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Rachel Sheerin: How To Be Great At Sales Without Seeming Salesy

Whether right or wrong, I think it’s what most people perceive and perception is 100% reality — no sense in fighting it or arguing semantics. I’d rather focus on building better — breaking the systems and old ways if we need to in the name of progress and getting more people on board with the […]

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Whether right or wrong, I think it’s what most people perceive and perception is 100% reality — no sense in fighting it or arguing semantics. I’d rather focus on building better — breaking the systems and old ways if we need to in the name of progress and getting more people on board with the immense power and opportunity being great at sales can give great people, teams and goals.

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 Rachel Sheerin.

Rachel Sheerin is an award-winning keynote speaker and team trainer who partners with companies and organizations that want to grow profits, success, and happiness. Named 2019 Speaker of the Year, you may have seen Rachel on the TEDx stage, featured in Inc Magazine for her sales coaching, or serving as Director of Global Awards for the Association for Women in Events. Focused on helping professionals thrive in work and life, Rachel’s served audiences from Spain to Seattle including Fortune 500 companies, associations, small businesses and creative entrepreneurs — most importantly, she takes her margaritas on the rocks.

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?

Oh, absolutely. It’s a tragic comedy — like many I fell into my career because I fell out of love with another career! I thought I was destined to be a leader of large sales teams — working for large Fortune 100 companies and crushing 8-figure goals — but along the path of leadership, I had a wake up call. Not only did I not fit into the corporate model of leadership but I also didn’t subscribe to the perspective traditional selling methods the world seemed to be insisting on. I found so much success in coloring outside the lines and embracing individuality — both of team members and clients — it became a huge contributing factor in my burnout. Burning out was the silver lining — it looked like (and felt like) failure, losing my career with no idea of what I was going to do next. What it turned into was the wake up call to what success really meant to me — helping people be themselves, be happy and succeed in ways that matter most — through making money, building businesses, and creating a life they love. It’s been incredible to help people build their dreams that provide profits way past their P&L and reach into their communities and the change they want to make in the world.

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 don’t know if this is interesting, amusing or horrifying, but on the way to my first ever national conference speaking engagement, the plane I was on had an engine malfunction. We had to return to the airport we’d taken off from and it was the longest 32 minutes of my life. The oxygen masks were deployed, people were freaking out, and I was silently crying in seat 12D. I remember it clear as day — and the reason I was crying wasn’t because I thought I was going to die (which I did think we were going to, despite the reassurances from the crew and captain) but it was because I was so thankful that I’d found my calling and chased my dreams before it was too late. That’d I’d hate the guts to leap from the safety of my career that was killing me slowly into the unknown, trusting that I’d find what was out there meant for me somewhere along the way. I’ll never forget that feeling — and then touching back down to ground safely. It was pretty memorable! I did end up making it to the conference, too, where all of the AV immediately went out the second I stepped on the stage (my mic, screen, laptop, EVERYTHING) but I went ahead and yelled my speech for the full hour — talk about memorable!

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

Yes, absolutely — there’s always something exciting at work when you love what you do! We’re currently in the 1st season of my podcast, F THIS S with Rachel Sheerin and it’s been a blast getting to deliver fast, effective and motivational advice so listeners can grow their success, happiness and career. Since I’m used to being on the road 250 days a year keynoting and training, I needed an outlet that I could speak with people and help them, even if just for a few minutes, get further in their journey of success. Some of my favorite moments on the road are with Uber drivers in New Orleans or the person who fate sits next to me on the long haul flight to Seattle — in the pandemic, there was less of those chance meetings to connect and help — so the podcast was born. It was always on my to-do list, so to be able to have the gift of time right now to do it is amazing.

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?

You are so right. 2020 has been an incredible year of seeing the hearts of people supporting each other, too — even when folks have had nothing to spare, I see them sharing what they have left with others.

When it comes to people who’ve invested in me and helped me get here, there’s so many but when it comes to sales, my mentor Suzie Price from Atlanta comes to mind. I met Suzie as I was starting my business years ago and got serious about behavior profiling so I reached out to her to see if I could learn from her — she’s a master in executive leadership coaching and professional assessments. I drove down to Atlanta to meet her for the first time, and as we were eating dinner, I was talking about my biggest goals and dreams. I mentioned flying in a private jet and having a million dollars in savings, but in the next breath I said, “But I mean, who does that?” — and she stopped me dead in my tracks. She told me the story of the first time she’d ever flown private and said, “Don’t ever dismiss your dreams because they’re someone else’s reality right now and that can be you, too.” I never felt ashamed or shy about those goals again and knowing her has truly changed my life for the better.

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

That’s a stellar question — I think in today’s world, being an authority or expert should come down to 3 things: have you done it ethically, have you repeated the results and have you taught others to do it. That’s yes-yes-yes for me — I’ve personally sold over $10 million for small businesses in my career and now on the way to a million in my own business since 2017. I’ve done it in ways that are honest, creative and bootstrapped — no ad spends, no fancy marketing firms and no smoke-and-mirrors — which is the way that I think all companies should do i Now as a keynoter and sales trainer, I’ve travelled the world working with small business to Fortune 100 clients helping them recharge and crush their sales goals. From new sales pros to veteran leaders, my clients are bringing me in because I’m high energy, authentic and I don’t tell people what to say — I teach people how to think in new ways and what to think about in order to sell in today’s fast paced world. They create their own sales machines and it works for each person best because they built it from the inside out — and I’d like to think that’s a skill that’s going to serve them long past our time together.

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?

Supporting others is a superpower great sales professionals have because sales is another word for advocate. If you’re good at selling, you’re good at advocating your ideas, your business, your perspectives and also, your good advice to your friends and family. One piece of advice I’d encourage would be to consume with clarity — whether it’s the news, movies, music, podcasts, articles like this — whatever you’re allowing your mind to consume has a large effect on your emotions and energy. The 24 cycle of news can take a toll, especially with the US elections happening in November, so I would just remind folks they have a choice in what they consume and don’t be mindless when tuning in, listening or reading. Overwhelm is real. Another suggestion to support others would be to send an unexpected note whenever someone crosses your mind. I can’t tell you how positive the response is when I send someone a text that says “You crossed my mind and I smiled so big thinking about you — hope you’re safe and well. Looking forward to a time we get together soon. No need to reply — know how busy life is right now.” Some people reply instantly, other take days or weeks, but it’s always appreciated and a connection that is real. Loneliness can be eradicated by a simple “I am thinking of you” whether in a text, email or note — so encouraging that reach out when you think of someone can give people the feeling of action and giving love when we feel disconnected right now. It’s really a win-win.

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 have always wondered this as well. The practical side of me thinks the teachers and principals couldn’t handle students who were good at sales! Could you imagine the selling we would have on our hands on why we didn’t have our homework or were late? It’d be great to see — especially because we see children as being so creative and uninhibited.

But the larger truth is that sales is not something that has a lot of respect or admiration in society, which is a shame, especially because sales is used in so many ways in life but not called sales.

A first date is a sale.

A job interview is a sale.

A closing argument in court is a sale.

A negotiation is a sale.

An eyebrow raised in a game of Poker is a sale. Bluff, or not? Sell it and the win is yours!

I could give thousands of examples — and the most successful people in society sell everyday to almost everyone they meet which means many of the least successful people are the ones getting sold to. If we taught sales, we’d have a much more equitable society — and much more ethical sales professionals, too!

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?

Whether right or wrong, I think it’s what most people perceive and perception is 100% reality — no sense in fighting it or arguing semantics. I’d rather focus on building better — breaking the systems and old ways if we need to in the name of progress and getting more people on board with the immense power and opportunity being great at sales can give great people, teams and goals.

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?

Being a rebel in the sales universe, I don’t subscribe to the stages as laid out — I teach my clients my PASS framework — aka Pretty Awesome Sales System — which has 4 steps:

  1. attracting clients who love you
  2. sharing your awesomeness
  3. pitching your best
  4. launching together

Personally, I think I’m strongest at attracting clients that love me. I mean, if you read the 1st paragraph of this article or clicked on my website, RachelSheerin.com, you’ll know quickly whether or not you’d like to grab a margarita with me. That’s important — you should want to work with someone you want to spend time with because that’s the kind of relationship I have with my clients — I don’t punch a clock on time with them. I take their goals, their team, their challenges and their dreams like I take my own and that means we go hard, fast and fun together. If you like slow, traditional and safe I’m not your girl. I’m OK with that because I’m A-OK with me — and I believe my success (and everyone’s) coming from being the best version of our real selves.

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 get so excited talking about lead generation because there’s so much opportunity online to pay with right now — especially as the world stays inside battling COVID (or makes the permanent shift to working from home, out of cities, or whatever the future may hold).

One strategy I wish everyone would employ is being comfortable with pricing on your website, or at least in the first email or phone exchange with prospects, using price ranges. Listen, everything costs something and our clients know this — and it can be between $1 and $1 million, but typically we can narrow it a bit more for them — can’t we? Do it — and stand out. Be bold enough to plant a stake in the ground and wave a flag. A bonus tip is creating ranges and making sure your offerings come in at the lower ends of the ranges — talk about a nice surprise for clients that they don’t often get!

Another idea I know works for every business, solopreneur and sales pro out there but rarely seen done well is asking for referrals! Somehow we let our awesome clients have a great experience with us and just waltz away without giving us their great friends information. The American Marketing Association year over year publishes their study showing referrals are 5 times more likely to convert into paying customers and on average spend 10%+ more than non-referred customers which can transform every companies P&L by leaps and bounds. So how do you do it? Muster up the courage to ask early on in the project, and when you ask, be specific about why you’re asking (you love working with them because…) and what kind of referral you want (industry, company size, personality, position in company, etc).

Almost every client hates doing it at first but then people are so excited to help out and refer someone that it’s an awesome experience that only enhances working together.

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’?

Show me someone who likes being rejected and I will show you someone who should be going to therapy.

Seriously, who likes rejection? No one! We’d reject ourselves before others a lot of the time, so it’s natural for many — including professional salespeople — to get uncomfortable in objection, negotiation and closing conversations.

To get better, a simple mindset has served me well for years — “I am the expert they need”

This mindset transforms objections from “They’re rejecting me, sound the panic alarm, I’m losing the sale!” to “I’ve got this, they’re curious and I know what to do to help — If I know, I can answer because I’m an expert and if I don’t know, I will find out the answer and become even more of an expert thanks to my network.”

When you switch from insecurity to welcoming challenge in sales (and life), there’s no objection that give you a sense of excitement where stress used to be. Mindset can change everything.

‘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.

I’m big on quick, actionable strategies that can be adapted to fit people’s natural styles of communication and comfort, so before I give a few things that work well for my clients, I’ll add a note here about my definition of a “pushy close” — a close where someone (the salesperson or the prospect) feels rushed to sign the contract/pay money for a reason that is real or perceived.

So how to close without being pushy? Here’s a few of my favorite tried and true successful closing strategies that I’ve developed with clients:

  1. Share your closing style — That’s right, tell your prospect how you like to close and ask if it’s OK with them that you go through your process, or if they have a preference. I have a client, Dan, in Boston that can close a deal in 2 minutes with a Dunkin Donuts coffee in his hand while driving his car. Safe? Maybe not but he’s direct, fast and not the guy who asks how your day is going. That’s what his clients loved about him — until they all started retiring and being replaced with younger executives who wanted to be taken out for golf and steak bro-time. You can see how this didn’t go over well until my training with Dan. Working out a strategic understanding of what they didn’t like (him rushing them, feeling impersonal) and what he wanted (his time back, respect and trust) gave him the words to explain why his closing style was a win for them while also seeing value in what they desired (he had 2 20-something kids of his own he didn’t quite understand). Fast forward to a couple dozen 5 minute convos later and Dan’s back to his fast-paced closings with his clients on board — with a few extra minutes added to ask about the weekend, too.
  2. Give the Behind-the-Scenes Tour of Contracts and Invoicing — Most of the time, when salespeople get to closing, they send it off with a hope and prayer via email (or maybe they’ll go over it via phone with the prospect) but the conversation is proposal-and-question focused only. Instead of being so direct, I encourage adding the Behind the Scenes info to your close — why you did what you did, added what you added, what is happening around the company and what you foresee as being big deals in the coming days/weeks for your client that may be good for them to consider. Being a great sales pro, you’re not just selling them — you’re partnering — which means that you’re stepping in as a consultant in a way, so be sure you’re giving them the eagle-eye scouting report where you can.
  3. Lay out next steps with start date — When people see a start date and project timeline in front of them, they get excited and understand the work that’s about to get done for them. This understanding of closing to move forward to the next level of relationship can be massively successful if you’re selling project and service-based agreements, large product sales and more. A manufacturing client of mine out of Atlanta found this a game-changer when they began sending this out with their machinery quotes — understanding that the machines made overseas would take 3–4 weeks to arrive once ordered at the beginning of the quoting process made for a much faster closing time on their 6-figure price-tag items.
  4. Make it easy to sign — If you’re not using an e-contract for clients, why not? If it’s legal saying no, keep asking. Don’t tell legal I told you that. (laughs). I use 17Hats for my contracts and invoices — 2 clicks and we’re locked in for a keynote or training and I’m paid. It’s beautiful — and from my perspective, making my clients life easier is top of the list on my job description and yours, too.
  5. Don’t think of it as closing, but instead think of it as launching — Doesn’t that FEEL different? It should because it is. Closing can be sad — from last call at the bar to finding out your favorite doggie daycare couldn’t survive the pandemic and everything in between, closing isn’t often positive — but getting a new client and getting paid is awesome! So I call for a REBRAND! Closing is out and LAUNCHING is in. When I did this for my business and laid it out in my client journey that I share with prospects, it always gets noticed with positive comments. Notably, one CEO shared, “The last launch we did required us to sleep at the office and exist off of take out for 11 days straight. I have a feeling working with you on this is going to be a lot more fun — and a lot less stressful.” I don’t even think they realized I was closing.

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?

Simple: Until they tell you no, keep checking in. People are stressed, distracted and busy. Emails get lost, diverted and marked read. Calls get dropped, phones get lost and voicemails forgotten. Keep following up if you want that sale. If you don’t, own that you not wanting it is why you lost that sale. But if you do, follow up until someone says no (and in an age of automation, customizable templates and calendars it shouldn’t be too hard. I have about 15 templates for follow up that take about 10–60 seconds to customize each time).

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?

Whatever you’re most comfortable with is going to be my first choice as long as it’s what showcases your strengths best. If you’re a cool, visual forward company, video is going to be stellar to show off your cool product or space. If you’re working out of your spare bedroom with your 9-year-olds Disney wallpaper behind you, I love phone for you right now (or a green screen maybe, but I don’t trust them after seeing fellow keynoters use them and have them fail mid-conference, exposing ugly backgrounds and cluttered desks). Hearing and seeing each other is proven to raise connection, so if you can show up on your prospects lawn safely, do that — bring margaritas. It helps (and yes, I did get a recent investment firm keynote out of doing just that — Happy Hour delivery surprise and delight for the win!).

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. 🙂

You’re not kidding! That’s a huge question.

In the past few months, I’ve spoken to thousands of people about their businesses and their lives. Sometimes it’s an association that brought me in for a keynote to their members, other times it’s a company who is doing their first ever women’s leadership conference and wants to motivate their leaders all over the US. Other times, it’s a global network of travel-focused business owners who’ve seen their industry halted as borders are closed all over the world and yet they’re coming together for inspiration, education and preparation for when we’re all back on the road, ready to explore and experience again.

And through it all, the question I get most is, “How can I be happy when this year is so…?” The words they use are different but they all feel similar — heavy, scary, stressful, sad, hopeless.

I am a sales trainer — but I base all of my teaching on a happiness-first model, because happiness is proven to be a precursor to success. It feels great and produces greater results in every aspect of our lives, from profits to points, sex to success. But what about when happiness is hard to find?

And so, with that, your question — inspiring a movement to bring the most amount of good to the most amount of people?

Happiness is an inside job. It requires courage and curiosity, to ask yourself without judgement, “What do I want? What will make me happy?”. Notice I don’t say “What should make me happy? What will make others happy?” — those questions have purpose, but cannot replace the important ones of your own personal desire and need of happiness.

When you ask yourself these 2 questions, there is only 1 I have left for you — and it may be the greatest of all:

Are you prepared to get that happiness for yourself?

When you unlock that realization, that awareness and commit to your own happiness, then it’s only a matter of time until the people around you rise in happiness. The success you enjoy is shared, the joy you experience spills over, and the world rises with you.

Why not start today?

How can our readers follow you online?

I’d love to keep in touch! I’m super active on LinkedIn and have a weekly newsletter I send out with sales tips and motivation at RachelSheerin.com — plus my podcast, F THIS S with Rachel Sheerin, which you can subscribe to anywhere you listen to your favorite podcasts.

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

Many thanks and love to everyone out there. Sell and succeed as yourself — and don’t forget: your happiness matters!

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