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Jay Nathan knows more than most when it comes to leading dynamic customer success teams – and one thing he’s learned along the way is that true leaders never stop learning about how to refine their approach.

“Leadership is a lifelong journey,” he recently told Update AI’s Josh Schachter on the “Unchurned” podcast. “And it will be constantly changing because the people you interact with will be changing.” 

Jay has seen that firsthand, whether it’s at Higher Logic, where he’s an executive vice president and the chief customer officer, or at previous stops including RainFocus and PeopleMatter; Jay is also the co-founder of Gain Grow Retain, a community for CS leaders to collaborate and share their work. It goes without saying at this point that CS is his passion. 

During his conversation with Josh, Jay said the key for anyone in a CS leadership position to remember is this: you have to empower your team. You have to be able to delegate and inspire your team to rise to the occasion, because you can’t do everything – even if you wanted to – when you’re scaling a business. 

Let’s jump into the three steps Jay said are critical in being a leader in CS or any field. And of course, you can listen to the full podcast – and enjoy the back-and-forth volley between Josh’s New York accent and Jay’s South Carolina accent – by clicking here

Lead With Questions 

The first principle of good leadership, Jay said, is realizing you don’t have all the answers. 

This is important to accept, because when problems inevitably arise, the sole focus needs to be on finding a solution. And the best way to do that – and to empower your team members in the process – is to “lead with questions,” Jay said. 

Don’t start off by immediately giving directions. Instead, ask questions. This accomplishes a few things right off the bat. First off, it “allows people to take ownership of their own problems,” Jay said. As a leader, you cannot afford to take ownership of everything; this will galvanize your team member to embrace the challenge and feel they have real stakes in the outcome. 

Secondly, asking questions often helps the answer come into focus. You can eliminate certain roads that aren’t worth going down while, at the same time, potentially sparking an “a-ha” moment for your team member. Asking questions also reinforces the line of communication between the leader and team member and helps to build a foundation for collaboration.  

For more insight on how asking questions can foster growth, Jay recommended reading “The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever” by Michael Bungay Stanier. 


Be Direct 

Here’s where it can be a bit tricky. Yes, it behooves you to get the input of your team members and let them take ownership of their work. At the same time, remember: you are the leader, and sometimes that requires being direct and giving a clear verdict on tough decisions when needed. 

Striking that “equilibrium,” as Josh and Jay both put it, is difficult – but it’s imperative for any leader. 

“Be collaborative – but also be deliberate,” Jay explained. If you want to be in charge, you have to be mindful of that balance. 

As legendary basketball coach Phil Jackson said once at practice, when a player told him their defensive game plan was difficult to carry out, “If it was easy, everyone would do it.” The same applies to leadership – if it was easy, everyone would be a good leader. 

If you struggle with this aspect, don’t get down on yourself, though. Again, this is an equilibrium that you learn to strike as you grow in your leadership role. Both Josh and Jay said they had to find that balance as their careers developed; Josh said he could be too lenient in the early days of his career, fearing he would come across as overly coarse, while Jay said he also had to learn to be more direct when the time called for it. 

“It’s so friggin’ hard,” Jay put it succinctly, on picking your spots.

Empathy Is Essential  

What’s the secret to striking that balance? Empathy, Jay said. 

To be an assertive and effective leader, your team needs to feel you care about them. This allows you to make tough decisions and have difficult conversations without jeopardizing your relationships or dampening an employee’s passion. 

“Intent matters. It matters more than what you say,” Jay explained. “It’s where you’re coming from. Does the person on the other end of the phone know you care first?” 

How do you go about this? One way to build this “care capital,” Josh added, is for leaders to be mindful of the position their team members are in. Put yourself in their shoes for a moment. If an employee is out sick because they’re battling COVID, for example, you could send them a little care package. 

View it as an opportunity to move your relationship forward, because that consideration will pay off in spades down the line; you create a better environment to have difficult conversations down the line, while also letting your employee know that you care. They’ll be more willing to go the extra mile towards finding a solution for your customers in that case. 

If you can keep these three facets in mind, you’ll be able to empower your CS team to reach new heights. 

To learn more about Dylan’s leadership essentials, listen to the full first episode of “Unchurned.” (Again, you can find the show on your favorite app by clicking here.) And you can find out more about the course “Being a Leader and the Effective Exercise of Leadership” that Dylan co-instructs at UCLA by visiting this link.)

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