The Journey: #23 All Systems Go

When I started my career as a CSM, everything felt manageable.

I had a book of business, a list of clear priorities, a schedule that I owned, and a feedback loop that showed me how I was doing.

It was structured. It was measurable. And it worked.

But when I got promoted to Director of Customer Success, things started to shift.

I moved into a player-coach role, still managing customers while now also managing people. It was challenging, but not overwhelming. I could still hold it all together.

Then came the big leap: Senior Director.

Now I was leading a growing team, owning strategic outcomes, sitting in exec meetings, managing up, managing down, and constantly context-switching.

And for the first time in my career, I felt like I was drowning.

I was working 12–15 hour days just to stay afloat.

I didn’t feel productive, just busy. I was always reacting instead of leading.

So I went searching for a better way. I didn’t need more tools, I needed systems.

And over the years, I found five that have changed the game for me as a CS leader.

Here they are, with real examples of how I use them to stay focused, intentional, and (mostly) sane:

1. The Eisenhower Matrix

What it is: Prioritization by urgency and importance.

Sort every task into one of four categories:

Urgent + Important → Do it now

Important, not Urgent → Schedule it

Urgent, not Important → Delegate it

Neither → Delete it

How I use it:

Let’s say I’ve got:

A strategic renewal at risk → Do

A team member requesting coaching time → Schedule

A random request from Sales Ops for last quarter’s MBR slide → Delegate

A Product newsletter I haven’t read → Delete

I use this to gut-check my day when it feels like everything is screaming for attention.

Spoiler: It’s not.

2. The 2-Minute Rule

What it is: If a task takes less than 2 minutes, do it immediately.

How I use it:

Approve a PTO request

Forward a customer reference to Sales

Add a quick comment to a shared doc

Send a 1-line “Nice job!” Slack message

These micro-tasks love to pile up and become noise. Knocking them out on the spot keeps my brain clear and my to-do list realistic.

3. Time Blocking

What it is: Structuring your calendar around intentional work blocks instead of letting it become a meeting free-for-all.

How I use it:

Mondays 9 - 11am: Weekly planning and report reviews

Tuesdays 9 - 11am: Customer deep dives

Wednesdays 2 - 5pm : Deep dive on renewal forecast

Thursdays 2 - 4pm: Community calls

I color-code my calendar so I can see how much time I’m spending in strategy vs. firefighting. It’s one of the fastest ways to spot imbalance.

4. The Ivy Lee Method

What it is: At the end of each day, write down the 6 most important tasks for tomorrow in priority order.

How I use it:

Let’s say it’s Wednesday night. My Thursday list might look like this:

1. Finalize CS metrics for exec meeting

2. Review strategic account QBR deck

3. Meet with CSM on performance goals

4. Approve 3 new success plan templates

5. Prep agenda for Friday’s team sync

6. Respond to a customer escalation

I do this before I shut down for the day. It gives me clarity, and it stops me from starting tomorrow in a state of panic.

5. The 1–3–5 Rule

What it is: Structure each day with:

1 big task

3 medium tasks

5 small tasks

How I use it:

Big:

Lead Q2 strategy review with exec team

Medium:

Review our customer journey updates

Audit team health score notes

Review CSM enablement agenda

Small:

Schedule exec outreach

Comment on product feedback doc

Check in on that stubborn red account

Congratulate a CSM on a win

Share a job posting

This framework helps me avoid the classic trap: writing a 42-item to-do list and feeling like a failure when I only check off 6.

The truth is, systems don’t give you time back, they help you spend it better.

And leadership isn’t about doing everything, it’s about doing the right things, at the right time, in the right way.

If you’ve made the leap into CS leadership (or are about to), know this: the chaos is normal.

But it doesn’t have to stay that way.

Pick one system. Try it for a week.

Then layer in the next.

Eventually, your days will feel less like you’re just keeping up and more like you’re finally leading on your terms.