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Episode 62: Work culture 101: Trust each other enough to fight

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All Xero Gravity episodes

Hosted by Elizabeth Ü

“There’s no key to success. Success is made up of very small decisions, thousands of little decisions. Disciplined, good decisions over a long period of time.”

That’s Matt Rissell, co-founder and CEO of TSheets, the mega successful time tracking app. On Xero Gravity #62, this (in his free time) pilot of a Piper Saratoga has amazing tips to help your small business soar.

You’ll hear his approach to finding mentors, starting with asking questions that are in their sweet spot. You’ll find out how something as simple as truly listening to your employees’ feedback after meetings can foster trust, openness and continuity throughout your company. Plus Matt’s take on the future of cloud solutions, and why you ought to jump in without a moment’s hesitation.

All of that and park rangers, game wardens, fly fishing, book clubs and the pickle suit. 

Small Business Resources:

Episode transcript

Host: Elizabeth Ü [EÜ]

Guest: Matt Rissell [MR]

Intro: You’re listening to Xero Gravity, a podcast for small business leaders :and entrepreneurs around the world. Now to your host, Elizabeth Ü.

EÜ: Hi everyone. I'm Elizabeth Ü and this is Xero Gravity.

MR soundbite: “You have to trust each other enough to fight. Which is interesting because you usually don't put trust and fighting in the same sentence. But the truth is if you're going to go fight and tell somebody why you disagree with them on something, there's a level of vulnerability that takes place. So I'm a big believer in having confrontation; good, healthy conflict face to face with each other.”

EÜ: Meet Matt Rissell. He's out to prove that innovative ideas and startup success don't always come from Silicon Valley. With a passion for building great teams, Matt co-founded TSheets, a time tracking cloud application that's taken the world by storm. Matt lives life to the fullest. When he's not busy working he enjoys being outdoors and he even has a pilot's license.

Matt also loves teaching and learning, and the constant creativity that comes from working with a productive team. He talks about the role of mentors in shaping his life personally and professionally, as well as the role he plays as a mentor to others.

MR soundbite: “You know, you always approach mentors and people who you want to learn from in different ways. And most importantly do some research before you go meet with them and figure out exactly what their sweet spot is. So make sure you come prepared with, ‘Okay, I'd like to learn this. Will you teach me this specific skill set?’"

EÜ: So we have all that and more coming up on Xero Gravity, right after this.

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EÜ: Matt, thanks for joining us on Xero Gravity.

MR: Elizabeth, thank you for having me on your show.

EÜ: So I was thinking about this. We both work in careers in the cloud and that's not something that existed at all when we were younger. I'm curious, what did you want to be when you were growing up?

MR: You know, it's funny when we were growing up, or at least when I was, I mean, they didn't call it the cloud, right? And believe it or not my co-founder — this was, like, 1986, 1985 — he was actually sending email packets over the telephone wire. Which is interesting and not necessarily what I wanted to be when I grew up. \So actually I love the outdoors. I love the mountains and I always wanted to be park ranger or, like, a game warden. Just so I could drive around and be in the mountains all day long.

EÜ: You're kidding me! Because I wanted to be a park ranger up until, I mean, all the way through college and I never actually did that. I did end up working for the US Geological Survey and the Forest Service, but I never got to wear what some people affectionately call the pickle suit.

MR: [Laughing] Well, good. If I were you I would claim you'd never put on a pickle suit as well. However, I never did either, but I got to go one day. I took an entire weekend and I got to go around with the game warden. And it turns out it’s a great job except that you never get to talk to people because you're in a truck and you drive, like, just all over the place. And so I thought maybe that might get a little bit lonely, and so I started to drift other ways.

EÜ: Wow, that's so amazing. In terms of talking to people, we've spoken a lot on this show about the importance of mentors and role models. So have there been any people in your life who have been fundamental to your personal and professional success?

MR: You know, no question. I'm a huge believer that you need mentors. And basically what I encourage people to do, and what I've done is I just, I break my life up categorically and I literally find the best, most successful people in that area, and I learn from them. And sometimes I can't get close enough and so I just have to learn from them remotely. For instance, like, Marc Benioff, you know, I'm a student of his.

He one of my mentors. But he may not know it per se, because it's not like we've ever spent a whole lot of time together. And the same person that I might get, let's say, financial advice or professional advice may not be the same person I'm going to get advice for in my personal life or in my marriage, or something like that. So I'm a huge believer in finding the most successful people in every area of your life and just learn as much as you can from them.

EÜ: So how do you approach them once you've identified those people?

MR: You know, you always approach mentors and people who you want to learn from in different ways. And most importantly do some research before you go meet with them and figure out exactly what their sweet spot is. Something that you know they would be really interested in telling you, and show genuine interest and ask those questions. You know, one of the worst things I think that you can do — and maybe I'm sharing this out of place — but I have a lot of, like, young, you know, men and women out of college and they're, like, "I want to become an entrepreneur."

And they sit down and they ask me questions. And the first thing they say is, "Will you mentor me?" And I have no idea what that really means. So make sure you come prepared with, "Okay, I'd like to learn this. Will you teach me this specific skill set?" Or how to interact or how to negotiate or something like that; have something specific. Because if it's really big and ambiguous, you’re never going to get somebody who’s really busy with a lot on their plate to just say, "Yeah, you know, just come shout on me all day long."

EÜ: So when you're not busy running TSheets, what do you enjoy doing?

MR: So I'm still an avid outdoorsman and we're a very active family. So, I mean, I'll, you know, probably work at TSheets between 70 hours to 90 hours a week legitimately. And so it doesn't provide a whole lot of time to just go play. However, I like living a really full life and so we jam as much in as we can. So one thing I am is; I'm a pilot. I love to fly planes. And I have a little plane that I fly. It's a Piper Saratoga, six passenger plane.

And basically what that enables for my family, and even some business trips, is the north west of the United States is all within about a two to three hours flight for me. So it brings everything a lot closer. It’s so much fun to go flying through the mountains for breakfast, that kind of thing. And I love to fly fish and take my kids camping and even hiking and hunting and those types of things.

EÜ: So will you take me camping and fly fishing next I come to your part of Idaho?

MR: Absolutely. You're a fly fisherman?

EÜ: Well I have a rod. I don't have a reel at this point but, you know, I'm sure you have an extra five weight that I could borrow.

MR: We can solve the reel issue, no problem. We have some great places to go to where you can catch some world-class trout.

EÜ: That’s fantastic! So what made you decide to build this productivity software? I can't imagine that you just woke up one day and thought, "Hey, I'm going to build an app.”

MR: You know, you're exactly right. And it even took a really long time to dawn on me. You know, some people approach their companies and their product and how they're solving a problem, and they see a need in the marketplace. And they go, "I'm going to go solve this great big problem in the world.” I think they're a lot smarter than I am, actually. So what I did is I had a business before this, where we had four locations and about 35 employees, and I needed a time tracking system to solve a timecard fudging issue that was going on.

And also just the ability to see who was working at any given time at these different stores. And so I went to Office Depot first and I said, "This is what I need. We have four locations, 35 employees, some mobile salespeople and delivery drivers, and I need to see everything that's going on. I need a time tracking system." And they said, "Oh, I've got the perfect solution." And they walked me back into this aisle and they handed me this old metal thing where you push a piece of paper into it and it goes, like, cha-ching, like, it reminds me of [laughing] the Flintstones.

EÜ: [Laughing] Right. Totally.

MR: Yeah. And I said, "Okay, well, thank you, but that's not going to work." Still optimistic I went to Google, you know, typed in timesheets, time tracking, that kind of a thing. Nothing existed. So I called up my buddy and I said, "Hey Brandon, this is what I need." He was a software architect. "Can you build this basic version of what I need?" He's, like, "Yeah. Sure. No problem." So he built it for me. We processed our first payroll. We saved $2,400 on our very first payroll.

EÜ: $2,400 saved because things were inaccurate before, or just from saved time?

MR: Saved on inaccuracies, not just on labor. So statistically what happens: everybody has great employees, and so did I and I still do. And everybody has a tendency to give themselves the benefit of the doubt, especially when it comes to their time card. So if you're, you know, using paper or spreadsheets that track time, the American Payroll Association says that you will save between two and six per cent right off of the top of your labor expenses.

EÜ: Wow.

MR: It's a big number. And it was a big number, you know, for us as a really small business trying to have some kind of margins. And so anyway, she looked at me and she said, you know, after using it, "This is absolutely amazing. Can you sell it?" And I wasn't — this was 2005. It was back before software as a service was a word. And so, yeah, I actually didn't know that you could take, you know, a software cloud solution and have, you know, massive distribution. I said, "Yeah, I don't know." So I called Brandon up and I said, "Brandon, can we sell this?" And he said, "Oh yeah." And that was the beginning in the TSheets.

EÜ: So what are some of the most common mistakes that you see small business owners making when it comes to growing a productive workforce?

MR: Well, as any human being and any CEO or any entrepreneur we all make a whole bunch of mistakes. But some of the most common mistakes: I see entrepreneurs and CEOs saying, "Oh, when I get bigger then I'll implement these different disciplines." And for instance, like, I'm a big believer that when you have one employee, two employees, that you should have, like, an executive meeting.

And I also believe that you need to have all-hands meetings. I know it sounds funny and you may be just sitting, the three of you, having a conversation, but it keeps everybody on the same page.

EÜ: There's so much research now about how all of these standing meetings are sucking up so much of a business' time. So clearly you've come up with some sort of a system that keeps those all hands meetings relevant. Can you share some of the tips that you have for either creating an agenda or mixing things up?

MR: It's easy to let meetings, if you've ever read the book, you know, Death by Meeting — it's easy to allow them to take over a company, so you have to be careful. But there are some things in place that you can do in order to help the productivity of those meetings.

Always be willing to allow feedback at the end of the meeting. So one of the things I always ask at the end of our executive meetings is, "Did this work or what worked and what didn't work?" And if you have a really good environment and culture where they're willing to give you, you know, point blank feedback and say, you know, "This was a piece of shit." Or, "This was completely ineffective and a waste of time." Or, "This was really good because of this." You constantly have a refining tool in place that will allow you to get better as a company and allow your meetings to become more productive.

EÜ: This is great — this concept of allowing feedback. And I imagine that one part of that that's really important is making sure that everyone in a leadership position is trained not to bite back if they hear something that's maybe not so positive.

MR: You know, it's absolutely true. I have an open-door policy here and we are very transparent. And one of the things that's in my core belief system about our culture here is that you have to trust each other enough to fight.

Which is interesting because you usually don't put trust and fighting in the same sentence. But the truth is if you're going to go fight and tell somebody why you disagree with them on something, there's a level of vulnerability that takes place. And people that don't trust each other, what they do is they go behind their backs. So I'm a big believer in having confrontation; good, healthy conflict face to face with each other.

Actually, you know, interesting anecdote; because I'm a pilot I study a lot of the crashes that take place. And one of the cultures that they actually had to put in place in a captain, in a co-captain or co-pilot environment is in the commercial airlines. It was something like 75% of all of the crashes, the co-pilot actually knew that it was going to happen prior to the crash.

EÜ: Oh no!

MR: But the reason that they didn't communicate it is they were afraid to break culture and tell the pilot. And so, you know, feedback is always embraced here.

EÜ: Right. So how do you encourage that type of vulnerability and transparency and the type of culture where feedback is not only expected, but freely delivered?

MR: I would say the most important thing to create that culture is not only to ask for it, but when you get it don't act defensive. Truly listen to them. And then take action on the things that you think are really good points. That will truly create a self-reinforcing environment.

EÜ: And what are some examples of things that have come out of that sort of feedback that you've now implemented into the culture at TSheets?

MR: One of the things that we do is a founder's lunch where I sit down with all the new recruits who have just joined TSheets. And one of the things that I tell them is that I say, literally, "Any time you're going to your onboarding period, if you ever ask yourself, ‘Why did I do it that way? Write it down.’” Like, write it down right now. Because there might be no good reason that we do it that way. It might be something that, you know, got created over time. And it may be something that we need to change. And it's a way that we have created this, you know, this increasing and consistent self-improving environment.

EÜ: So I imagine that you also encourage this increasing and persistent self improvement on the individual level as well. Can you talk a bit about that?

MR: I think that a company's potential is made up of the sum of all the individual people that are a part of that organization. And so if you look at something and you go, "Ooph, you know, I don't see a whole lot of potential there." That means somebody hasn't been learning and growing and has the desire to learn and grow. So at TSheets one of the things we look for is somebody with a tremendous amount of potential.

Whether it's something that hasn't been tapped into or just given the environment, you know, put them in an environment where they can flourish. We have things in place for actual mentorships and onboarding buddies, where they spend time with somebody who has been here for a long time.

We have a book club, basically, where the executive team always has a book that we're reading together as a group. And we always share that book with the greater staff; the all-hands staff and say, "This is what we're reading together." And then sometimes as an entire company, I buy, you know, all 120 of us a book. And we all read it together. And then break up in discussions and chat.

EÜ: So we've been talking about a lot of things that come back to soft skills and leadership development and personal growth and culture building. But how does this cloud solution that you've created, TSheets, fit into all of that?

MR: So, I mean, TSheets is a company. It's a cloud-based company that literally has limitless potential, much like Xero, in that basically we don't have to go create a bunch of widgets to sell. You know, we have unlimited inventory. And we really have a massive market. There are so many small businesses out there that use paper and spreadsheets to track and manage and schedule their employees' time. And in the accounting space the same thing. There's small businesses still having receipts in their shoe box, and still using spreadsheets to do their books to send to their accountant.

EÜ: I know. It's heartbreaking, isn't it?

MR: Well, it's heartbreaking because (a) not only the inefficiencies, but also because of the inaccuracies.

EÜ: As far as the bigger picture that you see, I mean, you're not just selling timesheet management software. You're selling something bigger. What is that?

MR: Well, I mean, our mission is to truly help businesses succeed; small businesses, mid-sized companies succeed all over the planet. And our goal, like, where we're at is, like, where we want to be as a company is to become the number one employee-rated and requested time tracking system on the planet. Because if you ever go to a small business and ask their employees, you know, do you love your time tracking system, I think most of them are, like, "Ugh.”

The way TSheets was created was always about the employee. And so our slogan is, "We heart employees." Which we actually do love our employees internally, and that statement was originally created about the end users; the employees using TSheets every day, day in and day out. And the way that they track their time has a direct impact on how they get paid.

EÜ: Yeah, I'm thinking back to my own personal life and there was a moment when I was making pizza in Yosemite Valley and I actually caught my employer cutting my hours. I mean, I had clocked in with a card and I caught them cutting my hours, so they were paying me less than I had actually worked. And I thought to myself, "Gosh, I have no idea how long they have been doing this. I have no idea to how many people they had been doing this." So what kind of visibility does your software give employees into that bigger picture?

MR: There is a log that's created inside of TSheets every time somebody does something, or anytime somebody attempts to do something. So no one can go in and make any changes to the log that's created in TSheets; not the employee, not the manager and not the administrator.

It's a big differentiator in the marketplace. We're actually the only time tracking system with that level of accountability. And so our logs have actually gone to court to protect both employers and employees in labor disputes.

EÜ: You said that a lot of small businesses that you're talking to say that they're not going to do something — whatever it might be — implement a better structure or adopt a certain type of technology until they reach some mythical point in the future. Why do you think we do that? Why are we always postponing this system that would make our lives so much easier from the get go?

MR: Well, I think any time you try to implement change, period; I think we as human beings deliberately procrastinate. And I think it gets magnified when that change includes technology. So in the cloud world, as people move from desktop based software to the cloud, part of it is, you know, cloud technologies are still evolving and getting better. And so there was the reason, you know, a few years ago that, "Geez, it's not quite as good of a product," which isn't the case anymore.

Cloud technologies are as good if not better than, say, desktop type technologies. And so then it comes down to the resistance to change, not always seeing the benefit, there's always a conversion time period as well where, "Gosh, I don't want to take the time to convert until the pain with my old way of doing this is high enough.” And one of the last reasons I think that people do it is there's still some myths about people thinking that their information is less secure in a cloud solution than let's say a desktop solution or even a piece of paper.

EÜ: And what do you do to help people overcome these fears?

MR: Well, it depends. It depends on the person and how technical they are. Because for a super technical person we walk them through the security of our system and that alleviates it. But if somebody's not technical they really can't understand all of those things. So then we give another analogy. It's, like, you know, if you have a piece of paper and it's in a file behind a locked door, do you think that that is more secure? Somebody could come in, break the window and grab all of the files. Or is it more secure behind a firewall with very sophisticated encrypted technology? There's a lot more security and protection in the cloud.

EÜ: I'm curious, how is cloud technology unlocking more productive ways of working?

MR: So cloud technology is literally revolutionizing the way small businesses can run. And it's not just a statement that goes in a magazine or on a blurb. It is a true statement. It gives you enterprise level software for a fraction of the cost, and it makes it substantially more accessible being in the cloud, because you could take it anywhere, anytime.

So whereas, let's say three or four years ago when you were doing your books as a small business owner, or your accountant was doing the books in order, as the small business owner, to get visibility into your books, you literally had to go to your accountant's office and physically get them. Get a copy of the software from them, get a USB drive. Literally now you both are logged in and you can see it real time from your house. That kind of visibility and knowledge, to be able to control and make decisions about your company, is off the charts.

EÜ: And how many small businesses do you see using a variety of these solutions?

MR: You know, it's interesting. Small businesses typically use, I think, three to four different SaaS or cloud-based solutions without knowing it.

EÜ: That's a great point.

MR: And one of the things we recommend to accountants, "Look, you know, go and vet your top apps, you know, whatever it is. Pick your suite of apps. Learn them. Trust them. Figure them out. And then implement them across your client base. Because you will create efficiencies. You'll create more value because you'll be able to keep that same value building in place. And it's a great opportunity to increase your profit, deliver better services to your clients, and give them information in real time."

This is a fantastic thing. For instance, and here's a perfect example: one of our customers — the reason they chose TSheets is that their store was supposed to open at 8.00 am every morning — the guy had, like, five or six stores and he didn't find out one of his stores didn't get open until his next employee showed up at one o'clock in the afternoon.

EÜ: Oh. Oh.

MR: Because there's no way for him to know. Right? So he was able to get incredible visibility into that.

EÜ: I'm really inspired by this vision that you're painting of managers and leaders and employees doing whatever they need to do to be most effective in their workplace from wherever they are, and the role that cloud software and solutions like TSheets can play in this. But I'm curious to hear more about what you think the future of working will look like. I mean, whether it's how employees in the workforce itself looks like or just work in general. Where do you think that's going and what role do you think that the cloud will play in shaping that?

MR: Well, that's interesting. There's a lot of different places I think it's going to go. I think workplaces, you know — we have the capability at TSheets actually to have remote offices and people work from home, which we do allow for at times. But nothing I don't think can ever replace the face-to-face interaction that you get when you're actually there face to face.

And so I do think that while cloud enables remote working, I don’t think it'll ever be able to replace the actual face-to-face interaction that takes place. Now, some of the cool things that I do think that it will enable from a technology standpoint: I actually think that software is going to get so good that, like, for instance, TSheets will be able to predict employees' behaviors the point where they won't even to use TSheets to track time.

EÜ: Oooohh.

MR: So people are creatures of habit. They clock into the same job codes when they get to the same locations, etcetera.

EÜ: That's sound super exciting!

Thanks so much for your contribution in moving the workforce into the future. And we're going to finish up with our question countdown, which is five quick questions and five quick answers. Are you ready?

MR: Let's rock and roll.

EÜ: [Laughing] What business book or idea made the biggest impact on your life, and why?

MR: How to Win Friends and Influence People. It's a timeless piece. It gives you the basics of human interactions and if you can't build relationships with people, I don't think you can lead and build and create the things that you want to create. At least I can't. So it was probably one of the best books I've ever read.

EÜ: What's the one thing you can't live without?

MR: Laughing]

EÜ: No pressure. [laughing]

MR: [Laughing] The one thing, I mean, is my wife going to be listening to this, because I probably need to say, like, you know, my wife and kids and I guess, the one thing, you know, that you can't live without, geez.

EÜ: What was the first thing that popped into your head?

MR: I would say relationships.

EÜ: Oh. Perfect. And the most useful app on your phone right now?

MR: Outside of TSheets, which is probably cheating, the most useful app is, there is an app called Things. That is a to-do list. And it's easily the best to-do app I've ever found and I have no tie to that application.

EÜ: Great. I'll have to check it out. In one sentence, what's the greatest lesson you've learnt throughout your small business journey?

MR: That's there no key to success. Success is made up of very small decisions, thousands of little decisions. Disciplined, good decisions over a long period of time.

EÜ: And finally, what skill do you want to enhance this year?

MR: Like, I have so many skills, so I'm a big believer in learning. I'm learning to fly better. I'm learning to ride — it's funny — I'm learning to ride mountain bikes better than I ever have, right now. I mean, there are so many things. How to be a better leader, you know, as TSheets goes from 120 employees to, you know, probably 300 to 400 employees over the next couple of years. I've got to become a much better CEO and leader.

EÜ: Well, what a great conversation this has been. I am so inspired. Matt, thanks so much for joining us on the show.

MR: Elizabeth, thank you so much for having me on your show. It was a great conversation. And I look forward to (a) fly fishing together and (b) hearing more about your days climbing and working in a pizza shop.

EÜ: All right. Well, I can't wait.

Promo: Are you a fan of Xero Gravity? Because we’d love to hear from you. Subscribe to the show in iTunes or SoundCloud and leave a review, sharing your favourite moment from the show so far.

EÜ: That was Matt Rissell, CEO and co-founder of TSheets. Thank you for listening to Xero Gravity. Make sure you join us next week, because we'll be chatting with Emma Sharley, small business marketing consultant and instructor at General Assembly. Emma will share tips on low-cost marketing as well as insights on what to avoid when marketing your small business. Have a great week and we'll catch you then.

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