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Becoming a great leader is easier said than done.

And when it comes to customer success – and business in general – leadership requires the ability to galvanize your team to perform at its highest level, both when you are present and also when you aren’t there, looking over an employee’s shoulder.

Fortunately, Dylan Stafford knows a bit about what makes great leaders, well, great. Dylan is the associate dean and director of admissions at UCLA Anderson School of Management, which is where he first met UpdateAI CEO Josh Schachter about 15 years ago. Their long friendship made Dylan a no-brainer selection to be the first guest on “Unchurned,” UpdateAI’s recently-launched podcast. (Get more details on where you can find “Unchurned” on your favorite podcast app by clicking here!)

One tricky thing about leadership, Dylan pointed out on the podcast, is that there isn’t a commonly agreed upon definition. What really makes a leader? Sure, when you are looking for guidance and inspiration, you can find quotes from a number of people who have steered successful sports teams, like legendary UCLA basketball coach John Wooden, to business and marketing geniuses like Apple’s Steve Jobs. 

Those are great, of course; Dylan often points to Wooden’s famous “Be quick, but don’t hurry” maxim, which applies just as much in the office as it does on the hardwood. Still, there will be times when you’re not able to immediately summon an illuminating or motivational quote. That’s not what makes a great leader, anyway. 

No, what Dylan has found is there are core aspects of leadership that are universal – foundational traits that true leaders are able to demonstrate on a day in, day out basis. These are the traits that make people want to go the extra mile and trust in your vision. Two of those essential characteristics he pointed to: integrity and authenticity

Let’s dive into each of those more:



How do you practice integrity as a leader? It boils down to the simple realization, Dylan told Josh, that “My word matters.” 

This is a critical axiom to understand, because it sets the foundation for trust to be built. Think about professions with low levels of trust for a minute. If a politician makes a campaign promise and doesn’t follow through on it when they’re in office, you lose faith in them. (In related news, polling shows Congress members have the lowest level of trust among any professional field.) 

Understanding this axiom also pays dividends when it comes to CS, especially, by reinforcing and strengthening the customer-company relationship. 

“Trust happens by giving our word and keeping our word,” Dylan said on the podcast, “and by honoring our word when we cannot keep our word.” 

This is another important aspect: keeping our word is always the goal, but honoring our word is absolutely imperative. What does that look like? 

For example, let’s say you scheduled an important meeting with a customer, but right before the meeting, you find out your kid broke their arm at school and needs to get to the doctor ASAP. You are breaking your word with the meeting, so how do you go about honoring your word? 

The moment you know you’re not going to keep your word, you should do two things:

1) Communicate: Let your customer know you’re not going to make it and that you are sorry the meeting has to be canceled; ask what you can do and here’s what they can count on from you moving forward.

2) Don’t lead with an excuse: This doesn’t mean you avoid sharing why you are canceling the meeting altogether; instead, it means you aren’t fixating on an excuse. If the customer wants details, you will happily share them, but you need to focus on moving the ball forward (to keep the sports adages going) rather than dwelling on why things have went sideways 

By being a leader who routinely honors their word, you will foster trust and lay the groundwork for success. 

“If I’m going to be a leader in life, my word is not a casual thing,” Dylan said.


Being authentic goes hand-in-hand with integrity. If you’re aiming to lead a team, you need to give them a real sense of who you are and where you are going. 

Think about it: You wouldn’t want to follow someone who comes across as a fraud, right? So don’t portray yourself as a wannabe-Steve Jobs by putting on a black turtleneck and going a week without shaving. It’s not about the uniform – it’s about being the real person who is in charge. That’s who teams buy into and follow.

As Dylan told Josh, authenticity comes from “alignment,” where “who I am publicly is who I am privately.” 

This is important because it helps to “minimize variance,” Dylan said. There is no guessing game here. Embrace your best qualities and don’t be afraid of self-expression; if you’re a brash New Yorker or a laid-back Californian at heart, let that come across. That genuineness will help cement the trust needed to rally a team or keep an unhappy customer onboard. 

What you’ve probably already noticed is that honesty is at the heart of authenticity. Again, this is important. You want to not only have a vision for your team but also communicate it effectively – and sometimes that requires being blunt and saying “Here’s our destination, but I’m not 100% sure my roadmap will get us there. Let’s find out.” That’s especially true in CS, which is a budding sector where the maps are still being made.

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.)

More [Unchurned]

Meet the Team : Emilia

A little about me Emilia I grew up in an entrepreneurial family. My parents don’t have degrees or training in anything in particular, but what