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Three Questions Sales Leaders Should Ask for Better Buyer Conversations

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Posted in:  Buyer Engagement, Sales
three questions sales leaders should ask for better buyer conversations

Virtual engagements are nothing new — for most businesses, they have been a primary channel for engaging a global customer base.

However, these virtual engagements were often augmented with in-person interactions where an event could strengthen relationships or give buyers a chance to explore a product hands-on. With these engagements no longer an option, businesses have leapt to replace them with webinars, virtual summits, and lots of emails. The result? An increasingly cluttered digital sales environment.

So, how can you stand out in our noisy reality? Sales leaders must empower their teams with renewed emphasis on expertise, empathy, and interactivity. Ask yourself these questions to get started.

How Can My Sellers Build Credibility?

Begin by looking for ways your team can build credibility with buyers. One way to do this is by refocusing sellers’ energy on social media.

This may seem counterintuitive to closing deals given social media’s reputation for being a place of community and connection. But those elements are exactly what make it the perfect environment within which to grow the influence of both your brand and your individual reps.

By sharing high-value content and insights, your team will be able to establish areas of expertise and keep your company at the top of buyers’ minds. Thought leadership assets like the following items will be your best bet to enhancing credibility with buyers:

  • Licensed analyst reports
  • eBooks and whitepapers
  • Blog posts and articles 


The key to succeeding on social media is to ensure that assets are easy to find and distribute. Often, reps stumble when they are unsure of what to post, how to post, or when to post. By providing relevant guidance or suggested social copy alongside content, you can lower the barrier to participation and ensure that reps are sharing stellar content that boosts their credibility.

How Can My Sellers Start Conversations?

Once your sellers have proven to buyers they are there to inspire and educate, it’s time to start the conversation directly with the buyer. This can be a challenging space for sellers even in the best of times, given that it’s a binary outcome: either reps manage to capture customer attention or lose it, potentially forever.

Empowering your team with actionable guidance on how to transition from social interactions to actual sales engagements — especially in regard to our new digital selling reality — is essential to achieving sales success. Keep in mind that customers will be receiving all types of messages from sellers, coworkers, brands, and more. Therefore, you need to ensure guidance is geared towards cutting through the noise.

Think about:

  • How can sellers reference a positive social interaction in a first touch?
  • Which assets are suitable for this stage of the buyer’s journey?
  • How can you get creative with subject lines?
  • What information does a buyer need to move forward? 


Rethinking your standard approach to igniting customer conversations will ensure reps are armed with everything they need to make a great first impression.

How Can My Sellers Make Engagements Interactive?

It’s no secret that interactive engagements are core to successfully selling in our new reality. A buyer’s time is more valuable than ever, and if they don’t feel heard during a sales call, they have every reason to walk away.

Many reps think they are engaging interactively, but asking for questions at the end of an engagement is hardly enough. Reps need to be able to bring empathy to every conversation — and use those more personal elements to draw buyers into the fold. To succeed, advise sellers to try:

  • Creating a distraction-free environment for calls
  • Customising materials for every engagement
  • Providing a meeting agenda and objectives ahead of time
  • Asking for questions after every slide 


Go the extra mile to secure your team’s success by testing your reps’ ability to engage interactively via roleplaying sessions. These activities are essential coaching opportunities to check whether reps are actually putting these tactics into play and provide feedback if they aren’t.

The more a sales call resembles a dialogue — not a soliloquy — the more likely your sellers are to form lasting relationships and more deeply understand customer needs during a time of rapid-fire changes.

Win the Digital World

With a strategic approach to virtual engagements, your sales team is more likely to authentically connect with buyers and close deals.

Ready to get started? Explore new research from Forrester on how to master digital and virtual selling.

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