What to Protect, What to Delegate, and What to Let Go Of as a CS Leader

This episode is a practical breakdown of how to structure your time as a CS leader with intention. What to protect, what to delegate, how your calendar should evolve as you scale, and what a high-impact CS leadership schedule actually looks like in practice.

You'll learn:

• How your calendar should look different in early stage versus when you're scaling and why leaders who never recalibrate get stuck
• The four categories of time every CS leader should protect as non-negotiable, regardless of what stage they're in
• A practical framework for deciding what to delegate fully, what to stay involved in, and what only you can do
• What it actually looked like to manage time as a VP of CS and the mindset shift that changed everything

This episode is for CS leaders who are tired of being busy without being effective, and who want a practical, intentional approach to designing a schedule that makes them a better leader, a better coach, and a more sustainable one.

Ways I Can Help You Level Up Customer Success:

1. Value Realization Framework Online Course:  Install a repeatable system your team can run: deliver value, prove outcomes, and drive retention and expansion. Self-paced with ready-to-use templates. Learn more.
2. Newsletter: Practical, revenue-driven CS strategies in your inbox. No fluff. Subscribe here.
3. 1:1 Coaching: Hands-on guidance to roll out value realization in your org. Book a free consult call.

For more information, visit my website: Explore more resources and insights. CS RevSpeak

Let's Connect on Linkedin:  Get weekly insights, templates and real talk on CS leadership. Follow Angeline on LinkedIn.

Until next time, keep driving success and speaking the language of revenue!

Transcript

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Are you a customer success leader?

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If so, I want you to open your

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calendar right now.

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Look at this week, look at what's on

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it.

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Now, ask yourself honestly, how much of what's

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on that calendar did you put there intentionally?

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How much of it reflects your priorities as

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a CS leader?

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The strategic work, the team development, the thinking

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time, the things that actually moved the needle,

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and how much of it just accumulated, meetings

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that got scheduled because someone needed you, recurring

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calls that nobody has canceled in 18 months,

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back-to-back-to-back blocks that leave

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no room to actually think.

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For most customer success leaders, the honest answer

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is that their calendar is a reflection of

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everyone else's priorities, not theirs.

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And the result is a leader who is

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constantly busy, constantly responsive, and consistently running out

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of time for the work that actually matters.

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Your calendar is not just a scheduling tool.

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It's a strategic asset.

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And if you're not designing it intentionally, someone

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else is designing it for you.

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That's what this episode is about.

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So let's get into it.

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Welcome to the CS RevSpeak podcast, where we

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talk about practical insights, strategies, and frameworks that

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will help customer success leaders who carry a

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revenue number, drive sustainable growth, maximize customer lifetime

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value, and crush their numbers.

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Let's see what is actually happening here, because

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I think it's worth understanding before we talk

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about how to fix it.

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Customer success leadership is one of the most

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cross-functional roles in a SaaS business.

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You're connected to sales, to product, to support,

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to finance, to the executive team.

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Everyone has something they need from customer success,

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and because CS is fundamentally a relationship-driven

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function, there's a cultural expectation, sometimes explicit, sometimes

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just absorbed, that a good CS leader is

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always available, always responsive, always there when someone

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needs something.

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And so the calendar fills up.

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Customer escalations, cross-functional things, team check-ins,

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leadership meetings, one-on-ones that run long,

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and somewhat in the middle of all of

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that, the strategic work, the work that only

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you can do as a leader of this

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function, gets squeezed into the margins, early mornings,

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late evenings, the gaps between meetings that are

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too short to do anything meaningful in.

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Here's what that actually costs.

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Not in terms of stress or sustainability, although

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those are real.

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In terms of outcomes, when a CS leader

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is perpetually reactive, the team feels it.

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Decisions take longer because the leader is never

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in a focused headspace to make them.

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Coaching gets rushed or skipped because there's no

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protected time for it.

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Strategic initiatives stall because every time the leader

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sits down to think, something urgent pulls them

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back into execution mode.

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And the function stays stuck at a certain

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level of performance because the customer success leader

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never has the bandwidth to lead it to

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the next level.

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A CS leader who designs their calendar intentionally

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is a fundamentally different kind of leader.

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They show up to one-on-ones prepared.

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They have time to think before they have

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to decide.

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They can work on the org instead of

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just in it.

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And that difference compounds over time into a

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team that performs at a higher level.

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So the starting point is this, your calendar

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is a leadership decision.

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Every block on it is either something you

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choose or something you're allowed.

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And the first step in designing it well

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is taking ownership of that distinction.

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Before I share what I protected in my

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own calendar, when I was a VP of

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customer success, I want to acknowledge something.

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The right calendar structure is not one size

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fits all.

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What it looks like depends heavily on where

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you are in your journey as a CS

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leader, specifically whether you're in early stage mode

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or scaling mode.

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Because two phases make very different demands on

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your time.

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And what serves you well in one can

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actually hold you back in the other.

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In early stage, when you're building a function,

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when a team is small, when processes are

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still being figured out, your calendar is going

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to be heavily weighted towards execution.

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You're in the details, you're in customer conversations,

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you're building playbooks and sitting in on calls

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and sometimes doing the work alongside your CSMs,

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because that's how you understand what needs to

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be built.

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That's appropriate.

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And that's right for that phase.

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But here's where a lot of CS leaders

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get stuck.

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They never recalibrate, the org grows, the team

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expands, the complexity increases, and the leader is

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still spending their time the same way they

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did when the team was three people.

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Still in every escalation, still reviewing every renewal,

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still running every customer call that matters.

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And the team never develops because the leader

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never creates the space for them to lead.

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Scaling mode requires a fundamentally different calendar orientation,

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less execution, more enablement, less doing, more developing,

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less being in the work and more designing

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the systems that make the work run without

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you.

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I remember when this shift happened for me.

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I had built a team that was strong,

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genuinely capable people who knew their accounts and

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cared deeply about their customers.

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And I realized one day that I was

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selling their work in a way that wasn't

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serving them anymore.

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I was in account reviews, they could have

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led.

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I was in calls, they didn't need me

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on.

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And by being there, I was signaling unintentionally

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that I didn't fully trust them to handle

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it, that I needed to be involved for

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things to go well.

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That shift I made was to ask myself

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a different question every time something landed on

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my calendar.

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The question was not, can I add value

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here?

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The answer to the question is almost always

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yes.

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You can almost always add something.

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The question was, is my presence here the

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best use of my time given everything else

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I'm responsible for?

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The question produced very different answers.

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And it started freeing space for the work

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that only I could do.

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Let's get specific because I think the most

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useful thing I can give you in this

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episode is a clear picture of what belongs

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on your calendar as a protected, non-negotiable

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block.

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And why?

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First thing is to protect your strategic thinking

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time.

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And I want to be direct about this

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because I know how it sounds.

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Blocking time to think feels indulgent when your

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team needs things and your inbox is full

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and there are fires to put out.

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But here's the reality.

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The most important decisions you make as a

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customer success leader, how to structure the team,

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how to position CS internally, how to respond

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to a pattern you're seeing across your book,

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how to coach a leader on your team

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who is struggling.

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None of those decisions get made well in

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the margins.

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They require uninterrupted, focused thinking time.

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And if you don't protect it, it won't

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exist.

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What this looks like in practice.

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I'm talking about two to three blocks per

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week, maybe 60 to 90 minutes each when

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you're not in meetings, not responding to messages

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and not available.

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This is where you work on the org,

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strategy documents, coaching prep, thinking about a difficult

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decision, reviewing the health of the team's portfolio

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with a fresh eye, whatever is most important

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that week for you to give focused attention

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to.

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Protect it like you would protect a customer

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commitment because it is one, a commitment to

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leading your function well.

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The second thing is to protect your one

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-on-ones with your direct reports.

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And I don't just mean having them on

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a calendar.

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I mean having them consistently on time fully

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prepared and never canceling them.

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Your one-on-ones are your primary leadership

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tool.

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They are where you coach, where you assess

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performance, where you build the kind of trust

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that makes a teamwork.

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When you cancel them, especially when things are

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busy, which is exactly when your team needs

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them most, you send a signal.

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You signal that their development is optional.

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That when things get hard, the first thing

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to go is the investment in them.

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Protect your one-on-ones.

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Reschedule before you cancel and you show up

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to them prepared.

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The third thing to protect is your customer

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time.

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Even as you scale and delegate more operational

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work to your team, you should never fully

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disconnect from customers.

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You don't need to be in every account

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or every call, but you do need to

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stay connected somehow to the customer experience and

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keep it grounded in what your team is

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navigating.

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It sharpens your coaching.

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It gives you credibility in leadership conversations and

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it signals to your team that customer relationships

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matter to you.

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What this looks like at the VP level

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is deliberately selective.

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I'm talking about a handful of strategic accounts,

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executive relationships, escalation reviews.

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You don't have to have a full book.

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You need a curated presence.

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The fourth thing to protect is your own

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recovery time.

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I'm naming this explicitly because CS leaders are

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among the most prone to burning out quietly.

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The work is relentless.

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The demands are high and the culture of

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the function rewards responsiveness above almost everything else.

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You need wide space on your calendar, not

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as a luxury, as a leadership requirement.

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A leader who is depleted makes worse decisions,

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coaches less effectively and models an unsustainable pace

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for their team.

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Protect lunch, protect the end of your day,

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protect at least one morning a week where

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you're nodding back-to-back meetings from the

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moment you open your laptop.

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Let's talk about delegation.

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Delegation is where the calendar conversation gets really

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hard because most of the things that eat

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CS leaders' time are things they genuinely can

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add value to.

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The customer escalation, the renewal that's at risk,

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the cross-functional thing that's going sideways.

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Being in those things isn't wrong.

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The question is whether being in those things

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is the best use of your time at

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this stage or whether it's time to hand

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them to someone on your team.

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Here's the framework I'm wanting to use.

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There are three categories of work.

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Work that only you can do.

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Strategic decisions, leadership team, representation, work design, executive

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relationships, coaching your direct reports.

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This is your highest leverage work.

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It should be the center of gravity of

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your calendar.

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There's also work that your team can do

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with your input.

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Account strategy for complex situations, difficult customer conversations,

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cross-functional escalations that need a senior voice.

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This is where you're a resource.

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You don't have to be the owner.

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Your job here is to coach and advise

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and not to take over.

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And then there's work that your team can

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own entirely.

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Operational reporting, standard customer touch points, renewal execution

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for your healthy accounts, team rituals and meetings

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that don't require your presence.

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This is what gets delegated fully, not partially.

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The challenge for most customer success leaders is

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the middle category.

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They stay too involved in work their team

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can handle with input because it's hard to

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let go of things you're good at and

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care about.

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And I understand that feeling, but staying in

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the middle category at the expense of your

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highest leverage work is one of the most

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common ways CS leaders limit both their own

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impact and their team's development.

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Now here's the piece most CS leaders miss

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entirely when they think about delegation.

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It's not just about handing off operational work,

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it's about delegating strategic initiatives to your CSMs

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and doing it deliberately.

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So think about a work that lives on

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your to-do list that never gets done.

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The playbook that needs a full revamp, the

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onboarding process that's been patched together and needs

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a complete rethink.

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The QBR template that's outdated, the customer feedback

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loop that nobody has formalized.

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These are real strategic projects that matter for

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the health of your function.

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And they sit on your list quarter after

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quarter because you never have the bandwidth to

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give them the attention they deserve.

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Here's the shift.

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Those projects don't have to live on your

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list.

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They can live on a CSM's list as

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a stretch assignment, a development opportunity and a

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genuine contribution to the function.

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Delegating a strategic initiative to a CSM does

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two things simultaneously.

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It gets the work done and it develops

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the person doing it.

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A CSM's who leads a playbook revamp is

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building project management skills, cross-functional collaboration skills

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and the system's thinking muscle they wouldn't develop

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from account work alone.

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A CSM who owns a process improvement initiative

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is learning how to think about the function,

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not just your book.

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These are the experiences that build future CS

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leaders and you create them by giving your

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team real work with real ownership, not just

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more accounts.

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What this requires from you is a very

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different kind of involvement.

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You're not doing the work, but you're also

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not fully absent.

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You're setting the brief, what problem are we

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solving?

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What does success look like?

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What are the constraints?

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You're checking in at key milestones.

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You're available as a thinking partner when they

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get stuck and you're reviewing the output and

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giving meaningful feedback.

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That's the leader's role in delegated initiatives.

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Non-ownership, sponsorship.

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One practical move I'd recommend at the start

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of each quarter, do a calendar audit.

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Go through every recurring meeting on your calendar

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and ask two questions.

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Does this require my presence or could someone

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on my team lead it?

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And if I stopped attending this, what would

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actually happen?

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You'll be surprised how many meetings survive that

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question.

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And once they don't, those are your first

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delegation opportunities.

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Do the same thing with your strategic project

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list.

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For every initiative sitting on your plate, ask,

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is there someone on my team who could

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own this with the right brief and the

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right support?

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More often than not, the answer is yes.

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And handing it over with real ownership, not

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just task assignment is one of the highest

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leverage moves you can make as a scaling

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customer success leader.

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I wanna close this segment with something that

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took me longer than I'd like to admit

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to fully internalize.

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Letting go of things is not a sign

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that you don't care.

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It's a sign that you trust your team

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and a team that is trusted to lead,

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whether that's an account, a process or a

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strategic project, develops faster, performs better and ultimately

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00:13:59,900 --> 00:14:02,860
makes you more effective as a leader because

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they're carrying more, which means you can focus

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on what only you can do.

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Let's bring this together.

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First, your calendar is a leadership decision.

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Every block on it is either something you

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chose or something you allowed.

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Taking ownership of that distinction is a starting

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point for designing a calendar that actually reflects

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your priorities.

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Second, what your calendar looks like depends on

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where you are.

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Early stage, you're close to the work and

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that's right.

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Scaling, the shift is toward enablement systems and

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developing your team.

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The leaders who get stuck are the ones

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who never recalibrate as the org grows.

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Third, protect the non-negotiables, strategic thinking time,

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one-on-ones with your direct reports, selective

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00:14:43,320 --> 00:14:46,640
but deliberate customer presence and your own recovery

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time.

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These are not optional.

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00:14:48,420 --> 00:14:51,600
They are the foundation of sustainable high-impact

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00:14:51,600 --> 00:14:52,720
CS leadership.

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00:14:53,400 --> 00:14:55,280
And fourth, delegate with intention.

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Know the difference between work only you can

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00:14:58,000 --> 00:15:00,180
do, work your team can handle with your

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00:15:00,180 --> 00:15:02,680
input and work your team can own entirely

408
00:15:02,680 --> 00:15:05,680
and do a quarterly calendar audit to make

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00:15:05,680 --> 00:15:07,860
sure your time is actually distributed the way

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00:15:07,860 --> 00:15:09,120
you intend it to be.

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00:15:09,480 --> 00:15:10,900
Here's what I know from being in the

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VP of CS seat and from working with

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00:15:12,980 --> 00:15:15,460
CS leaders who are navigating exactly this.

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Designing your calendar well is one of the

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00:15:17,500 --> 00:15:19,440
highest leverage things you can do as a

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00:15:19,440 --> 00:15:19,680
leader.

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00:15:20,140 --> 00:15:21,900
Not because it may be more organized, but

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00:15:21,900 --> 00:15:24,140
because it changes what you're able to give

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00:15:24,140 --> 00:15:27,620
your team, your customers and your function when

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00:15:27,620 --> 00:15:30,520
you're operating from a place of intention rather

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00:15:30,520 --> 00:15:31,320
than reaction.

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00:15:31,320 --> 00:15:33,060
If you're in a season right now where

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you have the opportunity to be deliberate about

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00:15:35,860 --> 00:15:38,100
how you build your role, or if you're

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00:15:38,100 --> 00:15:39,900
feeling the weight of a calendar that's been

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00:15:39,900 --> 00:15:42,900
designed by everyone else's needs, that's exactly the

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00:15:42,900 --> 00:15:44,740
kind of conversation I have with CS leaders

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00:15:44,740 --> 00:15:47,380
in my one-on-one executive advisory and

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00:15:47,380 --> 00:15:48,160
coaching program.

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00:15:48,520 --> 00:15:50,240
Well, look at how you're spending your time,

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00:15:50,380 --> 00:15:53,120
what's actually driving your highest impact and how

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00:15:53,120 --> 00:15:55,840
to build a rhythm that's both sustainable and

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00:15:55,840 --> 00:15:56,320
strategic.

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00:15:56,800 --> 00:15:58,620
If that's where you are, I'd love to

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00:15:58,620 --> 00:15:59,360
work with you.

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00:15:59,360 --> 00:16:00,760
If you want to see if this is

437
00:16:00,760 --> 00:16:02,540
the right fit for where you are today,

438
00:16:02,820 --> 00:16:06,460
schedule a free consult call at csrevspeak.com

439
00:16:06,460 --> 00:16:07,780
forward slash coaching.

440
00:16:08,380 --> 00:16:09,500
Thanks for being here.

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00:16:09,680 --> 00:16:10,940
I'll see you in the next one.

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00:16:11,300 --> 00:16:13,780
If you enjoyed today's episode and you want

443
00:16:13,780 --> 00:16:16,460
to learn more about CS RevSpeaks coaching and

444
00:16:16,460 --> 00:16:20,940
training services, head on over to www.csrevspeak

445
00:16:20,940 --> 00:16:21,620
.com.

446
00:16:21,920 --> 00:16:24,580
I specialize in working with customer success leaders

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00:16:24,580 --> 00:16:27,080
who carry your revenue number, and I look

448
00:16:27,080 --> 00:16:29,880
forward to helping you confidently run a revenue

449
00:16:29,880 --> 00:16:31,660
-generating customer success team.

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00:16:32,240 --> 00:16:33,940
Don't forget to connect with us on LinkedIn

451
00:16:33,940 --> 00:16:37,200
and join our customer success leaders hub for

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00:16:37,200 --> 00:16:40,380
more discussions, resources, and networking opportunities.

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00:16:41,120 --> 00:16:42,440
You can access the links on the share

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00:16:42,440 --> 00:16:42,700
notes.

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00:16:43,300 --> 00:16:44,080
See you next episode.