I've Been in CS for Over a Decade. Here's What I learned.

I've Been in CS for Over a Decade. Here's What I learned.

I started working in Customer Success before people knew what it was. All I knew was that I wanted to help people and create strong lasting customer relationships. At the time, Customer Success didn’t have any fancy tools to help manage accounts or design playbooks on how to structure a good QBR. We had to be creative and adapt to change quickly.

I’ve learned a lot over the years and today I am sharing some helpful tips I’ve learned along the way.

Know What Type of CSM You Want to Become

Every company has different objectives for the Customer Success team. When interviewing it is important to know what type of CSM they are looking for. I’ve been the ticket-chasing CSM, the upselling quota-retaining CSM, a technical CSM, and everything in between. I always remind myself that I am interviewing the company as much as they are interviewing me. I want to learn as much as I can before making any decision to move forward.

Here are some of my favorite interview questions:

  • What does it take to be successful?
  • How is CS involved in the ticketing process (Support and Engineering)?
  • How is my success measured? (KPIs)
  • What are the biggest challenges the CSM team is facing?
  • How easy is it to work cross-functionally and get the resources I need?
  • Can you describe your management style?

Try building a career profile before interviewing. Be clear and concise about what you’re looking for and what you want to achieve. Create clear intentions for the type of job you want and be sure to explore that during the interview process.

Prioritize Your Mental Health

There are many things that may affect your stress levels throughout the day: a difficult conversation, a stressed-out customer, or the dreaded customer-churning conversation. On difficult days, remember that this is business and that tomorrow will be a better day. I remind myself that customers are not upset with me, they are upset with external factors such as the product, the turnaround time, or something unrelated and they are just having a bad day. Try not to blame yourself.

How to handle tough days:

  • Take a breather: Go for a walk, treat yourself to your favorite cup of coffee, or watch something funny.
  • Get it out: If you want to say something nasty, go for it, write it down to get it out (but keep it private and use a pen and paper)
  • Celebrate You: I like to put together a list of positive feedback I’ve received from customers and internally. Every so often when I’m having a tough day, I look at it to remind myself that I am doing a great job. All those small accomplishments add up.

Connect With Your Manager

Your manager can have an outsized impact on your work experience. I’ve had first-time managers who were promoted because they were great CSMs, managers who barely spoke to me, and managers who cared so much they wanted to mentor and foster my growth (this obviously had a positive impact on my desire to stay). Your manager is your support, quarterback, and guide to help you succeed at your job, in other words, your CSM. They are a key ingredient to your success and a more enjoyable work experience.

To help foster these relationships, set weekly goals for 1x1 meetings, ask if there is anything you could be doing better, and go the extra mile by starting a new project that interests you. That could mean taking an online class to gain a new skill or seeing a gap in a process that you want to iron out. Managers appreciate when you are proactive, adaptable, and eager to collaborate and learn.

Additionally, it's a good idea to learn their working style, goals and personal preferences to digest information. This is called managing up, and it's a great way to ensure you have a solid two-way working relationship.

How to manage up:

  • What keeps your manager up at night? What are they held accountable for? Do they prefer email or slack? Detailed reports vs bullet points? The more you understand their goals, the better working relationship you will have.
  • Share what you need to be successful. Managers don’t like surprises. Be truthful and honest about what you need. Do you want more direct feedback? Is there something that's keeping you from doing your best work? Your manager needs to know so they can help you succeed.

Make Work Besties

Become friends with support, sales, product, and everyone in between. Let leadership know who you are. When I was in a new hire training we all sat down for lunch, I introduced myself to the person across from me and we started chatting about summer vacations, music, and camping. I asked what he did within the company and I found out that he was the head of my division! You never know who you will meet or when those connections will come in handy. Those small talks go a long way and the rapport you build is essential for the future.

Showing interest in someone's hobbies outside of work is a great way to connect. I want to get to know you as a person, where you like to travel, what you like to do, and your favorite sports teams. Keep the topics broad and let them do the talking, you’ll be surprised how much you will learn about a person. They will remember that you took the time to get to know them and in turn want to get to know you too. As you get to know your co-workers, you can ask them how your role in CS impacts them and where you may be able to find opportunities to make improvements.

Be a Good Listener

Customer Success managers are really amazing listeners. I’ve learned over the years that even over the phone, people know when you’re reading a script or trying to sell them something. Try to always be your genuine and authentic self. I’ve found the most successful growth comes from listening to the customer and digging deep into what they are asking of you. This in turn builds mutual trust and is one of the most powerful tools.

It’s important to understand what the customer is saying between the lines. When a customer asks what they could be doing better, they are really saying, “how do I get the most return on my investment?” When a customer is frustrated with support because every time they call in they have to repeat themselves, they are really asking for a change in the process. When a customer keeps asking about product updates, they are really saying they want more communication about where things stand. You can find hundred of articles and videos on this topic.

How to actively listen:

  • Ask clarifying questions to make sure you fully understand them
  • Repeat back to the customer what they are asking of you and provide actionable items so they know they can rely on you for a resolution.
  • Silence can be awkward but try not to always fill the empty space. Sometimes, people need a little extra time to gather their thoughts.
  • Take 5 minutes to yourself to digest the information and work on the recap email while it is top of mind. Customers will appreciate prompt responses.

Shoot for the Moon

Even if you miss, you’ll land upon the stars. As CSMs, we are not confined to our role and there is a world of opportunity at our fingertips. Maybe you’re interested in enablement or the onboarding process, or maybe you have new ideas for a lunch and learn series. Regardless of what it is, make your voice heard, and be your own advocate. You will be surprised at the results!

A great way to get noticed when you first start your new job is to document what you do every day to make it easier for the next CSM to onboard. When a new CSM starts, ask if you can mentor them. If a customer is showing interest in providing product feedback, start a customer advocacy program where they have access to connect with the product team. If you see a need, make it happen and use the STAR technique to track your work accomplishments. Not only will you be promoting yourself, but you will also get yourself noticed and maybe even be promoted.


Customer Success is a vital part of any organization and will continue to evolve. We are the face of the company that builds trust, partnerships, and growth. If sales are the lifeblood of the company then Customer Success is the heartbeat. The role provides an amazing opportunity to connect and learn from all aspects of the business. I am excited to see what the next ten years will bring!

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