When something has been obvious to you for years, it’s easy to assume it’s common sense to everyone else. But that assumption? It’s a leadership killer.
Early in my Customer Success leadership journey, I fell into this trap hard. I never wanted to treat my team like they didn’t know what they were doing. So instead of validating their knowledge and experience, I made assumptions. I mean, it was common sense, right?
Big mistake.
A few companies ago, I hired a manager to lead one of our CS segments. Given their background and experience, I guessed they could take high-level direction and execute flawlessly.
One of their first projects? Scaling our lower-segment customer strategy.
I laid out the business need:
✅ Same number of CSMs
✅ Maintain our customer journey and key milestones
✅ Track and measure key KPIs
✅ Support a 10% increase in customers over 12 months
Seemed clear, right? Turns out, not so much.
What I didn’t know was that this manager had never tackled something like this before. But instead of asking for help, they struggled—hard.
They iterated on the project three different times, missing expectations each round.
Finally, I had to take it over just to get it across the finish line.
What This Cost Us
The manager lost confidence and grew frustrated
We wasted weeks spinning in circles instead of making progress
I had to step in, pulling me away from other high-impact work
Everyone lost.
What I Changed to Be a Better Leader
This failure forced me to rethink how I lead and delegate. Here’s what I changed:
1️⃣ Assess Before Assuming
Before handing off a project, I now evaluate skill and experience levels. If I’m taking over a new team, I spend time understanding:
Their strengths and gaps
What they enjoy working on
Where they need support
This helps me delegate with intention instead of making blind assumptions.
2️⃣ Invest in Continuous Learning
I fight for a training and enablement budget every single year. If we expect our teams to level up, we need to give them the resources to do it. Otherwise, we’re setting them up to fail.
3️⃣ Delegate with Clarity
Now, when I delegate, I don’t just throw out a high-level goal and expect magic to happen.
Provide clear expectations on deliverables and timelines
Set check-in points for feedback and course correction
Create a collaborative environment, so they know I’m in their corner
4️⃣ Create a Safe Space for Feedback
That manager didn’t come to me for help because I hadn’t created a culture where it was safe to admit uncertainty. That’s on me.
Now, I make sure my team knows:
Asking for help isn’t a weakness—it’s a leadership skill.
Feedback is a two-way street. If something isn’t working, I want to know.
Their success = our success.
5️⃣ Define Success Upfront & Align on the "How"
One of the biggest mistakes I made was assuming that the manager knew what success looked like beyond the high-level goals. I told them what needed to happen, but I didn’t align on how we’d get there.
Now, before assigning any major initiative, I make sure we:
Define what success looks like in tangible, measurable terms (What does “scale” actually mean in execution?)
Co-build the strategy instead of handing over an ambiguous mandate
Align on the first steps to ensure they’re set up to move forward with confidence
This keeps projects from spinning in circles and helps my team move fast without second-guessing.
6️⃣ Post-Mortem & Iteration
Even when a project doesn’t go as planned, there’s gold in the failure. But only if we take the time to debrief, learn, and adjust.
Now, I always run a quick post-mortem on major projects with my team:
What worked?
What didn’t?
What do we do differently next time?
I also use this as a leadership moment—it’s my responsibility to reflect on what I could have done better to support them. If I missed something, I own it.
By doing this consistently, we create a culture of learning, not blame. And that’s how teams truly grow.
Bottom line: Leadership isn’t about making assumptions. It’s about setting your team up to win. I failed that manager, but I used that failure to become a stronger leader.
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