New in Your Leadership Role? The Essential Salesforce Questions to Ask in Your First 30 Days
According to the Harvard Business Review, the average tenure for a Chief Revenue Officer is 25 months, and for a sales leader, it's just 19 months.
Chances are, you’re fairly new to your sales or marketing leadership role. In the first few months, the pressure is on to understand the business and drive results. You’re focused on closing deals and making an immediate impact. But then, a frustrating reality sets in: you can’t get the clear, reliable data you need to make strategic decisions.
That’s the moment you realize your Salesforce admin is about to become your new best friend.
In our experience, your admin holds the keys to understanding the history, strengths, and weaknesses of your company's most critical system. They know who the super-users are, where the data gets messy, and which processes are frustrating your team. We recommend meeting with them within your first 30 days.
To get the conversation started, here is a comprehensive guide to the questions you should ask to get a true assessment of your Salesforce instance.
Your Salesforce Diagnostic Checklist
Instead of just asking for a demo, use these questions to dig deeper into the six critical areas of your CRM health.
1. Data Quality & System Structure
Your strategy is only as good as the data it’s built on. Your first priority is to understand the integrity of your data foundation.
What are the biggest data quality issues I should be aware of? (e.g., duplicate records, incomplete fields, outdated contacts)
How is data currently maintained, archived, or cleaned over time?
Which picklist values are actively used versus outdated?
Are there any underutilized fields or objects in Salesforce that could add significant value if used properly?
2. Pipeline & Opportunity Management
A well-defined sales process in Salesforce is non-negotiable for predictable forecasting and revenue growth.
What are the defined stages in our sales process, and how consistently does the team use them?
How is pipeline health measured? What reports track deal velocity or pipeline slippage?
How are territories assigned and managed within the system?
What are the rules for account and contact ownership? How is this managed?
Which specific fields in Salesforce support the commission process?
3. Lead Management & Marketing Handoff
For marketing and sales to be aligned, the handoff process must be seamless and clearly defined in your CRM.
How do leads get into Salesforce? (e.g., web forms, list uploads, integrations)
How are Marketing Qualified Leads (MQLs) defined and tracked?
What are the exact criteria for converting a lead to an opportunity, and what is the handoff process to sales?
4. Team Adoption & User Experience
If your team finds Salesforce frustrating, they won’t use it effectively. Adoption is everything.
How does the sales team really use the system day-to-day?
What are the most common complaints or frustrations you hear from the sales team about Salesforce?
Are there any validation rules or required fields that slow reps down?
How are new sales reps onboarded and trained on Salesforce? What reference materials exist?
5. Automation & Integrations
Automation should help your team, not hinder them. Understand what’s happening behind the scenes.
What key automations are in place to support the sales team? (e.g., task creation, email alerts, field updates)
Are there frequent errors or issues with current automations that I should know about?
What other systems are integrated with Salesforce (e.g., marketing automation, email, calendar), and how do they interact?
6. Governance & Strategic Alignment
Finally, understand how Salesforce will adapt and grow with your new strategic vision.
What is the process for requesting and approving changes to Salesforce?
Which key dashboards do our executives monitor?
What are the top 3-5 reports or dashboards I should monitor weekly to understand team activity and performance?
Turning Answers into Action
The answers to these questions will give you a rapid diagnosis of your CRM's health. You'll quickly learn where processes are broken, where data is unreliable, and where your team needs more support.
As a new leader, your time is your most valuable asset. Spending it trying to untangle years of technical debt isn't the best use of your first crucial months. If your discovery session reveals more problems than solutions, know that you aren't alone.
At Walden Edge, we specialize in helping sales and marketing leaders like you transform Salesforce from a cluttered database into a powerful engine for growth. When you’re ready to build a system that gives you clarity and control, let’s talk.
