An artful approach to Customer Success

Let’s get something out of the way. I’ve never been a big C, big S Customer Success leader, manager, or employee. But I’ve built my career by focusing on driving success for my many types of customers. Hear me out. 

Professionally, I’ve held a few titles (Chief of Staff, COO, Director of Commercial Operations) that all focused on strategy, alignment, and flawless execution. I’ve served customers including a global workforce, a Board of Directors, numerous vendors, and, of course, a variety of actual paying customers. 

Personally, I’ve been a lifelong student of what I call Artful Concerns, my term for well-run, inspiring organizations. We’ve all experienced them and many of us spend our time attempting to emulate them: the companies that everyone wants to work for because current employees can’t stop talking about how great they are, that create can’t-live-without products and services, and that seem to, without extra effort, make their communities and the world a better place. 

These Artful Concerns treat stakeholders like customers. Each functional area is tasked with creating success for their customers: employees, vendors, partners, users. Through studying these organizations, and through my own career, I’ve learned a few critical lessons that apply to anyone trying to create success for their customers.

Maintain a Hospitality Mindset

What makes a great experience? Great software and great restaurants share something in common: they nail the details. Both understand what matters most to their customers and invest in that area. Do you know what wows your customer? What is the “mint on the pillow” aspect of the service you provide? This can be a little less obvious if you’re selling software, but if you’re curious enough you’ll uncover it. If I’m a customer of your software, here is my shortlist:

  • Create opportunities for me to self-serve information and, if I can’t answer my own question, make it easy for me to feel heard. I hate sending an email or picking up the phone. 
  • If I have to send an email, I better be able to respond to anything you sent me. Don’t send me emails from unattended inboxes that I can’t reply to. That simply creates friction in an already frustrating moment. Which leads me to my next point…

Get and Stay Curious

If your customer is frustrated, and you begin to feel anxious or frustrated yourself, consciously switch to a place of curiosity. Remind yourself that on the other side of the email or help desk ticket or weekly call is a person who is doing the best they can, at that moment, at the job they have to do. Your customer is just a person and people change thanks to circumstances outside our control.

Look at how much our roles (and lives!) have changed since January 2020. What worked well before might not work well now. If something isn’t working as well as it used to, get curious until you understand what changed. If your customer is consistently late to a regular status call and you run out of time every.single.week, get curious.

  • Perhaps you’re catching him right after his child goes down for a nap?
  • Maybe regular calls don’t work well given other urgent business priorities. Would ad hoc calls be better for the time being?
  • Or maybe, because of COVID, your point of contact participates in an expanded 3-hour executive meeting just before your standing call and they’re fried by the time you connect. 

Your frustration is a sign that you’re shoehorning an old solution onto a new problem. Acknowledge the friction, get curious, and use what you learn to evolve your approach. Which is the perfect segue to my final point…

Meet your Customers where they are

Now that we’ve accepted that our customers change (just like we do as people!), let’s meet them where they are. Use your curiosity to be flexible in designing your approach to Customer Success. If your customers love the phone, why are you investing in a slick ticketing system and hiring people who hate the phone? If your Board reads only some of the materials you send in advance, take the time to ask why and adjust your approach. 

I worked with a CEO who did a cursory read of his email on his phone, while on the train, before diving in morning meetings. Have you ever tried to review a spreadsheet on your phone? Or an email the length of a short novel? I adapted to be successful given the constraints and coached the rest of our team to follow the best practice of structuring “must be read before he starts his day” emails as follows:

  • An instructive subject line, even if it’s a reply to a thread, such as “Read before 10 am product launch meeting”
  • Always start the email with a TL;DR… (the key takeaway needed before joining the meeting)
  • “PDF attached for easy viewing on your phone”

If I needed him to dive into something longer, such as a financial model, I’d schedule the email to send at 12pm, knowing he would spend quality time on his laptop after lunch. It wasn’t effective for him to see this email in the morning nor did I want to risk a distraction from  the more urgent pre-meeting message. 

I didn’t change my work, I simply used tools (Boomerang or Gmail’s built-in delay send feature) to meet my customer where he was and increase the chances of a successful outcome. 

Let me know in the comments (or on Twitter @artfulconcern) how you create success for your customers (big or little c). I’d love to start a conversation!

Alicia Diamond blogs about her journey to becoming the best leader she can be at She’s a 2x Chief of Staff to the CEO, former startup COO, and currently runs Commercial Operations at LTSE in NYC. She’s passionate about empowering artful leaders to build more great companies.


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