Spoiler alert: Main character Willy Loman dies at the end of “Death of a Salesman.”
Cause of death? Pride, delusion and the inability to reach his goals.
Loman believed that in order to be a successful businessman, he could rest his laurels on being well-connected and well-liked alone to accomplish his professional dreams. Had he taken a step back, analyzed his out-of-date skill set and dedicated ample time to consistent training for improvement, his grim outcome may have been different in the end.
While only a dramatization, there is a universal truth to what Arthur Miller was trying to convey in his 1949 play: In order to be great, you have to accept change, acknowledge that there is always more to learn and strive to sharpen your ever-evolving skills.
It also doesn’t hurt to have a seasoned and supportive sales manager in your corner.
“Great salespeople lead by example, set the tone within the organization and work in harmony with their sales peers,” said Barry Brown, director of sales at Procare Solutions. “You have to develop an agile framework that provides some structure to the sales process, but allow each individual sales rep to develop their own individual voice.”
That’s why Built In Colorado sat down with five experienced sales leaders to learn about how they improve the sales acumen of each rep, the most important lessons they’ve learned and the ultimate traits that craft a truly great salesperson — not a Willy Loman.
In your experience, what are the traits, experience, skills and mindsets that define a successful salesperson?
Successful salespeople show characteristics of being able to own the daily, weekly, monthly and yearly grind that comes with sales and have clear goals to achieve results. They can be OK with the massive amount of rejection and celebrate the small wins along the way to a sale.
Typically, I see great salespeople possess a high level of curiosity. Curiosity for the industry in which they sell in order to become a teacher and trusted confidant with prospects and customers always striving to solve problems. Along with curiosity, active listening is a must for a successful salesperson. The ability to listen, digest and then prescribe lends itself to align with prospects and customers’ needs and drive solutions for support and change.
Great salespeople lead by example, set the tone within the organization and work in harmony with their sales peers as well as within the entire organization. They work to establish relationships across departments and are true team players. Finally, I see humility exhibited in some of the very best salespeople.
How do you help your reps develop their own sales acumen?
To lead sales reps and teams, you have to develop an agile framework that provides some structure to sales methodology as well as the sales process, but allow each individual sales rep to develop their own individual sales voice. Not all sales reps are created equal, so you can’t assume to manage each the same. You have to manage and coach to each rep’s approach, voice and overall performance.
By establishing measurable metrics at the sales org level and cascading those down to each individual’s sales foundation, you can help sales reps develop and master their craft over time. For example, vanity metrics like “x number of dials per day” do not necessarily lead to improving sales acumen — they only drive reps further from their leaders. By connecting the specific metrics to the specific sales rep, they can easily connect their activity to performance based on their own efficiency and effectiveness. From those metrics, as a leader, you can help them strive for excellence by connecting specific coaching to drive marginal gains.
Vanity metrics like ‘x number of dials per day’ do not necessarily lead to improving sales acumen — they only drive reps further from their leaders.”
As a manager of salespeople, what’s a lesson you’ve learned that helps you bring out the best in your direct reports?
Active listening from a management perspective is imperative. As sales managers we are constantly pulled in different directions. The term “running and gunning” is the norm. One thing I have learned over time is that the best managers tune out distractions to focus 100 percent of their attention to a rep in need of support or help. Making this time non-negotiable — wherein you remove any and all distractions — is important. Slack messages, emails and pop-ins are all deterrents and anyone sitting across the desk can easily see you are not engaged; thus, driving demotivating behavior.
Treat your direct reports with respect and ensure you give them time. Be there for them, as you ask them to be there for the company and the customer. Build a foundation of trust with your team, be transparent in your efforts, have open collaboration, be accepting of feedback and show them the metrics that are meaningful to them on an individual basis.
Culture isn’t the free beer, snacks, ping pong tables and happy hours ... It’s the product of the conversations, connections and collaboration that happens and rises the tides for everyone on the team.
In your experience, what are the traits, experience, skills and mindsets that define a successful salesperson?
In my experience, the most successful salespeople always find a path to win where there isn’t always an obvious one. That comes with a heavy, resilient attitude since those who hear the most “yeses” also get the most “nos” but still manage to work toward their vision of the bigger picture. Our top sellers have infectious and motivational energy. They want to be the best on the best team, which means they are also leveling up their peers around them to outperform everyday.
How do you help your reps develop their own sales acumen?
I focus on building off of their unique strengths and guide them to identify areas where they need the most improvement. Although feedback is important, I find it is most effective when reps are given the space and guidance to do their own self-discovery. Part of their quarterly business reviews is to celebrate creativity that has been successful and to highlight skills that need sharpening. Their job is to outline how to hold themselves accountable and assign me roles where I can help them along the way.
Ultimately, people buy from people and flaws make us human. We aren’t striving for perfection; we are striving toward relatability, and that comes with bringing everything that makes an individual’s style unique.
It is most effective when reps are given the space and guidance to do their own self-discovery.”
As a manager of salespeople, what’s a lesson you’ve learned that helps you bring out the best in your direct reports?
Give them a safe space to be vulnerable and to mirror that behavior as a leader. We experience mindset challenges every day in our lives that often get in our way of accomplishing our goals and the level of success that we want. My job is to cultivate an environment where we can be transparent when we are missing the mark and to dig deep on the journey we need to take to overcome our obstacles.
I’ve learned that in order to have the most raw, uncomfortable conversations that help build us to be stronger, I need to model that as a leader and be vulnerable with my team when I’m working on new personal challenges as well. When we do the hard work together, we can celebrate the wins together.
In your experience, what are the traits, experience, skills and/or mindsets that define a successful salesperson?
A salesperson needs to be solutions-focused in order to support their client’s objectives to accomplish a certain goal. As a media sales rep, gone are the days where their work is transactional and one-offs. Salespeople not only need to have a great relationship built with their clients, but they need to be able to address their concerns, understand what their goals are for the upcoming months and years, and know what products or solutions are going to help their clients close those gaps.
It’s more important now than ever before to understand exactly what you’re selling and how that can translate into success. We’re asking our multimedia sales reps to train on more products, learn the capabilities and get even more buy-in from the partnerships they create with their clients. It’s imperative that they continue to learn, digest, grow and increase their own knowledge base of the solutions in their sales toolkit.
As a manager, we can help them grow quicker and be able to identify their progress by creating KPIs that will help to increase their own sales acumen. Creating a data-driven approach to management is crucial, especially as a manager adds new team members.
How do you help your reps develop their own sales acumen?
Easy! Practice, practice, practice. The best form of training is through real-life application.
First, focus on internal training. Managers and colleagues should be role-playing in a real life example of a sales call with their reps. Ask them questions, put their feet to the fire and be their toughest client. This salesperson will pick up a lot by joining sales calls and understand how others are overcoming objections and creating a flow to their conversation.
Second, practice on low-risk clients. We all have them. Let this salesperson cut their teeth on these low-risk conversations and give them every bit of feedback on how it went. It doesn’t need to be all positive feedback. Constructive feedback on every little thing is helpful.
Finally, trust them. Once your salesperson has had a decent amount of experience, let them go out on their own. Trust that they’re making the right judgments and do not micromanage every call or email. If they make a mistake, address it, fix it and move on. Make sure you know what their bandwidth is too! Do they need help?
Showing them that you care about their mental health on top of their regular duties goes a long way.”
As a manager of salespeople, what’s a lesson you’ve learned that helps you bring out the best in your direct reports?
With the new work-life balance that’s been created as a result of Covid-19, this virtual management and overseeing of people’s heads led to a unique style of management that requires much more trust than ever before. Virtual salespeople are typically working more hours in their homes and we need to be cognizant of how they feel beyond just hitting goals and completing tasks.
Personally, I’ve learned that I can trust my team to get their responsibilities done. I always check in with them and ask how their bandwidth is. Are they overwhelmed, stressed, want more responsibility or have issues with individual tasks? Showing them that you care about their mental health on top of their regular duties goes a long way. Our sales machine is only as strong as it can be when we know it’s performing at optimal capacity. If we can reduce stress or add more to the fire, that goes a long way with them and typically builds a better relationship, strong sales team and happier clients.
In your experience, what are the traits, experience, skills and/or mindsets that define a successful salesperson?
The most successful salespeople I have worked with are those with a relentless pursuit of winning. They operate off the win-at-all-costs mindset while also applying skills of critical thinking, adaptability and consultative listening. This type of attitude and acumen is usually achieved through a sales person being willing to acknowledge their strengths along with opportunities for growth, and being genuinely willing to put in the work in order to improve.
As a manager, I’ve found that empowering the sales reps as much as possible tends to bring out the best in them.”
How do you help your reps develop their own sales acumen?
I help my reps develop their own sales acumen by demonstrating how to sell our product in real time, while mixing in skill sessions, dissecting won deals and through weekly one-on-one coaching. Most importantly, I help them develop their sales acumen through real experience. I'll usually sit in on their first few presentations and review with them directly afterward to identify both the areas in which they excelled and areas of improvement.
As a manager of salespeople, what’s a lesson you’ve learned that helps you bring out the best in your direct reports?
As a manager, I’ve found that empowering the sales reps as much as possible tends to bring out the best in them. At Apartment List, we have processes and sales plays that ensure the reps have the best resources available to be successful in the role. We also encourage them to be creative within our current processes, allowing them to implement strategies that play to strengths of their own sales style.
In your experience, what are the traits, experience, skills and mindsets that define a successful salesperson?
The typical attributes we see listed on a job posting for an account executive are grit, tenacity, an outgoing personality, culture fit, previous results, X-factor and some sort of athletic and or martial arts background.
Aren’t we looking to hire and develop a sales professional, not a drinking buddy or a bodyguard? Where the heck is sales acumen and or sales skills?
Matillion’s perspective is that there are a few aspects of sales acumen that differentiate world-class salespeople from all other sales professionals: questioning skills, curiosity, process, active listening and coachability to name a few.
How do you help your reps develop their own sales acumen?
We are focused on building a world-class sales organization that leverages data and iterative processes to improve our customer and seller success. Instead of using our gut instinct to identify opportunities for improvement and coaching, we use data.
One way Matillion captures data and enables our sellers’ success is by leveraging Gong. When we started our journey with Gong, we identified an organizational need to improve our questioning skills. To do so, we implemented new enablement activities for our sellers and sales leaders.
First, sellers and managers jointly built out questioning playbooks for common selling scenarios. Bi-monthly sellers tagged their managers in questions they asked that went well, went poorly, what questions they wished they asked and what questions they would like feedback on. Then we held bi-monthly team call reviews where we focused on a particular stage in the buyers’ journey and coached the call while asking questions.
Finally, iterate! We are constantly looking at data to see where we can improve.
Instead of using our gut instinct to identify opportunities for improvement and coaching, we use data.”
As a manager of salespeople, what’s a lesson you’ve learned that helps you bring out the best in your direct reports?
One piece of advice we give to every seller is to be active in your own sales development. With tools like Gong, there is no need to wait for others to improve yourself as a seller. Listen to at least one of your calls weekly. Ask yourself: What went well? What could I do differently? What should I learn or work on as a result of this?
In short, don’t skip steps in your development. Make sure you are mastering the sales fundamentals before adding more complexity to your selling skills.
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