The Leadership Job No One Has Time For
By Kristen Hayer
Ask a CS leader about their week and you'll hear a familiar list: coaching calls with CSMs, reports for the executive team, a customer escalation that needed attention right now, and meetings stacked back to back that somehow still leave the important conversations unfinished. Most of it is genuinely necessary. But somewhere in that list, something quietly disappears: the time to actually think about where the program is headed, what's working, and what needs to change.
I run into this constantly in my coaching work, and the leaders I talk to aren't exaggerating or making excuses. Their calendars really are full of things that matter. The trouble is that the thing missing from the calendar matters more than nearly everything else on it, and it happens to be the easiest thing to cut.
Why this happens
Tactical work comes with a built-in clock. A customer escalation has a deadline. A report is due to your CEO on Thursday. A CSM is waiting on you before their next call. Every one of those has a visible consequence if you let it slide. Strategic thinking doesn't work that way. Nothing breaks today if you skip an hour of thinking about next year's segmentation strategy, so that hour gets pushed to next week, and then the week after that, until it disappears from your routine entirely.
Why this hits leaders harder than individual contributors
An individual contributor who spends the whole day executing is doing exactly what their role requires. A leader who spends the whole day executing is directing a team without any direction of their own. Every coaching conversation, every report, and every process decision you make depends on strategic thinking that either happened somewhere along the way or didn't. When it doesn't happen, you end up reactive, solving the same problems repeatedly instead of asking why they keep showing up. The tactical work never disappears in this scenario. It just turns into busywork dressed up as productivity, and you're moving too fast to notice the difference.
What actually gets lost
When strategic time disappears, specific things go with it. You stop noticing patterns across customer feedback and start reacting to whatever issue is loudest that day. You stop asking whether your program design still fits where the business is headed and keep running the version you built two years ago because nobody has stopped to question it. Team structure planning slides from something you did on purpose to something that only happens once a hiring problem is already urgent. And you lose the thread that connects your team's daily activity back to what the company actually needs from you. These are the things that separate a CS program that's evolving from one that's just spinning in place, and losing them rarely happens all at once. It happens one skipped hour at a time.
How to actually protect the time
Block the time on your calendar before your week fills up rather than after, and hold it with the same seriousness you'd give a customer meeting. If it's the first thing you move when something urgent comes up, it will never happen. This also doesn't require a full day away from your desk. A consistent 30 minutes each week will do more for you than waiting on a rare open afternoon that never actually shows up.
Change your location. Sitting somewhere other than your usual workspace does something to your thinking that's hard to explain but easy to feel once you try it, and it's often the difference between staring at the same inbox and actually stepping back to see the bigger picture.
Remove distractions completely for that block, which means alerts off, Slack closed, and email out of view. Strategic thinking doesn't survive a notification, and you can't hold a real thought about your program's direction while you're also half reading a message from your VP about a renewal.
Set a specific goal for the time, whether that's a problem you want to solve, a trend you want to dig into, or a competitor you want to understand better. Without something concrete to work on, it's easy to sit down with good intentions and drift for 30 minutes without landing on much of anything.
The stakes
Strategic thinking isn't a luxury you get to once things finally calm down. It's the thing that determines whether all the tactical work you're doing is worth doing in the first place. A leader who never steps back is just running faster on the same treadmill, and their team feels it even when they can't name what's wrong. Protecting time to think isn't indulgent. It's the actual job, and it's the part no one else can do for you.
Looking for CS Leadership training or personalized coaching? We’ve got you covered! The Success League is a customer success training and consulting firm that offers both. Visit TheSuccessLeague.io for a full list of offerings.
Kristen Hayer - Kristen is the Founder & CEO of The Success League, a global, customer-focused consulting and training firm. Kristen’s background includes leading award-winning sales, marketing, and customer success teams in early and growth-stage tech companies. She is the host of several podcasts on CS and leadership, and has written over 100 articles on the field of customer success. The book she recently co-authored with 5 other CS thought leaders - The Customer Success Talent Playbook - recently hit #1 on Amazon in 5 categories. Kristen received her MBA from the University of Washington and splits her time between San Francisco and San Felipe, Mexico.
