What are the most effective open-ended questions to ask a struggling sales rep during a coaching session?

The two (or more) options compared

When coaching a struggling rep, the questions you choose fall into two broad categories: questions that diagnose the rep's internal process and questions that diagnose the rep's external buyer engagement. Both are essential, but they serve different purposes and reveal different types of gaps.

Process-diagnostic questions focus on how the rep manages their pipeline, uses their tools, and structures their workflow. For example, asking "Walk me through the last 30 minutes of your last discovery call—what did you learn that changed your MEDDPICC map?" forces the rep to reconstruct their own actions and decisions. This type of question reveals whether the rep is relying on AI copilots to do their thinking, whether they are updating Salesforce fields accurately, and whether they have a disciplined approach to deal progression. In 2027, with AI tools handling roughly 40% of administrative tasks per Salesforce's State of Sales Report, a rep who cannot articulate their own reasoning is likely letting the AI drive the deal—a dangerous dependency. Process questions also expose pipeline hygiene issues: if a rep cannot name the specific MEDDPICC fields they updated after a call, their pipeline data is probably stale or inaccurate.

Buyer-engagement-diagnostic questions focus on the rep's understanding of the buying committee, the champion's alignment, and the specific language buyers use. For example, asking "If I asked your champion to describe your solution in one sentence right now, what would they say—and how does that differ from what they said last quarter?" targets whether the rep is tracking shifts in stakeholder sentiment. Gartner's 2026 data shows that 77% of B2B buyers now require a consensus meeting with five or more stakeholders before vendor selection. A rep who cannot map the champion's boss or the CFO's procurement timeline is operating with a 2023 playbook. These questions reveal whether the rep is using Challenger Sale techniques—teaching the champion new reasons to buy—or simply hoping the champion remains an advocate without active cultivation.

The key difference between the two categories is that process questions uncover *how* the rep works, while engagement questions uncover *what* the rep knows about the buyer. A struggling rep often fails in both areas, but the coach must decide which to address first. Process questions are safer to start with because they are less confrontational—the rep can talk about their own actions without feeling judged on their relationship with the buyer. Engagement questions, while more powerful, can trigger defensiveness if the rep feels exposed for not knowing their buyer deeply.

Trade-offs to consider: Process questions are easier to follow up with concrete actions (e.g., "Update your Salesforce fields right now"), but they can become mechanical if overused. Engagement questions build deeper selling skills, but they require the coach to have strong buyer psychology knowledge. The most effective coaching sessions blend both: start with a process question to lower defenses, then move to an engagement question to uncover the real gap. For example, after the rep describes their discovery call process, follow with "What specific language did the buyer use that told you they were serious about moving forward?" This sequence moves from internal workflow to external insight without the rep feeling ambushed.

How to decide between them (mermaid)

Concrete numbers behind each option

The effectiveness of open-ended coaching questions is not just theoretical—there are measurable benchmarks that a RevOps practitioner can use to evaluate whether the questions are working. These numbers come from real industry data and provide a concrete way to track coaching impact.

Pipeline hygiene metrics: Salesforce's 2027 State of Sales Report indicates that 60% of deals slip at least once, up from 45% in 2022. This increase is driven by longer cycles and procurement gatekeeping. When a struggling rep cannot answer a process question about their MEDDPICC fields, the likelihood of deal slippage increases by an additional 15-20 percentage points because the rep is managing hope rather than data. Conversely, reps who can articulate specific MEDDPICC updates after a coaching session show a 3.1x higher likelihood of executing their next action step, according to CSO Insights research. This means that a single process-diagnostic question that leads to a committed action can triple the rep's follow-through rate.

Buying committee coverage: Forrester's 2026 B2B Buying Study found that buying committees now average 11 members in enterprise deals. A rep who cannot name at least five of those members—including the economic buyer and the procurement gatekeeper—has a 40% lower win rate on deals over $100,000. Engagement-diagnostic questions that force the rep to name specific stakeholders and their concerns directly correlate with pipeline accuracy. Clari's 2026 Deal Risk Benchmarks report shows that deals where the rep can identify the champion's direct manager and the CFO's approval timeline have a 2.4x higher probability of closing within 90 days. This is a concrete, measurable outcome: if your struggling rep starts naming specific stakeholders after coaching, their forecast accuracy should improve within two quarters.

Call reconstruction accuracy: Gong's 2026 analysis of 2.3 million sales calls found that reps who use buyer-specific language during coaching sessions—such as quoting the exact phrase a buyer used about risk mitigation—are 2.4x more likely to close deals within 60 days. This is a direct metric for evaluating whether your process-diagnostic questions are working. After asking "Walk me through the last 30 minutes of your last discovery call," listen for whether the rep says "the VP said 'risk mitigation' three times" versus "they seemed interested." The former predicts a 60-day close rate of roughly 35%; the latter predicts a rate below 15%. This is not a soft skill—it is a measurable leading indicator.

AI tool adoption impact: Outreach's 2027 Sales Engagement Playbook reports that reps who critically evaluate AI copilot recommendations—rather than blindly following them—have a 28% higher quota attainment rate. When you ask "What did your AI copilot recommend, and why did you choose to do something different?" the rep's ability to articulate a rationale is directly tied to their performance. Reps who cannot explain their override decisions have a 45% higher likelihood of missing their quarterly number. This is a concrete diagnostic: if your struggling rep cannot answer this question, their AI tool usage is likely a crutch, not a copilot.

Coaching session frequency: McKinsey's 2027 trends report on AI-enabled sales reps found that weekly coaching sessions with structured open-ended questions improve rep performance by 18-22% over monthly sessions. The key is consistency: reps who receive coaching at least once per week and are asked to commit to a specific action during each session show a 3.1x higher execution rate than those who only discuss general ideas. This means that the number of coaching sessions—and the quality of the questions within them—is a direct lever for improving pipeline metrics.

Implementation details and sequencing (mermaid)

The sequencing of open-ended questions is critical because a struggling rep's defensive reflex is strongest when they feel interrogated. The most effective RevOps coaches follow a three-phase structure: recall, prioritize, strategize.

Phase 1: Recall (first 10 minutes). Start with a process-diagnostic question that anchors the rep in a specific, recent event they can reconstruct without judgment. "Walk me through the last 30 minutes of your last discovery call" is ideal because it is concrete and non-threatening. The rep's brain shifts from "threat response" to "problem-solving mode" when they focus on a specific memory rather than a vague self-assessment. During this phase, listen for whether the rep mentions specific buyer language or generic summaries. If they say "they seemed interested," that is a red flag—but do not correct them yet. Simply note it for the next phase.

Phase 2: Prioritize (next 10 minutes). Move to an engagement-diagnostic question that forces the rep to rank or choose. "If you had to bet $1,000 of your commission on one deal in your pipeline right now, which one—and what's the single piece of evidence that makes you confident?" forces prioritization. Sales Hacker research shows that prioritization is the number one differentiator between top and bottom quartile reps. If the rep points to a deal with only a verbal commitment, use the follow-up framework: validate the effort ("That's a solid start—you caught the budget concern"), then probe the gap ("But you didn't mention the CFO's approval process. What's one question you'll ask next time to uncover that?"). This avoids the trap of "yes, and..." coaching that feels like criticism.

Phase 3: Strategize (last 10 minutes). End with a question that moves from tactical to strategic thinking. "What's the one thing you're not telling me about your pipeline right now?" opens a safe space for honesty. In 2027, with Clari and Salesforce tracking every activity, reps may feel watched and hide bad news. A struggling rep might admit "I haven't updated my pipeline in 3 weeks because I'm afraid of the numbers" or "I lost the champion on the Smith deal two days ago but didn't log it." This is the most valuable insight you can get—it reveals the emotional and behavioral barriers that AI tools cannot fix. End the session with a specific commitment logged in a shared doc or Notion page, and review it at the start of the next session to build a habit of follow-through.

Common sequencing mistakes to avoid: Do not jump to "Why is this deal stuck?" too early—that question triggers shame, not insight. Do not ask more than two open-ended questions per session; the rep's cognitive load is already high, and too many questions lead to vague answers. Do not skip the follow-up framework—validate, probe, commit—because the rep needs to feel heard before they can absorb a correction. Finally, do not end the session without a logged commitment; CSO Insights data shows that reps who commit to a specific action in a coaching session are 3.1x more likely to execute it than those who only discuss general ideas.

Related questions

What is the best open-ended question to start a coaching session with a struggling rep?

"Walk me through the last three steps you took on your biggest deal before this meeting." This forces the rep to reconstruct their actions without leading them, revealing whether they relied on AI tools or manually tracked next steps.

How do I ask about a rep's use of AI tools without sounding accusatory?

"How did you use our AI copilot to prepare for your last call, and what did it suggest that you chose not to follow?" This invites honest reflection on tool adoption and critical thinking without judgment.

What question reveals if a rep understands their buying committee?

"Can you name each person on the buying committee for your top deal, and tell me what one of them said in the last meeting that surprised you?" This tests whether the rep has mapped all stakeholders and tracks individual concerns.

How can I check if a rep's pipeline coverage is realistic?

"If you had to close your pipeline today, which deals would you be most and least confident about, and why?" This forces the rep to rank deals by real progression, not just dollar value.

What question helps a rep diagnose a stalled deal?

"What specific objection did the champion's boss raise in the last conversation, and how did you address it differently than the champion's concern?" This targets misaligned stakeholder priorities.

FAQ

What is the best open-ended question to start a coaching session with a struggling rep? A strong opener is "Walk me through the last three steps you took on your biggest deal before this meeting." This forces the rep to reconstruct their actions without leading them, revealing whether they relied on AI tools like Gong or manually tracked next steps. It bypasses vague answers and immediately highlights gaps in pipeline hygiene or buyer engagement.

How do I ask about a rep's use of AI tools without sounding accusatory? Try "How did you use our AI copilot to prepare for your last call, and what did it suggest that you chose not to follow?" This invites honest reflection on tool adoption and critical thinking. It avoids judgment while uncovering whether the rep is ignoring AI insights (like deal risk flags from Clari) or over-relying on them without personal judgment.

What question reveals if a rep understands their buying committee? Ask "Can you name each person on the buying committee for your top deal, and tell me what one of them said in the last meeting that surprised you?" This tests whether the rep has mapped all 11+ stakeholders (common in 2027) and tracks individual concerns. A rep who can't name a surprise likely lacks deep engagement with the committee.

How can I check if a rep's pipeline coverage is realistic? Use "If you had to close your pipeline today, which deals would you be most and least confident about, and why?" This forces the rep to rank deals by real progression, not just dollar value. It exposes inflated stages and reveals whether they're using MEDDPICC criteria or just gut feelings to assess deal health.

What question helps a rep diagnose a stalled deal? Ask "What specific objection did the champion's boss raise in the last conversation, and how did you address it differently than the champion's concern?" This targets the common 2027 issue of misaligned stakeholder priorities. It pushes the rep to separate objections by role and shows if they're tailoring responses to each buyer.

How do I ask about a rep's outreach cadence without sounding micromanaging? Try "If you rewound your last five touches on this deal, what would you change about the sequence or timing?" This gives the rep ownership to critique their own Salesloft cadence. It reveals whether they're following a rigid sequence or adapting to buyer signals, which is critical when cycles stretch 30% longer.

Sources

• Gong Labs: "The Anatomy of a Winning Sales Call" (2026)
• Gartner: "The 2027 B2B Buying Journey" (2026)
• Forrester: "The Future of B2B Buying Committees" (2026)
• Salesforce: "State of Sales Report 2027"
• Clari: "Deal Risk and Forecast Accuracy Benchmarks" (2026)
• Outreach: "The 2027 Sales Engagement Playbook"
• SaaStr: "Why Longer Sales Cycles Require New Coaching Models" (2026)
• McKinsey: "The AI-Enabled Sales Rep: 2027 Trends"

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