What’s the secret to being a great sales leader?
Your immediate response might be something along the lines of being the person with the solutions. But in reality, nobody has all the answers. And so many leaders are occupied with the pressure of being the go-to person, only to realize later that it’s not very conducive to helping the team prosper.
What if the next time an issue surfaced, you countered a question with a question? Something like: “What have you tried?”
This is just one of the questions Kaileigh Taylor, a sales lead at Canva, has used as an efficient approach to help a teammate arrive at a solution. It’s a perfect example of her leadership style, which is built on learning and investing in her team — as a whole and as individuals. “Taking the time to talk out a situation with someone to allow them to come up with the answer on their own will always make a bigger impact,” she said.
Opting for a strategic process to navigate an issue is a logical method to get a team thinking. And Taylor, in particular, has found it to be a productive way to foster confidence and empower the people she is leading. “The way I see it, the answer is always in the room, and you are here to help bring it out of everyone,” she explained. By encouraging communication and collaboration, team members are more likely to find solutions on their own, thereby growing as leaders themselves.
You don’t need to have all of the answers, but being able to lead by asking questions can make a huge difference in a team setting. We met with local professionals from Canva and Levelset to learn exactly what characteristics they believe are the most valuable in a sales leadership role and how their career history prepared them to be better leaders today.
What is your career background, and how did it prepare you for a leadership role?
I started in the technology sales industry about seven years ago at a technology reseller in Austin. I was an individual contributor for three years and have held leadership positions since then ranging from front line manager to regional director. Earlier this year, I joined the Canva team as their corporate sales lead and it’s been an amazing experience! Starting off as an account executive not only taught me the ins and outs of the role, but also how to hold yourself accountable in a fast-paced environment with new challenges that pop up every day. I was fortunate enough to work with a variety of leaders and technology partners who helped shape who I am as a leader today. Making connections is important, but learning from those connections is impactful.
What are the most valuable sales leadership attributes and characteristics?
Being collaborative, leading from the front and empowering your people are important, as is cultivating a fun team culture. It’s key to help the team solve problems while also enabling them to act as leaders. Being a leader doesn’t necessarily mean you know every answer. However, strong leaders help facilitate discussions to encourage everyone to learn from one another’s strengths.
People also want to work with leaders they trust and respect. The most rewarding way to engender this is by leading from the front. Being involved in the business early and often helps you gain buy-in while sharpening your skills as a leader. Lastly, empowering your people to solve problems and hold themselves accountable should be the ultimate goal for leaders. This can take time, but it’s more motivating for team members to feel confident they have the knowledge to understand how to solve the issues themselves.
Strong leaders help facilitate discussions to encourage everyone to learn from one another’s strengths.”
What is one challenge that new leaders often struggle with when supporting their team with solving an issue?
I see this happen on a daily basis. Some leaders will just give out what they see as the right answer and quickly move to the next thing on their to-do list. It’s easy to do, especially when you’re busy. The best approach I’ve seen is taking the time to ask, “What have you tried?” and “How would you resolve this?” These questions get your team thinking, and almost every time they solve the problem themselves. Sometimes you have to ask more questions and guide them through the process, but it teaches them to think strategically. This will build confidence and empower your team to know what to do the next time they come across an issue or challenge. This is one of my favorite parts of being a leader!
What is your career background and how does it align with your current leadership role?
I was an individual contributor and then a sales leader for seven years in a high-velocity, inside-sales environment. Next, I sold software for a couple of companies at the small and mid-size business and enterprise levels as an individual contributor. Upon arriving in New Orleans, I found a role where I could lead a high-velocity inside sales team, and also work on more strategic deals. Levelset really is a perfect fit for my experience.
It’s important to understand that you work for your people, not the other way around.”
What are the most valuable sales leadership attributes and characteristics?
Empathy, drive and vision are key. It’s important to understand that you work for your people, not the other way around.
What’s a recent example of how your sales leadership skills helped you or a colleague solve an issue?
We recently repackaged our product based on issues and feedback my team shared with me. As a result, we hit a big annual company milestone and had our best months ever back-to-back.
