Four questions every digital media salesperson must ask

The work doesn’t stop once the sale is closed. Each month, illustrating to the client how your efforts are helping them reach their North Star Metric will be critical to maintaining trust and satisfaction. These four questions aren’t just a tool for closing deals; they are the foundation for building lasting, successful client relationships.”

Shannon Kinney, founder and client success officer, Dream Local Digital

In last month’s column, we discussed that becoming a trusted adviser is one of the most important keys to success in selling. To become this, you need to deeply understand your prospect’s needs and how marketing could help them achieve their goals. Effective digital media sales professionals don’t start by pitching solutions; they begin by asking the right questions. Uncovering a client’s motivations, goals and priorities can position your offerings as the perfect fit.

Here are four essential questions every digital salesperson must ask to build stronger relationships and close more deals.

1. What does success look like for you, and how will you measure it?

Every client defines success differently and rarely by “clicks” alone or other vanity metrics. For some, it may mean increasing website traffic; for others, it’s about generating more qualified leads or improving conversion rates. To truly become a trusted adviser, you need to be willing to dig deeper to show a return on investment (ROI) and value. Understanding how a client measures success helps you tailor your proposal to their expectations. It also sets the stage for tracking performance and demonstrating ROI later. More importantly, it helps identify the client’s North Star Metric — the key performance indicator that matters above all else in driving meaningful results. By aligning on this metric from the outset, you can ensure that all marketing efforts are focused on what truly moves the needle.

2. Who is your target audience? (Be specific here!)

A campaign without a clearly defined audience is destined to fall flat. While answers like “women” may work when buying traditional media, you need to be much more specific online. The more specific you are here, the more efficient and effective your campaigns will be. By identifying the demographics, motivations, habits, interests, geography and online behaviors of your client’s ideal customers, you can craft a digital strategy that reaches them effectively. This question also helps determine the best platforms and advertising formats, ensuring a more efficient use of budget and resources.

3. What is your most profitable product or service?

In many cases, your prospects will ask you to promote their business broadly, and they may or may not be able to get specific when you probe about their target audience. When I follow up a discussion about their ideal customer with what is your most profitable product or service, I uncover the real answer to that question. Some products or services have higher margins, better retention rates or greater demand. Understanding which products drive the most revenue and which types of customers buy those products allows you to align marketing efforts with the client's business objectives. This insight ensures you’re promoting what truly matters to their bottom line rather than focusing on less impactful products.

4. What is your budget to reach these goals?

Discussing the budget upfront prevents wasted time and unrealistic expectations. Many clients hesitate to disclose their spending limits, but framing the question in terms of achieving their desired results can lead to a more open conversation. When a prospect isn’t ready to discuss a budget, I must work harder to build trust and rapport. I will share that I will give them multiple options and we can refine once they see the proposal, but I need a place to start. Understanding budget constraints helps you recommend the most effective strategies while ensuring the client sees a viable path to success.

The takeaway

By asking these four questions, digital sales professionals can move beyond generic pitches and deliver solutions that resonate with their clients’ specific goals. More importantly, truly understanding the answers helps marketing teams define the client’s North Star Metric and get their buy-in. When both parties agree on the key performance indicator (KPI) that drives meaningful results, showcasing ROI and fostering long-term client retention becomes much easier.

The work doesn’t stop once the sale is closed. Each month, illustrating to the client how your efforts are helping them reach their North Star Metric will be critical to maintaining trust and satisfaction. These four questions aren’t just a tool for closing deals; they are the foundation for building lasting, successful client relationships.

Recommended book of the month: Each month, I’ll share one of my go-to resources for mastering your craft in sales. This month, I want to share “Some Will. Some Won't. So What. Who’s Next?” by Walker McKay. I loved this book and Walker’s highly experienced, yet no B.S. approach to selling. This book contains real-life stories and actionable steps I’ve applied and seen actual results. I also follow his podcast, which shares excellent tips on mastering your craft.

Dream Local Digital Founder and Client Success Officer Shannon Kinne, brings over 30 years of experience in leadership roles developing scalable digital marketing strategies and supporting and training media companies with scalable digital revenue growth. She played a vital role in the development of such internet giants as Cars.com, CareerBuilder.com, Knight Ridder Digital, LinkedIn, Google, eBay, and Microsoft and worked with media companies worldwide until pivoting to found Dream Local Digital. Since Dream Local Digital’s creation in 2009, Shannon has served on the Local Media Association board, been awarded the LMA Digital Innovation Award, appeared on hundreds of stages as a keynote speaker, and has helped media companies transform their business model. Shannon can be reached at shannon@dreamlocal.com.