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CSM from the Trenches: Mentors – McKayl Bergman; Head of Lucidpress Customer Success

For those just joining our blog series CSM from the Trenches, welcome. This series, now a community for frontline Customer Success Managers (CSMs), discusses trends, best practices, and advice that can help 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

We recently launched a new segment of the series that 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!

From: McKayl Bergman; Head of Lucidpress Customer Success
Company: Lucid Software
: South Jordan, Utah

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?

Lucidpress is a fast-growing SaaS startup and the second product offering of Lucid Software, so the members of my team each wear several hats, myself included. Because the needs of the business evolve so quickly, customer success is uniquely responsible for keeping all of product, engineering, marketing, and sales informed of the news on the frontline. It is especially essential that product managers and developers understand clients’ industries and the pressures that make this or that an appropriate solution to the biggest problems.

It’s difficult to share our expertise with 60 different individuals, so we started a 5-minute tip session in our weekly all-hands meeting Tuesday mornings. The tips are typically 2-3 simple screenshots that illustrate how one persona or the other uses a particular feature that came up in conversation the previous week. We embed our description in the context of the job that the user needs to get done and share notes of what else the user would like to see.

It’s been neat to see people chat about an industry persona afterward, and some of our best process and feature improvements were kickstarted when Lucidpress team members walked up afterwards with questions.

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 like to wake up early and have an unhurried start to my day. I find that starting my morning reading a chapter or two of a book, taking a walk, or even doing dishes helps me feel productive and happy before I come to the office. I like to take the last 10 minutes before I head out the door to review my notes from the previous day and skim my email inbox for critical tasks. I convert critical items into Google Calendar events so I don’t overbook myself later in the day, and star any emails that are important, but not urgent.

I use my first 20-60 minutes in the office to respond to critical email tasks, then don’t check email again until 11 am and again at 3 pm. I’ve found that blocking email to regular windows on my calendar helps me stay focused. Responding to clients is definitely important, but not every thing that they’re interested in is truly critical enough that it should take priority over creative efforts that will have a lasting impact. If something is truly urgent, clients and team members will find a way to get my attention and convey the rationale for the emergency.

In the meantime, knowing that the Gmail tab is muted helps me feel safe to put on my noise-canceling headphones and start into the creative or strategic tasks I’ve decided are crucial to my satisfaction at the end of the day.

Question 3

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

Thought leaders:

Greg Daines is my number one favorite thought-leader, and Lincoln Murphy’s Sixteen Ventures blog has an article on every client success topic you can imagine. I Googled a ton in the early days of the client success department for Lucidpress and learned most of the key concepts from either of these two.


If you hate business books, read “The Spark: A Mother’s Story of Nurturing, Genius, and Autism” by Kristine Barnett. It is a memoir by the mother of a son who has become a force to watch in physics. The key lesson is to watch for and encourage people’s interests because they might turn into strengths. It’s informed my management style and is the number 1 book I recommend across genres.

The most influential book was Patrick Lencioni’s “The Advantage”, but I call it a very close tie. I hadn’t heard the term “organizational health” before cracking the cover, but it’s a practical guide to solve personal problems on your team and get folks sharing and collaborating together with vigor. Though it is aimed at executives, I’ve found the same lessons apply to helping customers circle with you around a goal. You can apply the practical concepts in “Discipline 1: Build a cohesive leadership team” to any interpersonal relationship.


I’ll go the unconventional route with this pick. A key piece of career advice that I learned from the tv show Covert Affairs — ‘Do what is absolutely necessary, then consider the rest negotiable.’ I’m sure television is the world’s worst teacher, but something clicked while watching Annie disregard the tasks she disliked, and I accepted that my backlog of ideas will always be significantly larger than my available time. No one wins awards for answering 1 million emails. Get the essentials done, and spend the remaining time making the biggest impact you can.

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”?

A couple years ago, I planned speaking engagements at a conference that our client hosted each year and attended the event with my mentor. After the event, we were walking down the hall and I asked for feedback on the execution of the trip. He had plenty of experience planning events and pointed out moments where the schedule had been unsure, the client wasn’t where we thought they would be, and where we had accidentally caused an inconvenience for the client.

At another event, I was training a group of end-users on site and gave in to folks who asked if they could close their laptops and listen. The training went more poorly than previous sessions because I’d contradicted my instructions, given away control, and become flustered.

How are these related? I learned the following key points from these two experiences:

  • Propose a schedule right at the beginning and commit to it
  • Provide clear next steps so your client knows what to expect–and you do too!
  • Provide clear next steps over email after each call so your client sees you have taken notes
  • Convey enthusiasm and celebrate progress when you have to nag a client to follow through
  • Use your expertise to find the opportunity in answering “No”

Now I encourage my team to take the name of our department literally. We are here to ensure customer success — your expertise is why you’re mapping the plan and not the other way around! Don’t be afraid to take the lead.

Question 5

What do you find most fulfilling about being a CSM?

One of the most fulfilling perks of being a frontline enterprise CSM is to visit my clients at their offices around the world and watch them go about their business; there is so much to be learned from observing your target audience without interfering. Even here at home, my day to day work gives me a peek into how other organizations are run, and use those insights to craft better solutions for my clients.

Above all, I love learning from clients, using that to help build a fantastic product, and seeing successful behavior changes in their day-to-day lives. I care about the consequences of how a product is designed, both large and small, and all I have ever wanted in my career is to be working with customers and product teams to improve user experiences. It’s an incredibly satisfying feeling to be at convention or tradeshow with your client and hear them sharing their success story on stage, recommending your product to their friends.

Question 6

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

Understand your customer and communicate in their language. Allow yourself to be curious during an interview, don’t feel like you have to stick to your questions as written. Look for opportunities to say “Interesting! Tell me more about what you just said. Why is that so?”

Interviews are your best opportunity to really understand your client without making assumptions. Even if you can only do 1 per month, it is invaluable experience and my favorite way of bonding with a client.

Question 7

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

Have you ever had the pleasure of meeting a company that asked to give you a call and hear what you might need from their product? That is an incredible, memory-building experience that cannot be replaced. Giving clients opportunities to share their insights with you doesn’t guarantee they won’t leave, but it is invaluable to your product team and builds trust. At the end of the day, your client bought your product for what it could deliver. Your job is to find the gap between the actual and expected outcomes, and communicate the source of that gap to product teams effectively.


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


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 – 3 Best Practices that Drive Powerful Customer Experiences (How to Avoid the Dreaded Car Dealership Experience)

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

Mieke Maes, Intuo – 5 Keys to an Effective Customer Apology

Priscilla Zorrilla, 15Five – Asking the Right Questions to Challenge Customers

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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