Sit in the Front: Interview with Chris Litster, CEO of Dianthus

I recently went one on one with Chris Litster, CEO of Dianthus.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth? 

Chris: I have worked in software (on the business side - not the tech side) for about 25 years now. I’ve been fortunate enough to learn a great deal over the years from the variety of roles, experiences, and leaders I’ve worked for as I grew from an individual contributor to executive roles at a number of great software companies. I’ve known Rob May, the founder of Dianthus, for over 10 years now. As Rob was starting to pull together Dianthus, he originally asked me to take on the role of Chairman of the Board. However, after just a few months, I fell hook, line, and sinker for what we are doing here at Dianthus. I asked Rob if I could take on the role of CEO—and in January of 2022, I took the helm. 

There have been so many experiences throughout my career that I look to as watershed moments that have impacted my growth. The ones that come to mind immediately all center on either helping people achieve things they thought were beyond their own reach or when people went out of their way to provide incredible feedback when they thought I needed it most.  I am so proud of helping several former colleagues build their careers and watching them become leaders of other organizations here in Boston and beyond.   

Adam: In your experience, what are the key steps to growing and scaling your business? 

Chris: There are some basic steps that are commonly recommended to help folks scale their business. However, the most important thing to remember is that there is  single template that you can apply from business to business.

The first step is making sure you truly understand your customer and the unique value you bring to them. It’s also imperative that you (and the other leaders of your business) understand all the levers and components of your business model from the jump, and that everyone is aligned on which sectors need improvement and who oversees each component. 

From there, you can start down the path of working to find the repeatable model for each component of the business through testing and listening to your intended customer's feedback. Once those repeatable aspects are found, that's when you can start to dedicate resources, time, and money-- which should lead you to a flywheel situation. After that, it's rinse and repeat.

Adam: What is your best advice on building, leading and managing teams?

Chris: My best advice may sound like a ‘duh’ statement, but I truly believe that it is something that many leaders overlook or forget: remembering that we are all human. As humans, what do we all want? We want to feel fulfilled in our professional life. We want to be respected, listened to, offered the opportunity for growth, and offered the opportunity to contribute to and achieve something great. I truly believe that effective leadership and management requires us to remember this foundational concept. When we do, it fosters alignment, team cohesion, and the ability for folks to collaborate more and achieve greater success for both the company and themselves.

Adam: What are the most important trends in technology that leaders should be aware of and understand? What should they understand about them? 

Chris: It won’t come as a surprise, but I’m going to reference the growing trend of AI and machine learning.  We are only just learning the impact that AI and Machine Learning can have on organizations - not only externally with a company’s customers but now notably how it can impact a company’s own operations and workflows. At Dianthus, we refer to ourselves as an AI-first company, which means we look at all our workflows as candidates for automation. We say, “All workflows are just data streams waiting to be identified and automated.” Companies should understand this trend not only to drive the automation of repetitive processes but also because of the ability to do them at a scale that up to now has not been possible.

Adam: What do you believe are the defining qualities of an effective leader? 

Chris: Empathy, vulnerability, and the ability to set a clear vision and cascade that vision through the detailed levels of an organization so that folks can align around it and understand how they contribute and how what they do matters. Additionally, having a real passion for building great teams and for working to get the best out of those teams is a really important quality. And finally, critical thinking and logical thinking skills. Those last two drive a leader to think from A to B to C to D - and then help guide the organization smoothly through that process. 

Adam: How can leaders and aspiring leaders take their leadership skills to the next level? 

Chris: First, find a mentor that you really respect and ask them to be your mentor. Next, just observe and learn. Take the time to observe others you find are great leaders, analyze their behaviors and try to understand why they do what they do - and then mimic them. Finally, ask the leaders you respect what books and articles they read - and then read them.  I have found that there are always new nuggets of greatness to discover this way.

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders? 

Chris: When it comes to hiring, always hire those folks who are better than you and hire for the future. Obsess over what you think you will need in 6 or 12 months and hire those folks now.

Overcommunicate. The reality is, even when you think you’re saying something for the 100th time, someone on your team might be hearing it for the very first time. Your goal in communicating should be that you hear from folks something like, “Yeah, we got it. We’ve heard this before.”  

Be humble - but persistent. You are the person setting the north star for your company. You are on stage every hour of every day with folks watching your every verbal (and non-verbal) move. Use your influence to bring people along with you and align them towards your vision - don’t use your influence to push people aside because you think you can do something quicker or better

Adam: What are your best tips on the topics of sales, marketing and branding? 

Chris: A company will not be at its best if there is a rift between sales, marketing, and branding. As a leader, you must work to ensure that these areas of your business are more aligned and partnered than any other.

It’s important to create cross-functional teams made up of sales, marketing, and branding folks - so that they have other opportunities to strengthen their relationships outside of sometimes heated or reactive situations.

Adam: What is the single best piece of advice you have ever received? 

Chris: The best two pieces of advice I’ve ever received came from my parents, and I use them every day. First, from my mom: don’t waste your life by sitting in the back of the class. Sit in the front, raise your hand and contribute to the conversation. I used that advice not only in the classroom but also in my personal and professional life.

Next, from my dad: Outside of coding software, very few things are binary. The solution is usually found somewhere in between. It’s your job to foster conversations that find the best solution, bring everyone together, and move things forward. It’s your job to foster the conversations to find that best solution - to find that in between reality that brings everyone together and moves forward.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

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