Coaching underperforming sales representatives is one of the most challenging yet consequential responsibilities a sales leader carries. It requires balancing empathy with accountability, strategic thinking with tactical execution, and short-term pressure with long-term development.
When a salesperson is underperforming, the immediate impulse is often to reprimand or push harder to meet targets. That approach rarely works, and more often than not, it compounds the problem. A more effective path is one that addresses the root causes of poor performance, provides actionable guidance, and invests in the individual's development. Underperformance can stem from any number of factors: lack of motivation, inadequate skills, poor product knowledge, unclear expectations, or even personal circumstances outside of work. As a sales coach, your role is to identify which of those factors is actually at play, then build a response that helps the rep regain traction.
Start with an Honest and Open Conversation
The first step is creating a safe environment where the salesperson feels comfortable discussing their challenges. Rather than opening with metrics and missed targets, start with questions: "How do you feel about your performance recently?" or "What do you think is the biggest obstacle holding you back right now?"
The goal of this initial conversation is to understand the salesperson's perspective and gather as much useful information as possible. Listen actively. Resist the urge to jump to conclusions or offer solutions too early. When you approach the conversation with curiosity rather than judgment, you signal that you're there to support growth, not issue a verdict. That distinction matters enormously. It's what creates the conditions for honest answers, and honest answers are what make coaching actually work.
Identify the Root Cause of the Underperformance
Underperformance is almost always a symptom. Diagnosing the actual cause before developing any coaching strategy is what separates effective managers from reactive ones. Common root causes include lack of motivation, unclear goals, inadequate training, poor time management, and misalignment between the rep's strengths and their current role.
Consider a rep who's consistently missing targets because they're not prospecting enough. The issue might not be a lack of effort. It could be a lack of confidence in prospecting skills, in which case additional training and role-play exercises will accomplish far more than a conversation about call volume. If the issue is motivation, the more productive path is exploring what drives that person and setting goals that align with their intrinsic motivators rather than simply reasserting quota.
The Five Whys method is a practical tool here. Start by asking why the salesperson isn't meeting their target. When you get an answer, ask why again. Repeat five times. The depth you reach by the end of that sequence is usually where the real coaching work begins.
Create a Personalized Development Plan
Once you've identified the root cause, the next step is building a plan, and that plan should be co-created, not handed down. When sales reps are involved in setting their own goals, their commitment to reaching them is substantially higher. This is how the brain works: ownership activates follow-through in ways that compliance rarely does.
The development plan should include specific, measurable goals, clear action steps, and a realistic timeline. Keep the focus on building skills and restoring confidence. If product knowledge is the gap, the plan might include dedicated study time, shadowing top performers, or practicing product demonstrations in low-stakes settings. If time management is the issue, it might mean restructuring the rep's daily schedule and identifying the two or three activities with the highest impact on pipeline.
Setting small, incremental targets is often more effective than attempting a wholesale performance overhaul. A rep struggling to book 20 meetings per month can start with a goal of 5 per week. A smaller target creates a shorter feedback loop: the rep sees progress faster, positive reinforcement kicks in earlier, and momentum builds from there.
Provide Ongoing Support and Accountability
A development plan without consistent follow-through is just a document. The work of coaching happens in the space between check-ins: reinforcing new behaviors, catching setbacks early, and adjusting the plan when circumstances change. Scheduling regular one-on-ones focused specifically on progress, wins, and obstacles is non-negotiable.
During these sessions, ask questions that invite honest reflection: "What progress have you made since we last spoke?" and "What's getting in the way right now?" Use those answers to calibrate the plan and signal that continuous improvement matters more than perfection. Accountability should be framed around growth, not consequences. The rep who is clear on what they're working toward, and who believes their manager is invested in helping them get there, is far more likely to push through difficulty than one who feels monitored.
Leverage Strengths to Build Confidence
Underperforming salespeople often lose confidence before they lose their skills. The downward spiral, where low confidence produces poor results which further erode confidence, is real and common. One of the most effective ways to interrupt it is to anchor the coaching work in what the rep does well.
Take time to identify genuine strengths and build from there. If a rep excels at building trust with clients but struggles with closing, use that strength as a foundation. Help them develop a closing approach that's consistent with their natural ability to create connection. A strengths-based coaching strategy doesn't avoid weaknesses; it addresses them from a position of confidence rather than deficit. Reps who feel capable in at least one dimension of their work are more receptive to feedback and more willing to engage with areas that need development.
Implement Quick Wins to Build Momentum
Quick wins are small, achievable objectives that generate early proof of progress. For an underperforming rep, a quick win might be securing one new meeting this week or successfully handling a common objection during a role-play session. These small victories matter more than they might seem. Success produces the neurochemical conditions that make more success likely: the brain's reward pathways reinforce the behaviors that led to the win, increasing the probability that those behaviors repeat.
When coaching someone who is struggling, create early opportunities for success deliberately. Don't wait for a big result to recognize progress. Identify what a small but meaningful win looks like in the first week, celebrate it when it happens, and build from there. As positive outcomes accumulate, the rep's mindset shifts, and the whole coaching arc accelerates.
Know When to Make Tough Decisions
Coaching is an investment, and most of the time it pays off. But there are situations where improvement isn't happening despite sustained effort on both sides. When a salesperson consistently fails to meet expectations and shows no meaningful progress after thorough coaching and support, the honest conversation shifts from development to fit. That decision should never be made lightly, and it should never be made without having done the coaching work first. But it is sometimes the right call for the individual, for the team, and for the organization.
If your sales team is carrying underperformers who haven't been coached effectively, the issue may not be the reps. Braintrust works with sales leaders to build the coaching frameworks, behavior change systems, and rep development programs that turn performance problems into performance outcomes. Start a conversation with our team to see what that looks like inside your organization.
