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Top 4 Sales Enablement and Leadership Challenges


Of the many initiatives sales leaders try to implement, which ones are the most difficult? To find out, the RAIN Group Center for Sales Research surveyed 423 sales, enablement, and company leaders.

Here are the top four (out of 14) challenges, and the percentage of leaders who labeled them as very challenging.

  • Recruiting and hiring: 52%

  • Improving lead quality and quantity: 41%

  • Developing sales skills: 40%

  • Developing sales managers: 36%

As for what we see when working with clients, we agree — these challenges are difficult. However, when you get them right, they have a huge impact. Here are some ideas of what to do with each challenge if, indeed, tackling them is on your radar screen.

Recruiting and Hiring

Fifty-two percent of sales leaders say recruiting and hiring top sales talent is very challenging. This bubbled to the top as the No. 1 challenge faced.

There are a few factors to consider here: 1) It’s a strong economy, so finding top talent is difficult, and 2) Change is afoot in the world of sales, requiring top salespeople to be exceptionally better than they used to be in order to deserve the label “top talent.” 

In the new report, Top Sales Leadership Challenges and Priorities, we propose an alternative strategy to recruiting top sales talent: Develop your own top talent.

This can be done through improving seller productivity (research shows significant improvement potential here for the vast majority of people), developing multiskilled sellers, and leveraging sales managers. Do these three things from “The Extreme Productivity System: Keys, Habits, and Hacks” and you’ll address many of the remaining top sales challenges.

Improving Lead Quality and Quantity

No surprise here. Generating leads, prospecting, and setting appointments — these were challenging in the 80s and continue to be today.

That said, prospecting used to be more straightforward. Get a directory, make phone calls, and set meetings. Today, prospecting involves multiple modes of communication across numerous touch points with various types of messages. You need to do more to get in front of potential buyers and provide a compelling case for them to meet with you.

This is possible and some sellers do succeed at it. In fact, our Top Performance in Sales Prospecting study found that 82 percent of buyers accept meetings with sellers who reach out to them.

Maybe your sellers avoid prospecting because they don’t think it works. It’s probably not working because they aren’t doing it right. Luckily, lead quantity and quality can be improved and they can begin by following the six keys to prospecting success.

Developing Sales Skills

Forty percent of leaders say that developing sales skills — driving and winning sales opportunities, driving account growth, consultative selling, filling the pipeline, negotiating, and so on — is very challenging.

In “The Top-Performing Sales Organization” study, we found that, across the board, top performers are significantly more likely to have sellers with the skills needed to find and win new business. From prospecting to consultative selling to negotiation to account management and sales management, their sellers have much better sales skills. 

We also found that top performers invest in and focus on sales training much more extensively. While developing sales skills is a top challenge, it seems the best sales organizations have the combination to this lock.

Developing Sales Managers

Sales managers are a key leverage point for many organizations, yet across all of our studies we find a lack of attention and focus being placed on sales management. Going hand in hand with sales management, 27% of leaders report coaching their sales force as very challenging.

Sales managers have a tough job with multifaceted responsibilities. The one area where we see a huge gap when comparing what they should be doing to what they are doing is the area of sales coaching.

There you have it. These are the most difficult challenges facing sales leaders today. In the Top Sales Leadership Challenges and Priorities Report, we dig a bit deeper into these challenges and share three strategies you can employ to overcome these challenges and drive sales success.

Fifty-two percent of sales leaders say recruiting and hiring top sales talent is very challenging.”

Mike Schultz | President, RAIN Group
Hear from Salesforce's sales leaders on how they hire and retain the best in selling.



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