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8 Biggest Challenges Facing Sales Reps (And How to Overcome Them)

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Sales has changed a lot in the last few decades. Boiler rooms and desperate door-to-door salesman have given way to strategy-minded sales teams armed with technology and huge amounts of research about their prospective customers.

But those prospects also have access to tech and research, and they’re using it to make better buying decisions.

As a result, customers are more likely to buy something based on its value, and not because of a snazzy ad or smooth-talking salesperson. More and more, prospects ignore sales calls, install ad blockers, skip commercials, and live in neighborhoods with “No Soliciting” signs.

The key to success is adjusting to the new sales climate. People don’t want to be sold to—they want experts to help them make informed decisions.

That’s why I’ve compiled a list of the eight biggest challenges facing sales reps today, as well as practical solutions for overcoming each one.

With this step-by-step guide, you’ll be able to conquer your sales goals.

PC: Accent

8 Biggest Sales Challenges and Solutions

1. Emphasize research so finding qualified leads won’t be a struggle.

For companies who rely exclusively on salespeople—cold calls and routinely ignored emails are a huge problem.

Here’s how to approach prospects by making sure they’re interested in what you offer:

1. Have your reps do their research and create customer personas, so they can come to the prospect with a solution to a specific problem.

2. Sales reps should then contact the prospect directly to present their solution. Sales reps should know how the problems arised and if they’re due to changes in the prospect’s industry or a merger involving their company.

3. Ask the prospect if they’d like to try a demo, free trial, or schedule a followup sales call.

4. Suspend all emails or phone calls related to your product until the prospect responds.

5. Have your reps begin sending helpful content that establishes your sales team members as credible leaders the prospect can trust—and eventually buy from.

PC: Dynamics 365

2. Know how and when to move on from cold sales.

Every sales rep has dealt with a promising lead who agreed to one or more meetings, before the deal stalled and fizzled out with no explanation.

Waiting for a turnaround on these cold deals can be a huge waste of time, and can cause you to miss out on other, better opportunities.

Here’s how to handle cold sales:

1. If you think there’s still hope, urge your salespeople to reach out to prospects with timely events related to their company. These could be things like new product lines, office openings, or earnings reports. The goal is to find a legitimate excuse to re-engage them.

2. Continue having your reps show the lead that you’ve done your research and are still engaged by sharing helpful content. (Their goal is to build upon the trust they presumably had in your company when they agreed to your previous meetings.)

PC: Fileboard

3. If all hope appears to be lost, do your best to learn why the deal fell through—including, if possible, asking the prospect for feedback.

4. Make adjustments to your sales process to reduce the likelihood of it happening again. Ask yourself:

  • Does the pitch need to be more customer focused?
  • Are your customer personas accurate?
  • Do your reps need updated presentation documents and tools?

5. Urge your reps to quickly move on to the next opportunity.

3. Align your sales and marketing team to avoid subpar leads.

Marketing departments often tout the number of leads they’re able to produce without taking a deeper look at the quality of those prospects. While generating a bunch of leads is great, it’s pointless if those prospects have no potential to become customers.

PC: Incisive Edge

Here’s how you can align your sales and marketing team:

1. Get your sales and marketing teams to work together on the front end to create more customers on the back end. You can do this by:

  • Developing buyer personas as a team.
  • Collaborating on content creation.
  • Walking through your buyer’s journey together.

2. Have your sales and marketing team come to agreement about what constitutes as a sales qualified lead (SQL).

3. Host regular discussions on whether or not the leads generated by the marketing department are continuing to meet those parameters.

Related: 8 Steps to Close More Leads with Sales and Marketing Alignment

PC: Incisive Edge

4. Address any fears that can cause potential buyers to back out.

Fear of economic slowdowns have left more and more companies hesitant to buy.

While everyday consumers might not be stinging from the recession a decade ago, companies are still holding back on spending until all risk and measurable benefits are considered.

But every company faces risk, and to remind your leads of that, your sales reps should always:

  • Tout the potential rewards of making a buying decision.
  • Use data to show how the benefits can far outweigh the risks.
  • Demonstrate how similar moves benefited other companies in their position (whether those companies are your customers or not).

The case for change made by real-life case studies can trump theoretical examples, and cause potential customers to become real customers for the sake of their business goals.

PC: HubSpot

5. Rethink unrealistic and counterproductive goals to prevent rep burnout.

Sales goals can be big motivators for sales reps, especially when potential earnings and incentives are considered.

But aggressive sales goals can have the opposite effect, if they push experienced reps toward burnout or push new reps too hard before they have the tools in place to be good sellers.

At the end of the day, the two major goals your sales reps should focus on are:

1. Helping leads see value in your products or services, instead of pressuring them into making a decision.

2. Mastering each step of their sales approach before closing any specific number of deals.

Note how simple these two goals are.

Remember, if an experienced rep is feeling pressure to resort to high-pressure tactics to hit quotas, chances are those quotas are too high and will result in an increase in customers who’ll stop doing business with you sooner than they would have otherwise.

You’re better off having simple and attainable goals like the two above.

6. Be sure your coaching is top notch to increase your reps’ effectiveness.

For many companies, sales coaching amounts to little more than giving reps a quick round of onboarding and training, a few sales materials, and then letting them loose.

In these settings, the only time coaching typically happens is when something goes wrong, and even then, the “coaching” can be more threatening than helpful. When your salespeople are fully armed with the resources, data, and support they need, they are more likely to thrive.

The best sales coaching:

1. Makes sure your sales process is fully documented and your reps are fully trained—including giving them some hands-on experience—before they go out on their own.

2. Monitors your sales reps’ progress from day one.

3. Praises them for their successes.

4. Address any problems as soon as they arise.

5. Encourages sales reps to sharpen their skills by reading sales books and blogs, and to seek out other educational opportunities in their free time.

7. Cut non-selling, administrative tasks out of your reps’ agenda.

Did you know that today’s sales reps spend nearly two-thirds of their work time doing non-selling tasks, like data entry or creating reports? The more time your sales reps spend on administrative tasks, the less time they have to sell.

PC: Salesforce

To create more time for your sales reps to sale:

1. Look for any and all opportunities to automate the non-selling steps in your sales process, like:

  • An automated dashboard for pipeline management
  • An electronic calendar for listing and scheduling meetings and demo times
  • An automated channel for tracking order statuses

2. Create templates for certain portions of their emails, follow-ups, etc., and streamline their communication.

Related: 7 Ways Top Sales Reps Spend More Time Selling

8. Keep your reps motivated after rejections.

Even the best sales reps have to deal with rejection. And no matter how much they prepare for it, hearing “no” over and over again can take its toll.

Constant rejections can lead to stress, self-doubt, and burnout. And when sales reps are burned out, not only are they at risk of losing even more sales, they’re more likely to lose their jobs, quit, or seek other lines of work.

So how do you combat rejection?

Train your sales reps to:

  • Not take rejection personally.
  • Know their sales ratio.
  • Set long-term goals.
  • Always have several leads in their pipeline.
  • Do their homework on the front end to anticipate hurdles.
  • Immediately focus on the next opportunity, not the lost one.

PC: Salesforce

Keep Adjusting to the New Sales Climate

Remember, prospects don’t want your sales reps to sell them something—they want your sales reps to help them make an informed decision.

Reinforcing this new sales mentality, especially among your younger reps, will be your team’s key to overcoming modern sales challenges.

Related: 9 Steps to Get First-time Sales Reps Up to Speed ASAP