Craig Goodliffe On Overcoming Obstacles Entrepreneurs Face in the Digital Age

October 31, 2024

A study by Deloitte found that 90% of executives believe their industries are experiencing disruption, with 44% stating they are highly disrupted. So how can entrepreneurs overcome these challenges?

The Valiant CEO ranked Craig in their Top 20 Business Leaders, not to mention The Wall Street Journal, and he is a Forbes Business Council member and contributor. Craig is celebrated for his ability to transcend geographical boundaries and empower businesses worldwide.

We interviewed Craig about his start in business, founding Cyberbacker, cross-culture, fostering strong interpersonal relationships, the remote landscape, and more.

How will you as an entrepreneur, leadership expert, and business coach known for his expertise in cross-culture business?

My journey started out as being someone who started out in the real estate industry from being a sales agent to becoming a business owner, which are two very different things, and people tend to think that my grandfather and my dad that you went ahead and you were an electrician, and once you got really good you became a business owner and that was the natural progression without realizing that those are two very different skill sets. I had an opportunity to learn and make a lot of mistakes, and then in 2015, I started coaching real estate business owners and professionals, and right now I got well over 10,000 coaching hours, and having conversations with people about business, and about leadership, and about entrepreneurism. I have been a part of people starting businesses and ending businesses and a lot of those great conversations. And then becoming an expert in the cross-cultural business development. I worked with my first international team member back in 2012, and that was Daphne from the Philippines. We still work together today, to this day, but she really opened my eyes to how remote work could work. And over the years, you know, that led to 2018 starting the great company that had done exactly that, and I’ve really been fortunate to have an opportunity to create jobs in foreign countries and a lot of programs that are really helping people and doing some good.

Craig, can you share some of your insights on how remote work culture has transformed the dynamics of the modern workplace? What key strategies do you believe are crucial for building a strong team, or cohesion, in a virtual environment?

Remote has changed everything for the workplace and that happened with COVID because jobs that people thought couldn’t be done remote are, are now being done remote. And, all that, if you look at the jobs that companies like Cyberbacker are not able to staff or they’re ones that require a physical presence, or a specific license or certification that we just don’t find or do so we don’t make that promise. That’s how remote work has been done, and, that’s something that people are wanting more. So it’s important that companies communicate that and communicate that they offer it and what that looks like. And one of the key strategies, I’m gonna tell you about the biggest one it is a face-to-face video call where you’re seeing and you’re meeting with your people frequently, because, in this, in this work-from-home environment, visibility is huge, and then being able to see people.

And then, also, just literally asking people ‘how are you’ and meaning ‘how are you,’ and really getting to know them as a person and care about them because you lose, when you work virtually, some of the, that watercooler conversation, and in some of those ‘in-passing’ conversations that sometimes, are distracting, they are also relationship builders because when someone is walking through the office and you can see them stomping around and they got a big frown on their face, you know they’re not having a good day, well, in the virtual world you can’t see that. But, if you’re meeting frequently and you can see them, and you can observe the changes in a personality, you’re able to go ahead and build some strong team cohesion.

In your experience, what are some of the most effective strategies that are enhancing communication with remote teams, and how do you ensure transparency, clarity, and consistent engagement among team members?

The first thing to remember is that you give what you get. You can’t expect transparency from others if you don’t give it. And you can’t expect good communication with your people if you’re not giving it first. That can be true with everything, with every one of those, but give what you expect to get first and foremost, and being able to almost overdo it, so people feel that, that you’re really transparent and clear with them.

When people feel that the leader is completely unrelatable, it’s hard for them to feel that ‘they get me.’ When people feel like you don’t get them, it’s hard for them to go ahead and want to engage with you. So, they are gonna engage with people that they feel comfortable engaging with, and leaders who are vulnerable, and who are doing their best, and who are genuine and who are authentic are who they’re gonna engage with.

So how do you empathize the importance of recognizing and appreciating individual and team achievements at Cyberback and in what ways do you think that this contributes to a positive and supportive work environment?

We’ve got different divisions that do different types of awards, and as a company, we “gameify” as much as we can, and we put together contests, for, you know, who did the most number of transactions coordinated, and we put together contests, for, and I said divisions, we’re striking that from our vocabulary, we meant teams so I apologize. But when these teams meet, they’re awarding top performers and things like that, they’re getting shoutouts, they’re getting recognition, that’s constantly being shared out over social media plus meetings and those little things like, when our growth team and our career team, when they meet every Friday, they’ll talk about their numbers first of all. Then we’ll go ahead and share who did something really, really awesome that week, or who’s leading the pack in specific KPI or something like that. But really just bolstering that community where people feel like they’re a celebrity and they’re winning and people just want some recognition. So that’s that’s kind of what we’ve been able to do here at Cyberbacker.

What were some of the innovative approaches to virtual team-building activities that you found effective in fostering strong interpersonal relationships [s and creating a cohesive remote team?

One of my favorite games that we’ve played with people is called Apples to Apples. It’s a card game where people go ahead, and there’s someone who draws a card with a question, and then people have other cards with answers, and they pass in the answer that seems most like the question. And you can play a game like that virtually. When we were first starting the company, taking time to just play little games and stuff like that and just build a relationship with people was instrumental because that’s how we got to know people. As it’s continued and gone on, we’ll do quizzes and we’ll do stuff like that in our company just because it’s gotten too big to play games like that. But it’s been really fun when we can go ahead and engage with people on a pretty deep level and we can build those interpersonal relationships. The other most effective thing is actually getting out of the virtual world and going over there, having them come over here just to get a different perspective. So it’s still better if you can, for virtual teams, to meet in person when possible.

How do you encourage skill-sharing among remote teams at Cyberbacker and why do you think it’s significant for building the dynamic and skilled workforce?

(Craig): So skill sharing, the thing that we do that I’m really excited about is our head backer program. And what that is, is that it’s kind of like peer training. And when someone’s a head backer, they’re making sure that when a Cyberbacker has a job to do that they have the training, they know what classes they’re sending them to, they can show them things from their own experience, they can be there to answer questions, they can be their support person. And we’ve seen that when they’re the person who’s giving the answers and they’re the person making sure people go to training, they’re very skilled at doing their job and they get better. And so you’re actually getting a higher level of output from your people because they’re working smarter. And then we also have masterminds on Fridays where they can go ahead and bring something like yours, something I’m working on. Who else is having this challenge, and how do we get through it? And they’re really coming up with some amazing things. But it’s about holding the space that allows them to do that. And so one of the things we’ve done really well with that dynamic building of skills is being able to create an environment where those skills can be showcased.

Can you elaborate on how Cyberbackers established a feedback loop that fosters a culture of continuous improvement and what role do you believe active team member involvement plays in this process?

So we’ve got a couple of different feedback forms. When we first went ahead and we released a feedback form, we got all sorts of stuff and some of it was usable information, some of it wasn’t. And what we found is when it wasn’t usable information, people still wanted to know that it was important to us that we knew and that we heard it. We changed the feedback form. To go ahead and ask better questions, to look at, is it quantitative, the feedback, or is it qualitative? Because if it’s quantitative, sometimes we have numbers that just aren’t being shared and we need to be able to share those analytics. And sometimes there’s something we should be tracking that we’re not, be we need to take a look at. So for those, for the qualitative, sometimes it’s just a feeling and sometimes there’s something that needs to be reiterated or mentioned to people that was heard. But when we have those things, we can have the right conversation and being able to ask someone: is this quantitative or qualitative? Sometimes when it’s neither one, it’s a rant. It’s just not valuable feedback, and it’s able to be dismissed, but having that has been pretty critical.

Craig, please tell us what inspired you personally? To champion a culture of compassionate Cyberbacker and how does it influence your leadership style?

This is very simple. I just built a culture that I would want to be a part of, and I’m still building a culture that I want to be a part of. And what you don’t want to do is build a company that’s culture you want to hide from because you don’t like it. And so I think it’s every leader’s responsibility to create the world that they want to be part of. And that’s what makes someone a champion of culture and compassion.

Can you share a specific instance where you committed to an employee’s well-being and had a profound impact on them?

We went ahead and set up this fun backer division that was designed to go ahead and check in our people to look at the emotions they’re experiencing, to have a conversation with them, and to really just be better. And we had a team member who we thought was good. And we actually found out was not as good because he was skipping right past that and sending them an email. It was basically, are you feeling red, orange, blue, or green? And the, what color are you feeling goes from a chart that you should be able to read their emotion. That’s not a profound impact. That’s a negative impact. Well, here’s what was profound. We hired him to go ahead and get into his emotions. And what we learned is he didn’t care about them, which means we hired the wrong person. And that was pretty heartbreaking. And we got out of business with that person. Let’s see, commitment to an employee’s well-being. As much as I can tell you we’ve had a lot of Comments, people that say that mentally I’m happier because I’m a cyber backer, because I’m around good people. We’ve had a lot of instances where we’ve got specifically some transgenders in our company. And for me, I think if someone could do a job, you don’t discriminate for any reason against them, as long as they can do the job and they’re good at it. And we’ve had a lot of people tell us that they’re really happy just because they feel like they can do themselves here.

As a Business Coach, how has your personal journey and experience shaped your belief in the transformative power of compassion within organizational culture?

This is a hard one to answer as a business coach because the most powerful transformation I’ve seen in our company’s organizational culture is when we were all together and we were sitting in a home for children ages zero to two who were orphans, who were foundlings, whose parents were incarcerated. They’re kids and they’re in a bad situation and seeing the emotional connection with our people and how much we all cared about these kids really opened my eyes to just having compassion for other kids and other people in this world and being able to share those tears and want something better. I haven’t had that as a business coach because unfortunately, I don’t go along with a lot of my clients when they’re doing some of that work. But I can tell you as a leader, the personal journey and experiences, every time we’re doing something good in the community or we’re helping others, we’re giving things to like kids in kindergarten, we gave backpacks and toys and school supplies. That’s when we unite as a team. And every time we’ve been able to give back, that’s when you really get to know your people and you can really feel loved.

What specific practices have you implemented at Cyberbacker to foster empathy, understanding, and employee wellbeing, and how do these positive shapes come into culture?

We’ve had a lot of different people like our cyber care committee, and our cyber care team. And what they do is they’ll go ahead and just celebrate birthdays and work anniversaries, which are little things. But that goes ahead and it just reminds people that we care about them. And then we’ve done when someone we’ve lost cyber backers in our companies who unfortunately passed away, being empathetic to the families and making sure that financially they’re not cut off if they’re relying on that person to be the breadwinner. And I have a real hard time with this question because we did it because it’s the right thing to do. We didn’t do it to go ahead and how to positively shape the company’s culture. I think the company’s culture is positively shaped when leaders do the right thing and taking care of people will always be the right thing to do.

In your view, does a company-centric culture contribute to Cyberbackers success and innovation in the remote landscape?

Yeah, absolutely. People do business with someone they know, like, and trust, and people, when they like and trust people who are very compassion-centric. And they don’t like people who are not very compassion centric. When people don’t feel empathy and like they matter and that they’re cared about, they don’t like working for a company like that.

Could you provide examples of collaborative initiatives or projects of cyber backers where compassion played a key role in driving groundbreaking collaboration and innovative thinking?

Just giving you one of our first ones that I’m most proud of is we went ahead and there was a, there was city called Tondo and There were some kids who were playing with matches and shouldn’t, and they believe it or not, they burned the place down. They burned down a lot of homes that were very clearly connected. And so it had displaced a lot of people, and they didn’t have a place to live. So they were collected together in a basketball court. And we went into Tondo, our team. And we had coordinated to get food and supplies, to get sardines, get rice, get things, be able to feed these people. And a lot of our great people stayed up all night putting down these care packs so we could deliver them to everyone in the day. And just the fact that our team stayed up late, worked hard, sacrificed so much to be able to put that together. It really brought us all together. There was very collaborative thinking and it was very good delegation on who did what. And, I’m proud of our team every time they can come up with things like that. Understanding the link between compassion and employee retention.

What specific measures is Cyberback taking to reduce turnover and retain valuable talent?

If you do the right thing and you care about people and you exercise compassion, you’re going to have employee retention because it makes people feel good. If you want to keep people and not have turnover, just simply make them feel good. And if you want turnover to be high, make them feel bad. It’s very simple.

What are key leadership practices you advocate to promote compassion throughout the organization?

The biggest one that you can do is lead by example. When people see you doing it, they’re going to do it. And when you’re not doing it, people aren’t going to do it either. If you’re not compassionate, they’re not. And so it’s just being compassionate, being very visible with that compassion, and just setting a good example.

How has the emphasis on compassion within CyberBacker positively impacted the overall environment?

What benefits has the company experienced as a result? Well, I think the biggest thing with compassion is people are overall happier. And is it perfect? No. Does it have a long ways to go? Absolutely. Because our biggest challenge with compassion is sometimes people carry the biggest burdens. They don’t want to share and they don’t want to be vulnerable. It’s kind of like a pack of dogs. The wounded one doesn’t want to get left behind. So pretend not to be wounded. And so it’s helped and it’s getting better, but I still think we have a long way to go. And I don’t think we’ll ever be done going ahead and emphasizing compassion.

What strategies or initiatives are you considering to further enhance and sustain the culture of compassion, especially in the evolving landscape of remote work?

The big thing coming is having our nonprofit and giving people an opportunity to participate in that, both giving and receiving. We’re making it so that when there are economic disasters, we can step in and we can provide help. And if we do good at that, and we’re able to handle all that, the next place we’re moving, or if there are no economic disasters, is helping children. That’s what we’re always going to do. And that’s how we demonstrate our compassion and our culture.

Where do you consider to be home? Is there a specific place that inspired your pursuit in tech?”

My home is Ogden, Utah. And it’s because when I go outside, there’s a big, beautiful mountain called Ben Lomond. And to me, that’ll always be home. And that had nothing to do with what inspired my pursuit of tech. What inspired my pursuit of tech is just, I happened to be positioned in an age with a lot of innovation. From seeing cell phones be the giant brick phone to now this handheld computer that, you know, does a lot. It’s just been a passion, but I’m in Utah’s home and it really doesn’t have anything to do with tech.

How do you anticipate and prepare for potential disruptions in your industry caused by emerging technologies?”

Well, I think the thing that we do is we’re constantly keeping an eye out for what are our competition, what’s our competition doing and what are other things doing that are going to potentially challenge us, and we can either work with those things or work against them and ideally we’ve made the decision that we’re going to go ahead and work with them as things come like artificial intelligence and whatnot and building up proper training and instruction for being able to do that.

How do you balance the need for innovation with the risk of investing in technologies that might pan out?”

The first thing is you’re going to be going ahead and making sure that you’re doing a great proof of concept before you invest too much in a new technology. You’ve got to make sure that you’re going to get something out of it. And so the best way to do that is starting with a very small subset and seeing how it plays out and then investing at the rate of your understanding. The better you understand something that’s going to work out, I mean, absolutely invest more, but you’re going to naturally invest least when you’re not sure. Innovation though, lack of innovation is one of the things that starves companies. And companies that start with the ones that go out of business. So innovation is essential, but it’s being able to scale that investment.

What was the inspiration for the development of Cyberbacker?

It was truthfully just wanting to help out other people like me and being able to put together the things that I’ve done that have made my life easier and be able to help other people do that and seeing an ultimate win-win situation.

Describe a situation where a company successfully navigated a technological shift. What were the key challenges and how were those challenges overcome?

One of the biggest technological shifts that were hard for us was when we said that we were looking at people applying in our company and sometimes, with their schedule, they wanted to apply and, you know, get an answer yes or no, can I move forward and with scheduling and different people that was hard to do and so this isn’t well this is a little bit of a technological shift, but I said we want to do 24-7 Video hiring. I want to have it be so 24-7 someone can go online, have an interview and be able to know quickly if yes they can move forward with our company or at least you know we’re going to move forward getting more information or no it’s not a possibility for them. And so we have one of our very very talented team members the time Jennifer Caparo actually go ahead and build out that 24-7 And it was, you know, truthfully, her and a lot of people just working non-stop until we figured it out. But it’s one of the greatest things that we’ve done and I’m very proud of the organization doing it.

How do you measure the success of your marketing campaign? What metrics do you track, and how often? How do you use them to optimize your strategy?

So we measure everything on social media from awareness to influence to leads. We measure key target demographics. Who are our key target demographics and do they even know who our company is? And then if they do, are they someone that probably, you know, we’d like to do business with and they’d like to do business with us? And so we’re constantly looking at how many people we need to have as a key target demographic, meaning we’re trying to get them to know our company. And of those people, how many of those would actually be a good candidate to do business with us? We look at that every day. And that’s how we know things are working because it’s at least going ahead and putting us in front of new people in that demographic or it’s taking people in that demographic and introducing them to our company. Second, technology in itself is a success.

What does success mean to you? What are your rules for success?

Success is accomplishing something that you’re setting out to do. Meaning, I said I was going to go to the office, I got my car, I drove, I was successful in that. If I went ahead and I got in my car and drove to the office and it broke down then I was not successful in my trip to work. But it’s going ahead and saying here’s what I’m going to do and being able to do that as success. When you look at pursuing success, that’s that journey to the office. Sometimes it’s a long journey and sometimes it will take years. But that doesn’t mean you’re not successful because you haven’t arrived. Sometimes success lives in just the pursuit, the fact that you’re going to the office.

What advice would you give startups struggling to secure funding in a competitive market?

With that, I had a conversation with an entrepreneur when he was saying, I’ve got this idea. I know it’s going to work. I can’t find funding. What should I do? And the advice I gave him was to make sure you have a good customer base, you know, go out there and create your product in essence and put people on a waitlist to get it. Like, see if they actually want it, if they’ll commit financially to be on that waitlist. You see a lot of companies like Indiegogo promoting that. And ultimately, if you want someone to invest in your company, they’re going to have a lot easier time investing. If they know that you have revenue you’ll be able to make with that getting funding. When you’re looking for funding, and you don’t have a good plan, you don’t have a good customer base, or someone just can’t see how they get a return, it’s nearly impossible to get funding. So go make sure you have a good customer base and show someone a return and you’re going to be able to do that.

What else would you share for the next up-and-coming tech investor?

(Craig): The best advice I’ve ever gotten was from one of my friends, Pete Owen. Pete works a lot with hedge funds, and I asked him, “What should I invest in?”

And he said, “For you?”

And I said, “Yeah.”

And he said, “Real estate.”

I said, “You don’t invest in real estate.”

He says, “Yeah, but I don’t know real estate.”

And I said, “Okay.”

He says, “You’re always going to do better investing in the things you know and understand.”

And so for today’s tech investors or today’s tech inventors, cause I just realized I read that wrong. For the investor, don’t invest in anything you don’t know. And for the inventor, be crystal clear on what tech, what problem your tech is trying to solve for people and making sure enough people have that problem. I mean, I mean, if you’re working on tech that measures the, you know, Golf score on a specific course and people have limited access to that course and aren’t able to play it, then you have a small category of people who actually want what you’re selling. If they’re not clear on the problem, they’re not going to want the tech. So anyway, get clear on the problem and who has that problem so you can determine the market. Then Fox Magazine is all about inspiration.

What and who inspires you the most?

The people who inspire me the most are the wonderful team members here at CyberBacker. I’ve got their pictures on my wall. Every single day, them and their family, I look at them and they look back at me and I get a lot of inspiration. It’s my responsibility to help them have a secure job, and they trusted me to help them do that. And so I get very, very inspired by the great people in our company who come to work every day, trusting and believing in me that they’re going to be taken care of. That to me is very inspiring.

What’s something people would be surprised to learn about you?

I failed more than I succeeded, and I keep failing more than I succeed. I keep learning, and it’s because I’m human, and I’m okay with that. I’m constantly finding setbacks and working through them, and I think it’s one of the biggest advantages I have. It’s also one of the biggest heartbreaks I have: that I fail more than I succeed.

What is your favorite innovation-related motto, quote, or words to live by?