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Effortless Customer Success: The Case for Doing Less

February 22, 2025

Most of us have tried the “more outreach equals better results” approach: pumping out weekly check-ins, nudging users with automated emails, scheduling QBRs just to schedule QBRs.

p.s. If you are a leader goaling your team on QBR delivery, I beg of you, please stop!

And yet, despite all of this effort, churn still happens. As it turns out, more doesn’t always translate to better in customer success.

The Proof

Recent insights from multiple CS platforms and industry research point to a common theme: when organizations move from broad, schedule-based messaging to data-driven, event-based and value-focused outreach, they often see churn reductions or retention lifts in the 5–15% range over a few quarters.

This is such a game changer.

Wu Wei

When I was super down in the dumps last year, a dear friend of mine introduced me to a Daoist concept called wu wei, which can be translated as “effortless action.” This doesn’t mean doing nothing; it means reserving your energy for action precisely when and where you can make the biggest impact.

I’ve been thinking about this concept a lot, and trying to practice it in my own life. So of course I’ve also woven it into my work.

In customer success, the concept of wu wei translates to helping your customers exactly when they need it most, being very carefully intentional and soft, rather than hammering them with generic messages.

Four Steps

I’ve always preached “back to basics” but now I have more clarity about what that instinct can mean for clients: 

  1. Observe

    • Just LISTEN. Meaningfully tap into your product analytics, user feedback, health scores, and customer objectives. Identify any patterns showing where and when users tend to need support or guidance or when they are falling short of achieving their goals.

  2. Simplify

    • Replace generic blasts with a focused set of outreach moments. Clear away noise so that when you do communicate, users see immediate relevance and benefit. Ask your customers how they would like to ingest information, and meet them there. 

  3. Trigger

    • Identify those meaningful moments to trigger outreach. Here are a few value-oriented examples:

      • Inactivity & Value Prompt: If a user hasn’t logged in for 7 days, send a short tip on how a specific feature can save them time or streamline a workflow relevant to their use case. 

      • Onboarding Stall & Benefit Highlight: If a user fails to complete a key setup step within 48 hours, share a brief tutorial emphasizing why this step unlocks valuable functionality (e.g., “This integration saves you an hour every week”).

      • Usage Drop & Use-Case Showcase: If a user’s activity falls below a certain threshold, reach out with a success story or quick demo of features that could address their current challenge. Reinforcing the ROI of re-engaging.

      • Feature Milestone & Advanced Tips: When a user first tries a premium feature, follow up with advanced tips or a brief example of how others leverage that feature for even greater success.

      • Outcome Surveys: Ask your customers how completely they’ve realized their desired outcomes (or not), and then deliver guidance to get them back on track or pushing forward to unlock more.  

  4. Reflect

    • Track quantitative and qualitative data in aggregate. It’s so much easier now with the AI momentum so really dig into all the qualitative insights you can get your hands on. If you see positive shifts, refine and expand. If not, adjust your timing, messages, or the value you’re offering.

If you’re hesitant to totally can routine check-ins, start small. Pick one user segment –  maybe it’s new users in their onboarding phase, for instance – and swap out your weekly emails for these types of value-driven triggers.

Track onboarding progress after this change vs. the before benchmarks, along with user feedback over the next few weeks or months.

See if fewer yet more resonant communications deliver a positive impact. Concurrently track customer effort. My bet is you’ll see a lower customer effort score and increased onboarding velocity.

Closing Thoughts

It’s easy to lean on volume: send more emails, make more calls, set more meetings. But the principle of wu wei and the real-world results indicate that doing less, but aligning outreach around genuine value, is far more effective.

By carefully identifying the moments when customers truly need your help, you transform what feels like impersonal outreach into meaningful support.

Soften up, step back, and carefully focus to nurture strong, lasting relationships. You’ll save your own sanity and your customers will thank you. 

A Special Note

I recognize wu wei is a sacred Daoist principle and aim to approach it with respect. If I’ve misrepresented it in any way, I welcome feedback and the opportunity to learn.

What Do Plato’s Chair, Casablanca, Six Sigma, and Customer Success Have in Common?

January 23, 2025

Ok, hang with me for a second… this connection will make sense, I promise.

But first, let me set the stage.

Over the past few months, I’ve cleared the path and turned the dial up to 100 on my Customer Success consulting business, helping clients build healthy CS foundations. Basically, I’m like a preventative health doctor for CS organizations.

As I’ve ramped up, I’ve committed to investing 20% of my time in learning—like REALLY feeding my brain—so I can keep elevating Customer Success as a domain.

This means diving into reading, podcasts, conversations with brilliant founders and CS peers, and connecting ideas that might seem completely unrelated. Honestly, it’s one of the best parts of this new chapter.

I get to choose how I grow and what I focus on.

No more mandatory certifications or corporate enablement sessions that don’t move the needle for my career or my clients. Now I have the space to do real thinking and get heady about ideas I haven’t had the luxury to explore since my liberal arts college days, like when I took an Integrated Studies creative writing and philosophy of film class.

Which bring me to…

Plato’s Chair, Casablanca, Six Sigma, and Customer Success

At first glance, these four things seem totally unrelated. Quick refresher on this stuff:

  •  Plato’s Chair is part of his Theory of Forms where he investigates “chairness”.

  • Casablanca is an award-winning, WWII classic romance movie.

  • Six Sigma is a methodology for reducing defects, often used in supply chain management.

These things don’t exactly scream “connected.” But look harder. They’re all about the tension between the ideal and the real.

  • Plato’s Chair teaches us that perfection exists only as a concept—every physical chair is just an imperfect reflection of the “ideal chair.”

  • Six Sigma offers a path to reduce flaws and get as close as possible to that ideal. But even '“perfect” in Six Sigma is only 99.99966% perfect.

  • Casablanca conveys that life rarely aligns with ideals and instead is about navigating messy, human realities.

Customer Success Is ALL of These Things

In CS, we work tirelessly to facilitate the “ideal” customer journey, use frameworks to reduce variability, and, like Rick in Casablanca, navigate the complexities of human relationships and real-world challenges.

But perfect forms (in this case, the perfect customer journey and experience) only exists in concept. NOT IN REALITY.  

So what now!? Here’s how I cope:

Expect imperfection. Anticipate failure. Build resilience into your processes.

For example:

  • Bake tests into onboarding to measure progress and proficiency and use failures to iterate.

  • Plan for stalled integrations with early alignment playbooks.

  • Anticipate that if training doesn’t stick, shift training to bite-sized, use-case-driven content.

  • Perfect doesn’t exist, but moving the needle in that direction counts; tie everything back to customer goals and track relentlessly.

The Magic of Customer Success

The magic of Customer Success lies in this tension between the ideal and the real. Getting better, not perfect.

Getting great, even. But still, not perfect.

The work of CS is about bridging the gap, using frameworks and creativity to create as much “ideal” as possible while managing the messy, human reality of it all.

My ultimate message is stop chasing flawless execution and start creating processes that embrace, adapt to, and grow from imperfection.