the leadership and the communication. So what I do these days is I consult with organizations that are trying to figure out how do I get people and technology to work better together. How to change and get people to do new things effectively and all that stuff. And a big part of that is figuring out how you keep your skills fresh, how you get really good at what you do? Thinking about how you keep your passion level high in the work that you do and all of those things. So that’s what I love to do. That’s what I’m super passionate about. And I’m so glad to be here to talk about it.

Career Development

John Barrows: So let’s talk about career development. It’s very timely this week. This past week I was doing a bunch of training and a lot of times get reps come out to me and saying, John, let’s talk career advice. I’m either, “I am not happy with where I am right now and I’m wondering how I should look at things”. Or it’s, “Hey John, how do you stay so passionate for like it for so long? I mean, you’ve been doing this now”.  I’ve been doing training now for 12 years.

So how do you still have the energy to get out there and go do what you do? I always feel like saying “Hey, I love what I do, but B, I have a plan”. I’m working towards something. So one of the things that’s interesting to me is, that I tell kids that all the time in your 20s is time to try everything out. Because there’s limited risk, right?

So you know, you can sleep on your parents bay, you know, in your parent’s basement if your f*** up, whatever thirties you should start to figure out kind of really what you’re great at and go in on it kind of right. I’m doing buckets here and then forties if you kind of haven’t figured it out in your forties you’re kind of screwed. So how should, people between the ages of 22 and 28 years old be starting their careers in sales.

Katy Tynan: I hate the whole idea of that you can’t know what you’re going to like or not like until you do it. So, let’s just take me for an example. I have a psychology degree. The plan was 100% to be an elementary school teacher. I am so not an elementary school teacher. In fact, I’ve spent about 30 minutes in a classroom during my college career and just felt, let’s not do that. You don’t know until you try things. I would never have told you that I was going to get into it. If you’d asked me when I was in college and when I was in my twenties, what I was going to be doing in 10 years, I didn’t really know. I was sort of following that path of following things I liked.

You find yourself observing what you do every day, what things come really easily to you that maybe are hard for other people. Or what things when you do it, you just lose yourself in that work and you’re like, God, I could do this for days. So it’s really a self-observation process in your 20s and I agree with you. You’ve got to experiment, you’ve got to throw yourself into it and you’re going to suck at stuff the first time you try it.

The first time you do anything, you’re not going to be knocking it out of the park. Nobody gets in the pool and turns out to be Michael Phelps on day one but you that and try it. You’ve got to like it enough to keep trying it so it’s no good to keep banging your head against the wall on something that you don’t enjoy either.

John Barrows: One thing I am noticing is a lot less patience with career development right now. I think we’re living in an Instagram world right now where everybody shows the outcome of how awesome things are, but they’re not showing the journey of what takes to get there. So I’ll give you an example. In our world, sales development reps. That is a sh***y job, period. Depending on the company you work with, it can be fun. Obviously, I think it’s the most important job in sales but you’re banging away 50 dials, working hard.

So it gets really mundane. It’s not hard to see why reps would like to get out of that routine. But there’s, there also is something. To your point, I can see how a rep would be thinking about moving away from that work ASAP. “I can’t stand this” and that sort of feeling. How long should you go into something to determine whether you really don’t like it or to get really good at it?

Katy Tynan: I spend a lot of time in the startup space and I’ve mentored a lot of startups. One of the things that you find is a lot of bad habits. Because everybody tells you to keep beating your head against the wall. Even if you get a hundred no’s, you got to get a thousand no’s. Even if you got a thousand no’s, you’ve gotta get a million no’s because eventually you’re going to get there. And sadly, some people just aren’t ever going to get there. So there’s a balance. I think you need to give anything enough time. And to me, enough time is three months. That’s the habit amount. If you look up how long it takes to form a habit…

John Barrows: 21 days, right? Isn’t it 21 days in a row doing something to build a habit?

Katy Tynan: 21 in a row or a three month period of time doing something consistently. Three to five days a week. So if you’re building a habit, that’s how long it takes for you to basically get good enough that you’re competent at it. And if you’ve tried something for three months and you’re still not good at it, you still don’t like it and you still think it sucks, then I would start thinking about other things with a big, huge caveat.

And the big, huge caveat is every single person, sales, not sales, whatever, your role should have at least five to 10 people in their network that are ahead of them. A year, two years, five years ahead of them that you can go and talk to and say, “Hey, how did you feel when you were in this sh***y role? How did you feel when you are doing this work? Did it get better? When did it get better? What did you progressed to? How is it now?”. So that helps you if you’re going to keep beating your head against the wall, have some context to put around that and say, oh maybe it did suck for three months, but maybe six months.

Sales Skills Development

John Barrows: When I took my second job before Thrive, Xerox obviously was a very well known brand with an insanely well-known training program. And so when I was looking for jobs right before Thrive, I had Xerox on my resume. People would notice it and it was an immediate qualifier for me that I didn’t even have to talk during interviews. Whereas if you worked for some no-name company that nobody has any idea about, half of the interview on your next job is going to be what the company does and what you did there. And so just building the logos, if you will, on your brand early on maybe isn’t the worst idea?

Katy Tynan: Yeah. And I also think to go down that path a little bit more, what you just said about training is also important. You can get hired by a startup tomorrow as a sales rep because every startup is dying for people to go sell their stuff. And most startup Founders are not very good at sales. So you can get a job anytime, any minute of any day doing that kind of work. But if you can get yourself into an organization that is going to provide you with some, great!

There’s other stuff that maybe at first you don’t like, but then when you learn how to do it, you get much better at it fast. And so you could be banging your head against the wall because you’re just doing it wrong. And then you get some training or you work with somebody who knows what they’re doing and all of a sudden it’s a different picture.

John Barrows: You just nailed why I love doing what I do. Because from a training standpoint, I always say I don’t have all the answers, but I’ve made a sh*tload of mistakes in my career. And so my goal when I do training is to help reps skip a few steps. I used to try to, when I’m doing training with around 30 reps in a room to reach every single one of them. Thinking they would all pay attention for a bunch of reasons. And now I actually don’t give a sh*t about the 30 reps in the room. I only care about the ones that really want to learn. Cause there’s always the group in the back that’s sitting there on their iPhones. And I used to try to force that and now I’m like, Hey, that’s your problem.

But, the ones you can tell are freaking out right now because of their job and quota are the ones I’m talking to. Maybe they’ve been blasting out calls and template emails. And then I come in and I give them a little bit of guidance and some tips and tools and techniques that work. And you literally watch their facial expression change. The “aha moment”. It’s interesting that we don’t always like some things until we have been at least given some guidance. Then it becomes easier and more successful, more enjoyable with that.

Katy Tynan: Yeah. And I think that’s a really important element to understand, how we learn. How, because everything we do actually a learning curve in our careers. I say this all the time, work is just applied learning. So we’re out there trying to figure stuff out every day. Most of us don’t have jobs that we walk into and know exactly how we’re going to do it every single day. So knowing how you learn, knowing what tools and resources are out there is huge.

Knowing how people in general learn can be really valuable to you as you’re trying to build those skills. In the tech world, and you  know this because we both came from there, it can be hard to develop and thrive. Because you started out and you had to just know hard skills. If you could could fix a server, you could have a job in it.

John Barrows: And the same thing is true in sales. If you can sell anything, you could have a job in sales, but then you have to add onto that your soft skills. Now you know the tech inside and out. But can you relate to people? Do you have leadership skills? Do you have an understanding of how people, other people think and process and communicate differently from you?

And then finally, now everybody wants business acumen. On top of that. So you’ve got to have hard skills, you got to have industry specific skills, you gotta have your soft skills and now you have to have business acumen as well.

Sales skills are another thing altogether. And that means you better accept that you’re going to be in a constant state of learning for your entire career. You’re never going to be done. And that’s important if you’re going to be happy working because you can’t freeze and realize you have to learn again today. Yes. You have to learn every day, literally.

I have the 12 guidelines of success, I think you know about right? Because I came up at Thrive with them and one is “get 1% better every day”. Know who you are, know what your customer expects of you, and then get 1% better every day. If I can look at myself at the end of the day and say, was I better today than I was yesterday that’s great. No matter how bad my day went, that is still something to be pleased with. If I got a little in, even in the sense of the smallest, 1% it’s a good thing.

That’s why it makes it manageable. Things like did I make one extra call? Did I go that one extra mile? Whatever it is. And if I can say that, then I feel good about my day. If I give, I can’t say that I got better today than I was yesterday, then I am, you know, I know I have to do better tomorrow.

Katy Tynan: Yeah, then you’re better tomorrow. Actually do your 1%. It’s true.

John Barrows: But what do you do? I’m sure you get a lot of reps who ask you about what happens if their company doesn’t invest in them. They don’t invest in training. So how would you approach  educating yourself and having that learning mentality? From a resource standpoint or what would you do to integrate the business acumen and learning earlier in your career?

Katy Tynan: So two things. First of all, I think we give kids the wrong idea because of the way we set up the system for getting your first job out of college. We give people the idea that education comes from someone other than them to them, right? So first of all, you got to bust that right out of your brain and say the person that’s responsible for and accountable for your professional development is you, and you’re the only one that’s going to be able to make that happen. Your company may provide some stuff. But let’s face it, their goal, especially with people having short tenures is to just give you what you need to do, what they need you to do.

They’re not really motivated. Even the best of companies have a hard time teaching you all of those pieces and parts and keeping track of where everybody is on that path. So you’ve got to own that. That’s part one. Part two is thank God we live in the age of the Internet because there are so many resources, whether it’s free stuff that’s out there, whether it’s stuff like LinkedIn learning or Coursera or Udemy, all of those. There’s just tons and tons and tons of stuff that you can go and find. And John, I know you’ve got a ton of resources out there that you spent years putting together for people to level up their sales skills. So consider, what are the skills you’re trying to get? Where can you get them? And I think it is important.

Work Ethic

John Barrows: So one key thing in sales is work ethic of course. This is quite a big topic right now with the work / life balance debate but I think it requires some context. My “Why” is building the best opportunity and platforms for my Daughter. I do not work 25 hours per day but there are obviously times and have been times in my career that I have worked super, super hard. That is not uncommon in sales. But especially in the early days when you’re honing your craft and trying your hardest to succeed, do something on the weekend or do it at home. The learning side of things doesn’t need to be focused on at 9am on a Monday. Reps sometimes tell me that they don’t find the time for development but that is when I’ve found the extra hours or weekends can be productive.

You saw me, I worked pretty much seven days of work a week at Thrive. I was up at a networking event every single morning and every single night. Working until about one o’clock, two o’clock in the morning because I had a drive to be successful and, and better myself. But am I mistaken that that mentality is shifted and now it’s more about “what’s in it for me?”. Why should I do this? Why should I have to work off hours or, or am I just being an old f*cking back in my day guy?

Katy Tynan: I think it’s actually a little of each, right? I grew up the same way you did with the, your work day starts as early as you can get there and you, if somebody calls you at 10 o’clock at night, you answer the phone and you don’t resent that because you’re trying to get somewhere and prove yourself, all of that. And to some degree, I think that’s right and valuable. With that said, I think what we see is a backlash from people who saw their parents do that growing up. And who look at that and say, that’s not sustainable. That’s a sh***y way to live your life. That everything you do is work and you never have time. And you’re always sort of saying, in six months this will all cool down and I’ll have time. But you never ever get there.

So to me it’s how do you find your personal balance for this? Is it Monday to Friday? Nine to five if that’s when your personally most effective in any time beyond that makes you grouchy and makes you suck at what you do? If it’s like that for you, then don’t do that.

But if you love something and you’re really passionate about it and you want to answer your emails at two o’clock in the morning and drive for that, that’s great too. I mean, we haven’t touched on this, but sales is, and consulting is like this too. People who don’t want to do the work and don’t love it for the sake of it and aren’t feeling motivated by the rewards of doing those things aren’t going to want to be in it for the long haul and they probably should go find something else to do.

But I also think you’ve got to watch yourself. It is possible for people to look at you and think that what you do is impossible for them. And so you’ve got to set the bar high, but you’ve also got to say to people, look, you’re the best judge of your life and your goals and your priorities, and you figure it out.

John Barrows: I think that I’m 100% on Gary V’s tip around if you make 40 grand a year and you’re happy, then f*cking amen. You win. Like you and I, and I agree with that. I know plenty of people who live that model. They have a decent house, they live a nice idea. They played with their kids on the weekends. I go to their baseball games and all that other stuff and they’re happy book regardless how much money they make. If that’s you and you’ve figured that out, you are my definition of success. But if you’re making 40 grand a year and you’re moaning that you don’t get the opportunities or you’re not making enough money and you’re not willing to put in the work to get more than that, something has to change.

Katy Tynan: Nope, that’s right. You are dead right. Nothing is free. You’re never going to get given that corner office and that $500,000 a year salary, you’re just not going to get that by sitting back. And so you need to sit forward. You need to put your time and sweat into your career and you need to do that in a way that helps you get where you want to go. So that you see those results so that you don’t feel like you’re just doing this because that’s what your boss wants. You gotta be doing it cause it’s what you want to do.

Leadership and Vision

John Barrows: So what do you think leadership’s role is in getting people working to the right tune? I get a lot of questions about getting reps working as hard as leadership. And the answer to that is you’re never going to get your reps to work as hard as you, cause they’re not there. They’re not as inventive. If you’re owner and you own 30, 40, 50% of the company and some kid’s getting a commission check, you expect that kid to work as hard as you. So do you have any guidance on leadership on how they can get reps to buy into that and also understand where they fit in the big picture?

Katy Tynan: Yeah. I think there’s a couple of things there and you’ve touched on really well. So one of them is why did we do that at Thrive. I’ll tell you why I did it at Thrive. I didn’t do it for the money. I did it for the people. Yeah. I was there every day and busted my ass at 10 o’clock at night for two sets of people. Number one, our clients because I was on the hook for it. You and I had sat in a room with those people, solved their problems and then if something broke, I had to go fix that. Part of it was that intrinsic motivation. I loved fixing things. I love taking that worry from those clients who don’t understand that technology.

If you don’t have intrinsic motivation, if you don’t believe in the product you’re selling to such a level that you’re willing to spend some of your personal time and spend some of your extra energy on doing that, then you need to find a different company that sells a different product that you really give a sh*t about.

That’s part one. Part two from a leadership perspective is it is about a lot of different things for different people. So I was not as money motivated as I could have been, but I was certainly career advancement motivated. I wanted to be at the next level of my career and frankly that Thrive director level position that I had there way early in my career got me somewhere that I would never have gotten had things been different.

John Barrows: Yeah. I always joke that like I was the VP of sales and marketing at the ripe old age of 24 years old, which is a total joke, but at least have that title.

Katy Tynan: Yeah, basically some exposure. Exactly. So you have to think about all the parts. And if you’re a leader, you have to look at each of those people that are on your team and say, why is this person here? Why did they take this job? Is it because of the people?  The money? Is it the opportunity to learn and grow? Is it that they thrive in this particular environment? And then you’ve got to help them see the connection between the work they do every day. And that intrinsic motivation gets them out of bed and it’s going to be different for everybody.

Now that’s like Ninja management. Not a lot of managers are great at doing that. And so they fall back on, I’ll just throw money at this person. But it’s not always about the money, especially at that level in your career. You know, the money’s gonna come at some point, but you’re doing it in order to get somewhere. And I think that’s what leaders need to understand. And that’s your point about the vision.

John Barrows: I think about this a lot, we’re in a world right now where you just have to accept the fact that, that whoever’s working for you is going to leave eventually, right? And they’re probably not going to be at your company forever. So why not create an environment for them where you’re going to get the best out of them in the short period of time. And be open and honest with them about it. And so I’m wondering if it’s, if it’s almost like if you’re a manager out there, one of the things that I would do. This is what I did with Morgan, you know, I asked him, what are your life goals here? Forget about this job for a second.

Ultimately what do you see yourself doing? My job here is to help you get there. Now I want to get the most out of you for us here with this organization. But in doing that, I want to help make sure that you’re developing to get to that next level of your career. I’ll give you an example. Like Morgan, his number one goal when he came on board was meet was he wanted to be the number one motivational speaker on the planet, right? You want like Tony Robbins type of stuff and always cracks me up. And I said, all right Morgan, give me three to four years.

I said, give me three to four years and I want you to bleed for me. I literally want you to go out and I want you to go train and travel and generate as much revenue as you possibly can from my company. And in return for that, I’m going to show you how to run a business. I’m going to show you how to manage. I’ll show you the keys to the castle of how to do this, but I need you to do this for me. And there’s a plan for that. Do you suggest that managers take that approach with each one of their reps? It’s kind of taking a step back and saying let’s talk about your life goals here for a second and how I can help you get there.

Katy Tynan: Yeah, so I do a lot of management development and leadership development work and there are so many theories, dude. I mean, you know, everybody in their mother, myself included, has a book and all of these things that you’re supposed to learn and know and do, and it can be really overwhelming to managers. All the stuff that they’re supposed to know and think about. And what I tell people is you can forget all of it, every single drop of theory, you can let it go.

The only thing you have to remember is to care about those people on an individual basis. And if you personally care about an invest in their success, they will go to the end of the earth for you because that’s all people want. They want to know that somebody gives a shit whether they’re successful or not. And I think you’re right in that partnership idea, integrated vice for managers to sit down and say, where are you trying to go?

How can I help you get there and in return, here’s what I need from you. And it’s a really good win-win relationship. And if it’s not working, I have written a whole bunch of articles about why retention is stupid and why you should stop trying to retain people. I get it that companies know that it costs them money to replace people, but you know what costs them more money? Having people sitting there on the job who don’t give a sh*t and aren’t trying anymore.

So make an environment where the people who are the right people will be super successful and they’ll stay as long as they feel like they can be super successful and then be excited when they move on to something new. Because they’re achieving their goals and they’re going to help you make a really lovely warm handoff and they’re probably going to help you hire their replacement.

John Barrows: Yeah, I mean it’s funny because people ask me about Thrive. What was I most proud of at Thrive? It’s funny because it has nothing to do with the fact that we sold to Staples. That has nothing to do with how we were the fastest growing company in Massachusetts and all that other stuff. The thing I am most proud about is that I gave Kevin Ellis and opportunity to do what he did. Yeah. I mean I’m never going to take credit for Kevin being as successful as he was because that was him. But I put him in a position to be successful and watched him grow. And now where he is in his career. Like I take a lot of pride in the fact that I was

Katy Tynan: Yeah. And you should take pride in that. And you remember what I said to Kevin Ellis when he was there and he was whining to you because I was hard on him. It was because he wasn’t getting it right. I gave him a whole ration of Sh*t and he came to you and said, why is Katy so hard on me? The answer is because I wanted him to be successful. And so I was gonna hold him to that standard because I knew he could do it. I think that’s the management that needs to happen to help people understand that you’re buying into their success, that you’re not going to let them do shitty work because you want them to get where they want to go. So I think that’s important. Yeah.

That’s a wrap. Join us next time

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