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Sales - 9 min READ

How to improve your sales skills: 5 underused tactics

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Copper Staff

Contributors from members of the Copper team

Whether you’re new to sales or a seasoned professional, there’s always room for you to improve your sales skills and perfect your trade.

There are a lot of articles out there telling you how to do this. They give tips like, “Do your research” and “Listen to your prospects,” which is not only obvious, but also lacking in specific, actionable advice.

This is not one of those pieces.

The following approaches for leveling up your sales skills are fresh, fun, and definitely not boring. We’ll take a zoomed out look at what makes a successful sales professional and provide you with tools and exercises for building tertiary skills that will set you apart from the pack, including:

1. Learn from every success and failure

In truth, it can be hard to carve out time for reflection, but learning from the past can help you do better in the future—and that’s what this post is all about.

For salespeople this means reflecting upon each deal, whether failed or won, to reveal opportunities for improvement and growth.

You can do this any way you like, using any number of frameworks or exercises, but if you’re not sure where to start, try using the Scrum Retrospective and “How might we?” questions.

Scrum Retrospective

This approach is often used by teams at the end of a two-week sprint; however the principles can be applied and modified whenever you need to look back and evaluate something.

To begin, give yourself 10-15 minutes to jot down what went well (WWW) and what didn’t go well (WDGW) since your last retro. You can do this on a deal-by-deal basis or overall—just make sure to be specific. Some examples might include:

  • WWW: [Prospect] was really impressed with the new case study we published. Upon receiving it, they replied, “Those are impressive numbers—like to see how we can achieve similar results.”
  • WDGW: [Prospect] was having trouble implementing our solution with their current system. Troubleshooting with customer service was unsuccessful and they’ve gone to our competitor.

Once you’re done with your WWWs and WDGWs, you can then spend another 10 minutes brainstorming what you’d do differently next time, or you can skip ahead to the next exercise.

“How might we?” questions

Take your list of WWWs and WDGWs, form each statement into a “How might we?” question.

Using the examples above, possible “How might we?” questions might include:

  • How might we create compelling case studies for each of our customer personas?
  • How might we improve our onboarding so trial customers don’t get frustrated and leave before having the opportunity to see results?

Once you have a list of questions, spend another 10-15 minutes brainstorming solutions for each and separating them into things you can impact directly (e.g., your own behavior) and things you can’t (e.g., product design).

Identify future opportunities to test out the solutions you can implement, and pass along your feedback and suggestions for the ones you can’t to their respective owners.


  • Schedule reflection time into your calendar. Doing it daily might not be realistic or necessary if your sales cycles are generally longer, but be sure to implement a set frequency and stick to it. I recommend no longer than two weeks, since it may be more difficult to recall the specifics of each deal.
  • Keep a running list of all your “How might we?” questions and proposed solutions, and refer to them often to ensure you’re actually implementing your learnings rather than just recording and forgetting them.
  • When you implement a proposed solution, reflect upon that, too. Did it help? Did it not help? Why or why not?

Consider digging even deeper with a thorough win/loss analysis. Check out Copper’s free Win/Loss Checklist to help you discover exactly why a prospect bought—or didn’t buy—your product, and how to best circulate your learnings.

2. Brush up on your conversion copywriting

A few short decades ago, 99% of all sales conversations happened via just two channels: face to face and on the telephone.

Nowadays sales channels are plenty—and growing still. From social selling to email to targeted direct mail campaigns, sales professionals can no longer lean solely on their “gift of gab”—they also need to know how to write.

No, this is not to suggest a salesperson should take a creative writing course (although if that’s something they’re into, all the power to them). But they should understand some of the fundamental principles of conversion copywriting, since every email they write to LinkedIn InMail they send ultimately has a conversion goal.

Joanna Wiebe offers a fantastic (and totally free) Conversion Copywriting 101 course, which breaks down conversion copywriting into its core components.

This is a great jumping off point for understanding why conversion copywriting is so important, and will provide a solid foundation for branching off into more niche types of conversion copywriting relevant to your industry and preferred channel type.

And since email is still considered the most effective sales and marketing channel, check out our article on how to write sales emails that not only get opened, but also lead to conversions.

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3. Speak often, speak widely

Yes, this piece highlights the importance of effective copywriting, but that doesn’t negate the importance of verbal communication—quite the opposite, in fact.

Being able to speak intelligently about your product or service and effectively convey how it will benefit your prospect is still a fundamental sales skill—perhaps even the fundamental skill.

But spewing off your elevator pitch 1,000 times isn’t going to make you a great sales professional—it’s just going to make you really obnoxious at networking events.

Instead, find opportunities to talk about your product or service in different formats and to different audiences. This will allow you to be more agile, so not matter what situation you find yourself in (be it a boardroom sales presentation, casual video conference pitch, or BBQ-turned-sales-opportunity), you can adapt accordingly and put your best foot forward.

Here are a few ideas to get you started:

Host a webinar.

Because so many sales conversations now happen virtually, being comfortable behind your webcam is a huge advantage.

Hosting webinars is a great way to do this, since it gets you in the habit of preparing for important video events. Plus if you open the floor up for questions after, you’ll hear from a variety of different people with unique perspectives and challenges, which is great practice for when you’re on an actual sales call.

Pitch to be a conference speaker.

Speaking at a conference is no easy feat, but it forces you to distill whatever it is you want to say into the most actionable and relevant information to your audience.

If you then think of your prospects as your audience, you’ll never bore them with another spiel about your product and its many features, but rather, you’ll demonstrate how said features will actually improve their lives.

And don’t forget, just because you’re attending a conference as a speaker, doesn’t mean you won’t have opportunities to put to use your newly acquired sales knowledge. Check out these tips for collecting good leads at an event.

Give a lunch and learn at your company.

Perhaps you’re not in a position in your career yet to speak at a conference or host a webinar—no problemo.

Instead, host a lunch and learn at your office to help you overcome the nerves that arise when speaking in front of several people at once. Plus, again, you can open the floor to questions, giving yourself an opportunity to think and react on your feet.

Take improv classes.

Speaking of thinking on your feet, improv will help you develop the cool demeanor and agility to respond to whatever weird and difficult questions come your way during a sales call.

Of course, you won’t likely have the opportunity to discuss your product or service during an improv exercise, but it will get you more comfortable with the unknown.

4. Build resilience

Getting pushback, objections, and straight up rejection is all part of the job. And while we could just tell you “Don’t take it personally” or “Turn that no into a learning opportunity” that doesn’t really help in the moment when you’re this close to hitting your sales quota for the month and you just couldn’t close it.

Instead, take steps toward building resilience in life, so that these setbacks and disappointments don’t affect you in the same way.


Researchers around the world have demonstrated meditation’s positive effect on the human brain and nervous system.

Take this study, for example, in which 174 adults engaged in an at-home mindfulness meditation practice. The results showed “increases in mindfulness and well-being, and decreases in stress.”

Make SMART goals.

You’ve likely heard of SMART goals—that is, Specific, Measurable, Achievable, Relevant, and Time-based goals. But did you know that making SMART goals may also help build resilience?

Instead of wallowing in what you haven’t achieved, try brainstorming possible solutions and then break them down into SMART goals. Each time you check one off your list, you’ll feel more confident and sure of your ability to take your life into your own hands.

Write it out.

When we experience disappointment or anger, we tend to ruminate on it, playing it over and over in our minds.

By getting it on paper—or on a Google doc, whichever your preference—you release yourself from its burden.

Gratitude journals, in particular, can be particularly helpful, as demonstrated in a 2003 study which showed that participants who wrote about what they were grateful for exhibited heightened psychological and physical well-being.

5. Take advantage of passive self education

If you thought your education ended when you graduated college, think again.

The world is changing at an exponential rate, and professionals need to invest in continuing education to stay on top of their game. Sales professionals are no exception.

While formal education and in-person sales training may be some people’s jam, sometimes it just doesn’t fit with our busy lives. Podcasts are a great alternative, since episodes are short (typically less than an hour), feature a variety of expert opinions, and they’re often based on the latest news and research.

Add to that the fact you can absorb the content while commuting, working out, or cleaning your house. In other words, podcasts allow you to passively brush up on your sales skills while getting other important things done—it’s a win-win scenario.

And while could curate a new list of top sales podcasts to listen to in 2019, why reinvent the wheel when Sales Hacker has already done a remarkable job pulling together their fav 50?

Improve your sales skills, and have fun doing it

As you will have (hopefully) gathered, improving your sales skills extends beyond your step-by-step sales process.

A successful sales professional will not only employ proven tactics and strategies, but also approach their jobs and prospects with a sense of genuine curiosity and an always-be-learning (vs. always be closing) attitude.

The strategies detailed above are just five of the many ways to level up your sales game, but the biggest takeaway should be this: you can always do better, but it doesn’t have to be boring.

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