11 Key Questions Every Successful Sales Ops Leader Must Answer

In sales operations, all the data in the world isn’t going to help if you never take action on it. It’s easy to get caught up in analysis paralysis when you chase facts and figures and insight down every line of questioning. Like tracking hundreds KPIs, there’s no way that any of your questions can be considered ‘key’ when all of them are. Here’s how to optimize your sales operations questions so you can keep implementing, not just investigating.

sales operations questions

10 min. read

Sales ops are known for having the answers to sales success. But are you asking the right questions?

A good sales ops leader should question the status quo, asking questions not just of their team members and cross-departmental colleagues but also examining the data they’re collecting and the customers they’re serving.

Research and data are good but taking action is better. Without a framework, you can get caught in the research trap, always investigating but rarely doing anything with the answers you’re getting.

So, I analyzed more than 25 interviews with successful sales operations leaders to get insight on how they frame their approach to sales ops. What questions are they asking? What are the answers they’re seeking out?

Many valuable ideas kept coming up over and over again in these conversations. But here’s the best part: in this post, I’ve distilled them down to the 11 questions that are most vital to sales ops success.

10 questions sales ops leaders need to know the answers to


1. Are my strategies aligned with top-level company objectives?

You can’t be so focused on the frontline salespeople that you forget about the C-suite and overall company goals.

What are the priorities for the entire organization? For example, here at Proposify, the leadership team picks one big goal to focus on each quarter. We don’t abandon our ongoing activities but pivot them or pick up new tasks to work toward the goal over the 12 weeks.

It’s important to have good data so you can show what is or isn’t moving the needle on the higher-level goals. You’ll also need to be able to back up your data with insight and analysis to back up what you’re doing.

Have a separate dashboard that boils down your sales ops activities to show the leadership team how you’re doing on those big targets and save your more granular spreadsheet for yourself.

If you don’t have a good process in place for this, you’re not alone. Lack of back-and-forth flow of information between sales operations and company leadership appears to be a wide-spread issue. A full 60% of sales operations cite delivering key decision-making data to executives as a high-priority area for improvement in 2019 and 2020.

2. How aligned are your departments?

A common thread throughout the interviews with sales ops leaders was, how can we find better alignment between departments?

A common solution for this issue was to approach work areas like projects instead. For example, using this set-up, sales operations, sales, and marketing would all work on the sales pipeline project together. The project-based approach creates teams within and across departments to help with communication and alignment.

Delineating which KPIs and corresponding data will be shared and which remain with their respective departments helps keep information flowing without unnecessary overlaps or duplication.

Danielle Wegenstein’s role specifically straddles this gap as director of marketing & sales ops at Sight Machine. She explains how she and her team decide the level of detail included in each team’s CRM.

“A good example of what is captured in our marketing CRM versus the sales CRM is all the email content and nurturing tracks. This is specific to the marketing CRM and not necessary from a visibility standpoint in Salesforce. What is captured in our sales CRM is the campaign level detail, allowing the salesperson to see which campaigns an individual lead or contact has gone through.”

3. How well do you know how your salespeople are actually selling?

It’s hard to have a positive influence on people and processes you don’t understand. Do you know how your salespeople sell?

Not what’s on paper or in your sales playbook. How are they conducting their calls and doing demos? Are they following sales processes or are they going rogue? Is there a disparity between the analytics and the actual experience?

This is where sales ops leaders need to put in the time listening to calls and talking to reps. It’s impossible to create your strategy in a vacuum.

Data & Tech

4. Are there any gaps in your process or cliffs in your data?

Watch the seams of your sales process for any cracks that deals could slip through. Lead handoffs are especially prone to gaps, as marketing passes leads to sales and sales passes clients to customer success. How can you patch these processes?

Also, keep an eye out for steep dropoffs in your sales data to diagnose process issues. This time it’s gaps in your sales funnel that you’ll need to fix.

If the data shows that leads are entering the top of the funnel and then bouncing or making it to the contract stage and disappearing, you’ll know which team members (marketing and your account executives, respectively) you need to work with to get that data trending in the right direction.

5. How clean is your data?

What are you measuring? Is the data you’re receiving biased or clouded in any way? Is there enough context to know?

When Anna Inman started in her sales ops role, the jumping-off point was not just diving into the existing data but assessing and thinking critically about its usefulness. “Starting with lead gen, I had to understand what a good lead looks like,” says Inman, sales operations director, Tungsten Network. “Is this a real lead or is someone selecting the wrong information, and so on.

“For me, it was really understanding sales data, what our CRM was telling us and could tell us and what that could mean to the sales team.”

6. How can we improve our tech stack?

What tools are you using? How many? Do you have dozens of single-use apps or a couple robust but clunky tools?

You have to look at whether your tools are making your salespeople more or less efficient. High performing sales teams use three times more sales tech than underperforming ones. But don’t just throw apps and other tools at your team for the sake of building a bigger tech stack. Don’t assume that every step in the sales process needs a tool.

Brandon Bussey, director of sales operations at collaboration software company Lucid, says that involving his sales leaders and reps in the procurement process helps him make good tech decisions. Together, everyone agrees on where their biggest tech gaps are and then start identifying tools that will bridge those gaps.

Doing things this way “doesn’t feel like Brandon from his glass castle is making decisions by himself. It’s their choice as much as mine,” says Bussey.


7. Are we optimizing processes for the entire buyer’s journey?

A few sales ops pros mentioned how ignoring the urge to go for all ‘quick wins’ at the top of the sales funnel but ignoring bottom-of-funnel friction can torpedo your strategy.

For example, you could drastically reduce your team’s average sales cycle length, but that accomplishment won’t mean much if deals get tied up in endless negotiations at the point of sale because your contract is convoluted or your proposal is unproductive.

The pros suggest following the buyer’s journey and removing friction felt there first. Instead of making internal processes easier for your sales and success teams, focus on making it easy for your customers to buy.

Check out this post from Proposify’s own director of sales, Daniel Hebert, on how sales ops and enablement efforts tend to fall short mid-funnel and how to fix it.

8. How scalable and accurate are your sales processes and tasks?

Always be looking for ways to streamline your sales team’s processes. It’s a constant balance between moving fast and getting it right.

Administrative tasks are a great example. If your CRM process is too time-consuming, it will eat into your sales team’s selling time. If your reps are rushing through or ignoring this type of admin, your team won’t have the data and insights they need later in the sales process or down the road when there’s an opportunity for another purchase, a renewal or an upsell.

Sales reps at organizations with high CRM use nearly double the amount of time they spend selling and spend less time on post-sales and admin tasks.


9. What’s my ratio between analysis and action?

How much time do you spend collecting the data versus actually doing the things? And how actionable is the data you’re collecting?

Successful sales ops should move fast. You can’t get caught up in waiting for ‘perfect’ data, ‘ideal’ conditions, or 100-percent go-ahead. Experiment and try things out, while measuring and evaluating.

The sales ops pros agreed that you need data and insight, but too much leads to either analysis paralysis or information overload. How can you move things forward?

Get good context for your data and then get buy-in from the people the action will impact, says Stephen Haltom, director of sales operations at AppDynamics.

“In terms of articulating findings to the relevant people, data is only great to a certain point. I heard a great quote a couple of years ago at Dreamforce: if data is king then context is God.

“Anytime you show something, especially if it’s controversial or challenges the status quo, a sales leader is going to have questions. So, it’s about presenting the data in a way that’s very easy to digest while proving that you understand the context of what you’re talking about. Then if they disagree with the proposed solution, that’s fine, you can go from there and brainstorm the right solution but getting buy-in on the issue is really the key to me.”

10. Am I using my soft skills to my advantage?

Soft skills are often pointed to as an important factor in hiring for sales ops positions, but they shouldn’t be left sitting on your resume once you’re on the job.

You can’t spend all your time with your nose in a spreadsheet or dashboard, dissecting the data. Ideally, you have a mix of ‘hard’ analytical expertise and ‘soft’ interpersonal skills. Your hard skills help you create the strategy and then your soft skills help you implement it.

This means you need to be able to have difficult, yet productive, conversations with your team. Giving feedback or implementing change can be tough. Numbers are great to back up your strategy but the ability to convey your message with tact and persuasion will go a long way.

Internal politics is a big sales time-waster and barrier to success. More than a quarter of sales leaders and sales reps cite managing in-house power struggles as their biggest challenge, so any way you can build bridges, not fences, helps.

“Because it’s a very emotive piece, a salesperson arguing with sales ops, and it happens all the time. But if you can manage to take the emotion out of it and make it a very fact-based clear conversation, it makes things a lot easier. And that’s something I’ve learned over the years. Once you figure that out it becomes, it becomes a lot easier,” says Robin Yeoman, director of international sales operations at Snowflake Computing.

Measuring Success

11. What does success look like?

Sales rep success tends to be straightforward. Measuring sales ops success, however, is trickier, especially when you consider that many aspects are outside your direct control.

That doesn’t mean building a byzantine maze of processes, a pile of tools that just drive up acquisition costs, or so much content to dig through that nobody ever uses it. Pick your KPIs and stick to them.

Here are the most popular ones mentioned by the sales ops pros:

Conversions—average win rate, average deal size, revenue per sales rep

Velocity—average sales cycle length, lead response time

Benchmarks—pipeline value and efficiency, forecast accuracy

Behaviours—time spent selling, meetings set

But sometimes measuring success in sales ops can go beyond numbers and data. Jesse Schreiber, director of sales ops and program management at Ibotta, explains:

“A lot of what I’m measured against is feedback from all of the teams that I’m working with, related to what tools I implement, what tools I take away and enhancements my team drives.

We can gather that sort of peer and team feedback via survey at mid-year and end of year.”

Sales ops questions and answers

If there’s one thing I learned from reviewing dozens of interviews with sales ops leaders, it’s that the best ones are not only continually asking good questions, but they’re also seeking out better answers.

How will you step up your sales ops Q&A game?

11 Key Questions Every Successful Sales Ops Leader Must Answer

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