Dennis Bowers of The Bowers Group at Compass: “Teamwork ”

Teamwork — surround yourself with a solid team. Lawyer, mortgage, insurance, assistants to make sure that they are able to answer anything and everything for your clients. Allow the attorney to talk law, mortgage to talk numbers, and so on. Be an expert in your field and allow your team to excel in theirs. As a part of […]

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Teamwork — surround yourself with a solid team. Lawyer, mortgage, insurance, assistants to make sure that they are able to answer anything and everything for your clients. Allow the attorney to talk law, mortgage to talk numbers, and so on. Be an expert in your field and allow your team to excel in theirs.


As a part of my series about how to be great at closing sales without seeming pushy, obnoxious, or salesy, I had the pleasure of interviewing Dennis Bowers.

Dennis Bowers is a leading real estate expert in Southwest Florida and Principal of The Bowers Group at Compass. With more than a decade of industry experience, Dennis built his business reputation from the ground up while keeping his clients’ wants and needs at the center of his work. He attributes his success to his value of integrity, trust, and honesty. The Bowers Group saw a record year in 2020, serving 100+ customers with more than $70 million sales volume.


Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to this career path?

I studied Exercise Physiology and have a Master’s of Science in Exercise and Wellness Promotion. I moved from Western PA to Naples in 2002 in order to work at the wellness center for the hospital in Naples. After 3 years there, one of my personal training clients sold me on getting into real estate. I worked as onsite sales consultant for a production builder until the crash in 2008 and then I worked in high-end construction through 2015 and sold real estate on the side. I came to realize that I had a passion for connecting with people, understanding their needs, and helping them find their dream home or investment property. The next year, I went full time into real estate.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

I recently traced 60% of my earnings back to my very first customer. When I was handling project management for a custom builder, a couple bought a home that we built back in the 90’s. We worked with architects and designers to rework the house and do a renovation, but he ended up tearing the house down. I managed the project and made sure the land was maintained over a two-year period. During that time, he referred me to a friend and I did a small renovation on their villa — which wasn’t a big job but I gave it my all. When I hung my real estate license, the first gentleman used me to buy a $2.3 million dollar home and I sold the original piece of land for $2.1 million. The other villa owner has referred me over $50 million in business. My lesson is, no matter what you are doing, no matter the cost, no matter what you are making, do it at 100%.

Are you working on any exciting new projects now? How do you think that will help people?

I am working to organize my first Golf Scramble hosted by The Bowers Group and Compass to benefit local charities. We want to help bring awareness and support our community’s philanthropic efforts while bringing together family, friends and customers.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There are so many people who have helped and influenced me along the way including colleagues, friends and my family. I am always learning and adapting. Tina Deady, a personal training client of mine turned mentor back in 2005, is the reason I ended up in real estate. She is the one who told me I had the “it” factor — what it takes to be successful. Tina sadly lost a battle with cancer two years ago, but she is the person who inspired me to transition into this profession, believe in myself and keep pushing forward.

For the benefit of our readers, can you tell us a bit why you are an authority on the topic of sales?

My experience and results. I am a leading sales agent in Naples and have been selling services for 20+ years now. Originally, selling personal training services to help people achieve their fitness goals, then transitioning in home sales. In 2005, I sold 100+ homes in 2 years for a builder who I was working with. I then sold and managed over $30 million in construction projects of condos and single-family homes. Since 2011, I have sold over $185 million in real estate including $120 million over the last three years.

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the COVID-19 pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

I believe that the biggest aspect right now is staying positive and staying educated. Faith over fear is the way that my family has lived through this entire pandemic experience. The fear that has spread through the world is extreme and being empathetic to those who are fearful and anxious is a must, but also helping to see that the beauty of this world is still true and just. Overall, treating others the way you want to be treated, with respect, no matter what.

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know, nearly any business a person will enter, will involve some form of sales. At the same time, most people have never received any formal education about how to be effective at selling. Why do you think our education system teaches nearly every other arcane subject, but sales, one of the most useful and versatile topics, is totally ignored?

Sales is predominately relationship building, trust and communication. I feel that a lot of that is taught through other avenues and life experiences. Yes, you will have the salesperson who is very robotic and systematic about what they say and how they respond, but being good in sales will continually be contingent upon that repeat business, referral system, and long lasting trust from your customers.

This discussion, entitled, “How to Be Great At Sales Without Seeming Salesy”, is making an assumption that seeming salesy or pushy is something to be avoided. Do you agree with this assumption? Whether yes, or no, can you articulate why you feel the way you do?

You always want to be genuine and steer away from being pushy, however everyone responds differently. I personally cannot stand a pushy or salesy salesperson and therefore do not respond to that way of selling. I respond to someone who is an effective communicator, listens to the wants and needs of the individual and then assists in finding the right product that fits the bill. At times, you may have to push to get someone to make an offer, but if the total transaction is centered around the customer’s needs and the salesperson is able to educate and illustrate how a home or a certain product fits those needs, the sales experience should be smooth, easy, and less stressful and pushy.

The seven stages of a sales cycle are usually broken down to versions of Prospecting, Preparation, Approach, Presentation, Handling objections, Closing, and Follow-up. Which stage do you feel that you are best at? What is your unique approach, your “secret sauce”, to that particular skill? Can you explain or give a story?

My secret sauce is a combination of prospecting, preparation and follow-up. My business is 85% referral and therefore the care of my customers and the trust that I build softens the other aspects of the sales process. When you have earned the trust of others, and your word, character and integrity is not questioned, you are able to sell without pressure.

Lead generation, or prospecting, is one of the basic steps of the sales cycle. Obviously, every industry will be different, but can you share some of the fundamental strategies you use to generate good, qualified leads?

I have tried online lead generation and some cold lead strategies however tried and true comes back to your “Sphere of Influence.” I double down on Sphere every day over other avenues. Call the people who already know you and will refer you. If you are authentic, honest, and bring value to your clients — word of mouth leads will follow.

In my experience, I think the final stages of Handling Objections, Closing, and Follow-up, are the most difficult parts for many people. Why do you think ‘Handling Objections’ is so hard for people? What would you recommend for one to do, to be better at ‘Handling Objections’?

Most people hate conflict, therefore handling objections is one aspect where there is going to be push back — this creates anxiety for many people. Identifying the customers hot buttons and knowing what makes them tick is the most important part. If they are analytical, give them numbers and statistics. If they are emotional, paint the picture and illustrate their family there. Speaking their “language” will help with push backs and objections

‘Closing’ is of course the proverbial Holy Grail. Can you suggest 5 things one can do to successfully close a sale without being perceived as pushy? If you can, please share a story or example, ideally from your experience, for each.

Closing in real estate is different than many other sales positions. Closing is the Holy Grail, however too many people assume that once under contract, the closing will come naturally. The reality is, from the time of contract to the closing itself is the real challenge. Inspections, negotiations on the inspections, pricing of repairs, pricing of work to be done to the home, insurance, flood insurance, mortgage paperwork, appraisals, etc. are all challenges that can come up along the way. Some newer agents feel that the contract date is the closing, but that is where the real work starts.

My #1 tip is Preparedness. Schedule everything out, know your dates and timelines, and be proactive with completing checklists. Consider all angles and be prepared to address any issues that may come up.

2) Communication with all parties ensuring applications, paperwork and due diligence is completed.

3) Transparency to make sure that all parties understand the status of and any situations that transpire. Everything is searchable these days, customers will know everything about you and visa versa with properties and websites that provide, taxes, last sale, etc. You have the most informed buyers in history right now, be honest, don’t be afraid to say “I don’t know and I will get back to you.”

4) Education. Your customers are not professionals in this business, educate them on what to expect. Put yourself in their shoes. This brings value to the table.

5) Teamwork — surround yourself with a solid team. Lawyer, mortgage, insurance, assistants to make sure that they are able to answer anything and everything for your clients. Allow the attorney to talk law, mortgage to talk numbers, and so on. Be an expert in your field and allow your team to excel in theirs.

Finally, what are your thoughts about ‘Follow up’? Many businesses get leads who might be interested but things never seem to close. What are some good tips for a business leader to successfully follow up and bring things to a conclusion, without appearing overly pushy or overeager?

A CRM (Customer Relationship Management) system is a must for the busy salesperson. Technology has helped tremendously and investing in the right CRM is key to staying organized, and adding drip emails or text campaigns for buyers and sellers is also a great tool. Sending personalized letters and gifts to past customers and referral partners is also imperative in this fast-paced market. Being top of mind is key for repeat business. Handwritten cards are a staple that are under-used in today’s world but go a long way.

As you know there are so many modes of communication today. For example, In-person, phone calls, video calls, emails, and text messages. In your opinion, which of these communication methods should be avoided when attempting to close a sale or follow up? Which are the best ones? Can you explain or give a story?

To close a deal, I think it has to be a phone call or in-person to be the most successful. You cannot feel emotion or tone in text messages or e-mails. I like to ask people what they prefer (text, email, phone, etc.), however, to close the deal, you need to feel and hear the other person.

Ok, we are nearly done. Here is our final “meaty” question. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

I would love to create a movement where families stay together and do not have to rely on both parents working so that kids can spend more time with parents and family. I feel that this would help so many of the issues with our world and our society. There are too many split households, too many kids raising themselves and not enough love and support.

How can our readers follow you online?

You can find me on Facebook, Instagram @thebowersgroupnaples and Linkedin.

Website: www.dennybowers.com or www.bowersgroupnaples.com

Thank you for the interview. We wish you only continued success!

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