Mistakes and Lessons as a CSM
In this life, we’ve all made mistakes that take your breath away, wake you up in the middle of the night (if you manage to fall asleep), and keep you distracted during meetings, your mind stuck on a loop you can’t escape.
But like most things, it’s temporary.
And the best thing we can do is analyze it, identify the mistake, and figure out how to avoid it next time.
For those of us working with clients, we know that the perfect path often doesn’t exist. And we don’t always have the time to make the perfect decision either, which means some decisions, made in haste (though with humanity), are imperfect by nature.
That’s why today I want to share 3 real mistakes that truly hurt, mistakes I lived through as a CSM and how they turned into valuable lessons.
For me. For the team. For the product. And most importantly, for the customer.
🧩 Case 1: The onboarding was “so easy” no one understood it
In one of the projects I led, I was asked to create an onboarding flow. At the time, I had only 5 client accounts as a sample. They all knew each other, and we knew them personally.
Yes, I was inexperienced. And I built the onboarding based on their opinions, not on wider insight or instinct.
I put in a lot of effort and practiced active listening. When they tried the onboarding, it seemed perfect, because we followed up constantly with calls, NPS surveys, and real feedback.
But a few weeks later, once we scaled it to other clients… guess what we found? Co-rrect: it didn’t work at all.
I was monitoring platform usage, but saw barely any activity. Since we were in a holiday season, we assumed it was just a timing issue. We also blamed it on a few bugs after a major release.
Then, one week later, a message came in:
“I’ve been logging into the platform for weeks, but I don’t even know what I’m supposed to do or where to start.
Do you have any extra documentation that could help me?”
Truth is, we had designed an onboarding for a specific profile: Clients who already knew the product and understood the technical jargon.
Not first-time users.
What happened?
We redesigned the onboarding so it would work for clients with all types of backgrounds, with clear instructions, constant guidance, and regular value sessions to help them achieve their goals.
What did I learn?
We rebuilt everything from scratch: Simple materials, visual checklists, strategic sessions, and a clear journey.
Instead of teaching “how to use the product”, we started showing “how to apply it to your goals”.
Outcome:
- Questions after onboarding dropped by 40%
- Use of key features within the first week increased significantly
- Expansion became faster, easier, and more efficient
⚠️ Case 2: Active customer ≠ Happy customer
Yes, you read that right. An active customer is not always a satisfied one.
In this case, the client seemed happy.
They logged into the platform several times a week.
They received our newsletters.
In our calls, they told me they explored the new sections.
They liked our use cases.
They even contacted support from time to time.
But then, during a renewal meeting, they dropped this:
“I really like the product, but honestly…
I never managed to truly integrate it into my daily work.
And with the data we already got, I think we’re fine.”
What happened?
- We confused activity with adoption
- There were clicks, but no impact
- The product had a WOW factor — but not in their business
- Worst of all: we never checked whether they had truly reached their goals
What did I learn?
- We restructured our CRM to capture earlier signals
- We revamped discovery questions during onboarding
- We built quick wins
- We added post-onboarding interviews and activated better alerts
Outcome:
- Early risk detection, which helped reduce churn
- Better segmentation for personalized intervention
- More tailored follow-ups
- Most importantly: the client felt heard and supported at every step
💥 Case 3: Moving forward without validation can break trust
This time, I was working with a strategic client. The kind you absolutely don’t want to lose. The kind who asks for so much that you start losing focus on what to even show next.
We were in the middle of implementation. My internal team and I were overwhelmed. Several fronts open. Bottlenecks everywhere.
The deadline had already passed.
Tension grew with every passing day.
The platform still had bugs. Data looked suspicious.
And even though we explained what was happening… nothing was moving forward.
Then we received a clear directive from leadership: “We deliver today. Notify the client. Tomorrow we explain it.The errors aren’t that bad. The client is eager to see something.”
I had doubts. But between exhaustion and desperation… I said yes.
That “Hey, it’s ready!” message and the “We’ll walk you through it tomorrow at 11:00” were the start of our nightmare.
That same day, they replied:
“Perfect — tomorrow you’ll explain it to me,
because I can’t understand why it took this long
to deliver something that’s basically useless to us.”
What happened?
- We skipped critical validations
- We ignored signs that certain data needed to be cleaned
- During the call, we gave so much context that the client had to imagine what the future product might look like
- We lost the client’s trust — for weeks
What did I learn?
- We introduced a strategic pause policy — never move forward without full validation
- We ensured realistic commitments and proper review of starting points by key stakeholders
- We realigned expectations
- Every deliverable included a roadmap and context, so everyone knew exactly what was going on
Outcome:
- We did regain their trust — they became strategic allies
- But the journey was painful
- We improved our account handover process
- And our post-implementation satisfaction scores with strategic clients rose significantly
🔁 Epilogue: To err is human. To iterate is strategic.
Everything I’ve shared here actually happened. I’ve spoken to other CSMs who experienced similar situations. These mistakes leave a scar — but if you treat them right, that scar becomes your lever for growth.
I’m sharing this so that next time you face something similar, you’ll be more prepared. Or at least… on alert.
And remember:
- Onboarding isn’t about showing the product — it’s about proving its value
- If the customer loses that value at any point, they’ll walk away
- Dashboards don’t tell the full story
- Saying “Let’s wait to validate” can be an act of care — not a delay
✍️ And you? What mistake taught you the most as a CSM?
Drop it in the comments or write to me on LinkedIn.
One thing I’ve learned over the years: