Kyle Elliott of CaffeinatedKyle: How To Be Great At Sales Without Seeming Salesy

Authority Magazine
Jul 31, 2020 · 10 min read

I believe the education system grazes over sales because there is no size fits all methodology for sales. I also believe many people are uncomfortable about the topic of sales because they see it as a negotiation rather than a partnership. People believe they are trying to sell someone to do buy or do something. In reality, I see sales as simply having conversations with other humans in an attempt to find win/win situations. When you think about it, our education system focuses a lot on teaching us how to have conversations with others. That said, our education system could likely focus more attention on the win/win part.

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 Kyle Elliott, MPA, CHES.

Kyle Elliott is the career and life coach behind CaffeinatedKyle.com. His goal is simple — to help people find jobs they love. As a result of working with Kyle, clients have landed jobs at Facebook, LinkedIn, Amazon, Google, Microsoft, and nearly every other Fortune 100/500 company you can think of. They have also found happiness.

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 started my business on Fiverr. I charged five dollars to edit resumes, write LinkedIn profile summaries, and edit personal statements for students in college to support my Starbucks addiction. I never imagined this college side hustle would transform into a thriving coaching practice where I help some of Silicon Valley’s most prominent executives. While I help people across a range of industries, my expertise is the high tech space and Silicon Valley.

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?

Absolutely. I remember early on in my career spending $1,000 on a magazine ad to try and secure clients. I did not land a single client. My therapist called the mistake the ‘tuition’ of doing business. I quickly learned that my clients are not going to hire me from seeing an advertisement in a magazine. Moving forward, I focused on relationship building, relationship building, relationship building.

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

Yes! I am currently completing a Doctor of Education in Higher Education at the University of North Dakota. I am crafting my dissertation on the effect of sharing stores to reduce mental health stigma among college students. Studies show that mental health stigma is a huge barrier to students seeking treatment. My hope is that this research will provide a possible avenue for reducing stigma and increasing mental health help-seeking behavior and recovery among college students.

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?

Without a doubt, my parents. I am incredibly thankful and humbled to have parents who have supported me throughout my entrepreneurial and life journey. My parents truly believe in me, my abilities, and my fabulousness.

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

As I shared earlier, I started my business on Fiverr to support my Starbucks addition (soy, sugar-free vanilla lattes to be specific). Now, I advise some of Silicon Valley’s most prominent executives on their careers and lives. That transformation did not happen as the result of fancy sales funnels, thousands of dollars on social media advertising, or smoke and mirrors. Building a multi-six-figure practice came as the direct result of focusing on relationship building and delivering immense value to my clients.

Notably, I am also recognized by the industry. I am one of few millennials accepted into the invite-only Forbes Coaches Council. Also, I have been featured in dozens of leading publications, including Forbes, Fast Company, The Muse, The Ladders, you name it. This is what I am meant to be doing.

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?

As a career coach, my business has thankfully been positively impacted by the COVID-19 pandemic. However, I recognize that not everyone is as fortunate. If you are feeling anxious as a result of the global pandemic, focus on what you can control. You are powerful and in control of a lot more than it may seem.

Remember that you do have to go at it alone. Ask for help. People are willing to help you, but you have to communicate what you need.

Look for the silver linings. Personally, this has included spending less money on eating out, spending more quality time with family, and reassessing my values and priorities.

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?

I believe the education system grazes over sales because there is no size fits all methodology for sales. I also believe many people are uncomfortable about the topic of sales because they see it as a negotiation rather than a partnership. People believe they are trying to sell someone to do buy or do something. In reality, I see sales as simply having conversations with other humans in an attempt to find win/win situations. When you think about it, our education system focuses a lot on teaching us how to have conversations with others. That said, our education system could likely focus more attention on the win/win part.

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?

I am not a fan of being salesy or pushy. I am a fan of building genuine relationships. I want to work with clients who want to work with me and who do not need a push to feel like they need to work with me. I believe pushiness comes from a place of scarcity rather than abundance, which is where I prefer to operate. If you feel the need to be pushy when closing people, you are focusing on the wrong aspect of the sales cycle. The wrong people are entering the Presentation stage if you need to push them to close. It should feel like a natural fit.

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?

Presentation is one of my favorite parts of the sales cycle. As a career coach and business mentor, I help my clients figure out what makes them fabulousness so they can charge a premium for their service. I also help them own their fabulousness so they can get over Imposter Syndrome — for good.

The Presentation stage is an opportunity for me to showcase my own fabulousness. I am unique from other coaches in that I am a 20-something-year-old coaching some of Silicon Valley’s greatest talent. I am thriving in an industry where my peers are twice my age.

As a result of helping my clients own their fabulousness, they have successfully transitioned industries, landed top tech jobs, and grew their coaching practices from nothing to multi-month waiting lists.

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?

Former clients are one of the best sources of leads. My former clients are my cheerleaders because I deliver great results. In return, they sing my praises from the rooftops.

I am also a big fan of LinkedIn. Tons of job seekers and career coaches are hanging out on the platform. I naturally attract my ideal clients by showing up honestly and authentically on the platform.

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’?

Handling Objections is difficult for people because we so often sit on the same side of the table as our clients. In other words, as I shared earlier, people often treat sales as a negotiation rather than a partnership.

I am a fan of going into sales as a partnership. Aim to find clients who treat this work as a partnership rather than a negotiation. This makes negotiations easier and turns objections into questions and conversations.

‘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.

The most common mistake I see with new business owners is that they talk way too much during consults. Instead, focus on asking questions. “Why are we talking today?” “What do you need?” and “How can I help with this?” are all simple yet powerful sales questions.

Only once you have asked questions and clearly understood your prospect’s challenges should you then deliver solutions. As you deliver solutions, do not be afraid to also deliver value. I am not afraid of dishing out advice during consults because my ideal clients are coming to me for more than quick advice. They are in it for the long-haul.

Embrace silence. You do not have to fill in every silent gap. Before filling in a gap of silence, count to ten. This will allow your prospect an opportunity to share more about their challenge!

Don’t be pushy. Personally, I do not share my solutions until clients ask about them. If clients do not ask about them, which has only happened on a handful of calls, I do not share them. This may sound counterintuitive, but it works. I want the solutions to come up if and when it feels right for my clients.

Remember that you will not always close the sale right then. Focus on the long-term. You do not want to lose a sale today that could have been a successful sale had you given the client the night or weekend to think about it. Additionally, do not feel like you have to sell your client every single solution from the get-go. It is OK to up-sell them over time as you learn more about their challenges and how you can best serve them.

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?

I realize this goes against the grain, but I am not a fan of having a call-to-action (CTA) when following up. I want to avoid coming off as pushing. I also want to avoid prospective clients feeling pressured. I like to remind clients that I am here for them when they are ready. As I shared previously, I also strive to deliver value whenever possible. If I came across an article or resource that the person may find valuable, I will pass it along.

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?

I am a huge fan of phone calls for speaking with both current and prospective clients Phone calls allow me to really focus on what clients are saying. I have tried videos but I feel like I am too focused on visuals rather than the words and the underlying meaning. I am very empathetic and want to ensure I am in alignment with how my client is feeling.

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. :-)

My vision is lofty — to live in a world where everyone owns their fabulousness. This is why I am relentlessly authentic and share my whole truth with the world. I want to show others that it is OK to be your fabulous self. I believe every single human is fabulous. And, I believe the world deserves to experience your fabulousness.

How can our readers follow you online?

Readers can find me on LinkedIn, Instagram, Facebook, Twitter, or my website, CaffeinatedKyle.com.

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

Authority Magazine

In-depth Interviews with Authorities in Pop Culture, Business, Tech, Wellness, & Social Impact

Authority Magazine

In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

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Authority Magazine

In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.