What We Wish We Knew When Starting in Customer Success

In this episode of CSin15, Jason and Chris step away from the latest trends to share something more fundamental: the lessons they wish they'd known when starting their CS careers. These aren't theoretical frameworks—they're insights earned through years of managing customers, navigating internal politics, and learning from both wins and painful losses.

Whether you're new to Customer Success or seeking to elevate your approach, these six core lessons will help you establish a stronger foundation for long-term success.

The Six Lessons Every CSM Should Know

1. Keep Perspective: Nothing Is As Serious As It Appears

Jason's foundational mindset shift: "At the end of the day, if you are not a medical doctor, your work is probably not saving lives. So nothing is as serious as it appears."

While this might sound harsh, the underlying message is crucial for CS professionals. Jason admits he was "very hyper reactive" early in his career, either completely overreacting to customer issues or underreacting entirely. The solution? "It's okay if things go wrong. It's okay to just take a second and breathe and truly think about how to respond or how to react to a negative situation."

The anxiety bell curve concept: Someone Jason worked with introduced him to this idea—you want to be in the middle or just on the edges of the anxiety curve. You need enough anxiety to take appropriate action, but not so much that you're stressed 24/7. When a customer threatens to churn or a deal goes sideways, remember that while it matters for your business, it's not a life-or-death situation.

This perspective shift allows you to respond strategically rather than emotionally. Instead of panicking when a renewal looks shaky, you can step back, assess the situation objectively, and develop a thoughtful plan to address the issues.

2. Build Executive Presence From Day One

Chris's career-defining advice: "You will be aligned to the level at which you speak. And I think if you come in and you don't sound confident or you don't sound knowledgeable, you're not presenting yourself as kind of this expert in the field."

Executive presence isn't just about confidence—it's about presenting yourself as a prescriptive consultant with genuine expertise. This becomes especially critical during executive business reviews and day-to-day customer interactions where you need to command respect and drive action.

The imposter syndrome reality: Both Jason and Chris acknowledge that imposter syndrome is everywhere. As Jason puts it: "If you're here, if you're doing it, if you're actively working the job, if you are still in CS with an organization, leading customers and helping them, you're not an imposter, you're doing it." But you still need to project confidence and subject matter expertise.

How to build executive presence:

• Practice speaking whenever possible: Jason credits his college job in career services, where he had to go "dorm to dorm" and speak publicly about internship opportunities, as foundational to his ability to command a message.

• Learn deeply, not just broadly: Chris emphasizes the need to "learn the product, learn the industry, and come ready to […] deliver recommendations."

• Get real speaking experience: Chris recommends finding opportunities to speak in front of people in person.

The goal is simple: executives should feel like they want to speak to you again because you provide genuine insights and value.

3. Your Perception Matters More Than You Think

Jason's reality check: "How you're perceived both internally and externally matters a lot."

This lesson goes deeper than most CSMs realize. Your reputation directly impacts your ability to drive customer success and your job security within your organization.

External perception with customers: If you're not perceived as a subject matter expert or strategic advisor, "the likelihood that you're gonna be able to generate the movement you need within a customer, not super high." Customers need to be confident in your expertise to follow your recommendations and engage in strategic conversations.

Internal perception within your organization: This is where many CSMs get caught off guard. If you're perceived as someone who "can't necessarily talk intelligently about the product," it puts more scrutiny on your work. As Jason explains, "any mistakes are magnified because now here's a person who's messing up more and more." In today's environment with frequent layoffs, negative internal perception can be particularly dangerous.

The positive flip side: When you have strong internal perception, "it gives you way more room within an organization to operate how you need to operate, have a little bit more trust from your managers, a little bit more leeway if something does go wrong."

Chris's important caveat: When you build a strong reputation and get tapped for multiple projects, "do not say yes to every request." Instead, be strategic about what you take on and "be the directory rather than always the point person" when someone else is better suited for a task. This actually enhances your reputation as someone with good judgment.

4. You're a Program Manager (Whether You Like It or Not)

Chris's fundamental insight: "Be a program manager and acknowledge that you have to be a program manager... both internally and externally."

Most CSMs don't realize they're essentially running complex, multi-stakeholder projects. Accepting this reality and developing the skills to excel at it separates good CSMs from great ones.

Internal program management: "It is not going to be anybody's directive or thing on their mind to reach out to your customers." If you want strong executive-to-executive connections between organizations, "it is your duty to orchestrate having an executive reach out to another executive or having this leader reach out to this leader."

External program management: "You will likely be the person who cares the most about your tool" at the customer organization. This means you need to "hold them accountable through timelines, through actual due dates, get their agreement on them."

The mutual success plan approach: Chris advocates for using formal success planning tools: "We have a tool for mutual success plans. So I'll pull it up. I'll show it to them. I'll show them that there's like a Gantt chart and timelines and due dates." Even though customers likely won't log in independently, showing them the tracking creates accountability.

The psychological effect: When customers see formal project management, "it puts in their head of like, hey, one of my leaders will probably see this thing. And if we come into a meeting and I haven't executed on any of this, it's gonna look bad on me."

5. Technical Knowledge Is Non-Negotiable

Jason's hill to die on: "If you don't know how it works, if you don't have the ability to grasp different feature sets, how they might connect with each other, where do they integrate, how do they integrate... you're not gonna be of much help to your customers."

This goes far beyond surface-level product knowledge. You need deep technical understanding of your platform's capabilities, limitations, and integration possibilities.

Why technical knowledge matters: Without it, you can't drive meaningful outcomes or hold customers accountable. As Jason puts it, "you are not even accountable for how your own product works at that point." You also can't have credible strategic conversations if you don't understand what your product can actually deliver.

The day-to-day reality: You should be able to answer the vast majority of "how does this work?" questions on the spot. Jason has "gone into conversations with CSMs throughout my career and they're asking me probably the most basic functionality questions that I feel like we should know because you've been in the product."

The strategic connection: Chris adds that technical knowledge "assists you if you know what the product can do in depth, you can also align that strategy better and also be able to speak to it and kind of defend like, here's how this gets done."

What weak technical knowledge looks like: Constantly saying "I don't know, I'll come back to you" or "I'll follow up" destroys your credibility. While occasional follow-ups are fine, "you gotta know it" for the core functionality.

6. Your Champion Doesn't Sign the Contract

Chris's biggest and most painful lesson: "Your champion is not your decision maker. Your champion is a great partner... But at the end of the day, they do not sign that contract."

This lesson has "hurt" both hosts multiple times throughout their careers, and it's one of the most common causes of renewal surprises in Customer Success.

Why champions can be misleading: Champions are often personable and develop genuine relationships with CSMs. But "they might sugarcoat it because they don't want to have to tell you bad news." They're also not always in the room when budget and renewal decisions are being made.

The dangerous pattern: CSMs naturally gravitate toward champions because "they're willing to engage because we develop these great relationships." Jason admits, "even now, to some extent, I have a tendency to kind of latch onto the champion."

The hard truth about decision makers: "Go make sure that you are knocking on enough doors that if there is bad news or if there is a bad perspective you're hearing it... before it's resolving in renewal not being signed."

Jason's painful experience: "I've been hurt, I've been sad, heartbroken a million different ways on that exact thing." The emotional investment in champion relationships makes the renewal surprises even more difficult to handle.

Tactical Actions You Can Implement This Week

For Building Executive Presence:

• Record yourself presenting: Use tools available today to practice presentations on non-work topics. Remove "ums," "ahs," and moments of uncertainty from your delivery.

• Join a local speaking group: Look for Toastmasters, professional associations, or even organize presentation nights with colleagues where everyone presents on a topic for 5-10 minutes.

• Study industry leaders: Watch speeches and presentations from executives in your industry. Note how they structure insights and recommendations.

• Prepare three industry insights: Develop three current, data-backed insights about your industry that you can weave into customer conversations this month.

For Technical Mastery:

• Audit your product knowledge gaps: List the top 10 customer questions you've had to follow up on in the past month. Learn those answers completely.

• Create a technical reference guide: Build a personal cheat sheet of common integration scenarios, feature connections, and troubleshooting steps.

• Shadow technical calls: Ask to observe sales engineering or implementation calls to see how technical experts position capabilities.

• Test every feature: Spend time in your product weekly, exploring features you don't regularly discuss with customers.

For Program Management Excellence:

• Implement mutual success plans: If you don't have a formal tool, create a simple template with timelines, owners, and success metrics. Share it visually with customers.

• Map your customer's decision-making process: For each account, identify who influences budget decisions, who uses the product daily, and who signs contracts.

• Create accountability cadences: Establish regular check-ins specifically focused on progress against agreed-upon goals, not just relationship maintenance.

• Document everything: Start tracking customer commitments, timelines, and progress in a format you can easily reference and share.

For Relationship Expansion:

• Identify economic buyers: For each account, research and document who actually controls budget decisions. Plan specific outreach to these stakeholders.

• Ask direct renewal questions: This week, ask at least one customer: "If your renewal was today, would you feel confident signing?" Follow up with: "What would need to change for you to feel completely confident?"

• Map stakeholder influence: Create a visual map of each account showing champion, users, economic buyer, and decision influencers. Identify gaps in your coverage.

• Schedule executive connections: Orchestrate at least one executive-to-executive touchpoint this month, even if it's just a brief introduction email.

For Perception Management:

• Audit your internal brand: Ask your manager directly: "What's my reputation internally? Where can I improve my perceived expertise?"

• Choose projects strategically: Before saying yes to the next request, ask: "Am I the best person for this, or should I connect you with someone who has deeper expertise in this area?"

• Document your wins: Keep a running log of successful outcomes, customer feedback, and value delivered that you can reference during reviews.

The Bottom Line

These lessons represent years of trial and error from two experienced CS professionals. They're not just theoretical concepts—they're practical insights that can immediately impact your effectiveness as a CSM.

The common thread across all six lessons? Success in Customer Success requires more than relationship building. It demands technical competence, strategic thinking, political awareness, and program management skills. These fundamentals matter more than the latest CS trends or tools.

As Jason reflects, many of these are "soft skills" that become increasingly important as you advance in your CS career. Master these basics, and you'll be well-positioned to thrive regardless of what changes come to the CS landscape.

The question isn't whether you'll face these challenges—it's whether you'll be prepared when they arrive.

Have your own hard-earned CS lessons to share? Jason and Chris would love to hear from you. And if you're interested in being a guest on CSin15, reach out—they're always looking for practitioners with valuable perspectives.