Understanding your why

Take time this week to reflect deeply on your CS career. Not the metrics or the titles, but the moments that made this work meaningful. The goal is to understand your unique strengths and motivations so you can find your next role with clarity and purpose.

When have you felt most energized in your CS role?

Think about specific moments, like:

• That meeting where you helped a customer have a breakthrough. When you asked just the right question that uncovered the real problem, and you watched their whole perspective shift. The meeting that ran long because everyone was too engaged to stop.

• When you designed a new process that other CSMs now use. Maybe it was a new QBR format or onboarding checklist that others still use today.

• Recall a struggling account you turned around - not just the final win, but the detective work of figuring out why they were stuck, the strategy you developed, and that first meeting where you saw them start to trust you again.

• When you spotted an opportunity nobody else saw. Maybe catching a subtle shift in the customer's voice that revealed a bigger problem, or noticing their workaround that sparked a new use case idea. Or a new process that helped the team be more productive.

Don't just list big wins - focus on the moments that made you think "This is why I do this job."

Which accomplishments have made you proudest?

Don't just list your wins here. Dig into why they matter to you personally. The goal is to understand what kind of impact feels most meaningful to you.

Consider achievements where:

• Consider the times you threw out the standard playbook because you knew there was a better way. When you trusted your instincts and it paid off - like restructuring an onboarding process or changing how you handled QBRs.

• Think about projects where your unique background or perspective made the difference. Maybe you drew on past experience or connected dots others missed. What made your approach different?

• Remember solutions you created that others wanted to copy - training materials, email templates, or customer strategies that became team resources. Why did these particular contributions resonate so well?

• Look for times you solved problems in unexpected ways - when conventional approaches weren't working and you had to get creative. What gave you the confidence to try something different?

The key here isn't just what you achieved, but why it mattered to you personally.

What problems do you love solving?

Before listing your favorite challenges, think about those days when you looked up and somehow three hours had passed. The problems that had you sketching solutions on napkins or waking up with new ideas. These aren't just tasks you're good at -but also the ones that energize you.

• Think about those technical deep dives where you and a power user geeked out over advanced features. When you both got excited about pushing the platform's limits, and you found yourself drawing workflows on the whiteboard while the customer finished your sentences. Those sessions where your technical curiosity really shined.

• Remember those strategic planning sessions where you helped leadership teams see the bigger picture. The meetings where you asked the questions that shifted their whole approach, or mapped out a bold vision that got everyone leaning forward in their seats. Times when you weren't just planning features, but reshaping how they ran their business.

• Consider those major change management projects where you guided customers through scary transitions. When you broke down overwhelming changes into manageable steps, kept everyone calm during hiccups, and saw the relief on their faces when it all came together. The times your steady hand made big changes feel possible.

• Think about the adoption challenges that turned into creative campaigns. Maybe you designed that unique contest that finally got the skeptical team engaged, or created that simple workflow that turned reluctant users into daily active champions. When your creative solution became a case study for other CSMs.

Think about the problems where time flies because you're so engaged.

What makes CS deeply meaningful to you?

Take a moment to think beyond the day-to-day tasks. We're looking for those fundamental aspects of CS work that would make you choose this career path again, even if everything else changed. The elements that make you think "This is exactly where I'm supposed to be.”

• Remember watching that customer finally hit their big goal - maybe it was launching their new program, hitting a major milestone, or seeing their team fully transformed. Those moments when they shared success stories not just as wins, but as personal achievements you helped make possible. When their success felt like your success too.

• Think about those customer relationships that evolved from formal check-ins to trusted partnership. The ones where they started calling you first for advice, where you could hear the trust in their voice, and where you found yourself genuinely invested in their success. Those connections that made Monday meetings feel like catching up with colleagues you respect.

• Consider those times when you pieced together a creative solution that nobody had tried before. When you combined features in unique ways, or developed a new approach that solved multiple problems at once. The satisfaction of turning "we can't do that" into "I never thought of doing it that way."

• Reflect on those moments when you spotted a trend across customers and brought it back to the product team. When your front-line insights helped shape the roadmap, or when your detailed feedback turned into a new feature. Those times when you truly bridged the gap between customer needs and product evolution, making both sides stronger.

This is about the core elements that would make you choose CS again.

Quick reflection exercise

Take 15 minutes to write down:

1. Your best day in CS from the past year

   1. What happened:

   2. Why it was meaningful:

   3. What it taught you about your motivations:

2. A challenge you actually enjoyed tackling

   1. The situation:

   2. Why you enjoyed it:

   3. What it reveals about your interests:

3. A piece of feedback that really resonated

   1. What was said:

   2. Why it meant something to you:

   3. What it shows about your values:

Remember: There's no "right" answer here. The goal is to understand what genuinely motivates you, not what should motivate you.

Using these insights

Now comes the crucial part - turning your reflection into action. Set aside 30 minutes to look at everything you've written. We're not just pattern-matching here; we're building a compass for your next career move. Look for the threads that connect your best moments, biggest wins, and deepest satisfaction.

Identify your career patterns

• Review everything you've written and highlight recurring themes. Maybe you consistently light up when solving complex technical challenges, or perhaps your best stories all involve building something new from scratch. Notice which elements appear in both your proudest moments and your most energizing days.

• Pay attention to your natural momentum points - those areas where you consistently do more than required. It might be the extra documentation you create, the process improvements you initiate, or the team members you spontaneously mentor. These aren't just good habits; they're clues to your professional sweet spot.

• Look at the impact patterns in your work. Are you most fulfilled by immediate wins like solving urgent problems, or do you thrive on long-term transformation projects? Do you get more satisfaction from helping individuals succeed or from creating systems that help everyone?

• Notice where you naturally take ownership without being asked. These moments - whether it's jumping in to fix a broken process or creating new resources for the team - reveal where your genuine interests and talents align.

Put insights into action

Take these patterns and create three simple lists to guide your next steps:

1. Must-haves for your next role:

   • List the elements that energize you most.

   • Note the types of problems you want to solve.

   • Include the impact you want to make.

2. Red flags to watch for:

   • Roles that lack your energy-giving elements.

   • Environments that don't value your natural strengths.

   • Positions that would minimize your favorite types of work.

3. Questions to ask in interviews:

   • About opportunities to work on your preferred challenges.

   • Regarding the impact you've identified as most meaningful.

   • About how they value and support your natural strengths.

Remember: This isn't just about finding any CS role - it's about finding the right one that lets you operate in your zone of genius most often.

Career Reflection FAQs

Q: I barely have time for my regular work. How can I make time for this reflection?

A: You don't need to do this all at once. Start with just 15 minutes before your day begins or during lunch. Focus on one question at a time. Even short bursts of reflection can give you valuable insights.

Here are some practical ways to build reflection into your schedule:

• Keep a quick-capture document open during your workday. When something meaningful happens (a great customer interaction, a problem you enjoyed solving, or positive feedback), spend 30 seconds jotting it down. These notes become your reflection material for later.

• Block 15 minutes after your weekly team meeting. You're already in a headspace of reviewing work, so use this time to note which parts of the past week felt most energizing.

• Look at your calendar for the past week each Friday. Highlight the meetings or activities that left you feeling accomplished or energized. Add quick notes about why these moments stood out. Over time, you'll see patterns emerge.

• Start with just one prompt from the reflection guide. Work on it for a few days, adding thoughts as they come to you. When you feel complete with that prompt, move to the next one. Many CSMs find this gradual approach leads to deeper insights than trying to tackle everything at once.

If you're struggling to start, pick the easiest prompt: "What was your best day at work this month?" Write about it for just five minutes. Often, this opens up natural connections to the other reflection questions.

Q: What if I can't think of any standout moments?

A: Many CSMs feel this way at first, but your standout moments are there. They might just need a different way of looking at them.

Here are several approaches to uncover these moments:

• Check your sent emails folder for thank you messages from customers or positive feedback from your team. These often point to impactful work you might have forgotten about. Save them!

• Review your calendar from the last three months. Look for meetings that ran longer because everyone was engaged, or follow-ups that led to customer breakthroughs.

• Open your project tracking tool and look at completed items. Focus on the ones where you added extra details or went beyond the basic requirements. This often reveals work you were naturally drawn to.

• Talk to a colleague who's been with you for a while. Ask them to remind you of projects where they saw you really engaged or times when your work made their job easier.

• Look through your meeting notes, especially from customer calls. Search for phrases like "this is interesting" or "great idea" which often mark moments of genuine engagement. Think about the times you've shared work stories with friends or family. We naturally talk about things that matter to us, so these conversations often point to standout moments.

If you're still stuck, try reversing the question: What parts of your day do you look forward to most? Which meetings don't feel like a chore? These preferences often point to your standout moments.

Q: Should I focus only on big wins and major achievements?

A: Not at all. Often the smaller moments reveal more about what truly motivates you than the big achievements everyone expects you to be proud of.

Here are ways to identify revealing moments beyond the obvious wins:

• Pay attention to the types of customer problems you naturally jump to solve, even when they're not technically your responsibility. These show what kind of work pulls you in.

• Notice which parts of your job make you lose track of time. Maybe it's diving deep into analytics, creating new processes, or mentoring team members through challenges.

• Think about the customer conversations that energize you rather than drain you. Often these point to the type of work that comes naturally to you.

• Look for patterns in the small improvements you make without being asked. Whether it's documenting a better way to handle onboarding or creating email templates others now use.

• Consider which customer success stories you love telling others about. Sometimes, the wins that excite you most aren't the biggest on paper, but they showcase the kind of impact that matters to you.

• Reflect on the moments when customers or colleagues say "I hadn't thought of it that way." These instances where your unique perspective made a difference often reveal your natural strengths.

Remember the small fixes or improvements that others now regularly use. These "minor" contributions that stuck around show where you naturally add lasting value.

Q: What if my reflections show I'm not in the right role anymore?

A: This realization isn't a setback. It's valuable information that can help you make intentional choices about your next career move.

Here's how to handle this insight productively:

• Look deeper into which parts of your current role aren't aligned. Maybe you love the strategic work but not the day-to-day tactical tasks, or perhaps you're energized by technical problem-solving but spend most of your time in routine check-ins.

• Consider whether you can reshape your current role. Many CSMs have successfully carved out new responsibilities or specialties within their existing position by sharing their insights with their manager.

Use this clarity to explore related roles where your CS skills transfer well. Solutions architecture, implementation, customer enablement, or CS operations might offer a better fit while building on your experience.

Take note of which moments do energize you, even if they're rare. These point to the elements you should look for in your next role, whether it's in CS or adjacent fields. Practice articulating what you've learned about yourself. Being able to clearly explain what kind of work energizes you and why makes you a stronger candidate for roles that truly fit.

Discovering this now saves you from making the same misalignment in your next role. You can use these insights to ask better questions in interviews and evaluate opportunities more effectively. Consider talking with people in roles you think might be a better fit. Your CS experience gives you a great network to learn about adjacent roles where you might thrive.

Q: How do I actually use these reflections in my job search or current role?

A: Your reflections aren't just personal insights. They're powerful tools for steering your career and communicating your value.

Here's how to put your reflections into action:

Based on your reflections, create a concrete list of what you're looking for. Instead of vague criteria like "good culture," you might specify "regular opportunities for strategic planning" or "significant time for technical problem-solving with customers."

Turn your meaningful moments into compelling interview stories. When asked about your strengths, you can share specific examples of times you've created value in ways that energize you. Or, ask colleagues or select customers to write a recommendation on your LinkedIn page. It's always a good idea to reciprocate!

Build targeted questions for interviews that help you assess alignment. If your reflections show you love creating scalable solutions, ask about opportunities to build new processes or improve existing ones.

Use your insights to evaluate job descriptions more effectively. Look beyond titles and standard requirements to spot roles that match your identified patterns of success.

Prepare for salary discussions by highlighting the unique value you bring. Your reflection examples help demonstrate why your particular approach and strengths deserve competitive compensation.

If staying in your current role, schedule a career development conversation with your manager. Share specific examples of projects where you've had the most impact and discuss how to incorporate more of these opportunities.

Look for internal initiatives that align with your strengths. Your reflections might reveal you excel at mentoring, so you could propose leading new hire training or creating onboarding materials.

Review your current accounts or projects through this new lens. You might find opportunities to realign your work with your strengths while delivering better results for customers.

Q: How do I know if I'm being honest with myself in these reflections?

A: It's natural to worry about authenticity in self-reflection. Your mind might drift toward what sounds good on paper rather than what truly matters to you.

Here are ways to check if you're being genuine in your reflections:

• Notice your energy level when writing about different experiences. If you find yourself getting animated and adding more details to certain stories, that's often a sign of genuine enthusiasm.

• Pay attention to your go-to examples. When someone asks about your work, which stories do you naturally tell first? These instinctive choices often reveal what really matters to you.

• Look at what you do when you're tired. The tasks you still want to tackle at the end of a long day, or the problems you think about in the shower, often point to genuine interests.

• Check your language. If you're writing what you think others want to hear, you'll often use formal or buzzword-heavy language. Genuine reflections tend to be more specific and personal.

• Consider which parts of your job you do more thoroughly than required. Maybe you create extra documentation, dive deeper into analytics, or spend extra time mentoring. These voluntary efforts often reveal true interests.

• Think about what makes you lose track of time. The tasks where you look up and realize an hour has passed are usually aligned with your genuine interests and motivations.

• Listen to feedback from colleagues. They often notice patterns in your work style and enthusiasm that you might miss. What do they come to you for? When do they say you seem most engaged?

Review your reflection answers after a few days. Your initial responses might be what you think you should say. Coming back later often helps you spot where you weren't being fully honest with yourself.

Q: What if I'm good at many aspects of CS but can't identify what I love most?

A: Being versatile is valuable, but it can make it harder to pinpoint your true passions.

Here are ways to uncover what you love most when everything seems equal:

• Track your work for two weeks without judging it. Write down which tasks left you feeling energized versus just accomplished. Sometimes what we're good at isn't what fills our energy tank.

• Pay attention to where you go above and beyond. You might be good at many things, but notice where you naturally do extra work. Maybe you're creating better templates, improving processes, or helping colleagues even when it's not required.

• Look for themes in customer feedback. When customers praise your work, what specific aspects do they mention? Sometimes others spot our unique value before we do.

• Notice what you advocate for in meetings. The topics where you speak up most passionately often reveal what you care about deeply, beyond just being capable.

• Consider which skills you're constantly trying to improve. Being good at something isn't the same as wanting to master it. Where do you spend your learning time?

• Think about your dream projects. If you could design your perfect week, which types of work would get the most time? This often reveals preferences you might not see in your daily work.

• Ask yourself which accomplishments you're most proud of. Not just the biggest wins, but the ones that felt most satisfying. These often point to work that aligns with your values.

Reflect on when you feel most confident. The moments where you know exactly what to do, where your expertise feels natural rather than practiced, often reveal your sweet spot.