Some sales secrets never go out of style.

We’ve pulled together ten timeless sales tips to help your outside sales team stay ahead of the competition. They’re simple but shockingly effective! Read on to see which techniques your team can take action on today.

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Top Outside Sales Tips

1. Encourage Failure

It’s not enough to embrace failure—we need to aim for it. That may sound strange but as they say, you gotta risk it for the biscuit.

As a sales representative, imagine hearing these two statements from your team leader:

  • It’s okay if you fail—you’ll learn something!
  • You should fail. We want you to fail. Go out there and fail.

The first may help to alleviate some stress. You’ll know that, at the very least, you won’t be hounded for your mistakes. If you forget to follow-up with a client or hear “no,” you know you may catch a little flack but, overall, your team will just expect you to do better next time.

This is obviously important, but it doesn’t do much by way of encouraging you to push the envelope.

If you hear the second statement, though, you’ll know that you’re in an environment that strives for innovation. When failure is encouraged, you’ll be excited to think outside the box, try new things, and go big. You’ll be more inclined to try the latest technology, read blogs to find the most cutting-edge strategies, and perhaps most importantly, will generally be eager to put the rubber to the road.

On the ground, this can be as simple as encouraging your team to play around with technology and try new tools to see if they notice results—or as big as telling your sales reps to always go for the big upsell, just to see how it goes.

2. Hire Sales Consultants — Not Salespeople

You’ve probably heard the idea that you want to sell benefits, not features—that is, you don’t sell the drill, you sell the hole in the wall. Incorporate this concept into your entire sales cycle by encouraging your team to think of themselves as sales consultants rather than salespeople.

Instead of just pushing products at people, when your team thinks of themselves as consultants, you become all about helping clients find solutions to achieve the results they want and need.

Not only does this mindset help your team to find more success in their pitching, but it also increases team morale by demonstrating that you value all parts of their work beyond just selling. Team members will naturally enter client meetings with a “what can we achieve for you?” outlook rather than an “I desperately need this to close” one.

To drive this point home with your team, be sure that you are emphasizing more KPI than just ones related to selling. For example, consider measuring customer happiness and success through data like:

  • Customer business growth
  • Percentage of repeat customers
  • Referrals
  • Excellent testimonials

Get your team in on it by asking them what KPI they think your team should prioritize.

3. Focus on Your Current Customers

Upselling and cross-selling are your best friends and where you will generate the vast majority of your revenue.

Acquiring new customers costs your business somewhere between 5 and 25 times more money than selling to established ones. And in addition to simple repeat orders, there are two primary ways to sell to existing clients: upselling and cross-selling.

Upselling is when you get a client to upgrade their purchase for a more premium (and expensive) offering. For example, when you “supersize” your meal at McDonald’s or turn in your iPhone for the newest model, you were just upsold.

Cross-selling is when you get a client to add-on a complimentary purchase for an additional cost. For example, when you toss an unplanned stick of gum into your cart at checkout or say “yes” to “Would you like fries with that?” you were just cross-sold.

Upselling and cross-selling are both effective because the labor of convincing the client to trust you and invest their money in your offering is already done—they’ve already committed. Now, you’re relying on that momentum to get them to agree to upgrade or add-on something else to help them achieve even better results.

The trick here is to think critically about what upsells and cross-sells are going to be appealing, realistic, and beneficial to your clients. Effective upsells and cross-sells follow the logic of the customer’s intent behind their purchase.

For example, if a customer was renting a car for their large family on a road trip, you wouldn’t want to try to upsell them a souped-up sports car. Instead, a motivating upsell could be “Upgrade to our larger minivan so your kids have more space” and a cross-sell could be “For an extra X amount, we can toss-in an entertainment system to keep your kids distracted.”

4. Automate Daily Sales Tasks

There’s a scary statistic out there that only 36% of the average salesperson’s day is spent selling. While that number seems pretty bleak, it also means that if you automate those tedious non-selling tasks away, you can sell up to 300X more without changing any other habits.

So, embrace technology to save time, money, and headache. You can utilize tools to automate everyday sales tasks like:

You’ll be able to find most of these features already in your CRM (like Hubspot or Salesforce) or as affordable integrations.

A tip is to work with your sales team to automate a couple of tasks at a time. There can be a learning curve with some of the tools, and you want to be sure you’re actually saving time and not just spending it obsessing over new tech.

You may be wondering, how do you know which tasks to automate? Rather than thinking of it as an either/or scenario, try to think of technology and human reps as a one-two punch that works side-by-side at every step of the sales funnel.

Experiment and see what is most effective for your reps, and then encourage them to implement it on a larger scale!

5. Focus on the Right Leads

Not all leads are created equal—and not everybody at a target company actually has the ability to make big decisions. Close more deals faster by allocating your team’s energy towards only those companies and people that are an excellent fit.

Niching down—or narrowing your target market—can feel intimidating. After all, who wants to turn away potentially paying customers? But the truth is, at the end of the day, your customers are willing to pay much more for an offering they feel was tailor-made for people just like them.

Narrowing in on the right targets (and being comfortable with letting the rest go) is a great way to invest your resources more effectively.

Similarly, it takes a lot of time, energy, and money to pitch seven individual people at a target company when you could’ve just pitched one. Ask for the gatekeeper or decision-maker early in your communications to streamline your efforts—that way, success will actually mean a sale and not just getting passed a bit up the food chain.

Targeting a specific person within a specific niche allows you to really dig into pain points and needs unique to their situation and sell more effectively.

6. Get Confident With Your Pitch

You won’t ever have the perfect pitch. If there was a formula you could read out loud and close any deal, then most of us would be out of a job. The truth is, the “right” pitch for one given situation will never be the “right” pitch for another.

So, rather than aiming perfection, aim for confidence.

Instead of memorizing a spiel from beginning to end, get to know your offering inside and out. Understand the benefits it offers to your customers so you can capitalize on their unique needs.

One way to stay confident is to have a few killer statistics on hand that demonstrate the impact of your offering. For example, you may be able to reference similar case studies to the prospect you’re currently pitching—and toss in some impressive KPI they achieved.

Another tip for staying confident is knowing that you have the ability to make a powerful close, no matter where your pitch has taken you. For that, study empathy-driven sale closing techniques and have a few go-to options in your pocket. For example, you may choose to have visuals to help drive a point home or you may wrap with a compelling story.

Remember: failure is the goal. So don’t be afraid to try new things in your pitch! If it doesn’t work out, there will always be a new prospect to go after.

7. Set SMART Sales Goals

You always want to set intelligent sales goals for yourself and your team—and to do that, your objectives need to be SMART. That is:

  • Specific
  • Measurable
  • Attainable
  • Relevant
  • Time-based

Specific means instead of saying “sell more,” you’re saying “sell x-amount more than last quarter.” At the end of the day, there should be no question whether or not you achieved your goal.

Measurable means it's reasonably quantifiable. For example, “make customers happier” is not measurable while “increase repeat business” is.

Attainable means that your goals should be realistic. Sure, it would be nice if your startup outpaced Apple this year, but you should think critically about if that’s on the table. Without a doubt, you should push yourself and your team to succeed—don’t do throwaway goals! But make sure they are reasonable enough that your team feels motivated to pursue them.

Relevant means that your goals matter to your business. If your company only works with local clients, having a million Twitter followers might not be the most helpful objective.

And lastly, time-based means you give yourself a deadline. As a salesperson, you know what a great motivator urgency is—so give yourself some!

To tie everything together, imagine that you sell consumer goods. Your SMART goal could be: By Christmas, we will have inventory in 60% of our city’s box stores.

8. Practice Time Management Skills

Time is money. We already talked about the importance of automating daily tasks, but automation aside, there are literally dozens of ways you can save time throughout your day.

Time management skills are one of those things that we tend to assume will be intuitive or obvious but isn’t. Odds are good that you’re losing precious minutes in places throughout your day that you don’t even realize.

Don’t worry—this isn’t about squeezing cutting down on breaks and eliminating fun. The secret to time management is not cramming even more tasks into your day, but using the time you do have more efficiently. If you’re doing it right, you should end each day with more energy—not less.

Some effective ways to manage your time include:

  • Tracking your progress towards SMART goals
  • Scheduling follow-ups around your customers
  • Batching appointments to minimize windshield time
  • Focusing on one task at a time
  • Eliminating non-essential tasks (and delegating the rest to automation)
  • Avoiding distractions
  • Immediately finishing all tasks that can be done in two minutes or less
  • Giving yourself regular 15-minute breaks
  • Embracing the power of “no”
  • Using templates when possible

Try working in one or two time management techniques at a time and see how they go for you! Remember, the goal is to create new habits—so take your time with it (no pun intended).

9. Embrace Email Best Practices (and Templates)

You don’t need to reinvent the wheel with every single email message. Fall back on handy-dandy templates and then customize them as needed to fit your current situation.

Having a working knowledge of email best practices will take you a long way. For example, did you know that personalized subject lines (even for promotional emails) have a 29% higher unique open rate and a 41% higher unique open rate than non-personalized ones?

Personalization can look like:

  • Using the person’s first name
  • Referencing their transaction history
  • Mentioning their birthday or other important personal dates
  • Citing their location
  • Discussing interests or past conversations

Another great way to email better is to keep your emails tight. In a world that sends approximately 205 billion emails a day, your customers are on email overload. Show them you get it and respect their time by taking an extra moment to make your email concise.

In fact, Hubspot reported that emails between only 50 and 125 words had the highest response rate at 50%. One great way to do this is to always strive to put the most important information first. You can have an introduction, of course, but then don’t beat around the bush.

10. Try Out New Technologies (But Don’t Force It)

There are tons of incredible applications and software out there to help you stay organized and maximize your sales. Give yourself (and your team!) permission to try them!

There is a ton of awesome technology out there to help you with everything under the sun, like:

  • Expense management
  • Customer service
  • Sales data analysis
  • Order fulfillment
  • Network security
  • Human resources
  • Marketing graphics
  • Time management
  • Social media marketing
  • Email automation
  • Route mapping

Similarly, you’re always going to see write-ups about new sales techniques, like different closing strategies or pitch materials. Let your team try it out!

This goes back to what we discussed before about encouraging failure—not every new technology is going to be a home run for your team. Every other business in town could be absolutely raving about it and it just might not be the right fit for you for whatever reason.

That’s okay! When you create an environment of experimentation rather than rigid tradition, you give your team the chance to find awesome things that work.

11. Perfect the Follow-Up

Did you know that studies have found that 80% of sales require five follow-ups after the initial point of contact… but most 44% of salespeople give up after only one?

To consistently close deals, you are going to need to consistently be checking in on your prospects and clients with follow-ups. Follow-ups, simply put, are anytime you check back in with a client after your last communication. It can be an email nudge, a reminder phone call, an in-person coffee—whatever it takes to stay on your prospects’ radar.

To do an effective follow-up, all you need is a good reason to get back in touch. For example, you can:

  • Check back in (generic nudge)
  • Share a piece of content
  • Announce a new feature or offering
  • Offer a new call to action
  • Ask a question

If it seems overly simple… it’s because it is! By just making the effort, you put yourself head and shoulders above the competition.


Help your field sales team get ahead by utilizing these ten timeless techniques and tools. Remember, above all else, always try new things, think of how you can help your customers, and prioritize effectively focusing your resources!