Ashley Winkel of The James Agency: How To Be Great At Sales Without Seeming Salesy

Authority Magazine
Authority Magazine
Published in
12 min readMar 21, 2021


Drop some FOMO — Show them work you’re doing for someone else, or an idea that you had for them that gets them excited and make them feel like they’re going to be missing out if they don’t engage soon.

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 Ashley Winkel of The James Agency.

Ashley aligns potential client needs with The James Agency’s areas of expertise. Building on 15 years as a Client Services powerhouse, she understands both the big picture and the finer details. She collaborates closely with the directors to build strategies that produce tangible results and move the needle on clients’ business goals. Ashley has experience leading digital, traditional and fully-integrated marketing engagements ranging from local start-ups to global multi-million dollar brands.

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?

It’s funny, I actually never saw myself as a “sales” person or someone was good at what I traditionally considered sales. In fact, I had a negative perception of sales, even though up-selling and relationship-building were a huge part of my previous roles.

I went to college on a theater scholarship but quickly realized that while I loved performing, I would never make a living doing so. Luckily I discovered advertising, where my love for creativity and my natural talents with presenting and talking in front of people made me ideally suited for client service.

I grew up in the advertising industry always working on the agency side in a client services role. I started as an intern at VMLY&R and completely fell in love with the business and client services.

Enter COVID in March of last year and my CEO approached me about the opportunity to use my natural gifts to help her diversify our portfolio of clients. She saw that I had a gift for public speaking, for connecting genuinely with people, and for speaking naturally about how our various services can help business owners to achieve their goals. At the time I was so caught off guard, but honestly it’s the best thing that ever happened to me. I think my experience with relationship-building from my years in client service set me up really well to be a sales person.

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 tend to be a very bold and outspoken person. Often referred to as the “party fluffer,” I’m there to make sure everyone is having a great time, not taking themselves too seriously and feeling connected. However, sometimes my big mouth can get me into trouble. I’ll never forget our team was pitching a huge opportunity and there I was at the helm. The captain of the ship. There to set the example! So what did I do? I orated a beautiful opening statement and then handed it off to our Creative Director, Shane, for whom we have many nicknames. Feeling perhaps a little too loose, I called him “Shanus.” Oh yeah, I made a butt joke in front of a distinguished board of conservative, mostly over-50’s, decision makers. And rather than just leave it there and pray they didn’t hear me, I reiterated the fact by adding “Oh, that’s just what our nickname for him. You can call him that too.” It was mortifying. The good news is that we won the project, but I’ll never forget how ridiculous I felt letting that one fly! My CEO also loves telling that story… as a warning.

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

Yes! I’m working on a podcast that will help demystify marketing for people. I know podcasts feel overplayed, but I’m really interested in helping non-marketers to understand why what we do matters and how they can get more juice out of their squeeze.

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?

Honestly, there are so many people who have mentored me, believed in my abilities and encouraged me. Naturally I want to shout out to my CEO, Veronique James, who has continually invested in me and cultivated my talents. When it comes to sales specifically I have to thank Steve Hanrahan, the president of Reseco, who taught me what he knows about sales.

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

Having worked 13 years in the marketing and advertising industry before transitioning into a sales career gives me a unique perspective on what it means to “sell.” I know I’m not just selling services or products, I’m selling myself. I have to build a brand around my personality. People are buying me, my experience and my partnership. If they believe in who I am as a person and I’ve made a genuine connection with them, it will be that much easier for them to trust what I have to say.

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?

Firstly, it’s really important to acknowledge that every person’s experience right now is different. There are people living in a constant state of anxiety and loneliness all around us, and it’s more important than ever that we’re quick to listen and slow to speak. That said, connecting people to resources that can help them (books, podcasts, professionals) and reminding them that you’re thinking of them frequently goes a long way. Being seen and known is important. Sometimes just a little text message saying “I’m thinking of you” or sharing something encouraging or uplifting can be a silver lining. Personally, I’ve tried to fight the anxiety by focusing on gratitude and physically making a list of the things I’m grateful for. That said, I’m a person of privilege and I have to recognize that telling someone else to “focus on gratitude” may be incredibly trite and inappropriate for what they’re going through.

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?

What an interesting question! Honestly there are so many practical skills that aren’t taught in our education system — like financial literacy, nutrition and healthy relationships. I think people are uncomfortable talking about or teaching sales because it’s often mis-perceived as manipulative or forceful. That you are trying to convince people to buy something they don’t really need or want and therefore it’s not be encouraged.

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 absolutely do think this is to be avoided. If I find myself in a situation where I’m having to push someone along, I find I’m likely not talking to the right person, or they’re not in the right mindset to receive what I’m sharing with them. Sales is at its best when you’re in genuine connection with someone. Which means you shouldn’t have to push or “sell” them as much as share what you know. Ideally I’m presenting a solution to a problem, an answer to a question or making a genuinely well informed recommendation to someone who trusts what I have to say.

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?

Oh, I love me a good follow up. I find that most people don’t expect you to actually follow up and care about what they have to say, so it’s such a great opportunity to cement your relationship. Typically about 30 days into a partnership is when I start scouting for a chance to check in. I also use the follow up as an opportunity to make sure I’m selling what people are actually getting (i.e. the pitch and the experience align) and that I’m able to get ahead of any potential landmines. I can always tell from their voice if there’s something negative they need to get off their chest, and since I’m not involved in the day-to-day, it gives them license to be honest with me. Bonus points when I can actually address or course-correct for them because it reiterates that I genuinely care about the experience their having and reinforces that we value their feedback.

We recently had a client who was meandering off course, getting behind on deadlines, not providing thorough feedback, generally feeling disengaged, which is the first step in losing a partnership. It was the perfect excuse for a follow up from me. I was able to get some insight into why they were drifting away and pull them back in before we ran out of rope (to continue the metaphor) ,and it not only made them feel amazing that I cared enough to check in, but it allowed me to reiterate why it was so important for them to lean into the experience without it feeling like they were being scolded.

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’ve found that there’s nothing more impactful than a referral, so I really focus my prospecting time on deepening my relationships with former colleagues, former clients and friends. It’s easier to go to the well than to make it rain, and most of the time it’s as simple as a cocktail hour with an old friend that can keep your name on their lips. I keep it very non-work related, but the question of “how’s business” always comes up and it’s a great opportunity to toot our horns about all the great work we’re doing and new business we’re generating. A referral lead is the strongest lead!

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’?

Honestly, I love handling objections because the other party is literally putting their concerns on the table and giving you the opportunity to directly address them. What hardest for me are the perceived objections that don’t get voiced. The concerns I know they have but haven’t shared. Or clients who come with a lot of baggage from their previous agency relationships and have PTARD (Post-Traumatic Agency Relationship Disorder.) I don’t ever want to plant a seed of doubt where there wasn’t one, but at the same time, if someone has no objections at all, I’m skeptical.

The advice I would share with others relative to handling objections is to look at it as an opportunity. They are literally telling you the barriers you need to overcome. That’s a good thing! Now you don’t have to guess what might be holding them back.

‘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.

Here are 5 things I’ve tried that have worked for me!

  1. Create scarcity — Let them know that resources/schedules are filling up and you want to make sure you get them in for month/quarter/year whatever it might be.
  2. Create urgency — Share some news from a competitor that will help light a fire. Company X just made a move to do Y, now would be a great time for you to get head of them!
  3. The Touchstone — Remind them of their problem and how valuable it will be to them to address it.
  4. Drop some FOMO — Show them work you’re doing for someone else, or an idea that you had for them that gets them excited and make them feel like they’re going to be missing out if they don’t engage soon.
  5. The Price Hike — I only pull this one out if I really have to, and it works particularly well near the end of a fiscal year, but you can always warn them that your rates are going up to encourage them to lock-in the current pricing.

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?

Listen, I’ve been on the other end of a pushy salesperson who genuinely doesn’t understand what my timing and motivations are, so every follow-up feels like a sales tactic. Like most things, it’s not just what you say but how you say it. I would recommend using the phone over an email as much as humanly possible to avoid your note getting lost in their sea of emails. If you are going to send an email, I would recommend using an emoji in your subject line to help it pop out from the rest of their inbox. As much as possible, I try to keep my follow ups topically separated from the actual opportunity. I ask how business is going, what new opportunities have come their way, how they personally are navigating. Oftentimes if someone’s dropped off the map it’s because something awesome or something difficult has happened and their priorities have shifted. I try to ask about that, meaning the other things are their plate, before I ask about where they’re mind is at relative to my proposal.

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?

Oof. Remember that you aren’t just selling your product or service, you’re selling YOU. You are the brand. You want to establish trust, you want them to like you, you want them to hear what you have to say and then do what you’re suggesting they do. If they can’t see your face or hear your voice, you’re dancing without your legs. It can be done, but dang it’s so much harder. For that reason, I would avoid any communication methods where you can’t rely on your personality as a connective element. Avoid emails and LinkedIn messages because it’s just so hard to stand out from all rest.

In person meetings are GOLD because you’re working with a full deck, but most of the time I’m working up to an in person, so I really lean in on phone calls where they can hear my tone and start to build that friendship/relationship. I consider text messages to be very personal because you’re now in there with messages from their friends and spouses and family. For this reason, you should use them sparingly. Don’t overdo it on the messages or you’ll lose your privileges.

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 heart really breaks for people who have come to our country from other places seeking peace and healing and opportunity only to be met with prejudice, apathy and downright hate. I come from the middle of the country (Kansas) where I’m watching small towns fade away into the abyss because no one wants to stay there an open up businesses. I would love to lead a movement that connects these small communities that are in need of revitalization and growth with immigrants who will bring small business’ and innovation and families who will stay rooted in those small towns. I truly believe there is enough for everyone.

How can our readers follow you online?

Always on LinkedIn at Ashley Winkel, @moxiemoron on Instagram if you like Corgi content, @TheJamesAgency on Clubhouse, and soon to premier, the LevelUp Podcast.

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



Authority Magazine
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