Sales is an experimental art.
The past years have proven the demand for innovative ways as per the market trends (Remember how COVID pushed businesses online?).
Looking ahead to 2025 and beyond, it is essential to focus on data analytics, personalization at scale, and AI to improve your sales approach.
This blog discusses the top 19 sales challenges and solutions for reps to overcome obstacles, enhance their strategies, and achieve better results.
Let’s dive into how sales are changing and the new challenges reps face to close deals.
Changing sales landscape – Raises top challenges for sales teams
Let’s understand how these four trends raise the biggest challenges in sales:
- Economic shifts: The financial uncertainties lead to longer sales cycles and raise sales obstacles around pricing.
- Customer expectations are high on personalization: Granular-level personalization is the expectation of prospects, making it one of the biggest sales and marketing challenges.
- Value-driven sales in demand: People prefer products that offer value, suggesting a move towards a value-based selling approach.
- Integration of AI in sales: AI offers efficiencies but challenges personal connection, urging a balanced approach to tech integration.
Moving on to discover the most common sales challenges faced by sales professionals with their possible solutions.
19 Biggest sales challenges and their proven solutions
In every sales process, reps encounter a set of common challenges, from identifying the sales-worthy leads, effective nurturing to get prospects engaged, handling objections, etc.
Let’s explore how to overcome challenges in sales with strategic solutions:
1. Adopting the buyer-first approach in the sales process
Our modern buyers know what they want and expect reps to serve them what they’re looking for:
Shifting the mindset from what we sell to what you are looking for is a sales challenge for reps used to a push sales strategy.
A recent Sales Gravvy podcast with Carole Mahoney stressed the demand for the adoption of a buyer-first approach.
Selling isn’t just about selling anymore; it’s about genuinely solving problems for your buyers, building relationships, and gaining trust.
Solution:
- Research your target audience and create a customer persona to understand what your prospects are looking for.
- To tailor your approach, use CRM and analytics to understand your target buyer’s preferences and common pain points.
- Practice listening to your prospects’ thoughts to uncover their true needs.
2. Realizing a solid product doesn’t guarantee sales
This sales challenge is faced by reps who don’t follow any strategy and practice pitching their product benefits to the target prospects.
So, they end up empty-handed and losing the opportunity.
Solution:
- Firstly, find your unique value proposition to understand what makes your product different from competitors.
- Discover how you solve specific problems or meet the unique needs of your ideal customers.
- Focus on educating your audience and adopt a value-based selling approach.
3. Lack of brand reputation and trust
Building a brand reputation is one of the biggest challenges in sales and marketing.
For sales reps, closing deals for new businesses without brand awareness and reputation becomes a significant sales challenge.
However, it is not that you won’t give results without a brand image.
For a new business without a strong brand presence, overcoming trust barriers in the buyer’s journey involves strategic actions.
Solution:
- Sales reps can’t directly build brand reputation alone but can help by focusing on customer needs and ensuring a good buying experience.
- Ensure honesty and clarity in all communications (during phone calls or emailing).
- Leverage customer feedback to improve service and offerings.
4. Qualifying MQLs as sales leads
MQLs (Marketing qualified leads) show initial interest but haven’t yet demonstrated a readiness to buy.
The biggest challenge lies in focusing your efforts on leads with a higher chance of purchasing and ensuring sales resources are used most effectively.
Overcoming these sales challenges will help reps save more time and grow sales counts faster.
Solution:
- Using a lead qualification framework that includes lead scoring helps pinpoint which prospects are truly ready. This way your teams will likely focus on the right people and win deals.
5. Not getting enough time for prospecting
Prospecting is the first sales pipeline stage. It involves practices identifying and contacting potential customers (or prospects) to convert them into clients.
According to ZoomInfo, sales prospecting is one of the powerful ways to grow sales for 70% of B2B companies.
Effective time management is crucial for overcoming obstacles in sales, especially for prospecting.
However, with the pressure of converting the ongoing leads in their sales pipeline and other day-to-day activities, most reps find it challenging to dedicate time to prospecting.
Solution:
- Plan your to-do tasks and dedicate a specific time slot for sales prospecting (cold calls or emailing).
- You can use a Power Dialer to save time and increase efficiency.
- Set your email outreach on autopilot with the support of powerful cold email software.
6. Lack of time for selling
A sales rep does a lot in a day, including collecting details about leads, nurturing them, drafting sales emails, updating records, etc.
Besides, if things aren’t organized, more time is wasted searching for information, and sales reps don’t have enough time to focus on selling.
A study by Salesforce states that sales reps spend a mere 28% of their week actively selling.
Solution:
- Evaluate your daily routine and find the time-consuming activities. If all are repetitive tasks, automate them using a Sales Automation tool.
- A cold email outreach tool can help you with an email builder, customizable templates, and sequences.
Upgrade yourself to leverage tools for data organization, meeting scheduling, email outreach, and all your mundane tasks – Ever experienced what a powerful CRM can do? – Streamline the entire business and boost productivity.
Manage your entire business with Salesmate CRM!
Explore Salesmate and see how the platform streamlines your marketing, sales, and customer support tasks smartly.
7. Sales and marketing teams misalignment
Reps struggle in sales due to ineffective misalignment of sales and marketing teams within the organization.
For instance, if your sales and marketing teams are using two different tools for working and managing data, issues like data loss and duplication will be a day-to-day time waster.
To succeed with Smarketing (a business strategy that involves the close alignment of the sales and marketing team), you need to break these organizational silos and combat them to develop an integrated system.
8. Making every sales interaction personalized
A personalized offer more often attracts the right audience. Also, top-performing sales teams are 2.8 times more likely to focus on personalizing customer experiences.
But, personalizing each interaction to the specific needs and preferences is a major challenge for reps.
Also, managing the scale of personalization when targeting prospects with varied customer personas is a matter of challenge.
Solution:
- Develop buyer personas and segment the customer base to create more targeted communication strategies.
- For engaging with inbound leads, make sure your customer understanding is on point to hit their pain point, be a solution to their challenges, or more.
- Be an active listener to your prospect during discovery calls and meetings to propose personalized offers.
- Technologies like CRM, customer data analytics, and AI can help you understand your target customer behavior for personalized communication.
9. Not getting a response from the prospect
After a few initial interactions, most of the prospects stop responding. Several sales reps get demotivated by this silence.
They abandon the lead and start focusing on another prospect. Due to this, most of the leads aren’t converted. In fact, a study revealed that 79% of marketing leads never convert into sales.
Solution:
- Try to connect with somebody else from the prospect’s company.
- Connect with your prospects using different channels besides calls and emails, such as text messages and social media sites.
- Setting up an automated follow-up process with email and text sequences will boost your productivity and responses.
- Connect with the prospect at different hours. Find the best time to send sales emails or dial the prospect.
Boost responses with Sequences!
You can automate your outreach and follow-ups with Salesmate to drive more business opportunities at your door.
10. Securing the first meeting with the prospect
For every rep, landing that first discovery meeting with the lead they’re chasing is one of the biggest sales challenges.
Solution:
- Prioritize responses to inbound inquiries and thoroughly research the prospects to ensure your message resonates with their needs and challenges.
- Use targeted, value-driven outreach strategies that clearly express the benefits of meetings.
- To increase your chances of being noticed, implement a multi-touchpoint approach (emails, calls, social media, and direct mail).
Tip – Make your every message/pitch hyper-personalized to win the meeting!:
11. Nailing the discovery meeting
Securing a discovery meeting is one of the successful milestones in a B2B sales process for reps, so you can’t lose the chance to win the deal at this point.
Building rapport, impressive presentation, discovering pain points, and planning time in discovery meetings are some of the sales problems for reps.
Here’s how you should schedule to keep all things on track:
Solution:
- Prepare thoroughly by researching the prospect’s business, industry, and potential challenges they may be facing.
- Be an empathetic and active listener to understand their situation.
- Ask open-ended discovery questions to discover the challenges and desires of prospects.
- Summarize key points to confirm understanding and demonstrate active listening.
- Position yourself as a consultant rather than just a salesperson by offering initial insights or values that align with their expressed needs.
12. Inability to answer prospect’s questions
Modern buyers are intelligent and well-informed. They are updated with the latest market trends and popular technologies.
So, they tend to ask a lot of questions. Most of the time, sales reps go blank and cannot answer these questions.
Are you facing this issue too? If yes, then here are things you need to do.
Solution:
- First, ensure you have good product/service knowledge.
- Make a list of questions that you often get and prepare for it.
- Have a mock call session with your senior.
13. Winning at negotiation
Most of the deals are lost during the negotiation stage of the sales process.
Several prospects are unwilling to compromise or find common ground.
Besides, the prospect’s reluctance annoys the sales reps, who end up venting their anger in an unpleasant way.
Solution:
- Stay calm during the negotiation and think before you respond to objections.
- Research and explore various negotiation tactics to deal with reluctant prospects.
- Identify the prospects’ pressure points and make them visualize the consequences of not addressing the problem right now.
- First, quote a high price, then offer a low-price option with limited features. While the prospect is swinging between two offers, make the actual proposal.
14. Inability to handle criticism or rejection
Most sales reps often struggle with rejection and feedback, leading to discouragement.
This even affects their next deal as they cannot focus on communication due to the disappointment from the rejection or criticism they face.
Solution:
- Practice and prepare a good response when you hear a "no."
- Don’t get emotionally hijacked; work on your EQ (Emotional Intelligence) skills.
- Ask your senior to conduct a mock call session to prepare you to handle rejection on sales calls.
- Create many opportunities for yourself so that a few rejections don’t affect your target.
15. Competing with competitors
Most sales reps often hear statements like:
“The [X competitor] is offering a product at a much lower price.”
“[Y competitor is giving a 4-month free subscription to their service].”
From lowering prices to offering freebies, businesses are doing all it takes to surpass their competitors.
Eventually, potential buyers pick such points and use them as leverage to negotiate a better price.
Sales reps may go blank when faced with these challenges or make impulsive decisions that result in losing the opportunity.
Solution:
- Map out the strengths and weaknesses of your competitors through an in-depth competitive analysis with a sales battle card.
- Find out how you are better than your competitors and explain it to your potential buyers.
- Share case studies and testimonials of satisfied customers who chose you over the competitors.
16. Selling to groups over a solo buyer
This is one of the biggest challenges of B2B sales, and you’ll agree that convincing a group of key decision-makers compared to an individual is tougher.
The negotiation process becomes complex with endless questions, the sales cycle lengthens, and it is challenging to convince different people with varied perspectives.
This scenario requires preparation for multiple aspects to close more deals.
Solution:
- Examine group dynamics and understand each contact’s role and preferences within their company.
- Understand the company’s industry position, challenges, and goals.
- Address both collective needs and individual concerns during sales communication.
- Strengthen your case with relevant case studies and testimonials.
Set your mundane tasks on autopilot for high productivity!
Salesmate offers a powerful automation suite to set your marketing and sales activities in automated mode. You just keep track of the success graph.
17. To leverage social selling for broader sales growth
Sales reps sometimes miss out on leveraging social selling to its fullest potential.
However, not utilizing social platforms effectively is a common challenge that needs to be addressed and overcome.
Did you know that 72% of social sellers who leverage social media meet their sales quota?
Let’s explore which social platforms provide the highest ROI:
Solution:
- Evaluate and identify the best platform for your business to engage the audience, establish trust, and sell.
- Build a personal brand and engage with potential customers to gain trust.
- Share content that adds value to your potential buyer’s work and demonstrates thought leadership.
- Practice social listening to understand customer needs that align with your brand’s offerings.
- Leverage social selling tools to track metrics, measure your sales efforts, and optimize for higher ROI.
18. Ineffective training received by sales reps
Many organizations set high expectations but fail to provide proper sales enablement training to reps to handle today’s intelligent buyers.
This lack of proper training is one of the primary causes of low sales productivity.
Solution:
- Identify training needs and request management to invest in relevant programs.
- Thoroughly review sales collaterals to improve your product/service knowledge.
- Explore solutions from industry experts and collaborate with your sales team for skill improvement.
- Seek evaluations and genuine feedback from sales managers or leaders to enhance your performance.
- Attend live webinars to gain insights from industry experts.
19. Leveraging the right technologies to overcome modern sales hurdles
While sales reps are adopting progressive working styles, they often lag in utilizing technology effectively.
According to Harvard Business Review, “Sales representatives believe that technology has not simplified their job or made it less expensive; instead, it has just been an added thing to learn.”
This highlights significant challenges, especially as businesses expect sales teams to boost productivity and grow revenue.
Here are the four key challenges associated with resistance to modern technologies:
- Effective data management and utilization
- Engaging leads through longer sales cycles
- Tracking and managing deals efficiently
- Adopting AI for sales effectiveness
Solution:
Adopting a robust Sales CRM can address these challenges by offering:
- Lead management to organize and segment prospect details.
- Lead engagement tools like emails or texts to maintain interest through extended sales cycles.
- Sales pipeline management to visualize sales cycles and identify bottlenecks.
- Sales automation to streamline repetitive tasks by setting them on autopilot.
- AI integration to expedite activities like cold email drafting, response generation, and meeting scheduling.
Wrap-up on sales problems and solutions
Overcoming sales challenges requires a deep understanding of customer needs, strategic use of technology, and a commitment to personalization and efficiency.
Lack of time management and effective objection handling remain major hurdles for sales reps.
To tackle these challenges, focus on understanding your prospects, aligning solutions to their needs, and leveraging supportive technologies to streamline the sales process.
Sales reps must embrace technology and actionable insights to guide prospects seamlessly through the sales funnel.
Frequently asked questions
1. What is the most challenging thing in sales?
Dealing with constant changes and uncertainty in the market is one of the top sales challenges that impact client engagement and the decision-making process.
2. What are the top B2B sales challenges?
Here are the major challenges in B2B sales:
- Long sales cycles and complex purchasing processes due to multiple decision-makers.
- Demonstrating deep knowledge and expertise to engage educated buyers.
- Prospects don’t have enough budget.
- Prioritizing customer retention to leverage existing customers.
3. What is an example of a challenging situation in sales?
A major sales problem is securing a first meeting with a prospect, often due to ineffective communication strategies and the difficulty of presenting a compelling value proposition.
4. What are the top sales challenges for small business owners?
Here are the five biggest sales challenges for small business owners:
- Manage finances and funding
- Stand out against bigger rivals
- Hiring talented people and employee retention
- Handle legal compliance
- Keep up with digital shifts
5. What are the biggest challenges in sales for remote sales reps?
The top three remote sales challenges are:
- Getting engagement in virtual meetings
- Adapting to technology like digital tools
- Building relationships without in-person interactions
6. What are the three biggest ethical challenges in sales?
Here are the three biggest ethical selling challenges:
- Honesty and transparency: Struggling with truthfulness and full disclosure to customers.
- Conflict of interest: Balancing company goals with customer needs impartially.
- Data privacy and security: Handling customer data ethically and securely.
Key takeaways
Sales is an experimental art.
The past years have proven the demand for innovative ways as per the market trends (Remember how COVID pushed businesses online?).
Looking ahead to 2025 and beyond, it is essential to focus on data analytics, personalization at scale, and AI to improve your sales approach.
This blog discusses the top 19 sales challenges and solutions for reps to overcome obstacles, enhance their strategies, and achieve better results.
Let’s dive into how sales are changing and the new challenges reps face to close deals.
Changing sales landscape – Raises top challenges for sales teams
Let’s understand how these four trends raise the biggest challenges in sales:
Moving on to discover the most common sales challenges faced by sales professionals with their possible solutions.
19 Biggest sales challenges and their proven solutions
In every sales process, reps encounter a set of common challenges, from identifying the sales-worthy leads, effective nurturing to get prospects engaged, handling objections, etc.
Let’s explore how to overcome challenges in sales with strategic solutions:
1. Adopting the buyer-first approach in the sales process
Our modern buyers know what they want and expect reps to serve them what they’re looking for:
Shifting the mindset from what we sell to what you are looking for is a sales challenge for reps used to a push sales strategy.
A recent Sales Gravvy podcast with Carole Mahoney stressed the demand for the adoption of a buyer-first approach.
Selling isn’t just about selling anymore; it’s about genuinely solving problems for your buyers, building relationships, and gaining trust.
Solution:
2. Realizing a solid product doesn’t guarantee sales
This sales challenge is faced by reps who don’t follow any strategy and practice pitching their product benefits to the target prospects.
So, they end up empty-handed and losing the opportunity.
Solution:
3. Lack of brand reputation and trust
Building a brand reputation is one of the biggest challenges in sales and marketing.
For sales reps, closing deals for new businesses without brand awareness and reputation becomes a significant sales challenge.
However, it is not that you won’t give results without a brand image.
For a new business without a strong brand presence, overcoming trust barriers in the buyer’s journey involves strategic actions.
Solution:
4. Qualifying MQLs as sales leads
MQLs (Marketing qualified leads) show initial interest but haven’t yet demonstrated a readiness to buy.
The biggest challenge lies in focusing your efforts on leads with a higher chance of purchasing and ensuring sales resources are used most effectively.
Overcoming these sales challenges will help reps save more time and grow sales counts faster.
Solution:
5. Not getting enough time for prospecting
Prospecting is the first sales pipeline stage. It involves practices identifying and contacting potential customers (or prospects) to convert them into clients.
According to ZoomInfo, sales prospecting is one of the powerful ways to grow sales for 70% of B2B companies.
Effective time management is crucial for overcoming obstacles in sales, especially for prospecting.
However, with the pressure of converting the ongoing leads in their sales pipeline and other day-to-day activities, most reps find it challenging to dedicate time to prospecting.
Solution:
6. Lack of time for selling
A sales rep does a lot in a day, including collecting details about leads, nurturing them, drafting sales emails, updating records, etc.
Besides, if things aren’t organized, more time is wasted searching for information, and sales reps don’t have enough time to focus on selling.
A study by Salesforce states that sales reps spend a mere 28% of their week actively selling.
Solution:
Upgrade yourself to leverage tools for data organization, meeting scheduling, email outreach, and all your mundane tasks – Ever experienced what a powerful CRM can do? – Streamline the entire business and boost productivity.
Manage your entire business with Salesmate CRM!
Explore Salesmate and see how the platform streamlines your marketing, sales, and customer support tasks smartly.
7. Sales and marketing teams misalignment
Reps struggle in sales due to ineffective misalignment of sales and marketing teams within the organization.
For instance, if your sales and marketing teams are using two different tools for working and managing data, issues like data loss and duplication will be a day-to-day time waster.
To succeed with Smarketing (a business strategy that involves the close alignment of the sales and marketing team), you need to break these organizational silos and combat them to develop an integrated system.
8. Making every sales interaction personalized
A personalized offer more often attracts the right audience. Also, top-performing sales teams are 2.8 times more likely to focus on personalizing customer experiences.
But, personalizing each interaction to the specific needs and preferences is a major challenge for reps.
Also, managing the scale of personalization when targeting prospects with varied customer personas is a matter of challenge.
Solution:
9. Not getting a response from the prospect
After a few initial interactions, most of the prospects stop responding. Several sales reps get demotivated by this silence.
They abandon the lead and start focusing on another prospect. Due to this, most of the leads aren’t converted. In fact, a study revealed that 79% of marketing leads never convert into sales.
Solution:
Boost responses with Sequences!
You can automate your outreach and follow-ups with Salesmate to drive more business opportunities at your door.
10. Securing the first meeting with the prospect
For every rep, landing that first discovery meeting with the lead they’re chasing is one of the biggest sales challenges.
Solution:
11. Nailing the discovery meeting
Securing a discovery meeting is one of the successful milestones in a B2B sales process for reps, so you can’t lose the chance to win the deal at this point.
Building rapport, impressive presentation, discovering pain points, and planning time in discovery meetings are some of the sales problems for reps.
Here’s how you should schedule to keep all things on track:
Solution:
12. Inability to answer prospect’s questions
Modern buyers are intelligent and well-informed. They are updated with the latest market trends and popular technologies.
So, they tend to ask a lot of questions. Most of the time, sales reps go blank and cannot answer these questions.
Are you facing this issue too? If yes, then here are things you need to do.
Solution:
13. Winning at negotiation
Most of the deals are lost during the negotiation stage of the sales process.
Several prospects are unwilling to compromise or find common ground.
Besides, the prospect’s reluctance annoys the sales reps, who end up venting their anger in an unpleasant way.
Solution:
14. Inability to handle criticism or rejection
Most sales reps often struggle with rejection and feedback, leading to discouragement.
This even affects their next deal as they cannot focus on communication due to the disappointment from the rejection or criticism they face.
Solution:
15. Competing with competitors
Most sales reps often hear statements like:
“The [X competitor] is offering a product at a much lower price.”
“[Y competitor is giving a 4-month free subscription to their service].”
From lowering prices to offering freebies, businesses are doing all it takes to surpass their competitors.
Eventually, potential buyers pick such points and use them as leverage to negotiate a better price.
Sales reps may go blank when faced with these challenges or make impulsive decisions that result in losing the opportunity.
Solution:
16. Selling to groups over a solo buyer
This is one of the biggest challenges of B2B sales, and you’ll agree that convincing a group of key decision-makers compared to an individual is tougher.
The negotiation process becomes complex with endless questions, the sales cycle lengthens, and it is challenging to convince different people with varied perspectives.
This scenario requires preparation for multiple aspects to close more deals.
Solution:
Set your mundane tasks on autopilot for high productivity!
Salesmate offers a powerful automation suite to set your marketing and sales activities in automated mode. You just keep track of the success graph.
17. To leverage social selling for broader sales growth
Sales reps sometimes miss out on leveraging social selling to its fullest potential.
However, not utilizing social platforms effectively is a common challenge that needs to be addressed and overcome.
Did you know that 72% of social sellers who leverage social media meet their sales quota?
Let’s explore which social platforms provide the highest ROI:
Solution:
18. Ineffective training received by sales reps
Many organizations set high expectations but fail to provide proper sales enablement training to reps to handle today’s intelligent buyers.
This lack of proper training is one of the primary causes of low sales productivity.
Solution:
19. Leveraging the right technologies to overcome modern sales hurdles
While sales reps are adopting progressive working styles, they often lag in utilizing technology effectively.
According to Harvard Business Review, “Sales representatives believe that technology has not simplified their job or made it less expensive; instead, it has just been an added thing to learn.”
This highlights significant challenges, especially as businesses expect sales teams to boost productivity and grow revenue.
Here are the four key challenges associated with resistance to modern technologies:
Solution:
Adopting a robust Sales CRM can address these challenges by offering:
Wrap-up on sales problems and solutions
Overcoming sales challenges requires a deep understanding of customer needs, strategic use of technology, and a commitment to personalization and efficiency.
Lack of time management and effective objection handling remain major hurdles for sales reps.
To tackle these challenges, focus on understanding your prospects, aligning solutions to their needs, and leveraging supportive technologies to streamline the sales process.
Sales reps must embrace technology and actionable insights to guide prospects seamlessly through the sales funnel.
Frequently asked questions
1. What is the most challenging thing in sales?
Dealing with constant changes and uncertainty in the market is one of the top sales challenges that impact client engagement and the decision-making process.
2. What are the top B2B sales challenges?
Here are the major challenges in B2B sales:
3. What is an example of a challenging situation in sales?
A major sales problem is securing a first meeting with a prospect, often due to ineffective communication strategies and the difficulty of presenting a compelling value proposition.
4. What are the top sales challenges for small business owners?
Here are the five biggest sales challenges for small business owners:
5. What are the biggest challenges in sales for remote sales reps?
The top three remote sales challenges are:
6. What are the three biggest ethical challenges in sales?
Here are the three biggest ethical selling challenges:
Sonali Negi
Sonali is a writer born out of her utmost passion for writing. She is working with a passionate team of content creators at Salesmate. She enjoys learning about new ideas in marketing and sales. She is an optimistic girl and endeavors to bring the best out of every situation. In her free time, she loves to introspect and observe people.