The Journey: #36 Planning for Peace

We spend so much time talking about customer journeys, business outcomes, and retention strategies but what about our own team’s journeys? Specifically, the moments when someone needs to step away.

In Customer Success, “time off” doesn’t work like putting a project on pause, bumping a timeline, or waiting for someone to circle back. Customers don’t pause their goals. Their initiatives move forward. Their questions keep coming. Their renewals don’t wait.

So how do we honor the fact that employees need (and deserve) real time off, while making sure the show still goes on?

Over the years, I’ve become a self-proclaimed master of coverage planning. Whether it’s maternity leave, paternity leave, medical leave, sabbatical, or even an employee moving on, I’ve built repeatable processes and SOPs to ensure that employees can fully disconnect and customers still feel supported.

Let me share one example.

A while back, I had the privilege of hiring a woman in her first trimester of pregnancy (and let me pause here to say, I hope more leaders actively hire pregnant women). From day one, I knew we’d eventually need to plan for her maternity leave.

We prioritized her onboarding, ramp, and acclimation. But once she was fully successful in the role, it was time to prep. She was encouraged to openly share her pregnancy with customers at the right moments. That early communication planted the seed: she’d be out in a few months, and customers could expect a thoughtful transition plan.

By the time her leave came, she could actually leave work at work. She signed off confident that her customers were in good hands and that her new baby had her full attention.

The Peace Planning Playbook

Here’s the playbook we followed:

1.Coverage Model

We mapped who would cover which parts of her book of business and defined the engagement model. No ambiguity, no surprises.

2.Data Hygiene

Before she left, we ensured every account record was accurate, current, and usable. Clean data = smoother handoffs.

3.Forecast & Renewals

Closed what we could early, forecasted what was coming, and clearly documented ownership for renewals and growth opportunities.

4.Customer Communication

The most critical step. We started communication 6–8 weeks out. Multiple touchpoints, across channels. Customers knew who, what, when and never felt blindsided.

5.Next Steps Mapping

Every customer had next steps documented, with clear ownership assigned. Nobody got “lost” in transition.

6.Internal Alignment

Sales, Support, Product, Leadership—everyone was looped in. Alignment ensured continuity inside and outside the company.

Why It Matters

The outcome?

My employee could disconnect completely, without guilt or worry.

Customers felt supported, informed, and even impressed by how seamless the transition was.

The business didn’t skip a beat.

Peace, true peace, comes from planning. Not scrambling. Not hoping it works out. But designing systems that make “time off” possible without trade-offs.

Your team deserves it. Your customers deserve it. And frankly, so do you.