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Madeline Hilliard Of Grayscale Marketing On Five Strategies Leaders Use

Madeline Hilliard Grayscale Marketing Nashville

We are all competing in an attention economy. From pings and dings to blinks and rings, companies and content constantly compete for our limited time and attention. How do great leaders turn down the noise and tune in to the messages that matter most? What does it take to be heard above the noise? And how do we create communication that cultivates community and connectedness in a distributed, distracted world? To address these questions, we started an interview series called “Can You Hear Me Now?: Top Five Strategies Leaders Use to Diminish Distractions & Win in the Attention Economy.” As a part of this interview series, we had the pleasure of interviewing Madeline Hilliard. Madeline Hilliard, Director of Advertising at Grayscale Marketing, has a proven track record of selling over 500,000 event tickets and generating eight figures in revenue for her clients. She is an avid reader and a dedicated student of leadership, consistently seeking knowledge. Outside of her professional endeavors, Madeline enjoys music, literature, and quality time with loved ones. Thank you for making time to visit with us. Before we dig in, our readers would love to get to know you a bit better. What is one of your most memorable moments, and what made it memorable?

Wow, that is a great question! It’s hard to pinpoint just one moment as my “most memorable,” but one that certainly stands out is seeing the Grand Canyon for the first time. My family and I went on a road trip all the way from North Carolina to Arizona and it was my dad’s dream vacation that he had talked about since I was a kid. I remember seeing the canyon and it just took my breath away. It was a moment when you can feel so small, but I was also so amazed that even in the grandeur of this world, there’s still a reason for little ole me to be here. My dad and I rode mules around the rim — I highly recommend it by the way — and I loved watching one of his dreams come true. I also took tons of photos that just don’t do it justice. I sat there and gazed nonstop in simple wonder.

What is the most unexpected twist in your career story, and what did you discover from your detour?

The most unexpected twist was getting laid off from a job. I had been promoted 6 months prior so I thought I had a level of job security, but alas, my position was dissolved and I found myself unexpectedly jobless. I actually now am extremely grateful and think it was the best thing that could have ever happened to me. When I moved to Nashville, I had in the back of my mind that I would love to work in music marketing because I have a passion for both music and marketing. When I found myself back on the job market, I remember thinking, “if I don’t do it now, then when?” So I quickly started looking for marketing jobs within the entertainment industry and here I am now working at Grayscale Marketing and working closely with our parent company, Romeo Entertainment Group. Through this detour, I realized that I didn’t have to choose between just one side of me (the creative musical side vs. the administrative business-y side), but could merge all of my passions into one and it has been so fulfilling.

According to a recent Harvard Business School study, the most essential communication skill for leaders is the ability to adapt their communication style. How do you adapt your communication style?

I communicate differently with different people on the team based on their communication style. I determine this by observing and taking note of their communication style. Matching others’ communication style is most likely to be effective; I do add my own flavor though because I never want to come across inauthentic. Practically, I’m always asking myself: Do they respond best to bullet point lists, paragraph style, or a mix of both? If they are stressed and pressed for time — let’s keep this meeting short. If something was misunderstood, how can I explain it a different way or improve in the future? Also, I try to read the room. What does this person or team need from me at the moment and what will be best received? Now, by “best,” that doesn’t necessarily mean happy, but rather, heard, understood, and inspired to action. I try to be self-aware as to how I may make someone else feel as their supervisor, but also be aware of what will push those on my team to succeed.

Clarity is critical as well. What lessons have you learned about how to communicate with clarity in our distributed world of work?

Don’t forget the human aspect. I always check in on my team, whether we are in the same room or working in different parts of the country. I like to demonstrate that there are open lines of communication, not just say it. Sometimes, that is as simple as a “Good Morning” message in the company chat. I’ve learned that it’s very easy to feel isolated and not a part of the team — especially in the distributed world or work — so I make sure to put things into perspective by reminding myself that it is an actual person on the other side of the email, who is juggling a lot. I try to be friendly and detailed to anticipate their questions — while also being as concise as possible.

We often discover what works by experiencing what doesn’t. Tell us about a time when your communication didn’t lead to the desired results and what you learned from the experience.

While I do not mind having tough conversations, I am an encourager at heart. In my early days of managing and leading, I had some issues with someone on the team. I remember trying to nicely encourage this individual during a one-on-one meeting to show that I believed in them. Unfortunately, I leaned a little too nice and this person did not realize the gravity of the situation. My superiors started to notice and expressed that to me. Then, I had another more serious conversation, that I felt I had still mellowed some, but this individual was shocked and was very resistant to the feedback. I learned that it is never kind to withhold constructive feedback. Of course, I want to package that from a place of love, but just patting someone on the back when there is an area that needs to be improved is never going to help them grow or ultimately develop into their full potential. Now, I try to have those conversations as early as possible to prevent future issues or conflict.

What advice would you offer to other leaders who are struggling to have their messages heard and actioned? Start with self-reflection. It’s not easy to admit that we as leaders could be the problem, but really try to be the most objective with yourself as possible. Ask yourself: Am I adapting for my team or just dragging them along? Have I tried a different approach to communicating my message? If so, how did the response change? I can be pretty bold so sometimes if nothing is working, I’ll just express that I don’t feel like I’m being heard. How can I better communicate for you? Try not to be accusatory towards others before you look within and at your own actions.

Leading a distributed team requires a different communication cadence and style from leading a team in person. What are five strategies any leader can deploy to improve communication and clarity when leading a distributed workforce?

1 . Lead by example — People follow your actions more than your words. As I mentioned earlier, I want there to be an open line of communication, but it goes both ways. Some people may feel timid initiating a conversation with you as a leader when they face an issue. Instead, I try to make myself available by asking questions in a caring way.

2 . Set consistent touchpoints — Whether you are having company-wide or department meetings, it is so important to have consistent times on the calendar to meet with your team to connect. Then, create space for questions or concerns. While I chat with my team every day, I meet with my Ads Department once a week to really dive into every account for only ads-related topics.

3 . Write things down — Remember everyone has different learning styles. You may have verbally said 10 things during one meeting, but always write down important information so your team has something to reference. For example, when I am in a meeting, I am taking notes of action items that need to come out of this meeting and then I will add any applicable action items into Asana for both myself and the team to reference in the future.

4 . Follow Up — Be careful not to be a micromanager here, but ask your team for updates (maybe during that consistent touchpoint) and ask what they need to be successful. Assume that the very first time someone hears something is not the only time it ever needs to be acknowledged unless you see immediate action or results.

5 . Be both thorough and concise — This might sound like an oxymoron but I try to find a healthy balance here. I want to make sure I am anticipating any questions that my team might have in my communications while also removing as much of the excess as possible. I’m a detail-oriented person so I ask, “what would I want to know?” However, I’m also a “get the point” kind of person so I try to skip the fluff — this isn’t a college discussion board, but an executive summary.

What are the three most effective strategies to diminish distractions when there is so much competing for attention?

  1. Unplug — Sometimes, you just have to turn off the noise to reset focus. Periodically, I will pick one day during the weekend where I will not go on social media or watch Netflix (or whatever I’m noticing is taking up a lot of time in my week). At first, it’s hard as I realize how much I reach for my phone in my spare time. But by the end of the day (or weekend), my mind will be renewed and I feel so refreshed and more productive. As someone who works in digital marketing, it is so easy to continually think about how we can leverage trends or viral content — stepping away actually allows my creativity to flow in a new way.

  2. Rest and find a creative outlet — Do something for yourself, that is only just for you. Maybe it’s a side hustle or maybe it’s something you only do in your home that no one else ever sees. Everything does not have to be a side hustle. I’ve found I’m most creative when I’m simply doing it for the love of being creative. When I come into the office well rested and “full” creatively, my mind can focus so much better.

  3. Set and respect boundaries — With everything so accessible right now, it’s so easy to just send a quick text outside of typical working hours or check that one thing before bed. I’m not saying I never do this, but I really try to respect that people need their personal time, as do I, so I only reach out if there is something absolutely urgent. I’ve found if people feel like their personal time is truly their personal time, they are less likely to be distracted when “on the clock.”

What is one skill you would advise every leader to invest in to become a better communicator?

Active listening. Don’t just come to people with an agenda of getting your tasks done. Yes, that is important, but if you want your team to do their best, you must earn their trust and make them feel like you care for them as a person more than the task. That’s how you build loyalty and inspire others to bring their best. But it all starts with listening and not just bulldozing over what they say. As they say, listen to understand, not to respond.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

My life purpose is to make people feel valued and seen. I truly believe that each person has a unique purpose and I am passionate about empowering people to discover and walk in that purpose. Sometimes, I think the greatest movements are found when you make an impact on one person — or a group of people — who then make a similar impact on those around them.

How can our readers stay connected with you? I’m always happy to connect with people on my LinkedIn:

Thank you for these great insights! We wish you continued success.

Read the full article at About The Interviewer: Karen Mangia is one of the most sought-after keynote speakers in the world, sharing her thought leadership with over 10,000 organizations during the course of her career. As Vice President of Customer and Market Insights at Salesforce, she helps individuals and organizations define, design and deliver the future. Discover her proven strategies to access your own success in her fourth book Success from Anywhere and by connecting with her on LinkedIn and Twitter.


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