Written by Brandon Cestrone - Founder of CS Insider
There are few moments from my childhood that I remember more vividly than almost drowning. We were visiting Lake Erie in Pennsylvania. Foolish, I swam past the safety markers and a strong current pulled me underwater.
I don’t remember being afraid that I was drowning. I remember being shocked. Shocked that I couldn’t do anything. Shocked that life could be lost. More than anything, I was waiting for someone to save me.
Luckily, someone was looking out for me - my mom. I coughed and cried as she pulled me up from underwater and to shore.
Flash forward to 2021 as a new CSM. I’m gripped against the currents again. This time I’m underwater at work that I can’t seem to grasp and a sense of dread that I was drowning again. And this time my mother wasn't there to save me.
Am I in the wrong role?
Am I good enough?
Is this what it’s always going to be like?
You also might know what it’s like to experience overwhelming thoughts like these.
If this resonates with you, here are four things you can do to make it back to safe waters as a new CSM.
Learning the ropes is important for any role. Within a startup, you have to learn the ropes while half-blindfolded.
There are three challenges I see working at a startup:
There are also things that can compound these challenges. I'm currently dealing with:
As you get ramped up, reality will set in. You’re in the water, so the first thing you need to do is learn how to tread.
I transitioned into Customer Success from Customer Education. I trained customers on a simple app. I didn’t have experience working with APIs or navigating complex business needs. Even with these limitations, I tried to “figure it out”. I didn’t respect the current until it caught me off guard.
What about you?
That’s ok. Be honest about your current capabilities and remind yourself that it'll take time and practice to build your knowledge, skills, and confidence.
Here are few steps to get started:
Wherever your skills and knowledge lie, be open and honest with your limits. This is your floor from where you'll rise.
Every organization has a pool of shared knowledge. Each employee contributes to this pool from their background, time at the company, and natural ability. And these people have various degrees of expertise with your product, industry, and/or customer.
Find and befriend these people as soon as you can. Here’s how:
These people are your future BFFs. Meet them. Build rapport with them. Learn how they like to communicate when you have questions. And respect what ticks them off.
When you document your learning, you can do a couple of critical things:
Learned how to set up a new integration? Document.
Uncovered a small aspect of how your product works? Document.
Discovered who’s leading a new feature build-out? Document!
Take time each day to write things down. You can use Notion, Google Docs, or your company’s internal knowledge-sharing tools. Document this article too.
I made the costly mistake of waiting until I had a crisis before asking for help. Fear of appearing incompetent, I became slow to adapt.
I was operating under a “Fixed Mindset”.
It’s hard to ask for help. But asking IS a sign of professionalism. We ask because we care about our work. And within a healthy startup, there should be a lot of questions being asked.
As Francesca Gino and Alison Wood Brooks explain in an interview with Harvard Business Review, "This belief that if you go to ask for advice from someone, they're going to think you're incompetent and you can't complete the task on your own is misplaced."
"Ultimately, being asked for advice is flattering. It implies, as the questioner, you think the person you're asking is smart. Conversely, they'll think you're smart, because you're being proactive in completing the task to the best of your ability."
I found that when you ask for help or advice, people respond with kindness and understanding. The funny thing is, as I grew in the first 8 months of my role, I asked even more questions.
This may seem unintuitive. But as we learn more, we uncover what we don’t know. We learn how to ask better questions.
These types of questions spur conversation within the company about product and process improvement.
So if you are feeling overwhelmed, ask for help. Eventually, you'll need to. And wouldn’t you rather ask now so you have more time to ship great work?
There are few mistakes that you can make that are irreversible. I had numerous, “This is bad!” moments. But soon I realized it wasn’t the end of the world. It wasn’t great. But we’re not heart surgeons. No need to call a lifeline to another career.
When things go south, document, reflect and set a game plan for next time.
Some other things that helped me when anxiety crept in:
As you get more experience, you'll still make mistakes. But now you'll learn how to fix them yourself, faster. Maybe even help others avoid the same mistakes.
I wanted to make the transition from a CSM role to a manager for a long time. But how did I get there? Through many mistakes, one thing stood out above all: I had to be a CSM to myself. To treat my career the same way I treated customers. Here’s what that looked like.
As a leader, you’re never 100% sure what your reports think of you. But knowing who you should be towards them is of utmost importance. Here are three key things you should be as a leader in Customer Success.
Having domain experience can help you stand out when applying for your first Customer Success role. This could be expertise in retail, education, hospitality, accounting, etc. Here are some things to do and avoid when targeting a CS role in your domain.