Bill Dennis is an expert in cultural and generational selling, as well as cultural connecting and cultural management.

Secrets of Success with People Different than You

It is rare for someone to achieve success on their own.

Our success usually depends on being successful with an array of people.

Successfully developing a meaningful and supportive relationship with someone who is different than you can be one of the biggest challenges you face in becoming as successful as possible in life.

When someone is different than you, they can easily feel a range of negative emotions towards you.

It can be a feeling of simply being uncomfortable with you to a more extreme negative feeling such as seeing you as outright conflicting with something that is particularly important to them.

That includes such things as not aligning with their values, beliefs, viewpoints, expectations, unconscious and conscious biases, and etiquette “do’s” and “don’ts” to name a few notable features that make us who we are.

An effective way to understand why you are not successful with them is to realize each of us live in a personal “Comfort Zone.” It consists of our powerful cultural, generational, and personality style values, beliefs, values, viewpoints, expectations, unconscious and conscious biases, and etiquette “do’s” and “don’ts, etc.”

Our “Comfort Zone” is the only “Comfort Zone” we usually know and understand.

It “who we are” and determines how other people experience us.

When you are trying to engage with someone different than you, you are unintentionally not engaging with them according to their “Comfort Zone.”

They feel that you cannot relate to them. As a result, they will lose interest in you.

The secret to you becoming successful with them is for you to become aware of, and understand, how you are different than them. That requires you to listen carefully to them and mirror their body language and tone of voice.

Most people in Western cultures like the USA and Canada are culturally programmed to speak significantly more than to listen.

Our predisposition to speak more than listen can easily self-limit our success with people who are different than you. When you speak most of the time, you are expressing your values, beliefs, viewpoints, etc. No doubt, some of their values, beliefs, etc., will be different than yours.

To be successful with them, you need to hold back from jumping in and speaking more than them. Make yourself listen and find out what is important to them about whatever it is you are talking about.

Not only will you come to understand them more, but by careful listening to them they will appreciate you as a being respectful. They will usually reciprocate by respecting you more. Obviously, mutual respect is essential to building a successful with a person different than you.

Align yourself with their “Comfort Zone” is a sure way of significantly enhancing your chances of being successful with people different them you.

You will become noticeable more successful with people different than you.

Cultural and Generational Relationships

Different Cultures

In life developing a successful relationship with individuals from countries with cultures different than your own can be very important to your success. It can also be very challenging.

The only way to develop a successful relationship with someone from a different culture is to know and understand their cultural values, beliefs, etiquette, assumptions, and rules.

It is important to fully recognize how much the USA’s and Canada’s demographics have changed over the past 20 years or so. It will be demographically changing even more in the future. 

Individuals naturally align, accept, and trust people more easily when they are from their “cultural group”. If someone is from a different culture, they will accept and trust them more if they demonstrate that they have taken the time to gain a reasonable level of knowledge and respect for the other person’s culture.

If you show that you have not made the effort to understand the other person’s culture, you will naturally and automatically want to do business “your way”.  That is the only cultural you know. You probably will not even realize you are behaving only “your way” and not the other person’s “culturally appropriate way”.

The culturally-different individual will note your lack of appreciation and respect for their “cultural way”. They will tend to see you as being culturally insensitive – if not more seriously being “culturally inappropriate”.  Your lack of “cultural appropriateness” will significantly limit how successful you can be in developing a relationship with them.

Canadians and Americans are culturally programmed to develop a relationship with someone much faster than individuals from the vast majority of other cultures of the world.  They will spend 3 to 5 minutes “getting to know someone” and then want to “get down to business”.

That approach works fine when dealing with another native American or Canadian. But is a seen as poor, if not aggressive or insulting, to individuals from the majority of other cultures of the world.

It is a matter that the approach of each individual is culturally very different and is the “right” way according to their culture.

We are all strongly culturally-conditioned on how we see things as being “right” or “wrong”.  Each culture has its own unique perceptions and behaviours as to what is “right” or “wrong” in certain situations.

To individuals from the vast majority of cultures, being “culturally appropriate” is far more important to them than how important it is to mainstream Canadians or Americans.

Individuals usually do “what is right” according to their culture but what is “right” in one culture might be perceived as rude, aggressive, or just plain “wrong” in another culture.

Our cultural beliefs, values, etiquette can stir deep emotions.

For example, to someone who grew up the USA or Canada, when they are speaking with someone who consistently “looks them in the eye”, they see that individual is seen as being trustworthy.

However, to individuals from other cultures, such as Japan, someone looking them in the eye for any length of time is seen as being rude, overly aggressive, and/or disrespectful.

Another important area of developing a successful relationship with someone from a different culture is making a good “first impression”.

While creating a good first impression is always important when starting a relationship, creating a positive “first impression” with individuals from a different culture is more important than it in Canada’s culture.

Research has shown that if someone is not culturally trained, they will make three cultural mistakes in the first minute to 1 ½ minutes of meeting someone from quite a different culture.

The culturally different person will likely forgive you for the first mistake you make saying to them “oh well, s/he is not from our culture”; the second cultural mistake you make, say, 20 seconds latter is not as quickly forgiven. They will say to themselves something like “not again” and start to write you off as not being very relevant to them. When you make the third “culturally inappropriate” mistake shortly thereafter, they will usually “write you off” as not understanding them and not caring about them.  You are seen as pretty much being self-focused and therefore irrelevant. They will keep their thoughts about you to themselves. They feel it would be “culturally inappropriate” to tell you how they feel about you.

Conversely, if you know how to be “culturally appropriate” with them, they will see you as knowledgeable and respectful of their culture. They will appreciate you for your cultural sensitivity and awareness.  As a result, they tend to want to see if a meaningful relationship can be established with you.

To the individuals from the vast majority of cultures, the relationship process is to establish a trusting relationship first and foremost. Then, and only then, do business with an individual.

It takes significantly more time to develop a relationship with someone from most other cultures than is the case in Canada or the USA.

Why should you make that extra effort?

Because once a culturally different person has a relationship with you and begins doing business with you, they will typically send a lot of referrals from their “cultural group” to you. We are not talking about 1 or 2 referrals such as you might obtain from American or Canadian clients. We are talking about a lot more referrals. You will also find that referrals from most cultural groups of different countries will be very loyal customer thereafter.

Different Generations

The four generations have very different values and developing a successful relationship with individuals from each generation requires very different approaches.


Among other requirements, developing a successful relationship with Traditionalists requires that you to show a reasonable amount of formality.

Baby Boomers

One of the most important things you can do to developing a successful relationship with Baby Boomers is show that you admire the level of success they have achieved in life.

 Generation “X”

Generation “X” is the first generation where you find a strong value placed on one’s self.  Being self-reliant is seen as essential.

To break through their skepticism of depending on others, among other things you can do to develop a relationship with Generation “X” individual is show that you admire their “Get-a-Life” attitude.

Generation “Y”

Sometimes called the “Millennial Generation”, Generation “Y” also places a strong value on themselves.  Yes, they are a “Me” generation.

They believe they can do pretty much anything using the power of the Internet.

They will respect you if they decide that you deserve to be respected. You need that respect to develop a successful relationship with them.



Connecting with Different Generations

Connecting with people from a different generation than your  generation can be important for you since you want to achieve a solid relationship with them.

This can be difficult to do since each generation has a very different generational culture. If you do not understand the “Do’s” and “Don’ts” of the person who is from a different generation, you can struggle to connect with them since what is appropriate to one generation can be offensive to someone from a different generation.

For example, if you are a baby boomer, trying to connect with a Generation Y individual, your lack of enthusiasm, understanding and/or comfort using social media and the internet can make them see you as “old fashioned”. That may result in them not being particularly interested in connecting with you.

What is important to a Generation Y person is someone who enjoys  internet service and is comfortable discussing such topics as Facebook and Skype.

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Cultural Competency Training and Customer Service

Significant customer service “competitive advantages” in the marketplace exist for Customer Service managers who embrace cultural awareness training for themselves and their staff.

Many Customer Service managers and their staff in American and Canada are currently experiencing multi-cultural challenges they are not trained to understand and address.

Most of us grew up mono-cultural. We understand and function successfully in the one culture we know – our own culture.

Of the 190 countries of the world, relatively few have cultures somewhat similar to Canada – 15 countries at most.

We are all very culturally conditioned. One’s culture is ingrained strongly in them. One’s culture largely determines how we perceive, evaluate, and respond to things.

People from different countries are typically significantly culturally different. It is not a matter of one culture’s way being “right” or “wrong”. Rather, it is a matter of each culture being different in what they value, believe, expect, and the way they behaviour.

Customer Service managers are increasingly finding themselves responsible for building and managing a multi-cultural staff of employees  Individuals from each culture have a unique set of core values, beliefs, perceptions, expectations, etiquette rules, practices, and attitudes.

Customer service staffs are experiencing the challenges of serving prospects and customers from a wide array of cultures.  People from each culture want customer service aligned with their cultural values, beliefs, and expectations. After all, that customer service is normal to the “native culture” they grew up in and has had a significant impact on making them “who they are”.

Cultural awareness training will result in you and your staff becoming significantly more successful with individuals from a variety of cultures. People culturally different than you will appreciate you being sensitive and respectful to their cultural preferences … rather than wanting to provide service only in “your way”.

People from a different culture usually do not expect you be as knowledge about their culture as someone who grew up in their native country. If you show that you are doing your reasonable best to be “culturally appropriate” with them, they will trust you much faster than otherwise. People from the vast majority of cultures of the world are from a slow trust culture and they only do business with people they trust and with whom they have established a good relationship.

Once that relationship is established, they will typically be loyal, long-term customers.  As well, they will refer to you a lot of business from their cultural group.

In net, cultural awareness training can offer Customer Service staff important cultural competitive edges in customer service.


Building a Relationships with Different Generations

Each generation has very different characteristics and values which result in unique emotions and behaviours.

To develop a successful and lasting relationship with people from the different generations, a lawyer needs to know how the generations differ, why they differ, and how to best approach develop a relationship and earn their trust.


These individuals are generationally conditioned to be conservative, frugal, and silent.

They are conservative because of the rigors of the extremely tough times they experienced as they grew up and survived day-by-day.

They are frugal since they lived through fear and painful shortages of the Great Recession and/or World War II. Making sacrifices and delaying benefits was the “way of life” during those times.

They feel most comfortable being silent.  The Great Recession and, even more so, being in the military structure taught them to “hold their tongue”.

Traditionalists are typically very disciplined individuals. A person with authority was not to be questioned. Everyone’s word was above question – their word was “their bond”. Their handshake sealed their bond with you.

To develop a successful relationship with Traditionalists, show respect for them as well as other people. Being rather casual with them can be interpreted as being too familiar.

Baby Boomers

Baby Boomers have grown up and lived through a wide variety of life-shaping events such as double-income families, consumerism, and the invention of television.

There are lots of Baby Boomers in Canada (9.6 million according to the 2011 Census – 27.9% of the population).

Baby Boomers were very hard working. They have virtually “lived to work” because they were so driven to succeed. They highly value the good things in life and want to display that they can afford the best.

Unlike Traditionalists, Baby Boomers want to be admired for their success and appreciated.

To develop a successful relationship with Baby Boomers, show you will “do whatever it takes”.

After all, that is what they did to succeed.  They will tend to expect you as their lawyer to “do what it takes” to successfully win their legal challenges.

Generation “X”

There is a relatively small population of 2.9 million (8.5% of the population).

Generation “X” typically refuse to follow in their parents footsteps of “living to work”.

To many of them, it is foolish to be dependant and loyal to a company. They saw their hard-working, company-loyal parents get laid off by a firm “downsizing” during periodic rough economic times. They are typically skeptical of things.

Generation “X”  highly value taking care of yourself and your family first and foremost and live a work-life balance – namely  “work to live”.

They see having up-to-date computer skills as significantly enhancing their ability to be self-reliant – the key to living a good life.

To develop a successful relationship with Baby Boomers, show you are self-reliant and have computer know-how.

Generation “Y”

With a population of 9.9 million, they are the largest generation currently in Canada (28.7%).

While not as skeptical of organizations as Generation “X”, they are similar in that they are “Me” focused. They typically take care of #1 first.

They often believe they are special and feel entitled because that is how they were treated at home and in school.

They highly value and want immediacy. After all, they grew up getting answers fast on the Internet.

They want to be respected and are self-assured … although the current high level of youth employment is hurting their assumption of self-importance.

To develop a successful relationship with Generation “Y”, show you respect their opinion, have social media skills, and use up-to-date technology. They will trust and respect you if they think you have earned it –it typically will not be automatic.

Understanding Builds Trust

When interacting with individuals form different cultures than yours, people tend to highly underestimate how much differently these individuals from a different culture “see things” differently.

This is a big mistake. It is often the main reason you experience cross-cultural relationship breakdowns.

To be successful with individuals from different cultures, you very much need to understand what their values, beliefs and attitudes. That is the first step to earning their trust. 

Showing respect for their culture is critical to gaining their trust.

If you do, they will tend to appreciate and respect you for taking the time to understand them and respect their culture.

Without that trust, they will likely not be interested in building a relationship with you.


Selling to Different Personalities

Sales professionals are increasingly being challenged by the wide variety of individuals they are encountering having different personality styles.

One of the most important “competitive edges” a sales professional can develop in today’s highly competitive marketplace is to become significantly more aware, sensitive, and knowledgeable  the four types of personality styles.

Understanding and being skilled at interacting with individuals with different personality styles is essential in winning profitable business. After all, people typically buy from sales professionals who have a personality style like their own.


Personality Styles

Psychologists have determined there are four types (i.e. styles) of personalities and each person has a dominant personality.

Many people have two or three personality styles but there is only one style that is dominant.

Each type of personality has a preferred way they want you communicate with them.

The four personality styles:


A “Driver” is a control person.

They are interested in the “bottom line”.


An “Expressive” is a social person.

They want to be interactive and appreciated.


An “Analytical” is a technical person.

They want details and logic.


An Amiable is a supportive person.

They are relationship people.