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Top 13 Challenges Sales Leaders Face in 2024 and How to Overcome Them

Sales leaders today are navigating an unprecedented landscape of challenges and opportunities. The current environment has a number of wicked problems that challenge sales leaders, sales managers, and their sales teams. Even though most sales leaders are turning to artificial intelligence to find the improvement they need, so far, there is little evidence that technology improves results. You will have to look elsewhere for solutions to the many challenges that plague salespeople.

  1. Meeting Evolving Buyer Demands: Some will bury their heads in the sand and pretend that buyers want and need to hear from salespeople. When the environment is uncertain, decision-makers need greater certainty that they will succeed. Salesforce reports 80 percent of buyers say they are more likely to buy from a company that understands their specific needs. Buyers seek a better experience and salesperson performance.
  2. Establishing Trust and Credibility: These two character traits, whether innate or learned, will determine much of how you do when it comes to creating and winning a client’s relationship and their business. Without trust, you are not going to win a deal. Without credibility, something we describe as Being One-Up, indicating you are an expert. Our friends at HubSpot found that only 3 percent of buyers trust salespeople.
  3. Cultivating a Personal Brand on LinkedIn: If you spend time on LinkedIn, you will have no trouble identifying those who have a strong personal brand. You will also notice a lot of folks have no brand. This too speaks to your credibility. Our friends at LinkedIn found that 70 percent of buyers say they are more likely to buy from a salesperson with a strong personal brand.
  4. Optimizing Time Management: Why do we waste our one and only resource we can’t renew? When someone says they don’t have time, it means they don’t recognize that all we have is time. Pace Productivity reports salespeople spend 34 percent of their time selling. McKinsey found that the average salesperson spends 21 percent of their day on emails. Without an effective plan at the beginning of the week, you may fall into the time trap.
  5. Mastering Effective Prospecting Techniques: Some time ago, I started to alert readers that the cold outreach apocalypse is here. This is the result of automation, sequences, and outreach from dozens of companies. HubSpot found that 40 percent of salespeople say prospecting is the most difficult part of their job. The Brevet Group says only 1 in 50 calls results in a meeting. You can improve that by honoring the trading-value rule.
  6. Accurately Identifying Decision-Makers: Any time you have a problem that recurs, you should move it to the front of your sales conversation. The longer you go without the decision-makers, the less likely you are to win their business. You cannot win if the decision-makers are not part of the conversation. Gartner says an average of 6.8 people are involved in the buying process. Forrester reports that 70 percent of buying decisions are made before a salesperson is ever contacted.
  7. Navigating Prolonged Sales Cycles: The folks who believe nothing has changed, need to look no farther than long sales cycles. In part, this is because of the uncertainty, with another challenge of consensus within the company. CSO Insights found that the average B2B sales cycle has increased by 22 percent in the past five years. Harvard Business Review reports that 75 percent of B2B sales to new customers take at least four months to close.
  8. Successfully Closing Sales Deals: Ink. Contract. Commitment. No one succeeds in B2B sales without being able to close the deal. For help with this, see The Lost Art of Closing: Winning the 10 Commitments That Drive Sales. HubSpot reports that 27 percent of salespeople say closing is the most difficult part of their job. The marketing donut says 80 percent of sales require five follow-up calls after the meeting.
  9. Effectively Handling Sales Objections: I, for one, can’t remember the last time I heard an objection. That said, I have heard a good number of real concerns. Would you want to avoid what you call an objection by resolving their concerns? Sales Hacker says the average salesperson hears “no” five times before they hear “yes.” In a stat I hope is incorrect, the Brevet Group reports 44 percent of salespeople give up after one follow-up. You can find help here in The Only Sales Guide You'll Ever Need.
  10. Maintaining High Sales Motivation: We keep hearing about burnout. One way to help is to find meaning and purpose in your work. You must remember that you help people improve their results. CSO Insights finds 55 percent of salespeople missing their quota. The Bridge Group reported that the average tenure of a B2B salesperson is only 1.5 years.
  11. Delivering Engaging Sales Presentations: It looks like buyers are now looking for presentations. Microsoft suggests the average attention span is only 8 seconds, thank you TikTok. Too long, didn’t read should be too short, didn’t read. Rain Group found that 60 percent of buyers say they are likely to buy from a company that has a strong presentation.
  12. Negotiating Mutually Beneficial Deals: You can find my 17-minute negotiation course here: https://www.thesalesblog.com/free-negotiation-video. This may help you or your team with Sales Hackers’ stat that 75 percent of salespeople say they don’t feel comfortable negotiating.
  13. Building Lasting Customer Relationships: If you want to succeed in B2B sales, you may not find help from B2B sales training. Relationships come with a cost. Relationships cost you time and attention. Invesp found acquiring a new customer is five times more expensive than retaining one.

Before you leave this article, identify the challenges you are struggling to overcome. Once you have your list, do a search here on thesalesblog.com for articles that will provide you with strategies for each challenge.

If you are a sales leader, identify your team’s challenges and prioritize the challenges that have the biggest impact on your results. Build a plan to help your team improve their ability to handle these challenges.


Sales 2024
Post by Anthony Iannarino on May 11, 2024

Written and edited by human brains and human hands.

Anthony Iannarino

Anthony Iannarino is an American writer. He has published daily at thesalesblog.com for more than 14 years, amassing over 5,300 articles and making this platform a destination for salespeople and sales leaders. Anthony is also the author of four best-selling books documenting modern sales methodologies and a fifth book for sales leaders seeking revenue growth. His latest book for an even wider audience is titled, The Negativity Fast: Proven Techniques to Increase Positivity, Reduce Fear, and Boost Success.

Anthony speaks to sales organizations worldwide, delivering cutting-edge sales strategies and tactics that work in this ever-evolving B2B landscape. He also provides workshops and seminars. You can reach Anthony at thesalesblog.com or email Beth@b2bsalescoach.com.

Connect with Anthony on LinkedIn, X or Youtube. You can email Anthony at iannarino@gmail.com

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