The Order of Operations for Questions: A RevOps Approach

Last week, I had the privilege of speaking at the HubSpot Admin User Group on the topic of RevOps strategy. The session was an opportunity to unpack how effective RevOps can transform your business—but only if built on the foundation of asking the right questions, in the right order.

This blog post builds on that conversation, focusing on the role of questions in guiding strategy, with practical advice for leaders looking to unlock growth through alignment and thoughtful inquiry.

Context Matters  

Before diving in, let me share something I believe deeply: context is everything. To create meaningful change, you need to understand where you’re starting from and where you want to go. This principle applies to RevOps just as much as it applies to personal growth or team alignment.  

When tackling RevOps, many people jump straight into tactics—tools, reports, automations—without stopping to align their teams or clarify the goals they’re working toward. That’s a mistake. Success in RevOps starts not with what you’re doing but with who you’re doing it for and why it matters.  

This is where the right questions come in.

The Problem with Asking the Wrong Questions

We often rush to ask “what” questions:

• What tools do we need?
• What processes should we automate?
• What reports should we build? 

These are important, but if we don’t start with who and why, we risk creating solutions that miss the mark. Misaligned initiatives lead to unreliable data, fragmented teams, and a lack of trust in systems and processes—all problems RevOps is designed to solve.

The Order of Operations for Questions

Here’s the hierarchy I shared during my talk, which guides the type and order of questions we should ask when building a RevOps framework:

1. Who:

• Who is our best customer?
• Who needs to be involved in this process?
• Who stands to benefit most from this solution?

These questions anchor your efforts in relationships—whether with your customers, team, or stakeholders. They remind us that every process, platform, or priority serves people first.  

2. Why:

• Why do we need to address this issue?
• Why is this a priority for our team?
• Why do these customers choose us over competitors?  

Once you’ve identified the “who,” asking “why” ensures you’re solving the right problems and clarifies your purpose. Without a compelling “why,” it’s easy to lose focus or fall into “random acts of RevOps.”

3. What:

• What are the specific pain points or opportunities?
• What can we do to align our efforts with customer needs?

What tools or processes will help us execute our strategy?

Only after “who” and “why” should you define the specifics of what needs to be done.

4. When:

• When is the best time to implement changes?
• When should we expect to see results?
• When do our customers need us the most?

Timing is everything. Well-timed actions can amplify impact and prevent wasted effort.

5. How:

• How will we execute our plan?
• How do we measure success?
• How can we improve our approach?  

“How” questions address the practical execution, but they’re most effective when built on a solid foundation of the previous four steps.

Applying the Framework in RevOps

When you apply this order of operations to RevOps, it helps you align your people, priorities, processes, and platform—the four pillars of any effective RevOps strategy.

For example:

• People: Who needs to be involved in this initiative to ensure alignment?
• Priorities: Why is team alignment more critical than automation at this stage?
• Process: What workflows need to change to reflect our priorities
• Platform: How can we use HubSpot to support this strategy?

Starting with people and priorities ensures you’re building solutions that are scalable and meaningful—not just technical Band-Aids.  

Asking Better Questions, Consistently

To truly embrace this approach, develop a habit of asking intentional questions regularly. I’ve found that asking one thoughtful question each week keeps my team aligned and focused.

For example:  

• If our systems were down, what would you focus on today? Why
• What can we do this week to create a better experience for our best customers? 

These questions prompt deeper thinking and guide teams toward impactful solutions, making them better equipped to iterate and innovate.

Closing Thoughts

C.S. Lewis once said,

“You can’t go back and change the beginning, but you can start where you are and change the ending.”

Whether you’re just beginning your RevOps journey or looking to refine an existing strategy, it’s never too late to ask better questions and realign your approach.  

By following this framework—starting with “who” and working your way to “how”—you’ll not only create better alignment and stronger strategies but also empower your team to navigate challenges with clarity and purpose.  

Now, it’s your turn: What questions will you ask your team this week? Share them in the comments below—I’d love to hear your thoughts!