22 Sales Skills to Master for a Successful Career

What does it take to become an expert salesperson? Over the course of my career, I’ve found that the best sales leaders are the ones who learn how to improve their sales skills continuously throughout their careers.

Indeed, in my experience, great salespeople know that they’re never done learning. In this article, I’ll walk through 22 of the most vital sales skills that today’s sellers need to master, before exploring some of the most effective strategies they can use to develop these essential skills.

1. Effective Communication

The ability to communicate clearly and effectively across media is a non-negotiable for salespeople. From drafting enticing sales emails to nailing presentations and keeping conversations flowing smoothly, I’ve learned that sales professionals must continuously hone their written and spoken communication skills to perform well in their roles.

2. Product Expertise

Why should your prospects buy your product? If you aren’t sure what value your product offers and what its key features are, you’re going to have a hard time closing a deal. Plus, if you want to keep your customers happy long-term (and keep them coming back for more), you need to make sure you don’t misrepresent the product.

As such, I’ve found that it’s vital for salespeople to know the ins and outs of the products they’re selling. This helps you reach your sales goals and ensures that you sell your products to customers who are actually a good fit. Those are the folks who are more likely to be satisfied with their purchase.

It also enables you to give detailed help and recommendations to your prospects, making them more receptive to continuing these conversations.

Having deep product knowledge means you can answer any question that comes your way, devise creative solutions to customer problems, and offer consultations that’ll lead to new opportunities. Moreover, as buyers get better and better at doing their own research, product knowledge will help you better convey your unique selling proposition.

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3. Customer Service

Top salespeople are able to engage and build rapport with the clients and customers they aim to serve. This can look like taking the time to learn about your customers and how your offering can alleviate their pain points, as well as asking meaningful discovery questions during your initial calls to establish a strong working relationship.

4. Problem-Solving

As a sales professional, your ultimate goal shouldn’t just be to close the deal — it should be to solve your customer’s problems. That’s why I’ve always believed that sales reps should be expert problem solvers.

In fact, in my experience, great salespeople aren’t just able to solve the problems directly in front of them, such as helping customers overcome objections. They also anticipate future challenges that may arise, and they proactively prepare solutions to address those potential issues.

5. Business Acumen

When salespeople are armed with the critical business knowledge and expertise that informs a strategic outlook and understanding of the industry they’re in, they become unstoppable. Reps with strong business acumen are able to make strategic decisions, empowering them to serve their organizations effectively both today and in the future.

6. Sales Demoing

Walking potential customers through a product demonstration is a critical element of the sales process, and as such, it should be done with care. That’s why I always recommend that new sales reps invest in learning to take their prospects through an easy-to-follow sales demonstration.

Pro tip: Effective demos should both introduce customers to the product and set the stage for the deal’s next steps.

7. Negotiating

Wouldn’t it be great if your prospects immediately signed your contracts and agreed to your payment terms with no pushback at all? Maybe so — but that’s not how most deals work. Even after vetting prospects and laying out a thoughtful quote, many deals still end up in a negotiation phase before the dotted line is signed.

That’s why strong negotiation skills are a must for salespeople. When reps are able to effectively negotiate mutually beneficial terms with buyers and other decision-makers, they’re more likely to secure better outcomes.

8. Prospecting

If you reach out first, 82% of buyers will accept a meeting request. That’s what makes prospecting so effective — and so critical.

To be sure, prospecting can be a lengthy and time-consuming process. However, I’ve learned that all that work won’t be in vain, as long as you’re focusing on qualified leads who are a good fit for your product. As such, successful prospecting requires research, clear communication, and discernment.

9. Collaboration

While it can be tempting for reps to solely focus on hitting their personal numbers, sales is truly a team effort. Indeed, in my personal experience, collaboration is a must for creating a frictionless sales process.

From teaming up with your marketing organization to ensure a smooth hand-off to cooperating with a prospect to come up with a mutually beneficial agreement, the best salespeople are agreeable and able to work with people both internal and external to their organization to reach their business goals.

10. Social Selling

If you thought social media could only be leveraged by the marketing department, think again. Social selling, or researching and connecting with potential buyers using social media platforms, is an important skill for sales reps.

That being said, social selling is only effective when done properly. Don’t spam users’ inboxes with unsolicited messages or flood their timelines with promotional posts. Instead, reps should start by optimizing their professional social media profiles to attract potential customers and then take a thoughtful approach to outreach by engaging on the appropriate platforms at the appropriate times.

11. Relationship-Building

The ability to build relationships is critical for all reps, and it is especially important for those who sell higher-priced or B2B goods. I’ve found that the higher the value of a product, the more buyers want to establish trust with those they are buying from. So, when a rep is able to cultivate meaningful relationships with buyers and decision-makers, they become better equipped to navigate the sales process.

12. Following Up

Succeeding in sales takes tenacity — and that tenacity is especially important when it comes to following up with potential buyers. According to a recent report, only 2% of sales are made after the first contact, and 44% of reps never make a second contact attempt.

Pro tip: By failing to follow up with prospects, you’re sabotaging your chances at success. To boost your closed-won potential, be sure to invest in refining your follow-up skills.

13. Closing

Each stage of the sales process is important, and the close is no exception. Effective reps should constantly be strengthening and refining their closing techniques to make sure they’re ready to seal the deal.

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14. Adaptability

Working in a high-impact, people-focused field such as sales, reps need to be able to adapt to a variety of situations. Whether that means anticipating objections or questions your potential buyers may have or being willing to adopt a new strategy or technique quickly when what you’re doing isn’t working, flexibility is a key trait for goal-crushing reps.

15. Active Listening

Many of the tactics above — including communication, relationship-building, and collaboration — are not possible without active listening skills.

In my experience, the ability to listen to and truly understand prospects can make or break your ability to win the sale. Not only does listening help you clarify what your prospect is actually looking for but it also establishes necessary trust with your buyers.

When your prospect feels heard and listened to, it creates a sense of connection that can keep the sales process moving in the right direction.

As tempting as it can be to dominate the conversation and just rattle off all the reasons why your prospect should purchase your product, knowing when to step back and give them time to speak is a thoughtful approach that will serve you better in the long run.

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16. Emotional Intelligence

Emotional intelligence is a critical skill to nurture if you want to make a lasting (and profitable) connection with your prospects. As former Account Executive at HubSpot Shaun Crimmins explains, “Sales EQ is the ability to effectively read, influence, and control emotions.” He continues, “Being able to stand out above the clutter of sales messages prospects are hit with — that’s what EQ is all about.”

17. Data Analysis

Gone are the days when you could rely purely on intuition to guide you. The modern salesperson has a nearly endless amount of information about their prospects, and this data can be used to decide who to target and how to connect with them.

If you understand the actions your buyers tend to take, you can avoid happy ears and know who’s more likely to purchase … before beginning a long and potentially fruitless conversation.

For example, perhaps CMOs at SaaS companies close at a 2X rate compared to CMOs at consumer goods businesses. Or perhaps your win rate is 30% higher for prospects who attended an in-person company event versus a webinar. Insights like these are incredibly actionable: To boost results, reach out to more SaaS CMOs and aggressively pursue event attendees.

Of course, getting access to those insights requires accurate, thorough data entry and periodic analysis. So, take it from me: Don’t wait for your manager or Sales Enablement team to run reports for you. Instead, go to your CRM, apply the appropriate filters, and look for patterns yourself.

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18. Challenger Selling

“One of the most important sales skills is Challenger Selling,” says Ben Cotton, a former Sales Enablement Manager at HubSpot. Cotton explains many sales reps are still tactical order-takers, rather than strategic consultants. They don’t offer genuine insights. Instead, they try to become friends with their prospects.

“The relationship builder approach is becoming less effective by the day,” Cotton comments. “Prospects want actionable insight.”

Pro tip: To improve your Challenger Selling skills, make sure to read “The Challenger Sale,” the book that catalyzed the movement.

I’ve also found that it can be helpful to look for recommendations and/or perspectives you can offer prospects based on your unique bird’s eye view of their industry and space. If you start the conversation with this information, you’ll gain credibility, teach them something new, and earn the right to their time.

19. Framing Skills

In his award-winning book “Pitch Anything,” sales expert Oren Klaff argues that our brains operate by four simple principles:

• If it’s not dangerous, ignore it.
• If it’s not new and exciting, ignore it.
• If it is new, summarize it as quickly as possible and forget the details.
• Unless it’s truly unexpected, don’t send it to the neocortex for problem-solving.

The result? Not only do prospects miss 90% of your pitch (i.e., the details), but they’ll ignore it completely unless it’s different and interesting. Moreover, anything complex will be treated as a threat, because complicated information takes more mental energy to process and thus leaves less brain power for survival.

You can only avoid this outcome with framing. Framing is all about how, as a salesperson, you maintain control of the conversation throughout your pitch or sales process.

To get started, review your pitch. Is it easy to understand? Are you telling a story — or reciting a series of dry facts? Do you present your product as the answer? If you answered “no” to one or more of those questions, it may be worth thinking about reframing your approach!

20. Technological Savviness

Throughout my career, it seems like every year Sales Enablement rolls out a new tool for the sales team. And while technology can be a huge productivity booster, it can also be a huge productivity drain. Effective reps must be able to differentiate between shiny new tools that are fun but ultimately distracting and resources that actually improve their bottom line.

For example, imagine your organization invests in an app that analyzes emails and notifies you when a prospect’s language indicates they’re ready to buy. You use it a few times, but typically, the notification doesn’t come until after you’ve already decided to close. In this case, the app’s probably not worth the time.

Importantly, I’m not saying that you should dig in your heels whenever your organization asks you to change your tool suite — but it is important to invest your attention where it counts.

21. Video Skills

With the rise of remote work and remote selling, video plays an increasingly important role throughout the buyer’s journey. Reps use video platforms to connect with new leads, answer questions, follow up and re-engage with prospects who have gone dark, give product demos at scale, make their proposals more engaging, and more.

As such, I’ve learned that honing your video skills is a no-brainer. Practice your delivery, tone, and pacing. Experiment with different subjects — which are most effective? Find the best lighting, props, and filming area. Figure out the optimal length for each type of video. Mastering the video creation process will put you far ahead of your competitors.

22. Honesty

It can be challenging to walk the line between being yourself and connecting with people who are different from you. In the past, salespeople might get away with pretending they were major sports fans or using other cut-and-paste techniques.

However, today, “These strategies are no longer relevant,” says Tyson Hartnett, a sales professional who has worked with giants such as Yelp and Discovery Inc (owner of the Discovery Channel). “People know when you are playing tricks on them.”

And while anyone can do what Hartnett calls a “closing trick,” far fewer can be genuine. Rather than pretending to like something because your client does, Hartnett suggests being authentic.

“Say, ‘I’ve never been a big fan of museums and art, but I know you like it, so I'm willing to check it out with you,’” he advises. “It may seem like a weird thing to say, but push yourself out of that comfort zone, and they will respect you for trying to learn and do more, even if you don't like it. Then, follow up with something you learned or found interesting from the experience.”

Hartnett continues, “Your prospect will think, ‘Wow, they hated museums but kept an open mind.’”

So, how can you improve your sales skills? Below, I’ll offer several tried-and-true strategies that I’ve learned can help anyone develop their sales skills and improve performance on their team.

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1. Attend sales training.

Throughout my career, I’ve seen first-hand that sales training and other professional development opportunities are a great way to keep your skills fresh. Indeed, being a lifelong learner gives you a major competitive advantage in the game of sales.

As Aja Frost, HubSpot’s Director of Global Growth, describes, “Great sales training programs will help you and your team members sell at your full potential. From higher quota and revenue attainment and better win rates to lower sales force turnover, the return will definitely justify the cost.”

Consider purchasing in-person or online sales classes, or take free certification courses through programs like HubSpot Academy or Sales Engine. These courses or certifications can specialize in sales skills such as sales presentations, sales methodology, social selling, or sales coaching.

Pro tip: When choosing a sales training program, consider factors like how long the program is, what it’s focused on, its location, and its price.

2. Implement roleplay.

When I get on an exploratory call, I want to be prepared for every question, objection, or circumstance a prospect throws my way. And the only way to be ready is to practice the flow of conversation and to learn how to ask questions authentically (rather than making them sound like an interrogation).

In other words, it’s essential to implement roleplay on your team. Your team can practice roleplay on its own once a month, or you can find a sales training course that includes opportunities for roleplay.

There are several roleplay exercises your team can try. Here are a few of my favorites:

• Dealing with extreme situations.
• Getting comfortable breaking up with prospects.
• Challenging prospects on why they’re stuck.
• Overcoming common objections.

3. Practice public speaking.

According to recent reports, 75% of the global population has a fear of public speaking. That means that even among salespeople, who may be more likely to be naturally extroverted, it’s not uncommon to struggle with public speaking.

Pro tip: As with most things, practice makes perfect. The more you practice public speaking, the more you’ll get used to it, and the less nervous you’ll be.

For sales reps, it’s important to be a confident communicator, so you can empathize and sell to your prospects. During the sales process, you’ll need to give sales presentations, conduct product demos, and persuasively speak to several decision-makers. As such, confident communication is critical for success.

To practice public speaking, I’d suggest attending events with organizations like Toastmasters, which offers professionals opportunities to practice public speaking and learn tips to become more confident communicators.

4. Find a mentor.

In my experience, working with a mentor or sales coach can drastically improve your sales performance. If you’re not sure where to start, work with your manager or ask if they can recommend a few successful salespeople at your company who may be willing to mentor you.

I have also found that professional development events and networking meetups can be great places to connect with potential mentors who can offer invaluable guidance and support.

Then, once you’ve found a mentor, you can ask them for advice on sales strategies, ask them to roleplay with you, or even have them shadow a sales call and offer you direct feedback. This relationship will both help you improve a range of sales skills and provide you with the opportunity to get helpful feedback on your performance.

5. Ask questions.

Successful salespeople ask questions. When a sales call doesn’t go the way you thought it would, or when you get a question or objection you aren’t sure how to respond to, ask your manager or peers for advice. It’s important to ask questions like these, so you’re prepared to solve those problems when they come up again.

In addition to asking questions in your role, it’s also important to ask your prospect the right questions. Learn about their pain points, and find out what their goals are. Only then can you truly begin to find a solution and understand how your product or service can solve their problems.

6. Become a lifelong learner.

I’ve said it once and I’ll say it again: Being a lifelong learner is a vital ingredient to help you improve your sales skills. From advances in technology to cultural and social shifts, the sales industry is continuously changing.

To stay up-to-date, it’s important to read the latest articles and books, listen to podcasts, and remain active and engaged in your work. For example, if you’re a salesperson at a software company, reading articles on the software industry will help you prepare for questions that prospects may ask and position your product or service in context.

7. Improve prospecting skills.

Although prospecting might not be the most glamorous aspect of sales, it’s one of the skills that can increase your sales numbers the most. It’s also the task that many salespeople spend the most time on.

Indeed, in her comprehensive overview of prospecting, sales expert Cambria Davies notes that “It’s not just a nice-to-have — prospecting in sales ensures that the leads you’re communicating with have an immediate (or potential) interest in a solution like yours.”

That’s why I always suggest that sales reps should enhance their prospecting skills. In order to effectively prospect leads, you can use several prospecting techniques, including making warm calls, hosting webinars, and spending time on social media.

8. Review your sales calls.

You can learn a lot from reviewing what you did well (and what went wrong) in recorded sales calls. Film reviews allow salespeople to listen to and provide feedback on a recording of a sales rep’s call. Ask your sales manager if they host film reviews, and if they don’t, start one with your peers.

As HubSpot’s Aja Frost explains, “The same question comes up again and again: ‘Why did this prospect take the call?’ If the rep can’t answer this question, it’s usually because they’ve failed to identify their buyer’s most pressing need. And that indicates they may lose the deal. Without knowing what’s driving their prospect, the salesperson can’t effectively explain their product’s value.”

Film reviews give you an opportunity to improve your sales skills so you can become a more effective salesperson. You might get feedback on how personalized the sales call was, how well you understood buyer pain points, your overall attitude and authenticity, how well you set the agenda, or how well you knew the product.

Pro tip: When you're participating in a film review, listen more and talk less.

Go into film reviews with a rubric or template in mind so you know the specific items you want to cover. For example, you could ask colleagues to rank your questions, authenticity, and product knowledge on a scale from one to five. Then, you could ask for specific action items that you could implement to improve.

9. Listen to feedback.

In the same vein, if you are taking part in film reviews, it’s important to really listen to the feedback you receive from your peers and supervisors. I know it can be hard to hear critiques and criticisms of your performance — but that feedback is vital if you want to improve your sales skills.

Pay attention to people’s input on the questions you’re asking, the flow of the conversation, and your rapport. These are critical sales skills that sales reps need to master to achieve success.

For example, during a film review, you might get the feedback that the conversation felt more like an interview than an authentic conversation because of how quickly you went from question to question. In response, you might aim to adjust your sales calls going forward to include more follow-up questions or small talk at the beginning of the conversation.

10. Stay connected to the customer.

In order to make a sale, you have to build rapport with your prospects. Of course, I’ve seen time and time again that this isn’t easy to do in just a few minutes with a stranger on the phone. To improve your sales skills, consider your level of connection with your prospects. Have you done your research, thought of interesting questions, and practiced your exploratory calls?

The key to building relationships is authenticity. Having an authentic, productive conversation is one of the best ways to stay connected with your customers and improve your sales.

For example, if you’ve done your research, you can talk about something the prospect has posted online. Personalized conversation starters such as, “I saw on LinkedIn that…”' or “I read on your blog that…” can be a great way to strike up an authentic conversation with a prospect.

11. Prepare for objection handling.

During sales calls, I’ve found that getting objections and questions about the product or service is all but inevitable. That’s why it’s important to be as prepared as possible for those objections and have canned answers ready to go.

Pro tip: To prepare for common objections, learn about your buyer persona and take time to understand their pain points. Ask questions like “Do they need our help?” and “Can we help them?”

By putting care and attention into your prospect’s pain points and preparing for their likely objections, you’ll improve your sales skills and enhance your performance.

12. Play with your closing techniques.

In my experience, iteration is everything. As such, you should always be experimenting and iterating on your sales process.

Specifically, to improve your sales skills, I always recommend trying different closing techniques. Sales expert Adam Turkington recommends techniques such as:

• Now or Never Closes: When using this approach, salespeople make an offer that includes a special benefit that prompts immediate purchase.
• Summary Closes: With this closing technique, salespeople reiterate the items the customer might purchase (stressing their value and benefits) to get the prospect to sign.
• Sharp Angle Closes: Prospects often ask for price reductions or add-ons because they know they have the upper hand — and they also know you expect it. If you have approval from your sales manager, try the sharp angle close technique to catch these prospects by surprise.
• Question Closes: This strategy focuses on asking prospects probing questions.
• Assumptive Closes: This closing technique draws on the power of positive thinking. If you believe, from the first piece of email outreach, that you’ll close this deal, it can have an incredible effect on the rest of the sales process.
• Takeaway Closes: If you have kids, you’ve likely noticed that taking a toy away from them makes them want it more than ever. Use this similar psychological practice on your prospects.
• Soft Closes: The soft close is a way to show your prospect the benefit of your product, and then ask a low-impact question to ascertain whether they'd be open to learning more.

By playing with these different sales techniques, you’ll continue to grow and improve your sales skills.

13. Iterate on your sales cycle.

Your sales cycle is usually a tactical approach to the way you sell your product or service. Typically, this isn’t something that’s going to change very often. However, it’s still important to iterate at each stage of your sales cycle.

For example, if your sales cycle follows the trajectory of “prospecting, connecting, researching, presenting, and closing,” you should consistently study ways to improve your prospecting skills. You should also read up on how to have a successful exploratory call, practice public speaking, and try different closing techniques.

By iterating on each stage of your sales cycle, you’ll continuously improve your sales skills and reach higher numbers every month.

14. Track your progress.

Another important way to improve your sales skills is to track your progress. To do so, set sales goals and record your performance every week, month, or quarter. You can even implement a sort of A/B test on yourself.

For example, begin by working on one skill from this list. Let’s say you’re going to try different closing techniques. Record your current close rate and then track your close rate after using that technique. Has your close rate improved? A test like this can help you isolate what’s working in your sales process — and what isn’t having as much of an impact.

Every sales team will need to determine the metrics that are most relevant to their unique needs and environment, but some of my favorite creative sales goals include lowering customer acquisition costs, reducing the time it takes to turn a lead into a customer, and shadowing a certain number of high-performing colleagues. By tracking progress against goals like these, you’ll be on your way to improving your sales skills and boosting your performance.

15. Enhance listening skills.

To be an effective salesperson, you must hone the art of active listening. Unfortunately, in my experience, a lot of salespeople are too focused on thinking of their responses and generating answers to questions in their heads, when they should be listening to what their prospects are saying.

Instead, it’s vital to truly pay attention while your prospect is talking. In order to ensure you’ve understood them correctly, repeat what they said back to them. This can also help you understand what their problem is and determine whether you can solve it for them.

Grow Professionally by Improving Your Sales Skills

Of all these skills, my absolute favorite is listening. At the end of the day, I truly believe that you can only be successful if you learn continuously, and you can only learn if you’re able to listen to those around you — whether that’s your peers, your mentors, your supervisors, or your customers.

Indeed, by continuously working on your sales skills, you’ll be set up to grow in your current role and advance your sales career. Over the course of my own career, I’ve always found that it’s important to continue to learn not only as you face new challenges and nurture new types of buyers, but as you try to upsell current clients, too.

By cultivating the skills above, you’ll be able to craft a selling technique that will help you stand out on your team and achieve long-term success.

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