10 Sales Prospecting Challenges (and How to Crush Them)

min read
June 25, 2024

From finding quality leads to facing rejections and navigating buying journeys that change faster than a toddler’s mood, SDRs face a lot of challenges while filling the pipeline with quality leads. 

We interviewed several presales folks, including our in-house experts, to compile a list of top 10 prospecting challenges and fool-proof ways to overcome them. Let’s dive right in!

Biggest Sales Prospecting Challenges & Their Solutions

1. Identifying Quality Leads  

You have a large volume of leads passed down from marketing. Add to it the leads you got from referrals, networking, and attending events. How do you go about deciding which leads to prioritize? 


Implement a CRM system with segmentation and lead-scoring capabilities to compile and track those leads.

If you’re doing it manually, segment leads based on demographics, firmographics, behavior, and engagement level. Prioritize leads that closely match your ICP. 

You can also use intent providers like Bombora, Albacross, or Amplemarket to focus your energy on prospects who are closer to buying. 

Pro tip: You can also prioritize based on lead source. 

For example, In our outbound sales strategy, we prioritize leads that view demos on high-intent pages like product pages, home page, ad landing pages, G2 listing, etc.

These pages typically contain detailed information about your offerings, indicating that the lead is actively seeking a solution and is closer to making a purchasing decision. This higher level of engagement suggests a greater likelihood of conversion, making these leads more valuable and a higher priority for follow-up.

2. Finding Key Decision Makers 

Identifying the right individuals within an organization who have the authority to make purchasing decisions can be a time-consuming and labor-intensive process, especially when dealing with enterprise accounts.


Utilize lead database software like Kaspr, Consensus, or Apollo.io to search for contacts based on specific titles, departments, and seniority levels. Then, use your CRM’s data enrichment features to update and verify contact information. 

Here’s an interactive demo powered by Storylane to show how you can use Apollo.io to find contact information and build lists. 

Pro tip: Consider sharing an interactive demo with a lead capture form with your champion within the prospect company. As people engage with your demo, you get real-time information about the stakeholders involved in the buying process. 

If you’re using Storylane, you can create a multi-flow demo that empowers viewers to “pick their own adventure.” This approach enables engagement and reveals preferences, as stakeholders naturally gravitate towards their areas of interest.

For example, if a technical buyer zooms in on the integration capabilities, you've pinpointed their primary concern.

Also read: How to Close Complex Deals With the Miller Heiman Sales Process?

3. Maintaining Consistent Communication

There’s a very thin line between being consistent and being intrusive. Sure, you want to say top-of-mind of your prospects, but how do you do it without being pushy? 

Research indicates that 57% of people are encouraged to make a purchase from a salesperson who doesn’t try to apply pressure or hassle them when following up. 


Establish a clear and consistent follow-up schedule that respects the prospect's time and preferences. Avoid excessive contact and space out communications appropriately.

You can use email automation tools like HubSpot and SalesLoft to schedule personalized outreach sequences, ensuring regular and relevant communication. 

Also, pay attention to the prospect’s responses and feedback. Adjust your communication strategy based on their cues, and be ready to back off if they signal a need for space.

Pro tip: Add a demo to your cold emails. Don’t wait for prospects to schedule a call before you actually start talking about the product. 

Research their industry and pain points, and share a personalized demo to speed up the sales process. 

With Storylane’s Gmail plug-in you can add demos to your mail as links, gifs, or both, without leaving the email interface. 

4. Overcoming Resistance to Change

Prospects often resist switching from their current solutions, fearing the risks and disruptions associated with change.


Acknowledge the prospect's fears and reservations about the change up front. Actively listen to their concerns and provide thoughtful responses that address each issue. Demonstrate your understanding and empathy to build trust.

Use demos, case studies, and testimonials to show how your offering can solve the prospect's pain points and improve their business outcomes. Make a compelling case for why change is necessary and beneficial.

For example, Upmarket used Storylane interactive demos and increased engagement by 78%, turning 22% of demo viewers into signups and 12% into paying customers. 

Here’s the demo they used: 

5. Personalizing Outreach at Scale

In-depth personalization requires a lot of specific customer data, and ensuring that data is accurate and accessible across systems can be a hurdle.


Develop "industry-specific content libraries" with repositories of insights, case studies, and pain points. SDRs can quickly pull relevant information from these libraries to personalize their outreach efficiently.

Also, use email personalization tools such as Mixmax, Outreach, and Yesware to customize greetings, highlight relevant pain points, and showcase targeted case studies. Integrate these tools with your CRM to automate much of the personalization process.

Pro tip: Use builtwith.com for account research. This site allows us to check the techstack of any company and personalize the outreach

6. Differentiating from Competitors 

Prospects are often bombarded with outreach from multiple vendors offering similar solutions. 

This makes it challenging to stand out, capture attention, and clearly articulate your unique value proposition when you're not the only one vying for the prospect's consideration.


Create a "comparison matrix" that highlights not just feature differences but also the unique business outcomes your solution provides. 

This helps prospects understand the distinct value you offer beyond surface-level comparisons. 

Additionally, focus on building relationships and providing value upfront, such as sharing industry insights or relevant case studies, to differentiate yourself from competitors who may be using more aggressive or product-centric approaches.

7. Navigating Complex Buying Journeys 

In B2B sales, decision-making often involves multiple stakeholders with diverse interests, making it challenging to effectively engage and convince all parties involved.


Develop a "stakeholder mapping" strategy. Create visual representations of the decision-making process within target organizations, including key influencers, potential blockers, and their interrelationships. 

Pro tip: Utilize "micro-demos" tailored to specific stakeholders.

Create short, focused demonstrations that address the unique concerns of each decision-maker, allowing you to quickly adapt your pitch without overwhelming them with irrelevant information.

8. Time Management

Prospecting requires you to dedicate enough time to finding qualified leads but also ensure you're nurturing existing ones to close deals.


Implement a "prospecting power hour" technique. Dedicate one uninterrupted hour each day solely to high-impact prospecting activities, focusing on tasks that directly contribute to pipeline growth.

Use productivity tools like RescueTime or Toggl to track how you're spending your time and identify areas for improvement.

9. Staying Motivated

92% of salespeople give up after four "no's," but 80% of prospects say "no" four times before they say "yes."


Engage in role-playing exercises and practice different sales plays with your team. This not only hones your skills but also builds confidence and prepares you for real-world interactions.

Bonus: Consider reading "Go for No!" by Richard Fenton and Andrea Waltz. This book shifts the perspective on rejection and failure, encouraging salespeople to embrace “no” as a step towards success. 

It offers practical advice on how to handle rejection and stay motivated, making it a valuable resource for any salesperson looking to improve their resilience and persistence.


10. Reaching Out at the Right Time

Catching prospects at an inconvenient time can backfire and reduce the chances of a successful engagement.


Using marketing automation tools like Pardot and ActiveCampaign can help schedule outreach attempts based on prospect behavior and past interactions. 

These tools analyze engagement data to determine the optimal times for contact, increasing the likelihood of a positive response. 

Additionally, implement a "trigger event monitoring" system. 

Set up alerts for significant events within your target accounts, such as leadership changes, funding rounds, or new product launches. These events often indicate a higher likelihood of openness to new solutions, making them ideal times for outreach.

Key Takeaways:

  • Use CRM systems and intent data to identify and prioritize quality leads
  • Leverage prospecting tools like Apollo.io and Storylane interactive demos to find decision-makers
  • Maintain consistent, respectful communication without being pushy
  • Address resistance to change with empathy and compelling case studies
  • Personalize outreach at scale using industry-specific content libraries
  • Differentiate from competitors by focusing on unique business outcomes
  • Navigate complex buying journeys with stakeholder mapping and micro-demos
  • Implement time management techniques like "prospecting power hour"
  • Stay motivated by embracing rejection as a step towards success
  • Use marketing automation tools to reach out at the right time
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"Previously, there was scope for error and we’ve gone from a process that could be time consuming and painful to a process that’s super quick."

"Previously, there was scope for error and we’ve gone from a process that could be time consuming and painful to a process that’s super quick."


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