The Most Important Question in Sales Operations

September 9, 2016 Mark Emmons


Sales operations pros are usually the people with all the answers. They’re the ones who can explain everything about how the company’s sales process works . . . and, of course, provide password information for forgetful reps.

But the most important question can be the one they ask themselves. Brian Belli, the sales ops lead with DataFox, explained what that means in a recent webinar. Belli said he constantly challenges himself with one, simple word.


“I think it’s really important to be able to answer ‘Why?’” he added. “Why did you purchase that tool? Why is the sales org set up that way? If you can answer those questions, it means you’ve been really thoughtful in setting up that process and those tools. And if I don’t have a good answer, I know it’s time to re-evaluate.”

Elaine Mao takes that idea one step further. She believes that you better have a good answer for yourself because you’ll always be asked to defend why a system operates the way it does.

“If I don’t know why I’m doing something or I wouldn’t want to do it myself, then I’m sure not going to ask my sales reps to do it,” said Mao, the head of sales strategy and operations/business development at ride-sharing giant Uber.

56206868_9ea35e3694_zThink of sales ops as the “left brain” of the sales team. Logical. Analytical. Objective. And practitioners are always scouring through the data as they look for insights to either confirm that the team is on the right path, or if a course-correction is needed. They have an obsession with detail.

That kind of systemic approach ensures that critical decisions determining the fate of a business are not made on intuition or gut feelings.

“In some ways, your job is to be the Devil’s advocate and question everything,” said Jonathon J. Leon Guerrero, who oversees sales ops at LeanData. “Sometimes it can seem like you’re challenging your manager when you keep asking why we’re doing something in a certain way. But that’s not it. You’re questioning the process to see if we can do it better. That’s your role.”

There’s not one, single roadmap to building a sales machine. Every organization is different. And even when a business finds a formula for success, the search for a better way never ends.

So, there’s always a long laundry list of “why” questions. Why these territories? Why this SDR-Account Executive ratio? Why this round-robin system for leads? Why this comp plan? Why do some deals close fast while others never close at all?

“I even wonder sometimes why I’m running some reports and if they’re giving me the information I need to answer some of those other questions,” Leon Guerrero added.

And the answers are always changing because the data always changes. Nothing stays the same.

Dhiraj Singh, the inside sales and operations manager at real-time memory database MemSQL, said when you’re a startup that’s scaling the sales team quickly, you’re making decisions on the best-available information.

But the data is always evolving. So you need to be able to communicate why tweaks are being made, he added.

“Your team always needs to understand why a decision was made the first time and why it’s changing now,” Singh said. “It needs to be logical, straightforward and based on data. It shows that decisions are coming from a well-informed place. That gives you the freedom to experiment. All parties involved need to understand that sound reasoning and logic are being used.”

Doug Landis, the vice president of sales productivity and chief storyteller at online file storage company Box, agrees that it’s “super-important” to always be asking questions. But he also offers a caveat. Just because sales ops pros are the people living in the data doesn’t necessarily mean they know everything.

And sometimes a we’re-the-experts attitude can be a source of friction between sales ops and the reps, he added.

“You can’t be afraid to look to others to give you an additional perspective,” said Landis, who previously was the vice president of sales productivity at Box.

Let’s say sales wants to try something new or use a different tool. Sales ops doesn’t see the value. Landis argues that there shouldn’t be an automatic assumption that the sales team’s position has no merit.

“Sales ops needs to understand that they aren’t the only ones with answers,” he added. “But I find that happens a lot in sales ops. Remember at the end of the day, we all work for sales. Our ultimate goal needs to be to make their life easier so that they’re faster, smarter and better. So that ‘why’ question should be asked of the entire sales organization.”

The answer to “why” impacts everyone. But nobody feels that weight more than the people asking the question.





About the Author

Mark Emmons

Mark Emmons is the staff writer at LeanData. He previously was a reporter at the San Jose Mercury News, Orange County Register and Detroit Free Press. He can be reached at

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