For the one millionth time, “coffee is for closers” is not a motivational tactic. Of course, seasoned sales leaders already know this, but it’s worth repeating as the image of a sales executive in pop culture still focuses on hard-chargers who lead teams through fear and intimidation. Today’s sales leaders don’t succeed through bullying and by pitting account executives against each other in winner-take-all competitions. Instead, it’s soft skills that matter, particularly empathy, at least according to three New York tech sales leaders we recently spoke with.
These leaders hail from Ontra, Trustpilot and Cockroach Labs and have over four decades of sales experience combined, so it’s safe to say they know a thing or two about leadership. Continue reading to learn more about why all three of these leaders believe great sales leaders need to focus on mastering soft skills along with their number one piece of advice for freshly minted managers.
Great salespeople are promoted into leadership roles because, well, they’re really good at their jobs. While selling and leading sellers require similar skills, Jen Murphy, head of global channels and alliances at Cockroach Labs, believes newly minted leaders need to use their existing skills differently in order to become great sales leaders.
What are the key skills or characteristics of a great sales leader, and why?
Many attributes that make a good sales leader are tied to teaching their team the fundamentals of negotiation, deal structure and forecasting. But the skills that make a great sales leader are soft skills. Top leaders get to know their team’s strengths as well as weaknesses. They actively engage with their team, listen, provide constructive feedback and assist in moving the sales process forward — coaching each step of the way. A strong leader encourages creative thinking but with integrity and driving to a goal of a mutual win with the customer. Most of all, they make themselves available and lead by example.
Understand the skills that made you a successful salesperson need to be used differently to make you a great leader.”
What have you done to strengthen or improve these skills/characteristics in yourself?
I have realized that building soft skills is an ongoing process that takes place throughout your career. I stay current on new approaches to managing through reading and formal training. More importantly, though, I use my extended circle to see how I am doing. I regularly connect with my mentors to ask for advice on how to handle a situation, get feedback on an idea or learn about things they are doing. I speak with my peers to ensure we are sharing our experiences, positive and negative, so we can coach each other on ways to improve. Finally, and most importantly, I check in with my team. If my team does not feel supported and motivated then I know I need to change my approach.
What advice would you share with sales professionals who are just starting out in their leadership journey?
Understand the skills that made you a successful salesperson need to be used differently to make you a great leader. Your passion is now focused on helping your team win, and sharing the knowledge you have gained over time to coach them is imperative. Learn to listen differently so you can clearly communicate how they can succeed by reinforcing the positives and helping them improve on the negatives. Most importantly, have a positive attitude and to celebrate the wins!
A dogged work ethic and in-depth knowledge of a company’s products and services can see an individual contributor on the sales team move into a leadership role in no time flat. When it comes time to make that transition, John DeGasperis, sales manager at Trustpilot, notes that one of the top challenges people face is giving up control. Here’s what he means.
What are the key skills or characteristics of a great sales leader, and why?
Empathy is most important, by and far. It’s important to remember that you’re leading people, which means different personalities and different motivations, among other things. Get to know your team members and realize that each individual is different from the one sitting next to them. The same management styles, tactics, etcetera that work for one team member may not work the same for the next.
It’s more important to focus on your team’s advancement than it is to focus on your own.”
What have you done to strengthen or improve these skills/characteristics in yourself?
I do my best to understand what motivates the members of my team and do whatever I can to help them achieve their goals. Get to know people beyond just a professional level and understand who they are beyond the office. Not everyone is motivated by money. Some are motivated by recognition, others by career advancement, and because motivations differ, blanket management approaches don’t work.
I meet with individual team members every January to understand their goals for the upcoming year and how we are going to achieve them together. There are obvious topics like income or promotions, but there are also other motivations, like trips or big purchases. It’s a fun exercise that keeps us mutually invested in their success and we can work backward on small goals to achieve the greater one.
A mentor gave me a great piece of advice about leadership, which is that it’s more important to focus on your team’s advancement than it is to focus on your own. If you can help your team members to achieve their individual goals and/or get themselves promoted, it’s a win-win for everyone. I take a lot of pride in the promotions and accomplishments that my team members have been able to achieve. It’s honestly the most fun part of the job.
What advice would you share with sales professionals who are just starting out in their leadership journey?
The transition from individual contributor, or IC, to leadership is a complex one. The biggest challenge for me was coming to the realization that not every rep who reported to me was going to operate the same way that I did as a rep. You can’t assume that everything you did as an IC was the right thing to do or that you have all of the answers. It’s difficult to give up that control, but the sooner that you can do it, the more successful you'll be.
The same is true when it comes to helping your team. It’s easy to give them all of the answers when they ask, but that doesn’t facilitate growth or learning. A general rule of thumb for me when someone asks what they should do in a certain situation has been to ask them what they think they should do instead of telling them. From there we can come up with a creative solution based on both of our inputs.
Empathy is an incredibly important soft skill for a salesperson to possess because it makes it easier to understand a customer’s problems and guide them toward the right solutions. It’s also one of the traits that defines great sales leaders. Brian Korchin, managing director and VP of sales at Ontra, said this is because an empathetic leader is able to more fully understand the emotional challenges that come with selling.
What are the key skills or characteristics of a great sales leader, and why?
Being a great sales leader requires a diverse array of skills and characteristics. Among the most important of these are: the ability to develop a vision and inspire a team to achieve it; attracting, motivating, and retaining the best talent; creating systems and processes so that the team’s success can be measured and scaled; delegation; adaptability; a true love for the game; and empathy.
Empathy is a particularly important trait for a great sales leader to have. Being in sales is incredibly fun, but it can be emotionally challenging. As a normal part of your job, you get ignored and rejected. Deals you were sure would close fall through. Your territory can be adjusted as new team members join and strategies change. Your livelihood and even your self-worth are on the line, and they can be negatively impacted by forces out of your control. There are few people in a company outside of its sellers who experience these challenges daily.
A great sales leader understands that the team needs empathy and emotional support — not only sales skills — to succeed in the face of these difficult challenges.
Spend a lot of time reading and learning from the greats.”
What have you done to strengthen or improve these skills/characteristics in yourself?
After leaving corporate law, I quickly fell in love with sales and began spending a lot of time outside of work learning about sales, marketing and how to lead a sales organization. However, sales is mostly a contact sport, and the deepest learning happens while doing. A lot of my learning came from trying new things, seeing what worked and what didn’t, synthesizing my experience with what I had learned from my outside reading and coming to my own conclusions. Like all crafts, you can learn a lot from others, but ultimately you have to make your own way that fits with who you are and the organization you lead.
It’s also critically important for a great leader to be honest about their weaknesses. Great leaders know that they aren’t perfect. A huge part of their team’s success depends on their ability to identify their own weaknesses and gaps and solve for them by attracting and retaining the right talent. The humility to acknowledge where you are weak and the confidence to hire people who are better than you is crucial.
What’s the number one piece of advice you would share with sales professionals who are just starting out in their leadership journey?
Become a true student of the game and allow yourself to fall in love with sales and marketing, which I think is distinct from, but inextricably linked to, sales. Immerse yourself in what great sales leaders have thought about the field, from tactical questions like the best ways to cold call to strategic questions like conceptualizing go-to-market strategy. Spend a lot of time reading and learning from the greats.
At the same time, remember there are a lot of opinions, and there are no silver bullets. You have to learn to hold these two ideas in your head at the same time. There is a lot to learn from others’ experiences, but someone else’s approach is not going to be a perfect fit for your company, your market or even for you as a leader.
Figuring out the right recipe is a science experiment: You create hypotheses based on what others have done and your intuition, and then you test and iterate. It’s a never-ending journey. Even things that work for some period of time eventually need to be changed, so it’s important to have the data and operational piece nailed down. The data will show you what is and is not working and lead you in the right direction.
