What Coaching CSMs Has Taught Me About CS and Myself

Leona Leong
Director of Customer Experience

Interview Highlights:

  • Customer Success is a high-reward profession where people can come in from different backgrounds and thrive. 
  • The best CSMs are those that are curious and take it upon themselves to learn things.
  • Many people who don’t think they have what it takes to be in CS actually do - they just need to be more confident.

Can you please introduce yourself and what you do?

My name is Leona Leong, and I’m the Director of Customer Experience at Coconut Software. 

What kind of learning process did you have during your career? 

My transition to CS was really just, “Here are your customers. Go.”

That probably wasn’t the best way to move into the CS world. This was 10 years ago, during a time when CS wasn’t really a formal practice yet. But I got more comfortable working with customers over time and was very lucky to be able to learn by osmosis. I shadowed a number of the more senior CSMs on their calls and picked up their best practices. 

For instance, I watched Achievers’ Senior Customer Success Manager, Paula Kwan, who I really looked up to. She managed some of Canada’s Big Four accounting firms. She created really great advocates and customer success stories for Achievers. 

Just watching Paula --especially as a woman of color--was inspiring to see. I was impressed at how much of a bad-ass she was in her job.

But my CS career really took off when I shifted from “osmosis learning” to “playbook learning” at Influitive under Sydney Strader, who was my manager at the time. She formalized a lot of the CS structures at Influitive in terms of how we did adoption playbooks, how we consulted with customers, and digging into the “why’s.”

Sydney put together a lot of the frameworks for the teams so that we all followed similar approaches, which included developing a consistent success plan. 

You coach other CS professionals as part of Coaching Corner. In your time coaching, what positive moment has stood out to you the most?

Just the sheer amount of people who want to go into CS. When I first started on my CS journey, I spent a lot of time explaining to people what CS was and what I did. They didn’t understand at the time. But now, there’s a lot of active folks who want to move from different industries into Customer Success. 

The CS community is really open and inviting. You don’t need to go through hoops and be a lifelong CSM to do well. People with different industry experiences perform really well because they bring a different approach and can help us refine our best practices. 

How do you think people from other verticals will do in CS?

Because CS utilizes a number of soft skills, people with different work experiences can and do succeed. That’s inspiring to watch!

One individual who comes to mind is Kristin Biddie. She was in retail working at Winners/TJ Maxx but was able to make the switch really quickly using the skill sets she had, like strategic planning. She became a CSM and now manages a team of 10-ish individuals at Loopio. And she did this in less than 3 years!

Another example is another former colleague of mine. He moved from being an accountant/consultant over to CS. Customer success is an inspirational career in that you don’t have to go through a pre-defined path like an SDR would have to do in order to be an AE. You can actually come straight in from a different practice, apply a different perspective, and do well.

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What qualities do you think would help a CSM best when making that kind of switch?

I would say innate curiosity about how things work. There are frameworks on how to conduct discovery conversations and what to ask, but at the end of the day it’s just being truly curious about the customer contact you’re working with, their company, that individual’s specific career goals, and tying that all back together. 

You take the things you learn about your customer - both for their company and for themselves - and draw those different data points together in order to figure out what the best solution is and what would motivate them to execute. There’s a lot of problem-solving and lateral thinking involved. 

What challenges have you encountered as a CS coach?

I wouldn’t say it’s been a challenge, but I’ve been paired with both men and women as mentees, and you can definitely see a difference in approach between the two genders. I would speak with women that are looking to move into CS and they tend to hesitate more and think their past experiences can’t apply. The men I’ve spoken to are not like that. 

How has coaching other CS professionals helped your own career?

Coaching others has made me realize that I sometimes undermine my own experience when I really shouldn’t. 

There was one time when I was chatting with a woman mentee and she said, “Oh, I don’t think I have the experience I need. What should I work on?”

I replied, “Actually, you have tons of experience. You worked in account management, sales, and have like 20 years experience. You’re going to kill it. You just need to find the right company to pivot into, but you have experience.”

As I was coaching her, I realized that I should take my own advice instead of being so self-critical. I’ve become more aware of my own tendencies since. 

Who do you think would benefit the most from this kind of career coaching? 

I would love to open CS career coaching up to students. 

I’ve been doing a lot more networking with recent grads, and there’s a lot of stuff they don’t teach you in school. I think farming CS recruits straight from university is a great idea. There’s a lot of talent at the undergrad level. It would be fantastic to help them start to understand how to get into the CS career path and why it can be so beneficial to them. 

What would be your advice for people who want to be a coach in Coaching Corner, or at least learn how to be a mentor to others?

I would say to treat them like your clients. I just spend most of my coaching time asking questions so that they come to their own realization. Oftentimes, the people with whom you’re working already have a lot of experience. They just need the right questions to frame up how they’re thinking about themselves.

About 
Coconut Software

Our cloud-based customer engagement platform combines your on-location and digital channels, providing self-service booking, online and physical queuing, wait time tracking, callback requests and virtual meeting support as well as contact center integration. We focus on financial institutions to seamlessly schedule, measure and manage client, prospect and staff interactions.

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