My Grandmothers’ 17 Step Checklist for Winning at Sales and Life


Both my grandmas came to America with nothing. They had to work hard for a better life.

Sales works the same way. Your prospects owe you nothing. And if you want to be successful in business, you need to take massive action.

In this post, I will share my ultimate checklist for winning at business (and life) — curated by life lessons I’ve learned from both of my grandmothers.

What can the life of an Italian Grandma teach you about sales?

You’re likely wondering what Italian grandmas know about sales. And while neither of them ever studied sales or marketing, they both taught me immense amounts about life.

My life would not have been the same without my two grandmothers, Luisa & Crisia. So, before I go on, let me tell you a little more about my two grandmothers.

Grandma Luisa:

My grandma Luisa was the chef of her own Italian restaurant for 30 years. She worked 12+ hours a day, 6 days a week. From her I learned what it takes to have an entrepreneurial mindset in sales.

Local newspaper featuring DiNardi’s Restaurant – 1991.

Grandma Crisia:

My grandma Crisia worked as a seamstress in various factory jobs in the Bronx, New York. Despite never learning English, she was a highly proficient Spanish speaker (outside of Italian). She passed away in 2018 after a tough battle with Alzheimer’s.

Grandma Crisia and I sharing a moment together – 2016.

Both of my grandmothers taught me to practice gratitude in my daily workflow. They never took anything for granted, and they appreciated the positive micro-moments within each tough day — like having morning coffee with the family.

They lived life to the fullest and had a lot of wisdom to share — wisdom that has helped me in every aspect of my life.

Now, it’s my turn to pass their wisdom on to you.

My Grandma’s Checklist for Winning at Life and Business:

  1. Be likable.
  2. Be authentic.
  3. Be disciplined.
  4. Be organized.
  5. Be adaptable to change.
  6. Become numb to rejection.
  7. Keep your promises.
  8. Never make excuses.
  9. Never worship money.
  10. Prioritize education.
  11. Prioritize family.
  12. Prioritize sleep.
  13. Always make time for your passion.
  14. Say less than necessary.
  15. Choose your friends wisely.
  16. Greet people with warmth.
  17. Part ways, with love.

#1 Be Likable

My Grandma, Luisa DiNardi, had a warm, infectious energy that was undeniable. She would always greet longtime customers by name, always in her signature white apron (often not so white from cooking all afternoon).

Everyone loved my grandma, not because of her cooking ability but because of how she made people feel. She didn’t have to try. She was naturally likable.

This energy impacted everyone that visited her restaurant and kept people coming back for years.

This is a Facebook message I received from a guy who used to work at my grandma’s restaurant in the 80s. He looked me up on Facebook to offer condolences after hearing about her death.

Grandma Luisa and Steve – a former employee at DiNardi’s restaurant.

Being likable isn’t rocket science. It often just involves you being yourself and being… well, nice (shocker, I know).

That being said, there are a few things you should remember for a business environment.

Listen actively during meetings and resist the urge to speak out of turn. That means avoiding being on your phone or your laptop while others are speaking.

Don’t challenge everything just for the sake of being a challenger.

Promote inclusivity and invite your most introverted colleagues to speak and share their ideas in team discussions.

Really, though, being likable boils down to one thing — consider the goals and priorities of others.

Remember, the world doesn’t revolve around you.

#2 Be Authentic.

This fits perfectly with being likable, but Grandma Luisa and Crisia were both unapologetically authentic.

I credit much of my business success to this important trait.

In business, but especially in the world of B2B sales & marketing, it often feels like folks are putting on an act (or trying to be something they’re not) — I often share videos of me playing the guitar on LinkedIn.

Why would I do this?

I lead demand-growth-marketing at Nextiva, a leading cloud communications company. A video of me playing the guitar has nothing to do with virtual phone systems at all!

That’s the point.

Business is personal now. People want to do business with people they can relate to, not corporate robots.

The key here is to always be yourself.

#3 Be Disciplined.

For grandma Luisa, preparation and discipline were the cornerstones of being a successful restaurant owner.

If fresh-dough wasn’t made daily, pizza wouldn’t be served that evening. And if customers weren’t happy, they wouldn’t return. And without happy customers, there wouldn’t be any money to feed the family.

Both of my grandmothers would wake up every day at 5 AM. There were no vacations. No going out to clubs. No fancy dinners. No partying. No watching weekend marathons of random Netflix shows. It was all business, then family (not saying I completely agree with this, but it was reality).

It’s easy to see how discipline can benefit your career, but it’s a lot harder to actually do it.

Start by avoiding digital distractions. Only check email at certain times of the day. Only allow a few browser windows open at a time. Set my iPhone to airplane mode. Wear noise-cancelling headphones. And consistently decline irrelevant meetings.

Next, you need to avoid real-world distractions. Remove all clutter from your desk and surrounding areas.

Being disciplined is all about playing the long game! Prioritize long-term organic growth over shortsighted gains.

Politely say no to things that don’t align to your core objectives and key results.

Add due dates to projects you’re working on to keep you focused and stay on track. Try a tool like Asana (or any great alternative) to prioritize your tasks and deliver them on time.

And probably my number one rule for staying disciplined — don’t wait until the last minute to get important sh*t done!

#4 Be Organized.

Both my grandmothers, Luisa & Crisia were clean freaks. Every detail in the house was spotless. The dishes never piled up in the sink. And each item was stored in a specific place.

You could ask for the most random item, like a rubber band, and they’d know exactly where to find it.

Attention to detail is a highly underrated trait in business. You’ll be surprised at how much easier things are when your life has organization and clarity. If you have a messy workspace, messy inbox, and a messy workflow — it will bring messy results.

Don’t be one of those people that rely on email communication for everything. Important. Crucial details are bound to get lost in the ruffle.

I would highly recommend leveraging a project management tool to stay organized, keep all your communication centralized, and store all pertinent notes and documents in one place.

#5 Be Adaptable to Change.

Imagine moving to America from a foreign country and not speaking a word of English! That was reality for Luisa & Crisia. They had to figure it out on the fly.

That’s why I admire the story of Nextiva CEO, Tomas Gorny. He came to America from Poland when he was a kid and didn’t speak English.

He shares the same mentality as both of my grandmothers — perseverance, discipline, and never giving up.

Given the current global pandemic, companies must also practice unprecedented adaptability to change as employees across the globe are forced to work from home for the foreseeable future.

While this is a challenging time for all businesses, you have to adapt and continue moving forward.

I don’t have any snappy tips for this one, because at the end of the day, this one is a choice. You need to choose that no matter what happens, you’ll find a way to make things work.

Failure isn’t an option.

Choose your mindset and make something happen.

#6 Become Numb to Rejection.

Outside of my profession as a digital marketer, I’m a music producer and songwriter. It used to be a dream of mine to be signed to a record company and earn a publishing deal.

It almost happened. I was invited to Atlantic Records for a series of meetings with label executives. And then, without explanation or closure, they ghosted me.

I was devastated.

During that painful moment in my life, I thought about my grandma Crisia.

When she first came to America, she was unable to get a job because she couldn’t speak English. She couldn’t do basic things, like get a driver’s license, due to the language barrier.

And then it hit me — my experience with rejection was insignificant in comparison to hers.

Rejection is nothing new in sales and marketing. In fact, it’s the norm. And if you’re going to be successful, you need to be numb to it.

Today, whenever I get rejected in life — whether it be personally or professionally, I just think of what my grandparents went through when they first moved to America. And suddenly, my rejection seems a lot easier to handle.

Ultimately, I turned my rejection into passion. I started blogging about my perilous journey in the music business. I published deeply tactical articles on my website, such as “How to Become a Songwriter and Make Money” – this allowed me to find my passion for SEO, as I realized these articles were growing in popularity due to being found in search engines.

#7 Always Keep Your Word..

For Luisa & Crisia, deadlines were not optional. Missing a deadline meant losing money. If a deadline was missed, the consequences would be severe.

Most sales & marketing professionals do not treat deadlines as seriously as they should.

Project deadlines are missed frequently in today’s business environment, and nothing bad really happens (most of the time). Usually, all that happens is you decide to push back the due date a few weeks, and everything is okay.

But sometimes that doesn’t cut it. And when it doesn’t, it can cost you big.

A deadline is a promise. It’s your word, and that is something you don’t want to tarnish. It can take a long time to build a good reputation, but it only takes a minute to lose it.

#8 Never Make Excuses.

When I was young — around 10 or 11 years old — my visits to grandma’s restaurant were no longer only to eat but to work.

My grandma would gently explain to me how to wipe down tables, how to shadow servers, and how to ask patrons if they were interested in having an extra serving of bread. She even trusted me with the cash register.

One time, I miscounted a customer’s change and gave back an incorrect amount of money. It was an honest (but careless) mistake.

My grandmother made sure a valuable lesson was learned, though.

To make up for the lost amount, I had to do extra chores, which meant staying late.

She was fostering in me a no-excuses mindset.

It didn’t matter that I was just a young boy. I made a careless error and needed to learn from my mistakes.

It’s the same in sales. If you’re getting rejected like crazy, or missing your numbers, don’t make excuses about it!

Figure out what you’re doing wrong, and improve. No excuses!

#9 Never Worship Money.

This lesson comes from grandma Crisia. She was truly a woman who appreciated the simple things in life — like sitting on the porch and catching the afternoon breeze or taking an evening walk with my grandpa.

Grandpa Luigi & Grandma Crisia.

While the men in my family would often preach about money, grandma Crisia was the opposite.

She lived a comfortable life, minus all the bells and whistles. She worked hard, remained humble, and found happiness without the hefty price tag.

In fact, this early teaching helped me navigate a critical career decision back in 2017.

I had two job offers:

  • Offer A: Very high salary, but brutal commute.
  • Offer B: Respectable salary, but work from home.

I went with offer B, which ended up being the right choice. But if I would have chased the money, I probably would have been unhappy with a 3 hour daily round trip commute.

Chasing money — and especially tying your self-worth to it — in an industry as volatile as sales and marketing is a recipe for disaster.

Money is great but focus on the things that really make you happy.

#10 Prioritize Education.

Luisa & Crisia were forced to drop out of school and work on the farm in order to help support their families. They didn’t make it past a 3rd-grade level, and therefore their reading and writing skills suffered tremendously.

While I was growing up, my grandmas would always stress the importance of continuous learning & development. They explained that education would provide me with the skills needed to be successful in life.

It was their dream to see me graduate from college. And while I don’t believe a college education is the best measuring stick for success, earning my degree was still a proud moment for my family.

When I think about education today, I believe it’s critical to remain curious. Especially in the fast-changing world of B2B sales & marketing — you need to stay up-to-date on everything that’s happening.

I do this by reading marketing & sales blogs like:

You don’t need a fancy degree to prioritize education. You just need to get into the habit of becoming a life-long learner, especially if you want to future-proof your career.

#11 Prioritize Family.

This should come as no surprise, but Italian culture is extremely family-oriented, and a grandma’s love serves as the nucleus of the family.

Have you ever thought about what it takes to put your family before everything you do, including your own wants and desires?

Luisa & Crisia sacrificed everything for our family, and they did it with pride.

For me, I’ll never forget Christmas dinner with my grandma’s famous “Zuppa di Pesce” as the main attraction. There’s nothing like the smell of Italian food wafting throughout the house as the whole family gets together for a feast.

Family often gets lost in the hustle and bustle of work. We get so caught up in metrics, reports, and the daily grind that we can forget about what’s most important.

Given the circumstances with COVID-19, the entire world has shifted to working remotely. And given the advancements made with remote work tools , now is the perfect opportunity to save that time you would have spent commuting and repurpose it with your family.

Grandma Luisa with me and my brother.

#12 Prioritize Sleep.

Going to sleep at 9 PM was routine for both grandma Luisa & Crisia. This wasn’t optional for them. After grueling days (Luisa in the restaurant, and Crisia in a factory), I doubt they had energy for anything else.

For most working professionals, sleep often gets deprioritized. In fact, the startup culture often glorifies no sleep and hustle as a fake badge of honor.

Unfortunately, this is a direct path to burnout, and it’s a route that should be avoided.

For the good of your mental health, don’t get caught up in the hustle-mentality. Guard your sleep, and make sure you always get enough of it.

Full disclosure: sleep is something I struggle with. I suffer from insomnia, and I’m trying to figure out how to turn it around.

#13 Always Make Time For Your Passion.

For me, this is unquestionably about music. I absorbed my love for music through both of my grandmothers.

When I was a kid, they would always play the Italian classics — everything from Nino D’Angelo to Andrea Bocelli to Renato Carosone.

At a young age, I learned how to sing in Italian and play the guitar. I was always jamming out and having fun.

Despite being a busy digital marketer, I still make time for doing what I love.

I’ve even played classic Sicilian songs on my LinkedIn, in a cool series I’ve created called #MusicMondays

It can be easy to get caught up in a work-first mentality, but to keep yourself from burning out, you need to make sure you make time for the things you truly love.

This goes hand-in-hand with being your authentic self and will attract more people to you than you would ever imagine.

#14 Say Less Than Necessary.

I noticed that the men from my family would often dominate the table conversations, while the ladies were less interested.

Rather than trying to force-fit into those male-dominated conversations, both my grandmas adopted a style of communication that was scarcity driven yet impactful.

For example, while my grandfather would ramble on, I always found myself craving more perspective from my grandmother.

This lesson is also a well-known teaching within the 48 laws of power.

“When you are trying to impress people with words, the more you say, the more common you appear, and the less in control. Even if you are saying something banal, it will seem original if you make it vague, open-ended, and sphinx-like. Powerful people impress and intimidate by saying less. The more you say, the more likely you are to say something foolish.”

You can take this lesson right from the Italian-family dinner table to the executive board room. Say less, listen more, and speak with impact.

Leave people wanting more.

#15 Choose Your Friends Wisely.

Both of my grandmothers would always caution me to choose my friends wisely. They didn’t have many friends outside of the family, but the few friends they did have were carefully chosen.

In the words of motivational speaker Jim Rohn:

“You are the average of the five people you spend the most time with.”

Eventually, you will start to think and behave just like the people you hang out with.

I’m so grateful my grandmothers embedded this concept into my mind at a young age. Consciously being aware of this throughout my life has been an absolute game-changer.

Like Gary Vee says in this video:

“Audit your circle of friends. Cut one loser, add one winner.”

If you want to be successful in business, you need to hang out with successful people, or at least with people who are also committed to success.

#16 Greet People With Warmth.

DiNardi’s restaurant was a melting pot of people. And while most customers were kind, some were not. Regardless, grandma Luisa handled them all with grace and respect.

She had a special skill for making strangers feel welcome. I can’t explain exactly how she did it, but simply welcoming them with a smile and asking if they’d like to hear about the daily specials always seemed to do the trick.

I learned about empathy and compassion at an early age by watching my grandma’s interactions with her customers. She was masterful with her approach.

I’ve tried to employ this philosophy in my own life. Simply saying hello with a smile and asking someone about their day are two basic steps you can take to ease tension with a stranger.

I’ve also learned that each person has something that makes them tick. I’ve found that if I can tap into the things people are passionate about, it creates authentic connections that develop better relationships.

The way my grandma treated her patrons at the restaurant is how businesses today should think about creating authentic experiences for their own customers.

Even just being downright funny can go a long way with your fans and customers.

Wendy’s is a hilarious example of a brand that goes the extra mile when engaging with their customers on social media.

I love their brash, antagonistic approach. If you look at this particular Twitter thread, you’ll see all the raving Wendy’s supporters jumping in, eager to bash McDonald’s.

I thought this was absolutely brilliant!

#17 Part Ways, With Love.

You know those people who are awkward at saying goodbye? That wasn’t the case for either of my grandmothers.

Both Luisa & Crisia were oddly good at making me miss them as soon as I left the house.

Every time I left, I would be given a mandatory “to-go” plate of food. I’d get the biggest and warmest hug I’ve ever gotten in my life. They would inspect my jacket to ensure it’s fully zipped as far up as possible. They would watch me drive off from the window. And I’d see their protective eyes following me until I exited the driveway.

How could you not miss someone after that?

In business and sales, you always want to have a graceful exit and leave people wanting more. They should be sad to see you go, not relieved.

My friend and colleague Amy Volas preaches this point often — when you’re ending a business relationship how you do so is as important as the ending itself.

A well-delivered ‘no’ can be the difference between referrals, revenue, and relationships — or massive fallout.

As the saying goes, people won’t remember what you did for them, but they’ll remember how you made them feel.

Take My Grandmothers’ Wisdom Forward

All credit goes to grandma Luisa & grandma Crisia for the man I am today.

The wisdom I shared here can be applied to almost any business or life situation. It would take a book for me to fully share all their lessons, but these are the things that have helped me most in my career.

Not all of these things are easy to implement, but in my opinion, these lessons are crucial to long-term success in business and life.

So, once you begin to implement these in your life, it’s time to take the final step. The step my grandmothers took — sharing this wisdom with someone else.

Gaetano is the Director of Demand Generation at Nextiva. With a proven track record of success working with B2B SaaS brands, Gaetano leverages a unique hybrid of expertise in both SEO & Content Strategy to win business results. Outside of marketing, Gaetano is an accomplished music producer and songwriter. To get in touch, follow him on Twitter via @gaetano_nyc

Join Us Today

Insider access to the GTM network and the best minds in tech.

Join Us Today

Insider access to the GTM network and the best minds in tech.

Trending Now

You may also like...