Leadership: Many people want it, some people have it and few people harness it correctly. So what does it take to separate the true greats from the “so-so’s?”
Being a strong leader is not as simple as being born with a certain skill, reading the right books or having the most lucrative connections. Rather, it is circumstantial in nature and based on diverse learning opportunities, trying and failing, being part of a collaborative culture and having a support system in your corner.
In sales especially, many factors can sway a team’s productivity and motivation without the guidance and strategies that an experienced leader provides — whether that be a fumbled negotiation, a disjointed sales pipeline, or a lack of recognition from a big client win. However, a leader who is unable to let go of the sales chase after being promoted or practice quality coaching one-on-one can be just as detrimental to a sales team’s success. So what holds the secret to the ideal person in charge?
Built In Colorado did some digging and discovered three sales experts who have figured out the art of kindling their teams’ fires based on their unique experiences and acquired skills throughout their career journeys.
“Sales teaches you early on that if you want to improve, you must own your work ethic and ability to change things that may not be working,” said Ryan Morrissey, inside sales manager at ezCater.
Looking to evolve your career into leadership? Read on below.
What is your career background, and how did it prepare you for a leadership role?
After undergrad, I knew I wanted to go into sales because I could clearly define my own success there. I started leading a small team doing door-to-door sales that summer. From that experience, I learned the value of hard work, which was critical for launching my sales career.
My first job was at Brocade doing cold calls. Then I moved on to big companies like Dell EMC and Oracle. Although big organizations have tremendous sales enablement programs, I felt boxed in and decided to further my career at a startup. I became an early-stage employee at Sumo Logic, and was promoted to my first management role. All of the tribulations I faced up to that point had prepared me for that position. I continued to listen to successful leaders at Sumo Logic who helped me build sales teams with defining attributes, and who taught me the principles of persistence, heart, and desire.
This background helped me be an extremely successful leader in multiple organizations, including my current position at StackHawk. Today, I still always take a step back and think about how I can strategically enable my team and walk in their shoes to help with whatever task they have on hand.
What are the most valuable sales leadership attributes and characteristics?
I follow four main practices from the book “Leadership and the One Minute Manager” that enable me to have different leadership styles depending on the person I’m managing and the task at hand. I’ve found them very helpful in previous roles and still helpful to me now as a leader.
The first practice is directing: providing specific direction to a task and closely monitoring it. I walk someone through the task and make sure they have everything they need to be successful.
The second is coaching: continuing to closely monitor performance of a task, but also explaining decisions, soliciting suggestions and supporting progress. This works for someone who may have some experience but needs a push.
The third is supporting: This tactic is unique because I continue to listen and provide encouragement while giving the other person the ability to solve the problem, so it’s still a shared responsibility. Then, they debrief with me afterwards and I facilitate the things they need to be successful moving forward.
The fourth and final practice is delegating: delegating to someone else who will own the decision-making process until the end result. This style is for those later in their career growth who have shown high competence and commitment.
I lead by example and end with reinforcement so that each person feels equipped to do it on their own the next time around.”
What’s a recent example of how sales leadership skills helped you or a colleague solve an issue?
Recently, there was a case where I had to move between management styles as circumstances changed. I was managing a deal that someone on the sales team was working on in a supportive nature; he was navigating the deal, and I was providing support.
Before the negotiation stage, he expressed to me that he didn’t have experience with negotiation and he wanted my guidance. So, I moved back into a directing type of role and did some of the negotiation live on the call. Eventually, the deal was closed.
I know what it’s like to be in the shoes of someone who’s still learning a new skill. So after the call, I took a step back and gave him praise and specific feedback. Then I said, “In the future, I know you have what it takes to close these deals. I will always support you, but I have confidence that you can take charge moving forward.”
This scenario shows how critical it is to use different leadership skills to approach different circumstances, and how important it is to have a relationship with my team where they feel comfortable asking for help. I lead by example, and end with encouragement and reinforcement so that each person feels equipped to do it on their own the next time around.
What is your career background, and how did it prepare you for a leadership role?
I’ve been in sales since college where I had jobs selling group sports tickets or apartments as a real estate agent and have never looked back. I don’t care who you are — starting out in sales is uncomfortable because you have to learn to lose before you can start winning. Who wants to do that? I guess, me.
But in all seriousness, to get to where you want to be as a seller, you need to embrace feedback and appreciate quality coaching. Sales teaches and ingrains into you early on that if you want to improve or hit goals, you must own your work ethic and ability to change things that may not be working.
Sales is a great path for anyone to build a foundation for a career in leadership as it forces you to problem solve on a daily basis. The thousands of curveball questions, objections or unexpected tech problems you might experience during a demo force you to develop a craft in communication navigation which is very helpful when leading a team.
What are the most valuable sales leadership attributes and characteristics?
Active listening and authenticity.
I think most sales leaders initially struggle to go from being in the game to overseeing those playing in it, and want to try to do both. It’s impossible. If you want to be a good sales rep, you need to be a very good listener when your customer is speaking on the call. If you want to be a good sales leader, you need to be an even better listener when you are meeting with your reps both individually and as a team. Your customers won’t trust buying from you if you just ignore their pain points or roadblocks. This applies to your team of sellers, too. The sales dashboard never tells the full story and it’s on you to ask the questions, uncover roadblocks and work together to remove what could be holding back your team.
I’m a big believer that people buy from people and not companies. You want your customer walking away from the buying experience recommending your name to someone — not just the company — because of the experience you gave them. Being authentic and not robotic as a sales manager is important. You’re in this role because you’re committed to the growth of your reps and to do it confidently, you have to be yourself.
It’s on you to ask the questions, uncover roadblocks and work together to remove what could be holding back your team.”
What’s a recent example of how sales leadership skills helped you or a colleague solve an issue?
Slumps and rough patches can happen in sales. As a rep, I would start to want to do too many things or overextend myself during those times. Recently I was working with a rep who wasn’t happy with their performance, and after listening to each other’s feedback in our first meeting of the new month, we built a plan of attack for the month ahead. It was clear the rep was juggling too many tasks. We left the meeting having agreed upon one metric to drive towards, and not only did they beat that target, but other metrics improved as well.
When things seem to not be going your way, it’s important to simplify what you are doing and refocus. I think at times sales reps can overcomplicate the job for themselves by trying to do too much. It’s crucial as a sales leader to have those conversations and advocate for them to go back to the basics to reset their confidence in doing the job they do best.
What is your career background, and how did it prepare you for a leadership role?
I’m the son of a sales executive. As a child, I imagined myself playing in the Premier League more than in corporate sales, but life comes at you fast. Once I finished graduate school, my calling was in advertising — or so I thought.
I accepted a role as a sales development representative making more than 200 phone calls a day, and oddly I was hooked. I’ve served in various sales leadership roles around the world across my tenure since my SDR days — from building a landing team in a new country to earning a SaaS IPO — and they were all building blocks leading to my current role.
The various roles taught many lessons, and perhaps more impactful was living around the world both as a child and an adult; these experiences yielded perspective. Specifically, I learned the power behind building inclusive and highly effective teams. When done right, it’s magic. The term “servant leadership” tends to get overused, yet at the core it’s a superpower. Teams expect inclusion, clarity, flexing communication styles and learning how to build trust, faster.
More than 20 years later, I’m still learning yet my lessons have collectively prepared me for today. Change is constant and the best musicians adjust to the beat of their drummer.
What are the most valuable sales leadership attributes and characteristics?
Let’s break out valuable attributes across four key pillars: strategy and planning, talent management and culture, operations and customer management.
Of course, depending on the maturity of the business, these attributes or pillars could shift when asked, “What’s important right now?” Holistically, two key attributes today fall within talent and culture are creating impactful employee value propositions and talent acquisition. The Great Resignation is real, and according to the Harvard Business Review, roughly one in five mid-career employees resigned or will resign in 2021. Sharing how employees can be productive anywhere today is less insightful given the modern tech stack, yet attracting talent to your revenue organization should feel different.
Field sales and conference marketing will not return to its meaningful level anytime soon. Yesterday’s playbook warrants new and fresh ideas. Waiting for “the good ol’ days” to return could be a mistake when attracting high performing talent. Job seekers both expect and are far more attracted to modern perks like new tech stacks, company mission and purpose, enablement, access, flexible schedules and remote work, exciting compensation and more.
Teams expect inclusion, clarity, flexing communication styles and learning how to build trust, faster.”
Give an example of those sales leadership skills in action. What’s a recent example of how they helped you or a colleague solve an issue?
A problem many companies face today is engagement given the culture shifts with distributed working. Co-worker bonds created through a quick happy hour or casual walk to grab coffee during the day seem harder to achieve. To many successful revenue teams, earning trust is the foundation of organizational health. Companies which prioritized culture pre-pandemic are rewarded today and others which may have ignored organizational health are feeling some pain.
An example of bringing inclusion, clarity and overcommunication to our team was structuring weekly revenue-wide “ask me anything” time, and then bi-weekly “ask me anything” time for the company led by our founders. These meetings allowed authentic answers to difficult questions in today’s uncertain environment. Our strained human connection due to our distributed nature does not grant permission to ignore hard truths. We must be intentional about what used to grow organically.
We have a lot more work to do and lessons to learn about employee preferences as we find our way through the global pandemic, but this is a step in the right direction.
