Lessons of a Customer Success Manager

Delores Cooper
6 min readFeb 24, 2021

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Thinking of making a career change to Customer Success? Do it! My first year as a CSM has been a whirlwind and I attribute my success to a host of people as well as the lessons outlined below.

Remember those “most likely to…” statements from high school yearbooks? Well, I was least likely to work in tech, and I definitely never thought I’d end up in Customer Success. I didn’t even know what Customer Success was or what a Customer Success Manager (CSM) did!

By sophomore year of college I had it all figured out. I would work in the nonprofit field with a focus on rehabilitation, youth and disabilities. I’d have small career changes, but that’s how I thought I’d spend my life. Then one day, while at an event for my nonprofit, I would walk into a building that I had passed countless times before — never knowing (or caring really) what was inside. I had entered Tech.

There’s some nerdy stuff that happened after — caressing a moss wall, learning that kombucha was a thing, and staring lovingly into the window of a vending machine filled with Apple products. But fast forward about 5 months and I was starting my first day at a SaaS company!

I’ll admit — I didn’t think I would last long. To be very honest, I still have moments when I doubt myself. It’s no secret that the tech industry is male dominated, and Customer Success tends to lack racial and ethnic diversity. How did I ever stand a chance of excelling when my surroundings looked so different from me? How was I supposed to excel in an industry that I knew nothing about? As I cross the three year mark in tech and the one year mark in Customer Success, I reflect on some things that I learned that have been crucial to my success.

Know that you’re the sh*t! Don’t undermine yourself

I’ve spent a lot of time believing that I suffered from Imposter Syndrome, and I’ve spent about the same amount of time trying to erase its existence from my being. I’ve been very fortunate in that every manager I’ve had at my current job was nurturing and supportive, and quick to call me on my self-doubting bullshit. Seriously, some would just literally ignore me when I started spouting out reasons why I thought I couldn’t do something. I’m not “cured” by any means, but with supportive colleagues and articles like this, I’m much better at identifying when I get in my own way and when I need to be a bit more gentle with myself. Conclusion: Be your biggest fan!

I’m much better at identifying when I get in my own way and when I need to be a bit more gentle with myself. Conclusion: Be your biggest fan!

Get used to ambiguity

I used to have an adverse physical reaction to ambiguity. I hated not knowing “the plan”. I didn’t know how to effectively operate in that space. I needed to know every detail before even thinking about taking action. Now I laugh at my past self for having that reaction. The more I’ve accepted how much I don’t know about a situation, the better prepared I actually was. The calmer I was in meetings. The more confident I appeared.

Don’t get this twisted with showing up completely unprepared. This isn’t that.

However, if a customer isn’t specific about what they want to discuss with me, I am no longer crippled with anxiety. I no longer spend hours preparing every topic under the sun just in case they mention it. I just come prepared with questions about their business goals and usually that opens the floodgates. Tech is constantly evolving, and in Customer Success, we’re dealing with humans. Things and minds are always changing. Embrace it.

Reset often — remember the customer; practice empathy

Customer trust and loyalty are what drive renewals and expansion. Sometimes you’ll feel the pressure of quotas or the burn to win a SPIF, and lose sight of the most important part of the job — the customer. In Customer Success, we pride ourselves in being able to build genuine and honest relationships in order to have an effective partnership with customers. We are trusted to inform on best practices, strategy, and goal alignment. If you see yourself morphing into the animated character with the drooling tongue 🤤 and dollar sign eyeballs 🤑, it’s time to reset. Take a step back and imagine if you were the customer in this instance — how would you want to be treated? How important is it that you trust your CSM? Be an empathetic human being and prioritize the relationship. Adjust accordingly to keep that as a priority.

Now reset yourself

A total of 768 million PTO days went unused in 2018. This article reports that in 2020 employees worked harder and took less time off. One could argue that using PTO was more important in 2020 since the COVID-19 pandemic completely shifted the work/life balance.

For many workers, myself included, going into the office was a tangible separation. At work, I worked; at home, I “homed”.

Now those lines are muddied. If I couldn’t go anywhere to recharge, I needed to take time and (safely) create a space at home to do it. It took one pandemic and 17 years in the workforce for me to understand and believe that it isn’t bad to use PTO. It’s literally a part of your benefits package, and in most cases, you accrue it as you work. It’s YOUR time! Take it! I try to take a few days each quarter and it really does help to reset and freshen my mind.

Ask (better) questions

Before Success, I had a 1.5 year stint in tech support/customer service where the interactions were mainly transactional. By far one of the biggest shifts I had to make when migrating to Success was how I prepared for customer interactions. In tech support the flow was pretty unsurprising.

Courtesy of Zendesk

You know — the usual reactive call with a problem and then fixing the problem. I asked questions of course, but they were almost always centered around the issue at hand. In Success, the interactions are far less transactional and much more consultative. I needed to learn how to take a proactive approach and ask better questions — ones that dug a little deeper and shed light on the bigger picture. Questions that pointed to the customer’s short and long term goals, internal processes, and pain points. The shift from transactional to consultative is a necessary and fun move in order to set yourself up for success.

Compartmentalizing is overrated

This is a big one. Being a Black woman I had learned through many experiences that it was safer to compartmentalize — don’t bring personal stuff into work, and don’t take work home. There was a lot at risk if the lines were blurred. Due to the COVID-19 pandemic, that is impossible because work is now literally in the home. And then there were the extreme and traumatic social injustices committed against BIPOC. I can’t stress how important it is to your healing that you have a space at work to express these feelings, even just for a few minutes. This space can be in a team meeting, a few moments of acknowledgement at a town hall, or a dedicated Employee Resource Group. Additionally, it’s equally as important to feel seen and heard by the company that you work for.

Employees cannot be expected to contribute at their full potential if they are expending effort hiding parts of themselves from their colleagues. Ask and advocate for what you need. Use one-on-one time with your manager to temporarily adjust your workload. And again, use PTO for that mental health day.

Remember there are people behind the laptops; put the human before the software.

Even though I’m only three short years into my tenure in tech, I’m absolutely loving it! Customer Success is the perfect blend of structure and autonomy, familiarity and innovation. I’m able to collaborate with my fellow CSMs, but also spearhead my own projects. The muscles exercised and skills developed are invaluable, and I’m sure I’ll be adding more learnings to this list.

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Delores Cooper
Delores Cooper

Written by Delores Cooper

Scaled Customer Success Manager | CX Professional | DEI Advocate | Content Creator

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