Executive Assistance & CSM Support Maturity Assessment

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1. Executive Time Protection

How much of a leader's day is protected for real, focused work?

Leaders' calendars are wide open to whoever books time, little is protected. Some time is blocked, but it gets overridden often. Focused time is protected and defended, even under pressure. Other / Describe

2. Decision Follow-Through

Once a leader makes a decision, how reliably does it actually get carried out?

Decisions get made but often stall without anyone driving them forward. Follow-through happens, but the leader has to check in to keep it moving. Decisions move forward without the leader having to track them personally. Other / Describe

3. Inbox & Calendar Ownership

How much day-to-day management does a leader's inbox and calendar require from them personally?

The leader manages their own inbox and calendar day to day. Someone helps, but the leader still makes most of the calls. Inbox and calendar are run end-to-end by someone else, with minimal leader input. Other / Describe

4. Delegation Clarity

When a leader delegates something, how much direction does it take?

Delegation requires detailed, step-by-step instructions every time. A stated outcome works sometimes, but often needs follow-up direction. A stated outcome is enough, the details get figured out without the leader's input. Other / Describe

5. Travel & Logistics Coordination

How is travel and event logistics handled for leadership?

Leaders book and manage their own travel and logistics. Support exists, but the leader still fields last-minute issues. Travel and logistics are fully coordinated, with issues resolved before the leader knows about them. Other / Describe

6. Onboarding & Handoff

When a deal closes, how does the customer move from sales into onboarding?

Information gets lost in the handoff, and the customer repeats themselves. A handoff process exists, but it isn't always followed. A documented handoff protects scope, stakeholders, and timeline every time. Other / Describe

7. Health Scoring & Risk Visibility

How do you know a customer account is at risk before they tell you?

We usually find out when the customer raises a complaint or churns. Some health signals are tracked, but action on them is inconsistent. Health scores flag risk early and trigger a clear response plan. Other / Describe

8. Renewal & Expansion Process

How does your team approach an upcoming renewal or expansion opportunity?

Renewal conversations start reactively, close to the renewal date. There's a general process, but timing and ownership vary by account. Renewals and expansion are planned well ahead, with a consistent, owned process. Other / Describe

9. Customer Playbook & Documentation

If your most experienced Customer Success Manager left tomorrow, what happens to their account knowledge?

It leaves with them, most of it lives in their head. Some documentation exists, but it's outdated or inconsistently used. A living playbook captures account knowledge and is used to onboard replacements fast. Other / Describe

10. Escalation & Support Response

When a customer issue needs to escalate, how does that happen?

Escalation is ad hoc, it depends on who the customer happens to reach. A path exists, but response time and ownership are inconsistent. Escalation has a clear path, owner, and response time that's consistently met. Other / Describe

How mature is your executive support and customer success?