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CSM from the Trenches: Mentors – Ben Winn, Founder & Executive Director, CS in Focus

Welcome to our blog series CSM from the Trenches, a community for frontline Customer Success Managers (CSMs) that discusses trends, best practices, and advice for the frontline.

Being on the CSM frontline allows us to directly influence the success of our clients. I love that; as our clients are successful, we’re successful. Each day we learn from the trenches what it takes to make clients happy and successful.

Mentor Questions

This segment of the series focuses on 7 mentor questions for the frontline. The goal is that by sharing our experiences we’ll be able to learn and apply more practical advice / practices to our careers.

Let’s get started with this week’s post!

FromBen Winn, Founder & Executive Director
Company: CS in Focus
: Toronto, ON

Question 1

What is one customer success best practice you’ve applied in the last few months that has had a positive impact on your success in your role? How has it helped you?

I’ve become much less professional…at least in the traditional sense. I do my best work when I’m being my authentic self, and that means dressing comfortably,  being honest when I don’t have the answer, keeping things light-hearted and fun, and being transparent about the fact that I’m just doing my best to get the job done well. I used to be so uptight about what clients, colleagues, and community members would think of me, and looking back, I can honestly say it’s a much better (and more productive) time for everyone when you stop caring about how others see you, and just be your authentic self.

Question 2

What are one or two things you typically do during the first hour of your day that leads to a productive day?

I wish I could say that I wake up at 6am, go to the gym, drink some protein sludge, and then start my productive day, but that’s not me – I need my beauty rest and my morning carbs.

The most important thing I do every morning is check my lists. I live and breathe lists. If something is not on a list, it’s not getting done. I have “Personal” lists and “Work” lists, and each one is subdivided into “Today”, “This Week”, and “Backlog”. Each morning, I review and update each list and then I get to it.

The only time I change this method is when I have a particularly crazy time ahead of me, in which case I throw away the lists and use only 2 categories: “Urgent” and “Not Urgent”. This allows me to prioritize only the items that HAVE to be done ASAP, while ignoring things that can wait.

Question 3

What are one to three books, blogs, or thought leaders that have greatly influenced your career, and why?

I get so many micro-influences from all of the books I read and people I meet, that it’s hard to nail down 1-3 that are truly profound, but here are a couple that come right to mind:

Extreme Ownership by Jocko Willink taught me about taking full responsibility for everything in my life, and that abdicating myself from responsibility, while tempting, will ultimately impact me negatively.

Sapiens/Homo Deus by Yuval Noah Harari gave me perspective by helping me to understand where we’ve come from as a species, and where we’re going (or at least, might be going).

Never Split The Difference by Chris Voss was my first foray into learning negotiation strategy, and I absolutely loved it. Negotiating has since become one of my favorite things to do, and when you combine that book with The Like Switch by Marvin Karlins, it’s a pretty killer combo.

Question 4

How has a failure, or apparent failure, during your time as a CSM set you up for later success? Do you have a “favorite failure”?

My favorite failure was a time when I lost an account due to my lack of confidence. I knew what was wrong and what needed to be done to fix the situation, but being the youngest and most inexperienced person in the room, I didn’t feel that I could plant both my feet firmly and say “This is what needs to happen, capisce?” So instead, I lost the account (and my retention bonus), and I learned a valuable lesson.

Nowadays, people have a harder time getting me to shut up…

Question 5

What do you find most fulfilling about being a CSM?

What could be more fulfilling than having “how well you help others succeed” as the yardstick for your own success? It’s a job that requires you to work hard, build relationships, and establish trust, all with the purpose of ensuring that the customer succeeds. In fact, I found being a CSM so fulfilling that I started CS in Focus, which is an organization dedicated to helping CSMs succeed!

Question 6

If you had to give one piece of advice to another CSM, what would you say and why?

The best thing you can do for yourself and your company is to become best friends with your customers. My yardstick used to be Instagram…if I can get to a point with my customers where we’re following each other on Instagram, they’re not going to churn (at least without good reason and lots of warning). Determine what your friendship metrics are going to be, and then go for it!

Question 7

What is one customer success principle you try to live by?

Keep things as simple and straightforward as possible at all times. Don’t use paragraphs when bullet points will do, don’t beat around the bush when you can say something directly, and always be 100% honest and transparent with your customers.


Want to share your mentor advice? Submit your answers here.

Join the conversation on our LinkedIn CSM from the Trenches group page.


Here are other customer success resources:

Customer Success eBooks:

Customer Success as a Culture: Customer Success Leaders Edition

Ultimate Guide to SaaS Customer Success Metrics

Other CSM from the Trenches Posts:

Sam Feil, ClientSuccess – Why User Adoption & Change Management Might Be Equally as Important as Achieving Objectives

Cole Sanders, ClientSuccess – 3 Principles I Learned in My First Year as a CSM

Erica Newell, EveryoneSocial – 5 LinkedIn Best Practices to Build, Grow, and Improve Client Relationships

Mieke Maes – 5 Keys to an Effective Customer Apology

SoapBox Team Shout-Out

Learn more about how ClientSuccess can help your company develop a strong customer success methodology and strategy with easy-to-use customer success software by requesting a 30-minute demo.

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