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Global Business Coaching Challenges and Issues: A talk with Tom Finn of Leggup

Tom Finn

When coaching business leaders in 20 countries and ten languages, issues surely arise. Tom Finn, CEO of LeggUp, an international coaching platform, explores management styles and issues in Canada, Switzerland (Do you know about dining etiquette?), India/Asia and Europe, and cultural challenges across the world. Yet as he explains, coaching is ultimately about encouraging clients worldwide to examine what they can do differently and allow themselves to lose control when going international. Tom’s final advice: Relax. All will be OK at the end.


Tom’s journey

Coaching in different cultures

Success in international coaching

Similarities and differences in coaching cultures

Advice for the younger person

Tom Finn Bio:

Tom Finn is the Co-founder and CEO of LeggUP, a professional coaching and wellbeing platform with a global presence. Possessing a wealth of experience in employee benefits, insurance market trends, business development, and revenue strategies, he is the thought leader behind two of LeggUP’s innovative product offerings, the LeggUP Platform and Talent Insurance®. His mission is to move professional coaching from an elite executive experience to an inclusive company-wide opportunity and move companies away from outdated leadership styles of talent management to talent empowerment.

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Full Transcript

Hello everyone, and welcome to Global Gurus. Every Friday, we explore stories of international business and speak with industry leaders operating around the world. I’m your host, Philip Auerbach, at Auerbach international (

If you’re tuning in for the first time, we start each podcast with a running segment called “Faux Pas Fridays,” where we explore a funny blooper or mistranslation that does not quite convey the professional image that your organization wants to project. And since today’s guest has a business in the insurance industry, I’d like to present a quote or a blooper from the auto insurance industry which does not match his version of insurance but still illustrates the point. This was a real excuse given in English as a reason for an accident, it was again conveyed to an auto insurance company where the writer said, “The guy was all over the road. I had to swerve several times before I hit him”. 

So, with that, today’s guest is Tom Finn, co-owner and CEO of LeggUp, a professional coaching and well-being platform with a global presence and a wealth of experience in employee benefits, insurance market trends, business development, and revenue strategies. He’s a thought leader behind two of LeggUp’s innovative product offerings: the Leg Out platform and talent insurance. 

His mission is to move professional coaching from an elite executive experience to an inclusive company-wide opportunity and to move companies away from outdated leadership styles to talent management and talent empowerment.

 I’m delighted that you could join us today, Tom.

Phil, it’s great to be with you. Thanks for having me on the show.

So, before we dive in, could you tell us a bit about your background, your international background, how you grew up, and how you gained some of your global experience?

I’d be happy to. Well, I’m sitting here today in Newport Beach, CA, which is just about an hour south of Los Angeles. So, if you want to put a pin on a map for where I’m sitting today, you’d find me just south of LA. 

But my journey began internationally. My parents were both in Athens, Greece. I was born in Athens, and at the age of 18, I did have the opportunity to join the Greek Army, which I respectfully declined, and went to college instead. But before that, we lived in London for about a decade in my childhood before we moved to the States. 

So, my father was always involved in international business, shipping, and trade, working for airlines all over the world, and I believe that as I grew older, I developed an interest in these fields as well. As a young boy, I was interested in business, and as I progressed through college, and graduate school, and finally started my career with that same international eye.

And Leggup is international. It’s a coaching platform, but apparently, you’ve got coaches from all around the world. Is that correct?

That’s right, Philip. So, LeggUp is a professional development and coaching platform designed for the next generation of employees. We are very focused on providing an inclusive and diverse option for employees around the world. And so, a lot of our customers are in the US, but we certainly have customers and coaches on international soil, and so we now serve 20 different countries. Our coaches speak ten different languages, and that serves our international community quite well.

And can you give some examples of what countries you’re in and perhaps some issues dealing with coaching in different countries?

It’s primarily global in Canada and the European Union. We have coaches in Australia, New Zealand, Japan, and India. So, I believe we have a good global distribution. And Canada brings up a great example because it’s so close to home for us here in the US, but it is an international country. So, when we think of Canada, what we tried to imagine when we arrived was what does this look like? It’s going to be too early to enter Canada? What are the watch outs? 

And I think one of the things we did poorly was … Do you know? Perhaps not. Understand that the Queen’s English is very important to Canadians, and you’re going to have to add a lot of “u”s  into your vocabulary as you go into Canadian English, which is primarily the Queen’s English from the UK, which is different from American English 

You mean, U, the letter in spelling.

I do. That’s exactly what I mean. and so on. If you’re an American company and you’re thinking, it’s just so easy to enter Canada: they speak the same language and they’re just nicer. And there may be some truth there, but in terms of spelling and changing your documents or your website, etc., there is an expectation that you certainly are in Canadian English, spelling-wise.

I run a translation company, and since I’m in the language business, I’ll ask you a question and see if you know the answer. In Canada, what is a hydro bill?

What is a hydro bill?

You get an invoice every month from your hydro company. What is that?

I’m hoping you’ll tell me, Philip.

So, hydro means water in American English, right?


In Canadian English, your hydro bill is your electric bill. 

There we go.

So, there’s one place one could stub their toe when heading into Canada. I think the other one that’s perhaps very simple, and not everybody thinks through this, is that when we invoice our customers or when we put proposals on the table, very simply, here’s a proposal for goods and services in Canada, you’ve got to do the translation into Canadian dollars. You can’t offer a package of services or products. and say, “Here’s your U.S. dollar invoice.” It doesn’t work that way. It makes you feel foreign instead of making you feel local, which is advantageous for your company.

Well, in any company, in any international situation, it’s always beneficial to appear local.

Many Mexicans, by the way, think Coca-Cola is a Mexican company. Just because it’s so omnipresent in Mexico and they do such a great job branding it locally. 

Can you give us some examples of some great successes that you’ve had in your coaching and international coaching?

I think one of the things that we’ve been successful in doing is making sure that we do localize our coaches. So let me give you an example of what I mean. It’s fantastic to have a US-based employee working with a coach in Spain who speaks great English and has a different take, and that’s OK and supported by our platform. 

But I think there are some nuances in business that you want to look to localization for. One of those is understanding the local management styles and the local structures within organizations. And so, one of the successes we’ve had is taking folks that are in Switzerland and giving them coaches that understand the Swiss culture and the varied languages there in Switzerland because they speak German, French, and a little Italian. 

And I think understanding that and putting coaches around people that are in that space makes a lot of sense because taking an American coach and having somebody try to support a Swiss makes a lot of sense nationally, for example. They don’t understand the nuances of that culture. I’ll give you one example that we ran into. Certainly, in Switzerland, they are known in American culture as making great watches, you know, beautiful timepieces. They’re known for their wonderful trains. And of course, you know the Swiss Alps that we see on television, and it’s all true, all true. 

But one of the nuances of Swiss culture is that you absolutely cannot show up late. There is no excuse for showing up late, and of equal value, you cannot show up early. So let me give you an example: If we’re all in Switzerland and we’re going over to a friend’s house for dinner, dinner’s going to be at 7. We’ve been asked to arrive at 7. You can wait outside if you arrive at 6:56. You wait on the sidewalk, and you look at that beautiful Swiss watch that will tell you exactly what time it is. And then at 7:00, not 7:01, you walk up to the door. And you, you knock or ring the doorbell, which is very much a part of Swiss culture. And one more thing, if you didn’t know, trains are always on time, so don’t be late.

Yeah, that’s fascinating. I did not know that about Switzerland. That is fascinating. What about, I guess, some major differences between coaches and different coaching styles or different countries? What have you encountered there?

Let’s start with the similarities, because it’s always nice to have things that feel familiar, and I think one of the nice things in the coaching space is there’s a large global organization called the International Coaching Federation which is sort of the governing body of ethics and values and continuing education for this emerging profession. There are 50,000 global coaches in the world. And the ICF does a beautiful job of having local chapters and then also providing a platform where these coaches get the same types of training around how to deliver coaching, how to be effective, human-behavior type science. As well as all of the ethical components that are so important to all of us when working in privacy and working with people. We have access to our personal information.

So that’s how we’re all tied together through this sort of association, I think how they’re different is that coaches within each given market will have their style, they’ll have their methodology, and they’ll understand the local business and the culture of the companies that they operate within. 

So let me give you an example. You know, we were chatting about how, for example, in Japan, we would never match a young female coach to a very senior male executive because, culturally, in Japan, that just won’t work. So, what we need to do is match somebody of equal generation. And typically, the same gender or perhaps a male gender in this example, so that that culturally will be a match versus perhaps my original example wouldn’t work.

In the case of Japan, China, Korea, or East Asia, people are much more reluctant to share their business and some mistakes, let’s call them. I mean, they are mistakes because there’s a tremendous need to save face, and so one doesn’t like to admit to doing anything wrong. So, in this case, how do the coaches cope with that? Because to be an effective coach – I assume all these are in the business environment – you need the client to be open and frank with you, the coach, about issues that are going on. But do you find, or do coaches find, that their Asian clients are less willing to share difficulties?

I would say that you are 100% correct on that. 

In addition, in the East, and particularly in India, Japan, China, and Singapore, as you said, people don’t want to admit mistakes. But in coaching, you’re not looking for people to admit mistakes. What are you looking at? It is for them to self-identify that they could do things differently and that doesn’t work. Something was wrong before; the work I’ll do in the future may be slightly different because I now have more information. 

And so, I think that’s a key principle to ensuring that people don’t feel like they’re being attacked or something along those lines. This is a violation of their value system. Whether that’s their personal or their cultural value system, we’re very thoughtful about how we do that.

Now for our science. And all of our intellectual property is subjected to productivity and well-being assessments. And it’s done in a way that helps support the growth of an individual, no matter if you’re in some sort of eastern or western culture.

That’s fascinating. And do you coach in the Middle East as well, or in Arab countries?

That’s a great question. We’ve had a couple of inquiries from the Middle East, but we have not actually on-boarded an account in the Middle East, and there are differences there obviously based on a variety of factors, one of them being religion and location.

Yes, very much so. What about Latin America? It is traditionally not always, but traditionally it’s a very, top-down, macho culture. And I guess it’s the same situation where many of the senior executives probably would not take well to a female coaching them.

We haven’t explored Latin America primarily because it’s driven by those characteristics that you just highlighted; it’s not a rich coaching market. The largest coaching markets in the world are the US, the European Union, Canada, and Australia. So, we focused our efforts there, but we do serve our customers. We have some folks in Mexico who are coaches themselves, but we may not have any customers on any sort of Latin American soil today.

What about cultural issues? Either similarities or differences between how, for example, an Indian coach might serve a client versus one from Mexico, for example. 

Well, I think we all have our preferences and our backstories, Philip, whether it’s you on the East Coast and me on the West. Right, perhaps the East Coast and West Coast, even in the United States, look at things slightly differently, and from that, we create our own culture in our communities. 

You know, Philly is different from New York. That’s different from Boston, and that’s different from LA, right? And certainly, Dallas, right there in the middle, is going to be a little different from all of those. And so, we sort of pick what’s familiar to us. 

It’s no different globally, right? So, if you just think about the US as a microcosm of different cities having different looks and feels, now just expand that into different countries having different looks and fields, and it sort of makes sense in that way. 

And so, for us, when we look at expansion, what we’re looking for is people that are familiar with that localization of the product. So, we want Canadian coaches to coach wonderful Canadian employees, but that doesn’t limit us from saying, “My goodness, we have some terrific coaches in Mexico, and somebody wants to speak Spanish in their coaching. They can select somebody from Mexico,” and they do that based on language preference as well.

In terms of coaching styles. If an Indian coach is coaching an Indian client, does that differ much from, let’s say, a German coach coaching a German client?

It does, yeah. 

And then there are those two great examples because they’re very extreme. And so, let’s just unpack that a little bit. So, if an Indian coach understands the culture of India where they don’t like to admit mistakes and they certainly want to put on a show, good face. And so, they’re going to understand that, recognize it, and coach in a way that doesn’t put the person on their heels going through the process. And these are nuances. These are the ways you phrase questions. These are the ones. This is the feedback that you give, and coaches are trained in this methodology and understand it. 

And then in Germany? You’ve got to be a little more direct. If you’ve had conversations with German leaders, you know that they do not have a whole lot of time for small talk. Most of them want to get right to the point. They want to know that you’re trustworthy and competent, and they might want to move quickly through a process. They don’t have a lot of time for fluff. They’re also a lot more top-down than we tend to find as well. 

And so, you’re going to have a much more frank and direct conversation if you’re a German. If you’re an Indian coach with a German leader, then you are, perhaps, an Indian coach with an Indian leader, and we are generalizing a little bit here, right? So, do I want to add that? “Out there,” we were making some generalizations. This isn’t all-encompassing, of course. We all have different human characteristics that drive this for us.

One of the management styles in the United States is empowerment, where a senior is a senior leader, CEO, or senior vice president and, in general, delegate and try to trust the junior managers to either figure out how to solve an issue or at least trust them to. The juniors implement whatever the challenge may be in contrast to Europe, and certainly in India too, in Asia and so forth, it’s much more top-down where the senior managers make the decisions and the junior managers are not expected to make a lot of the decisions, and are expected to implement what the higher-ups tell them. 

So, does it ever occur, for example, that an American coach might suggest, let’s say, to a German or Frenchman or a Spaniard – but not a Brit – that here is another way of structuring your company or another way that could be effective. Or does that mean that these management styles do not cross cultures or borders?

I think you’re right about the management style. One of the things that you’ll see in the US is this empowerment movement, and I host a podcast called The Talent Empowerment Podcast. This ties directly into what you were saying, Philip, and it’s all about elevating leaders so that they can elevate their teams, and that’s exactly what’s going on in the US, and I believe you mentioned it briefly in the UK as well, and when you venture into Mainland Europe, you do still have a top-down, industry model. I think that will change over time. 

So, to answer your question directly, coaches in the US, we understand that, but they’re trying to give the best advice for the individual in a private setting, right, and that will mean to the employee, hey, look, these are the cultural norms within your company that may be different than what you and I are talking about today, Phil. 

The same thing will happen in Mainland Europe here. Here is some advice. Here’s some conversation on how you could fix this, but it needs to be within the call, in the context of how your company operates and what your company culture is within the company, not just your societal culture but your culture within that company. 

Because there are certain things you could get away with in one German company that you certainly could not get away with in another German company that might be in the same industry, simply because cultures are so different within a company structure and so on. All of those nuances are considered in these coaching models, and it’s important that you have the right coaches that understand this because you have to source through 50,000 coaches out there in the world, and there are not 50,000 great coaches in the world. 

So, part of being a platform is being the principal and making sure that you’re hiring good teachers and weirding out those who don’t understand these cultural language localization competencies, as you mentioned, preferences that apply in your example to Mainland Europe also apply to Australia. 

But please understand that they also apply in San Francisco and Dallas.

And New York, so very much so. 

If you had the chance to give your current self some advice from the past, what would you tell yourself now?

I think this one you hear from a lot of entrepreneurs, and it’s no different from me. 

Relax, everything is going to be OK. I think that’s the advice I would give myself. You know, take a step forward, and step forward, and step forward. Because it’s going to be OK.

And we tend to most of us, certainly, entrepreneurs or business folks, tend to put more pressure on ourselves than anybody else can put on us. And that’s just the nature of who we are as people. And so, I would tell myself to relax, that everything is going to be OK in the end. And I’ll tell you, I still tell myself that I’ll tell my future self five years from now that everything is going to be OK. Just keep pushing forward.

Well, you’re also in Southern California, so you’ve got the image of the reputation of surfing. In the afternoon, anyway.

So yes, that’s right. Although I have only surfed once in Hawaii on vacation on a longboard on a wave that was, I don’t know, 12 inches high, after some wonderful surf instructor taught me how to do it. So that was the only time I’ve ever surfed a handful of years ago in Hawaii.

So, you do work during the day and don’t just take off on the beaches in the afternoon? 

I do. I’m like many fellow entrepreneurs, this is. I work half the day, about 12 hours during the week, and then half the weekend, about 12 hours the weekend. And you know that that is the life of people building things. And it’s a life I chose. And, you know, for me, I’m very grateful for it. I get to speak with and talk to people all around the world, which enhances my network. It enhances my learning and understanding of how things work.

It’s wonderful. Well, on the subject of what you do during the times you’re not working in your so-called off hours: What gets you excited? What do you enjoy?

Well, for me it’s very simple. I have a large family at home and kids of all ages, and I love attending my kids’ events and just spending quality time with my family. But you’ll find me in the kitchen, so my way to unwind and relax is that I love to cook, and that, for me, is relaxing and it allows my mind to settle down, my hands to move, and my creativity to flow, and that’s a space that doesn’t take too much time, like four hours playing golf, which I still love but don’t get to do as much anymore. 

Cooking is also a relaxing activity for me.

That sounds marvelous. Well, when I next come to Southern California, I will meet your family and have a home-cooked meal. Thank you.

Come on over, Phillip. We’d love to have you. We’ve got a big table, and we’ll save perfectly a spot for you.

It sounds great. Before we close, is there anything else you’d like to share?

Well, I think as long as people are thinking about going international or they’re already international, just try to make sure that you understand what loss of control you may have in different languages, different cultures, or countries within your brand setting. So, the one thing I’ll give you is an example: we call our product in the United States “Talent Insurance,” and in French Quebec, they want to call it The Show Has Talent Assurance, which doesn’t have quite the same ring to it. So, you know, one of these things is OK, but you just need to make sure that as you’re branding globally, you’re thinking about the cultural differences and how those impact where you want to take your brand.

Very true. Thank you. That’s a very great insight and thank you so much for your other wonderful insights about doing business in other parts of the world and different cultural issues as well. Thank you, Tom, for joining us.

Philip, thank you so much for having me, and best of luck to everybody as you look to expand or maintain your business internationally.

This has been Phillip Auerbach of Auerbach International ( . Please join us again next week for another edition of Global Gurus and their stories of international business.

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