I’m not going to lie and pretend I crushed every role I’ve ever had. The truth is I’ve failed plenty of times, and I’ve even been let go a couple of times.
Sales has been a roller coaster. Earlier in my career, I was a junior Account Executive, pitching to hedge fund COOs and CFOs — and I remember feeling completely out of place. I thought something was wrong with me, but the truth was… it was just a skill gap. I hadn’t yet invested the time, energy, or resources to become the best version of myself.
Now, as I reflect on how far I’ve come, I want to share the sales skills I believe are essential for building a successful career — not just in sales, but in any profession where influence, communication, and growth matter.
Spoiler: Lasting success in sales is built on emotional intelligence, business acumen, and a commitment to personal growth. The best sellers I know are also the most committed learners. They’re constantly refining, experimenting, and staying curious.
Here are the top skills you need to master.
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Sales Skills
- Active Listening
- Linkage
- Storytelling
- Business Acumen
- Creating a Compelling POV
- Curiosity
- Laying the Planks
- Coachability
- Follow-Through
- Account Planning
- Time Management
- Protecting Your Energy
- Public Speaking
- Reflection
- Responsibility
- Strong Discovery
- Problem-Solving
- Negotiating
- Prospecting
- Social Selling
1. Active Listening
This is harder than it sounds. Most of us listen to respond, not to understand. I’ve been guilty of this myself.
It takes a conscious effort to truly zip your mouth and be fully present with the prospect. When done right, you might find yourself barely speaking while the other person talks for ten minutes straight — about their problems, stressors, and what’s keeping them up at night.
The magic happens in the linkage, or when you apply what they shared to show them that you’ve solved this exact issue before. That’s where trust is built. (See my next point for more on this.)
2. Linkage
This is where many reps miss the mark. They default to features, benefits, widgets, and dashboards. But unless you can link it to a real-life, specific use case, it’ll fall flat.
The more specific you are, the more confidence the buyer has. When they hear a story about a real client who struggled with the same issue and came out the other side, they start to believe, “Okay, they’ve done this before.”
But here’s the key: You have to believe it yourself. Not just intellectually, but viscerally. That belief comes from doing the work, going deep with your current clients, and being able to speak to the before and after without hesitation.
3. Storytelling
Leverage the to connect the dots in a way that resonates deeply with your clients. In the hero’s journey, the character leaves their familiar world, faces challenges and transformation, and returns home with newfound wisdom.
That’s exactly what your client is experiencing. When you frame your narrative this way, it becomes less about pitching and more about guiding them through a powerful story of transformation … with your solution as part of the journey.
4. Business Acumen
Business acumen isn’t just something you gain from years in the trenches (although that helps). You can build it intentionally, starting today.
Use tools like ChatGPT and AI to summarize 10-Ks. Read earnings reports. Listen to quarterly forecast calls from public companies in your space. Make The Wall Street Journal part of your daily scroll.
And put yourself in rooms that stretch you. Talk to more senior stakeholders. Don’t be afraid to apply for that Enterprise AE role — you’ll grow into it faster than you think.
5. Creating a Compelling POV
At , we define a POV as a hypothesis you bring into the conversation.
Let’s say I’m meeting with the head of cloud at a Fortune 100 consumer products company. My POV might sound like this:
“I’m guessing you’re leading a fast-growing 800-person org, with a tech stack expanding so rapidly it’s tough to keep track of what’s current. Your Center of Excellence is solid, but to truly keep up with the pace of innovation, you’re looking to leverage additional resources. You probably asked around your network, which led you here today. Are you open to hearing how we’ve helped [insert their competitor] solve this?”
This not only shows you’ve done your research, but it invites them to validate or correct your thinking, which builds collaboration. It also demonstrates that this isn’t your first rodeo — and that you’re competent and credible.
6. Curiosity
Curiosity is one of the most underrated sales superpowers.
There’s a certain energy that comes from people who are genuinely curious. They ask questions not to pry, but to serve. I have a friend who asks incredibly personal questions, but no one ever feels uncomfortable, because you can tell it comes from a place of love and presence.
The best sales reps are the same. Their questions make people feel seen and heard — not interrogated.
7. Laying the Planks
One of the most impressive sales reps I’ve ever worked with was at TriNet. He consistently ranked #1 in the company, sometimes making close to a million dollars a year. The funny thing? You never felt like he was selling you anything. He carried this calm, trusted advisor energy. He knew exactly what he was talking about and made it feel effortless.
The secret? Mastery and repetition.
While others jumped from company to company, resetting each time, he stayed and became a true expert in his industry. He understood medical insurance plans inside and out. He had his metrics dialed in, knew how to run a discovery like a surgeon, and put his prospects through a seamless process that removed resistance. His implementation timelines were crystal clear. You could feel his quiet certainty, which was earned through years of delivering on promises.
Great reps make selling look easy because their foundation is rock solid.
8. Coachability
Every top seller I know is relentlessly open to feedback. Period.
When I went through , I learned that my ego was often the biggest thing standing in the way of my growth. It was humbling, but transformative.
Coachability is a superpower in sales, especially if you can take feedback without making it mean something about you.
Take our CEO, for example. He’s likely on track to generate over $2 million in profit this year, and yet, he still invests in coaching, attends seminars, and shows up to masterminds eager to grow. That mindset is contagious.
But it’s not only about being able to receive feedback — you must also be able to filter it. Watch people’s actions, not just their words. Be smart about who you take advice from. The best feedback often comes from people who are doing the thing you want to get better at.
9. Follow-Through
I’ve recently closed several deals where the common thread wasn’t fancy sales tactics. It was nothing but follow-through.
I cared. I followed up. I stood for the client’s success, even when it was uncomfortable.
During a recent lunch, a client told me one of the reasons she joined — despite the hefty investment — was that she felt we genuinely cared. It wasn’t about pressure; it was about persistence and presence.
People can feel when you’re in it for the right reasons. That sincerity builds trust faster than any pitch ever could.
10. Account Planning
Winning complex deals is strategy, not luck. It takes intentionality, deep thinking, and time.
The best reps I’ve seen don’t treat every deal the same. They go deep. They map out stakeholders, uncover political dynamics, and understand internal roadblocks. They know when budget opens up, who the real champions are, and what internal conversations are happening behind the scenes.
When I shifted my approach to fewer and deeper accounts (especially in enterprise), it changed everything. I stopped surface-level discovery and started solving real business problems. That’s when strategic partnerships are born.
11. Time Management
I’ve learned a lot from our CRO, . One thing I deeply admire about him is how fiercely he protects his time.
He doesn’t just talk about prioritizing. He actually lives it. He executes on what he says he’s going to do. That consistency creates trust and drives results.
As a rep, when you consistently follow through, people believe in you. Over time, that builds into a reputation that gets you more opportunities with less effort.
Like everything else on this list, the good news is that this is a skill you can practice and improve over time. For instance, I used to be terrible with time management, mostly because of recovering from people-pleasing tendencies. But now, I have no problem keeping my phone on Do Not Disturb pretty much all the time.
Pro tip: Even something as simple as downloading an app to block your LinkedIn or Facebook newsfeed can be a powerful hack — especially if you know you tend to distract yourself with social media.
12. Protecting Your Energy
Top performers aren’t just managing their time — they’re also managing their energy.
They batch tasks, ruthlessly prioritize high-ROI activities, and say no to anything distracting from their goals. For me, structuring my day into focus blocks has been a game-changer. I set aside time for prospecting, deep work, and creative tasks — and I protect that time like it’s a meeting with a client.
Focus is a competitive advantage in a world full of noise.
13. Public Speaking
In today’s world of content overload, being able to communicate clearly and confidently from the heart is a massive differentiator.
The best public speakers aren’t flashy. They’re real. They share from experience. They speak to their younger selves.
I’ve found that sharing lessons I’ve learned — from struggling with structure to building confidence after rejection — helps others more than I realize. People don’t need perfection; they need your truth.
Forget the clickbait. If your message comes from service, it will resonate.
14. Reflection
Sales is emotional. The best reps don’t just grind, but they also give themselves time to reflect.
After a tough month, I ask myself:
- What did I learn?
- Where did I hide?
- Where did I lead?
This simple act of reflection helps me grow faster. I journal, revisit key calls, and get honest about what worked and what didn’t. Without reflection, we’re just reacting. With it, we’re evolving.
15. Responsibility
Let’s be honest — blaming external circumstances is easy. I’ve done it, too.
“I didn’t vibe with that manager.”
“I don’t have the right tech stack.”
“That person said something that felt off.”
But none of that moves the needle.
What changed everything for me was asking: What would a top performer do in my situation?
Instead of blaming, I started tweaking. I cut low-value activities. I stopped chasing unqualified leads. I got clear on my POV. I stopped being lazy with messaging and started showing up intentionally.
You don’t need to be perfect. You just need to take responsibility. There are thousands of prospects out there who need your help. You owe it to them to show up fully.
16. Strong Discovery
This is arguably the most important skill to master in sales. Most of us love to talk, but the more we talk, the less we learn.
Even if the prospect is firing questions at you, it’s crucial to set the stage early. I like to say something like, “Just like a good doctor wouldn’t rush to prescribe medication without understanding the symptoms, I want to make sure I fully understand what’s bringing you to us before jumping into features or solutions.”
If you skip discovery and dive into features too soon, it won’t land because you haven’t earned the right or uncovered the real pain yet. Great discovery builds trust, surfaces urgency, and sets you up for a solution that actually resonates.
17. Problem-Solving
Closing the deal is great, but the ultimate goal of a great sales professional is to solve real business problems.
That’s why I believe top sales reps are expert problem-solvers. It’s not just about handling objections in the moment. It’s about anticipating future roadblocks before they show up and proactively preparing for them.
This takes practice. It also takes curiosity and the discipline to think ahead. Before every dial, take a moment to brainstorm: What might this prospect be struggling with? What’s going on in their business, based on what I know?
Don’t overthink it. But don’t just wing it either. The best reps stay agile. They’re willing to adjust when new information comes in, but they always come in with a solid POV.
18. Negotiating
Great negotiators know their worth, and they don’t operate from a place of need.
One of the best negotiators I know charges $30K a year for coaching — and people pay it gladly. Why? Because he doesn’t need the client. That posture changes everything. It makes the interaction feel more natural and aligned.
Too often in sales, we’re taught to “do whatever it takes” to win the deal. But discounting doesn’t build trust — it undermines your value.
What works better is deep discovery, alignment, and showing how your solution drives impact. When there’s real value, price becomes a smaller part of the equation.
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19. Prospecting
Prospecting is about volume, but it’s also about precision.
It’s easy to fall into the trap of just “checking the box.” But top performers slow down to speed up. They build systems that streamline their process while staying hyper-targeted.
Yes, rejection is part of the game. Even the best reps feel it. But the key is being resilient while also staying strategic — multi-threading, focusing on the right accounts, and personalizing based on buying triggers.
With AI, you can now . Use that to prioritize the people most likely to convert.
20. Social Selling
In an age where inboxes are flooded with automation, the human touch matters more than ever.
If you’re not staying in touch with your network — or if you’re only reaching out when you need something — don’t be surprised if your messages go unanswered.
Social selling is about community, not transactions. Are you showing up with value? Are you spotlighting others, giving thoughtful comments, and making introductions?
I once knew someone who was fundraising for a cause she cared about, but her approach made people feel guilty instead of inspired. She could’ve tapped into her network more effectively, but instead, she got blocked by people who felt drained by the interaction.
The takeaway? Lead with service. Be generous. If you do, your community will show up when it matters most.
21. Adaptability
I’m not going to lie — I was slow to adapt when the pandemic hit. Those were some of the hardest years for me, largely because I resisted the changes happening around me. I learned the hard way that resistance to change can cost you. And the truth is, most of us struggle with change. It’s natural, normal, and expected. But growth starts when we stop resisting and start adapting.
Things are moving fast. Tech is changing. Buyer expectations are evolving. Internal orgs are reorganizing faster than ever.
If you’re stuck in how things used to work, you’re going to fall behind.
One pattern I’ve seen: Reps who’ve struggled over the last five years often cling to outdated playbooks. What worked in 2013 doesn’t fly in 2025. The buyers have changed. The tools have changed. The process has changed.
You have to be willing to evolve fast. That doesn’t mean chasing every shiny object, but it does mean being open, curious, and committed to growth.
22. Technological Savviness
The reps who stay curious, adaptable, and open to learning new tools will always have an edge. Being tech-savvy doesn’t mean jumping on every shiny new thing. It means being intentional about the tools that help you optimize your workflow, increase your output, and create more leverage in your day.
The key is to stay in the know without going overboard. There’s a fine line between being an early adopter and getting caught in analysis paralysis. I’ve learned this the hard way: Spending too much time testing the latest tech stack or automation tools can actually pull you away from your core goals.
For example, I’ve had moments where I signed up for five different AI platforms thinking they’d each transform my outreach. But it wasn’t until I simplified and focused on using ChatGPT intentionally — like creating role-play scenarios based on real objections or drafting personalized outreach for enterprise AEs — that I actually saw results. Now, I use ChatGPT to prep for conversations, tighten messaging, and even streamline content creation like this article.
Tech should serve you — not the other way around. Use it to amplify your strengths, not distract from them.
How to Improve Sales Skills
- Attend sales training.
- Implement roleplay.
- Review game tape.
- Find a mentor.
- Ask the hard (and deep) questions.
- Become a lifelong learner.
- Improve your prospecting skills.
- Be able to prove ROI.
- Ask for and listen to feedback.
- Stay connected to the customer.
- Address the elephant in the room.
- Experiment often.
- Lead with integrity and honesty.
- Track your progress.
1. Attend sales training.
There are so many great sales trainings out there. My advice? Ask the top reps you’re close with, or the ones who carry a certain energy you admire. Grab lunch or coffee with them. They’ll likely tell you which courses and programs helped them shift from operating in survival mode to selling from a place of abundance.
2. Implement roleplay.
I’ll admit this can feel super cringey initially, especially if you’re not used to it. But if you’re in a role with tons of at-bats — like I was at CoachHub as a mid-market AE in New York City — you’ll improve much faster by practicing intentionally.
Thanks to the marketing dollars we invested, we had a flood of meetings. Looking back, I wish I’d role-played more often to make the most of those opportunities. Sometimes, slowing down to speed up really is the game.
Lately, I’ve been using roleplay to tackle the objections I still struggle with. And yes, you can even roleplay with AI now. I use ChatGPT by feeding it context based on the personas I’ve had trouble closing. It’s helped me sharpen my language and get more comfortable navigating those friction points.
3. Review your game tape.
Replaying your sales calls can be confronting. Most of us don’t like how we sound or look on camera. And let’s be honest — many salespeople start off as people pleasers. We like getting along with others, which can make self-criticism uncomfortable.
But growth lives in the details. Watch for filler words, tone shifts, and awkward pauses. But here’s the key: don’t beat yourself up. Be critical and kind. Think goldfish memory. Tweak what you can, and let the rest go.
Don’t overcorrect. You’re a work in progress — and that’s a good thing.
4. Find a mentor.
Mentorship is one of the biggest unlocks in my journey. A great mentor helps you avoid costly mistakes and accelerates your learning curve. But it only works if you truly listen and apply what you hear.
It still amazes me how many people go through life without a mentor, or wait until they burn out to seek one. I genuinely can’t imagine doing this work without the mentors who’ve guided me. It’s a gift. Don’t take it for granted.
5. Ask the hard (and deep) questions.
This one sounds simple, but how many times have you held back from asking something real because you were afraid?
Thanks to platforms like LinkedIn, it’s never been easier to connect with people. But people can feel your intent. Are you reaching out because you want something? Or because you genuinely care?
When you lead with curiosity and service, people open up. Ask the question. Go there. You’ll be surprised what doors it opens for both of you.
6. Become a lifelong learner.
I’ve said it before and I’ll say it again: Being a lifelong learner is essential. With constant shifts in tech, buyer behavior, and culture, the sales landscape is always evolving.
The best reps I know are students of the game. They read the latest articles, listen to mindset and industry podcasts, and stay engaged with trends that impact their customers. For instance, if you’re selling software, staying current on the industry helps you anticipate objections and position your product in context.
A few of my personal favorite podcasts that help me grow:
- – Inspiring guests that elevate your frequency. A wholesome, soul-nourishing listen.
- – I attend his Summit of Greatness every year. The community is amazing. I’ve met lifelong friends there.
- – She’ll help you level up your business acumen with no-BS strategies and frameworks.
7. Improve your prospecting skills.
Prospecting isn’t glamorous, but it’s what fills the pipeline. And without a pipeline, nothing moves. It’s also where many reps spend most of their time, so it pays to get sharp here.
Cambria Davies said it well in this blog post: “It’s not just a nice-to-have — prospecting ensures that the leads you’re communicating with have an immediate (or potential) interest in a solution like yours.”
My advice? Try different prospecting methods — warm calls, webinars, social selling. Use data, but lead with heart. Curiosity and relevance will always outperform automation at scale.
8. Be able to prove ROI.
Being able to articulate ROI in a simple, confident way is a game-changer. Let’s say I’m talking to an enterprise AE making $265K who hit 80% of plan last year. She’s back from maternity leave, low on support, unsure about new product launches, and pacing to hit just 50% this year.
If her OTE is $300K and she’s on track to earn $185K, that’s a potential $80K loss. Suddenly, a $10K coaching investment doesn’t seem so expensive — it becomes a no-brainer.
Don’t be afraid to talk numbers. If you don’t, they’ll be doing the math in their head anyway. Help them connect the dots, casually and confidently. Share stories, especially of people in similar situations. A quick video or testimonial can go a long way toward building trust.
And remember: People buy emotionally, but they justify it logically. Lead with both.
9. Ask for and listen to feedback.
Whether it’s a film review or a Slack message from a peer, feedback is gold if you’re willing to hear it. I get it — it’s not easy to hear that you asked too many questions in a row or didn’t build enough rapport. But that’s how you refine.
If someone says your call felt like an interrogation, reflect on that. Try adding a bit more warmth or curiosity next time. Build in moments of genuine connection, even if it’s just a light touch of small talk upfront.
Even beyond calls, ask your current clients what’s working and what’s not. Feedback surveys are great, but often the best insights come from quick, casual check-ins. Yes, it takes more effort, but you’ll grow exponentially from the insight.
10. Stay connected to the customer.
As AEs, we’re often incentivized to move on once the deal is done. But staying in touch with your customers is powerful.
You get to see the real-life ripple effect of your work. That kind of impact — the “this deal changed their team’s entire workflow” kind — gives your work deeper meaning.
You might not get comped for it, but fulfillment is its own kind of ROI.
11. Address the elephant in the room.
If you know an objection is coming, bring it up first.
Let’s say I’m meeting with a commercial AE at Salesforce. I already know they might feel they’re “too junior” to benefit from our coaching at Unlock Your Sales Potential. So I’ll say upfront: “39% of our community is in the same segment as you, and many of them are closing deals at an enterprise level just by shifting their mindset and daily habits.”
It’s a powerful reframe, and it builds instant credibility.
Proactive transparency removes friction.
12. Experiment often.
Sales isn’t a rigid science. It’s a living process. Iteration is everything.
Every Monday morning, I reflect on the past week during my accountability calls. I rate how effective I was, and not just based on results, but on effort, mindset, and process. That reflection time helps me stay focused on the inputs, not just the outcomes.
Try the Pomodoro Method for 12 weeks. Give Bullet Journaling or the 12-Week Year a real shot.
If you just got promoted from MM to enterprise, don’t copy-paste your old process — adapt it.
Evolve it. Test. Tweak. Repeat.
13. Lead with integrity and honesty.
Say what you’ll do and do what you say.
It sounds simple, but in high-pressure sales environments, it’s easy to cut corners or prioritize short-term wins over long-term trust. I’ve talked to reps who “win” deals because of contractual loopholes, only to lose trust later.
That’s not sustainable.
Play the long game. Doing what’s right for the client — even when no one’s watching — is what makes you a true professional.
14. Track your progress.
If you can’t measure it, you can’t improve it.
Set clear sales goals and review them weekly, monthly, and quarterly. Track not just your output, but your consistency and growth. Consider running A/B tests on your own messaging. What resonates? What falls flat?
Use that data to improve your process. Not everything will be a home run, but if you commit to honest reflection and continuous learning, your skills will compound over time.
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, mentors, supervisors, or customers.
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.
Editor's Note: This post was originally published in October 2019 but has been updated for comprehensiveness.
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