Everybody loves a good challenge. In fact, at Performio, we have what we call, “The Weekly Challenge.” It’s a culture building event everyone takes part in and teams accumulate points each week that culminates into a quarterly team champion. It’s a mix of trivia via Kahoot! And sharing your experiences on any particular topic via Slack. Last week’s challenge was, “What’s the most adventurous thing you’ve ever done and would you do it again.”
Well if there was ever a challenging adventure, I’d have to say, it would be sales. Unpredictable, highly complex, competitive, the list goes on. But to run an effective sales team, you must have a solid foundation in order for the adventure to be a success. Nobody’s going skydiving without being assured proper safety procedures were in place to ensure the parachute opens. Just like ensuring your sales team is built right from the ground up and given the support they need to be successful.
The world of sales is full of challenges, but some loom larger than others. A recent study by RAIN group identified the five biggest challenges facing sales leaders today, which is a great start, but we want to take it a step further by offering solutions.
At Performio, we’ve helped hundreds of sales organizations navigate some of their trickiest problems, giving us a wealth of experience to draw on. So we sat down with our CEO, Grayson Morris, to talk through these challenges, identify ways to solve them, and suggest additional resources from Grayson’s stack of favorite sales books.
Here are the five challenges sales leaders find most difficult, and how to overcome them.
1. Recruiting and hiring
The first and biggest challenge revealed by the study is recruiting and hiring, with 52% of sales leaders saying they find it very challenging. We’ve previously discussed the challenge of hiring, noting how expensive and time intensive it can be, as well as how the problem is exacerbated by poor retention rates in sales. But there are ways to address these issues.
Be clear and specific about what you need
Recruiting and hiring presents a challenge across all industries and positions, but sales presents a particular challenge due to the uniqueness of each role and each sale. Past success selling one product doesn’t necessarily translate to success when selling another.
You could find someone who did great when selling to marketing leaders, but discover that they’re unable to replicate their success when selling to sales ops. Or they may have had success selling a high transaction volume of $15,000 deals, but they can’t manage to sell a $150,000 deal at all. And by the time you discover the problem, you’ll have already spent countless resources hiring and onboarding them, not to mention that you’ll have turned away other candidates who may have been a better fit.
The solution here is to be as upfront as possible about the specific requirements for the role they’ll be filling. The more granular you can be on the details, the more likely it is that you’ll find a candidate with directly applicable skills and experience, who will be a good fit for your position. Doing so requires more work upfront, and it may take a little longer to find the ideal person, but that’s far better than having to start over from scratch when it doesn’t work out.
Foster the right kind of culture
Once you’ve found the ideal candidate, you still have to convince them to join your organization. And once they’re onboard, you want to make sure they stick around. After all, lower turnover rates mean less recruiting and hiring that you have to do in the first place. And one of the best ways to secure these results is by fostering the kind of culture that makes sales reps feel valued and cared for.
We’ve written a whole ebook on how to do this, which you can download for free, but here are some of the key takeaways:
- Offer competitive compensation. All else being equal, sales reps are most likely to want to work for the organization that will pay them best. If you’re able to offer above-average compensation, put that front and center in your recruiting pitch. If not, be sure to make up for it with these other elements.
- Provide plenty of growth opportunities. Sales reps need to know there’s a clear path to advancement. If they put in the work and show proven results, they should be rewarded accordingly. Be ready to communicate exactly what that path looks like to potential hires.
- Give your team the tools they need to succeed. Your sales reps don’t want to waste their time fighting with outdated or lackluster products—they want to stay focused on making sales and earning commissions, and the tools you use can make their lives easier or harder. When recruiting, it goes a long way if you can point to best-in-class solutions in your sales tech stack, like Performio’s ICM software, which saves your reps time and hassle while providing transparency into their sales performance and earnings.
- Promote a healthy work-life balance. You want to drive your sales reps to succeed while avoiding burnout. That can be a tricky balance to strike, especially when dealing with various personality types on your sales team, leading to different ideas about what an ideal work-life balance looks like. Wherever you end up landing on this, it’s important to be upfront during the hiring process about what your reps can expect.
Suggested resource
For more advice on recruiting and hiring, check out Who by Geoff Smart and Randy Street, which offers a method for hiring that goes further into what we’ve described—how to become really clear on what you want and then find candidates who’ve been successful doing that.
2. Selling in an uncertain economy
Selling is hard work at any time, but it’s made especially difficult in an uncertain economy. Individuals and organizations alike are far less likely to make bigger purchases when they aren’t able to plan for what’s coming next. So understandably, 43% of sales leaders find selling in such an environment to be very challenging.
Make a clear appeal to value
When faced with uncertainty, the easiest thing to do is nothing. You don’t rock the boat, you don’t make big changes, and you just continue on as you’ve been doing until you have a better idea about how things are going to play out. For customers, this means delaying purchases, even if it could be making their lives easier right now.
To break through to reluctant leads, you have to show them exactly how your product or service will improve their current situation. Instead of focusing on what your offering does, you need to demonstrate the value it provides. For example, rather than simply telling you that our ICM software streamlines the process of calculating sales commissions, we’d explain how it can turn a week’s worth of work into hours, reduce errors, prevent overpayments and underpayments, and provide a proven ROI for your organization.
Customers have to see how your product or service will help them become more efficient, reduce their risk, generate more revenue, or whatever it is that “value” means to them. This changes your proposition from a risky purchase in the midst of uncertainty into an obvious choice for better navigating the uncertainty.
Suggested resources
For selling in an uncertain economy, Grayson recommends The JOLT Effect by Matthew Dixon and Ted McKenna, as well as The Challenger Sale by Matthew Dixon and Brent Adamson. These books detail specific sales methodologies geared toward presenting value, highlighting opportunities the customer may not have been aware of, and delighting them with experiences that create a lasting impression.
3. Generating qualified sales-ready leads
Qualified sales-ready leads are those that are ready to buy from your organization. As opposed to a cold lead, who may or may not have any interest in what you have to offer, a sales-ready lead is already primed with an understanding of the problem they face and how your solution could help them. They’re the best kinds of leads to have, but 40% of sales leaders find generating such leads to be very challenging.
Cut through noise with a distinct point of view
One of the biggest obstacles to lead generation is simply all the noise that customers face. They’re constantly bombarded with competing offers for their time, attention, and money, and you have to find a way to break through. They need to understand that your product or service is not merely one solution among a mass of others like it, but the solution best suited to their needs.
And one of the best ways to help leads reach this point is by drawing them in with high quality content that offers a distinct point of view. When potential customers come to your blog, read your LinkedIn posts, or download your ebooks, you don’t want them to see more of the same rehashed material they’ll find from anyone else in your industry. You want to teach them something new, provide a valuable insight they never encountered before, or help them reframe a familiar concept in a new light. You don’t want to simply repeat information, you want to become an authority on it.
When readers come across content like this, it stands out in their mind, causing them to associate your organization with original thinking and insightful ideas. This then naturally leads them to transfer that association to your products or services, creating a clear differentiator between you and the competition.
Suggested resources
For more on these ideas, Grayson points to Obviously Awesome by April Dunford and Killing Marketing by Joe Pulizzi and Robert Rose. They expand on these themes of cutting through the clutter and positioning yourself in the market with a clear point of view, and they walk you through best practices for achieving these ends.
4. Developing sales skills
This fourth biggest challenge in sales comes with a little additional detail. The study clarifies “developing sales skills” to include “driving and winning sales opportunities, driving account growth, consultative selling, filling the pipeline, negotiation, managing and coaching sellers, etc.” And 33% of sales leaders consider it to be very challenging.
Do the hard work of one-on-one sales coaching
This is an area we talk about a lot because we really believe it to be crucial. Investing in one-on-one sales coaching is the best way to develop the kinds of sales skills you want your sales reps to have. Nothing else can replace it.
Group training sessions certainly have their place as well. They allow you to quickly move through a lot more teaching, and they’re a great option for introducing new concepts. But actually honing and developing those skills over time requires more dedicated attention. Reps need a coach to sit down with them, take inventory of their strengths and weaknesses, and form a personalized plan to help them master core competencies.
“Frankly, the way to do that is good old fashioned hard work. You just have to do the hard work of reviewing the tape or sitting on the calls and then giving them feedback. And a lot of people just don’t want to do that. It’s hard work, right? But it’s a big part of developing sales skills.” Grayson Morris, Performio CEO
Suggested resource
For developing sales skills, Grayson recommends ProActive Selling by William “Skip” Miller as a good example of a true sales process. Skip introduces the concept of a buyer’s journey, helping you understand what sort of feelings, emotions, and activities people go through when making a purchase. And then he shows you how to align your sales process with that buyer’s journey.
5. Developing sales managers
Finally, the study identified developing sales managers as the fifth biggest challenge, with 32% of sales leaders finding it very challenging.
Find the right people and give them the support they need
A big part of why it’s so hard to develop sales managers has to do with promoting the wrong people to the position. There’s a tendency to look at the performance of a sales rep and use their selling success as a metric to move them into a leadership position. And to an extent that makes sense, as a sales manager should certainly have sales skills. However, sales skills don’t automatically translate into managerial skills.
This is the premise of the TV show The Office in a nutshell. Michael Scott was promoted because he was such a great salesman, but he had no idea what he was doing as a manager. And while the show was obviously exaggerated for comedic effect, the basic problem it portrays is a very real one that plays out in countless sales organizations.
So the first step in developing sales managers is to identify people who actually exhibit the traits of a leader, not merely a good salesperson.
Having done that, it’s crucial to ensure that your sales managers have people they can look to for help and direction. We’ve already discussed how important sales coaching is, but that need for coaching doesn’t go away once someone becomes a manager. If they’re promoted to a leadership role but not given guidance, they’re sure to flounder.
One great way to alleviate this problem is by pairing sales managers with mentors—more senior members of sales leadership who have been where the new managers are now and can give them that one-on-one guidance on what they need to know to be successful.
Additionally, Performio helps with developing sales managers by providing unparalleled visibility into team performance. It allows you to see at a glance how each team is progressing, and you can stack managers against each other to learn who’s doing what well. Then you can have the top performing managers work with the lower performers to help them replicate their success.
Suggested resources
To develop sales managers, Grayson points to High Output Management by Andrew S. Grove and Leadership and Self-Deception by the Arbinger Institute. High Output Management is written by an engineer who explains management in the way only an engineer could, breaking it down into its component parts. And Leadership and Self-Deception helps managers stay focused on who their people are, rather than merely what they do.
Develop the sales culture you want to see
Many of the challenges sales leaders face can trace their way back in one way or another to the kind of culture that a sales organization fosters. But you don’t have to leave that chance. You can take an intentional approach to developing the kind of sales culture you want to see, and we’ve written an in-depth guide to help you do that.
Retention through Culture: Why Sales Reps Leave, and What to Do about It walks you through the biggest issues that cause high turnover among sales reps, and explains four key aspects of company culture you can focus on in order to improve it.
Download the free ebook to learn more.
And to see what Performio can do for your organization, request a demo today.