Important questions to repeatedly ask your sales teams every day, week and month

Want to boost the value of your sales team? Get their feedback.

Your sales team isn't just a revenue engine - they're your frontline intelligence unit. Every conversation they have with prospects and customers is packed with insights that could reshape your product, refine your messaging, or unlock new markets. But too many leaders waste this goldmine of information by not asking the right questions. These daily exchanges contain vital clues about what's really working, what's falling flat, and where your biggest opportunities lie. And your sales reps? They're sitting on answers that could transform your business. You just need to know what to ask them.

These questions work best in a regular rhythm - some for weekly one-on-ones, and the more strategic ones for monthly reviews. The key is consistency in asking them so you can spot trends and changes over time.

Question 1: What are your top three deals closest to closing this week? Don't waste time reviewing the entire pipeline. Focus on what's hot and what needs immediate attention. This helps you identify where to concentrate resources and spot any last-minute roadblocks you can help remove.

Question 2: What’s the status of major in-progress deals? This was highlighted by Shreyas Doshi, who led and grew products at Twitter, Google and Stripe.

Question 3: What's the biggest obstacle preventing you from closing more deals? This cuts straight to problems you can actually solve. Maybe they need better sales collateral, faster response from technical teams, or help with pricing approval. Your job is to clear these roadblocks.

Question 4: Looking at last week's goals, what did you hit and miss? Start with a review of what they committed to. This builds accountability and helps identify patterns - are they consistently missing certain types of goals? Are they sandbagging? Setting unrealistic targets? The patterns tell you where coaching is needed.

Question 5: What support do you need from me this week? Make it specific to this week. This question shows you're ready to help while keeping the focus on immediate, actionable needs rather than vague wishes

Question 6: What are your specific goals for the next week? Make them commit to clear, measurable targets. Not just revenue goals, but specific actions: number of new prospects to contact, meetings to book, or proposals to send. This creates a clear benchmark to measure against in your next check-in.

Question 7:  Any new or surprising findings about the competition? Because your sales reps speak to many potential customers, their answer to this question will give you insights on what your customers are thinking.

Question 8: Which parts of your sales process are taking the most time? Time kills deals. If your rep is spending hours on proposals that could be templated or waiting days for internal approvals, that's where you need to focus your operational improvements.

Question 9: What's one thing we could change about our sales process to help you sell more? This is an improvement-focused question. Reps in the field often spot inefficiencies or opportunities that management can't see. This also shows you value their strategic input, not just their numbers.

Question 10: How are you tracking on your activity metrics? Whether it's calls, meetings, or proposals sent, these leading indicators tell you if future pipeline issues are brewing before they hit the revenue numbers.

Question 11: What's working well in your outreach that others should know about? Great reps often develop effective techniques that could benefit the whole team. This question helps you identify best practices while giving recognition to your top performers.

Question 12: Do you have any feature/pricing concerns? Because your sales reps speak to many potential customers, their answer to this question will give you insights on what your customers are thinking.

Your sales team speaks with ideal customers everyday. But this information often gets lost. By building a system for sales feedback, you are not only improving your sales team but also your core product and services.

Asking these questions repeatedly every week will give you many insights that will make you a better leader. With Progress Updates, you can customize the B2B Sales Feedback template, and send it to your team to automatically start getting quality feedback from your team everyday. 

Progress Updates has listed the important weekly questions and automatically set the schedule to Friday at 5:00 PM, so that everyone in your sales team will get these questions every week. Become a better leader by asking the right questions today.