Conquer the Obstacles: Overcoming Common Lead Engagement Challenges

By Aldwin Neekon

Engaging your audience over time isn’t without its challenges. These roadblocks, if left unaddressed, can hinder your efforts and prevent you from realizing the full benefits of creating the lead engagement strategy that wins lost sales for your company.

Here are four common challenges you might encounter on your lead engagement journey:

Challenge #1: Keeping Leads Engaged

Imagine having a captivating conversation with a friend, only for them to lose interest and scroll through their phone halfway through.

Or basically any conversation with a teenager. (Don’t worry, I guarantee they’re not reading this).

That’s what happens when leads get disengaged. The challenge is keeping their attention and getting them to see enough value in your interactions to keep them motivated to continue them.

Here are a few Lead Engagement Strategy Pointers:

Offer Value First, Promote Later: Focus on providing valuable resources and insights that address your audience’s pain points. Build trust and establish yourself as an expert before introducing your sales message.

Variety is Key: Don’t bombard your audience with the same message. Mix up your content formats with blog posts, infographics, videos, and even interactive quizzes to keep things fresh and engaging.

Another reason for variety is because different people prefer different formats at different times. Sometimes I just want to scroll through a blog post and pick up the top 3 points. Sometimes I want a well told story in a video. Other times I’m in a commute and I want to hear it in a podcast. Give your leads choice.

Challenge #2: Identifying Disengaged Leads

Not all leads are created equal. Recognizing and addressing disengaged leads quickly is crucial to optimize your efforts and focus on those with higher conversion potential.


  • Monitor Key Metrics: Track essential metrics like email open rates, click-through rates, and website visitor behavior. These indicators can reveal a decline in engagement and help you identify leads who are losing interest.
  • Analyze User Behavior: Pay attention to how your audience interacts with your content. Look for signs of disengagement, such as abandoning website forms halfway through or failing to open multiple emails in a row.
  • Conduct Surveys: Directly reach out to your audience through surveys or polls to assess their level of engagement and understand the specific reasons behind potential disinterest.
  • Talk to Your Sales Team: This one’s for the marketers. Talk to sales. Talk to any other customer-facing people. Find out what they’re hearing. What are their frustrations? Today I talked to a senior sales guy who told me about his challenges in getting ghosted by leads who were previously deeply engaged. Figuring out what happened there can unlock all kinds of things we can try to prevent it from happening next time.

Challenge #3: Personalizing Lead Engagement

A generic “Dear Valued Customer” email might have sufficed in the past, but today’s audience craves personalized experiences. Tailoring your communication to individual needs and interests is crucial for effective engagement.


  • Segment Your Audience: Divide your leads into groups based on demographics, interests, and buying stage. This allows you to tailor your messaging and content to resonate with each segment on a personal level. Let them choose their own path. I’ve had over 300% increase in conversion rates, for example, simply by allowing visitors to pick what kind of customer they are by clicking on one picture vs. another. Your leads don’t want to waste their own time. Let them show you how to be more relevant to them.
  • Dynamic Content: Use marketing automation tools to personalize website content and email campaigns based on user behavior and past interactions. For example, if a lead downloads a specific white paper, you can send them follow-up emails with related content.
  • Use Personalization Tokens: Personalize email greetings, subject lines, and even blog post recommendations with the lead’s name or company information to create a more personal touch.
lead engagement is a team sport

Challenge #4: Measuring Lead Engagement ROI

Without quantifiable results, it’s difficult to assess the effectiveness of your lead engagement efforts and justify their continued investment. Measuring your return on investment (ROI) is crucial for demonstrating the value of your strategy. This is a longer-term thing. A lot of what you do as a marketer impacts sales, but in B2B that might not hit the books for months or years.

That’s good news by the way.


  • Set SMART Goals: Start by defining specific, measurable, achievable, relevant, and time-bound (SMART) goals for your lead engagement efforts. This might include increasing website traffic, boosting conversion rates, or generating a specific number of leads.
  • Track Key Performance Indicators (KPIs): Identify relevant KPIs that align with your goals and track their performance over time. This could include lead generation cost, customer acquisition cost, or lead conversion rate.
  • Utilize Analytics Tools: Leverage data analytics tools to measure the impact of your campaigns. Analyze the data to identify which strategies are most effective and optimize your approach for better ROI.
  • Find interim or leading indicators: One of my favourite metrics is how quickly leads get through the various steps of their buying journey. If they used to get stuck on step 5 but now get to step 6, that’s a huge improvement. It will let you finally get enough data on step 6 to solve it. Once those obstacles are gone, you guessed it, they’ll zoom right to step 7 and you’ll hear a whole new set of complaints from the sales team!

Addressing these common lead engagement challenges is crucial for any business aiming to convert leads into loyal customers. Try out the strategies outlined above, and let us know if they helped you overcome these obstacles.

Remember, consistent communication, valuable content, and a focus on personalization are key ingredients to building lasting relationships with your audience and driving sustained business growth.

Which, ironically, I do a lot more of on my LinkedIn profile than here, mainly because I don’t hear from you hear. But I’m always looking forward to our next chat. Give me a call.

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