Madeline Pratt: How To Be Great At Sales Without Seeming Salesey

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In our western society, we still see selling and talking about money as tacky or taboo, which is ironic given the capitalist construct we operate under. Historically speaking, our education system was designed to prepare people for life as a worker for someone else’s company, and for being compliant to their rules and orders of operation. Even though entrepreneurship has always been a vital part of our economy and the American success story, our culture is based on the belief that success comes from people that pull themselves up by their bootstraps and figure these things out on their own, rather than being taught it in school.

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 Madeline Pratt.

Madeline Pratt built her career at the unique intersection between technology, sales enablement, and channel development. As a business development leader, she has worked with companies from startups to Fortune 500s that were aiming to offer innovative products, partner programs, and marketing to their target consumers. Today Madeline serves as the founder & CEO of Fearless In Training, a creative consulting company that focuses on working with female founders, technology innovators, and ambitious entrepreneurs to help them start, grow, and scale their businesses by aligning with their true market potential.

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?

My first job out of college landed me in the world of technology, and I’ve never truly left. I built my career literally from the bottom up, working as an inside sales rep in the basement of a growing software company. From there, I grew into the world of business development, and eventually joined a Fortune 500 where I built my skills strategizing, teaching, and training accounting professionals how to leverage cloud technology. I quickly realized though that corporate life isn’t really my thing. I love the innovation and energy of earlier stage companies, and found a better fit in the small start up world where I spent the next three and a half years leading the business development strategy, customer success, and marketing initiatives for an Australian start up that was looking to move into the American market.

While I loved the company and the team that I had built, over time, I recognized that my biggest passions were within my work educating customers and developing creative marketing strategies, and I could see how many other businesses could benefit from the expertise I had built in the world of tech. After seeing how many of my friends were starting businesses but lacked the confidence or know how to scale successfully, I realized I wanted to create my own company that focused on offering ambitious entrepreneurs the education, strategies, and resources they needed to grow a business model that truly brought their vision and values to life. Today, my company Fearless In Training offers online education, communities, consulting, and coaching for entrepreneurs and tech companies from around the globe.

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

I grew up being told that I could do anything my brother could do, and I believed it right up until I started my career in tech. As my career unfolded, I was often the youngest or only woman in the room, and I quickly realized that bias still had a sizable impact on how people perceived my abilities as a leader. Once, I was at an industry event where one of the most influential leaders in the accounting space extended an invitation to the company I was working for to be a part of a major annual event his organization was holding in New York. I knew about the event, and what an honor it was to attend because the guest list was invitation only, so I was thrilled to accept.

To my surprise, I was told I couldn’t attend, but this leader suggested that one of my male counterparts would be able to come instead. After much back and forth, and one of my bosses insisting that it was my job to be there to represent the company, I finally was allowed to go to the event. As soon as I stepped foot into the conference room on the first day of the gathering, a realization dawned on me as I looked around and realized that everyone was white, and out of the fifty attendees, I was one of five women in the room, and younger than almost everyone there by a decade or more.

A huge component of this event was a pitch competition, where the representatives from tech companies would have five minutes to provide details on their company’s product and strategy, as well as deliver a small speech that answered a series of questions provisioned by the same leader that had tried so hard to keep me from attending. He was known for disqualifying anyone who went over time, and the room was equipped with a bright red buzzer that would resound the second you’d hit the limit. I’ve always enjoyed a good challenge, and I had spent extra time preparing and practicing so that I could recite my speech from memory, and not go over the allotted time. With fifty of the most respected leaders in our industry in the room, I took a deep breath, remembered what I’d practiced, and pitched my heart out.

I was the youngest attendee there, and only one of five women, and I won that pitch competition. Afterwards, the leader gave me the award and prize, and said in a surprised tone “I had no idea you could speak like that.” I remember smiling in return, and saying something to the effect that he had no idea what I was capable of.

I look back on this moment as one of many in my career where bias has been present and people who are rooted in the past have tried to hold me or others back from progress. While I realize my life has afforded me certain privileges to even be able to be in that room in the first place, I’ve always seen it as my responsibility as a woman and leader in tech to show up fully prepared, hold my head up high, and stand up and stand out as an example of what women can do so that folks are forced to question their biases. I know that there are so many hurdles of inequality that we still have to overcome in the working world, but I learned in that moment to seize any and all opportunities to change the conversation about what women are capable of.

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

This year, we launched a new program called Learning Lab, which is an ongoing education program designed to help ambitious entrepreneurs gain the skills & resources they need to grow a modern brand and business. The program focuses on topics like how to structure a proposal or how to uncover your brand story, and is designed to be accessible and beneficial to anyone starting, growing, or scaling a service based business. The thing I love most about the program is that it has given me the opportunity to draw on the relationships I’ve built over my career with amazing industry experts on topics like pricing, business development, and marketing, and get to bring their insights to our members in a really engaging way. The thing that excites me most about the model is that our members are learning from each other and from our experts, and will have such a stronger foundation in business. Typically 50% of new businesses fail, but I know that our members are getting the knowledge they need to build their business intentionally and developing the skills they need to thrive.

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?

So much of my success would not have been remotely possible if it weren’t for my mother. Shortly after I started my career in tech, I divorced my first husband and was juggling my responsibilities as a single mother while also trying to build a better life for me and my son. When big opportunities came my way, my mom always stepped up to help care for him so that I could travel and accomplish what was needed in my career. Even after I remarried, my mother has been a constant source of support for our family, and I am forever grateful for her presence in our lives.

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

My entire career has been built around my ability to build relationships that lead to sales. I started my career as an inside sales rep, smiling and dialing my days away trying to qualify potential customers to take a further look at software solutions. Over the years, I got into more strategic sales roles, where I had to focus on selling to entire organizations and helping them navigate the steps it takes to make the shift to cloud technology. The further I’ve gotten in my career, the more consultative my conversations have become, and I’ve spent the last five years focusing a lot of my energy towards training sales teams from around the globe as well as teaching entrepreneurs the skills needed to deliver a relationship based sales experience to their customers.

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 think one of the simplest and most important things we can do is to check in on each other and not assume that everyone is okay. Everyone navigates anxiety and stress differently, so it’s crucial to just reach out and ask our friends and family how they are doing. Even just a simple text that says “I’m thinking of you. No need to respond, but I’m here if you need me” can go a long long way during this trying time.

Another thing we can do is send our love to others. My friends and I have also been sending letters or little care packages with coloring pages for our kids, and it is such a small gesture but it makes us feel loved and connected even if we’re far apart from each other.

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 versalite topics, is totally ignored?

I think this has a lot to do with our cultural connotations around selling and money in general. In our western society, we still see selling and talking about money as tacky or taboo, which is ironic given the capitalist construct we operate under. Historically speaking, our education system was designed to prepare people for life as a worker for someone else’s company, and for being compliant to their rules and orders of operation. Even though entrepreneurship has always been a vital part of our economy and the American success story, our culture is based on the belief that success comes from people that pull themselves up by their bootstraps and figure these things out on their own, rather than being taught it in school.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesey”, 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 don’t think anyone enjoys the experience of being coerced. We’ve all experienced it at some point or another, whether it was buying a car or being bombarded by someone at a beauty counter. We as consumers want to make informed decisions that feel like they’re of our own volition, not like they were something we were forced into.

I believe that we should sell like we would want to be sold to. If someone is offering something that I genuinely want and value, I’m going to purchase when the time is right. But I don’t believe that our role in selling is to push people to buy things that they don’t want or need or aren’t ready to buy. Great selling is about educating and empathizing with the customer to build connections, and when the time is right that customer will trust you enough to transact with you. It should never be about pushing or selling someone on something they don’t need or aren’t ready to invest in.

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?

I have my own approach to selling, and it’s broken down into Qualifying, Engaging, Discussing, Proposing, Closing, and Onboarding. I am an absolute ace at Engaging, because this moment is really about hearing the story of what the client is struggling with, and then offering up information about what you have to offer that could help. The key to this comes down to really listening.

Recently, I was working with a newer client that came to the table thinking that they needed help hiring and building a sales team and strategy to take their product to market. However, as the conversation progressed, they came to share that their company had simultaneously been building a secondary product and they were starting to feel uncertain about which one they should be focusing the bulk of their energy towards.

Over the course of the call I helped the client to see that what they really needed to spend their time on was evaluating the potential of each product prior to investing any additional funds in building and training a sales team, and I shared with them how we coach and consult with clients to make these key types of product decisions and offered up a story of a recent client that we’d help bring one focused and successful product to market. In the end, the client ended up purchasing a service that they hadn’t walked into the conversation expecting, but it ended up to be exactly what they needed and we were able to help them focus their energy around the secondary product and set them up for a successful and tailored launch to their intended market.

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?

One of the most important ways we generate leads that are of quality is by being crystal clear in our marketing who we’re meant to serve. A common mistake that businesses make is thinking that lead generation is about quantity, so they mass market and pull in as many leads as possible. However, I strongly believe that there is nothing worse than wasting our time talking to folks that aren’t a fit for what we offer and never intend to become customers, so we make it a huge focus in our company to make sure our marketing is designed to repel away people that aren’t a fit for us. That way we’re only focusing our energy and attention on leads that actually have the potential to become paying customers that we actually enjoy working with.

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’?

I think folks struggle at handling objections because they assume it means that they are at opposition with the customer, and then it’s their job to convince the customer to move forward with a purchase. My belief is that great selling doesn’t involve coercion of any kind, it involves education.

In a moment where a client is hesitating to come onboard with us I know one of two things are occurring:

1) They are uncertain of the value and credibility of what we offer OR

2)They’re not a fit for us or ready to purchase at this point.

As I mentioned before, we make a point to repel away as many people as possible but occasionally some folks that aren’t a fit for us or aren’t ready to commit to a purchase still show up in our pipeline. I make a point to never chase these people. We’ve got enough ongoing content education in our marketing to nurture these folks to reach out or sign up when they’re ready or move on if they aren’t a fit. But if we’ve had an initial conversation with someone and they’re still feeling unsure, that’s when I know I need to focus on delivering them more details to educate them on how we work, and the benefits of what we have to offer by providing them with another opportunity to discuss our services or introducing them to an existing customer that was facing a similar problem prior to working with us.

‘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.

  1. Set clear boundaries & expectations. — This is a critical way to let potential buyers know that you mean business. The more clearly you can communicate with customers about the timelines, the information that is needed to prepare them to purchase, and the value that will be delivered, the more they will trust that you have a process in place to support them as a customer and live up to the conversations you’ve had thus far.
  2. Confirm you’re on the same page. — Sometimes things change during the sales process. A virus happens. Someone leaves the company. Budget numbers are reconfigured. Part of being empathetic is understanding that things change, and checking in with your prospects to see if something has shifted so that you can both adjust your plans accordingly.
  3. Leave space to ask further questions. — Questions are always going to come up after the fact. Folks will forget what was said on a call or come up with an idea or issue that needs to be addressed in the days after you propose to them. That means that you need to do your part to be accessible and available to demonstrate your value by asking if they have any further questions and answering them as they arise.
  4. Offer more education & resources. — Just because someone is uncertain about making a purchase does not mean they’re a “no” or that they won’t be a “yes” in the future. One of the easiest ways to demonstrate that you’re the right person for the job is to offer them education and resources upfront for free. Whether this is free training or just a whitepaper that could help them make an informed decision, it is always a good idea to offer resources that make your prospects see you as a source of valuable and trustworthy information.
  5. Ask them if there are obstacles you can help with. — You know the adage, it’s not you, it’s me? Well sometimes that “me” is a manager. Or a boss. Or a team member. Or some other obstacle inside of their organization that can’t seem to come onboard with the purchasing decision, even if your prospect is ready to purchase. Make a point to ask the folks that you’re engaged with if there are obstacles blocking your way, and show them that you’re on their side by offering them support and resources to remove them from your mutual path.

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?

Whenever and wherever possible, provide value. Don’t just “circle back” with folks for no reason, they’ll sense that you’ve got a sales agenda and that it’s disingenuous. Instead, offer value. I like to circle back with previous prospects and share articles or other information like a radio segment that I’ve come across that I believe would interest them. I also make a point to see prospects as people, and whether they work with us or not, I always keep an eye out for ways to connect them to other folks and opportunities in our network so that they always associate their relationship and experience with me and my company as being one that is valuable and beneficial to their business.

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 think that texting is the most invasive means of communication, and should be avoided entirely when selling. Nothing repels me more than a company texting me without my permission. Again, the goal is to sell like you’d want to be sold to, so don’t be that person texting someone to sell them something they never indicated any interest in.

For me, I’ve found a lot of success in video calls, where I can make a human connection with the person I’m aiming to bring onboard. Clients who have heard about me or my company’s work appreciate the opportunity to connect with me and get a sense for who I am as a person, and I get an opportunity to get to know them and get to check my gut if they’re actually a fit to work with me and my team. I’ve also learned over time that potential clients don’t always remember what we’ve discussed, so I make a point to always follow up with a clearly detailed email that outlines what we covered on our call and the next steps we’ve outlined whether that’s signing a proposal or setting up another call.

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 greatest beliefs are that we all come into this world with a unique light that we’re meant to shine and share with the world. I also believe that we can use business as a way to bring that light to the world in bigger and more powerful ways. My hope for my work is that it inspires other people to look inwards and discover their own values, and in doing so uncover a vision for how they could build a brand and a business that allows them to share that on a global scale. We have so many inequalities in our society that can be undone by the actions that individuals and entrepreneurs can take, and it all starts simply by believing that we have the power to change the world for the better.

How can our readers follow you online?

I can be found on Instagram & Twitter at @madelinekpratt.

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


Madeline Pratt: How To Be Great At Sales Without Seeming Salesey was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

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