Strategies for Coaching Underperforming Employees

When an Employee Isn’t Meeting Expectations: A Conversation, Not a Confrontation Let’s be real—managing someone who isn’t meeting expectations can feel awkward. No one enjoys those conversations, and for the person on the receiving end, it can be nerve-wracking. But before jumping straight to feedback, pause for a moment. What might be going on for them? Have expectations shifted? Are they aware they’re not quite hitting the mark? Before we assume, we need to listen—really listen. Understanding their perspective is the first step towards a productive conversation. Performance isn’t just about ticking boxes; it’s about alignment, clarity, and support. If someone on your team isn’t quite where they need to be, chances are they know it too. So, instead of approaching it with a ‘fix them’ mindset, start with: “Let’s have an open dialogue. My goal is to understand where you’re at, share clear feedback, and work together on a plan that sets you up for success.” This isn’t about pointing fingers—it’s about trust. When people feel heard, they’re far more open to change. Here’s how to make that happen: 1. Set the Stage for Success Before jumping in, get clear on what success actually looks like. Have expectations been clearly communicated? Have they changed over time? No one can improve if they don’t know what ‘good’ looks like. 2. Get Specific Vague feedback like “you need to step up” won’t help. Instead, bring clear examples: ✔️ “In the last three projects, deadlines were missed, which affected the team’s workflow.” ❌ Not: “You’re not proactive enough.” Being specific makes the conversation about actions, not character. 3. Make It a Two-Way Street Instead of assuming the worst, ask questions with genuine curiosity. Maybe they’re struggling with workload, lack of clarity, or something personal. Try: 🔍 “How do you feel about your recent performance? What’s getting in your way?” You might uncover something that completely shifts your approach. 4. Build a Plan—Together This is where collaboration truly kicks in. Work with them to set clear, achievable next steps. Instead of saying, “You need to improve,” try: ✅ “Let’s focus on meeting deadlines for the next two projects. I’ll check in with you halfway through—how does that sound?” When improvement feels like a shared effort rather than a demand, accountability follows naturally. 5. Support, Don’t Just Supervise Most people want to do well. If they’re falling short, be a leader, not just a manager. Offer mentorship, training, or resources if needed. Recognise small improvements—it builds confidence and momentum. No one wants to feel like they’re failing. When someone isn’t meeting expectations, it’s an opportunity to connect, reset, and grow together. Addressing issues with empathy, clarity, and collaboration makes all the difference. Have you ever had to manage a tough performance conversation? What worked (or didn’t work) for you? Let’s talk.

Your best people are failing. And it's not their fault. As an Olympian, I learned this truth: When athletes underperform: - We don't question their talent - We check their support system Business got this backwards: - We blame the people instead of examining what they need to succeed. I spent years frustrated with "underperforming" teams. The real problem? - I was giving tasks, not tools - Assigning work, not purpose - Expecting Olympic results with recreational support The truth: - Your people want to deliver the best they can. - They took this job to contribute something meaningful. - When they're struggling, they're probably more frustrated than you are. ❌ The question isn't "Why aren't they performing?" ✅ The question is "What support are they missing?" 8 Things You Can Do Right Now: 1. Ask them directly: ↳ "What's blocking you from doing your best work?" ↳ Then listen without defending 2. Clear the path: ↳ Remove one bureaucratic barrier they face daily. Just one ↳ Watch what happens 3. Give context, not just commands: ↳ Explain the why behind every request ↳ People perform better when they understand the mission 4. Invest in their growth: ↳ Send them to that conference. Buy that course ↳ Your investment shows you believe in their future 5. Create psychological safety: ↳ Make it safe to fail, question, and suggest improvements ↳ Innovation dies in fear 6. Provide the right tools: ↳ That software they've been requesting? That upgraded equipment? ↳ Stop seeing it as an expense. It's an investment in results 7. Set clear expectations: ↳ In sport, vague goals kill performance ↳ Be specific about what success looks like - just like a coach setting clear race times or technique benchmarks 8. Recognize effort, not just outcomes: ↳ Acknowledge the work they put in, especially when external factors affect results ↳ Be amazed by what your team can achieve The best leaders I know - like the best Olympic coaches: ❌ Don't manage people ✅ They remove obstacles ❌ They don't control outcomes ✅ They create conditions for peak performance Remember: 💡 Your team isn't broken. 💡 They're waiting for you to help them shine. What's one thing you'll change today? Share your experience below ⬇️ ♻️ Repost to help others advance their teams 🔔 Follow Eva Gysling, OLY for more

Last week I led a session on #PerformanceManagement for senior leaders. One of them reached out with the following important question about #PsychologicalSafety in the context of managing underperformance: "Psychological safety is an extremely difficult concept to pin down, especially in a setting where we have to strike a balance between supporting human beings under pressure, while at the same time being accountable for results. I would like to have more guidance on is how one manages the psychological safety element in a situation of underperformance - which often requires (at least partially) withdrawing that safety, to the discomfort of the staff member." Here is my advice to those of you wondering the same thing: In the context of managing underperformance, having psychological safety means feeling that you won't be punished or humiliated for making mistakes or for underperforming. That being said, having a conversation with a supervisor about your performance when you’re not meeting expectations is inherently stressful. It is psychologically difficult for people to focus on where they are coming up short; this undermines their sense of self as a competent person, particularly when they feel that they have been working diligently or when they have been negatively affected by situations beyond their control. While it may not be possible to make a staff member completely comfortable during feedback conversations about underperformance — and indeed, a total lack of discomfort with the status quo may not be optimal for motivating improvement — these conversations are much more likely to achieve their aim of helping the staff member perform at a higher level when the supervisor does the following:   ⋙ Provide Actionable Feedback ⋘ 👉 Give specific, timely, and constructive feedback on performance gaps, not just vague criticisms. 👉 Clearly outline expectations, metrics, and deadlines for improvement. Maintain an empathetic, development-focused tone even as you increase accountability. ⋙ Focus on Development, Not Just Evaluation ⋘ 👉 When addressing underperformance, emphasize how you can support the employee's growth and improvement. Make it clear the goal is to help the employee succeed. 👉 Collaboratively identify obstacles (e.g., by asking questions like, “What is most difficult about this for you?” and “What’s getting in the way?”) and craft a plan to overcome them through coaching, training, or other resources. 👉 Engage the staff member in articulating what help they feel they need and what path forward feels most motivating and productive. This helps to build employee ownership over their plan for improvement rather than thrusting it upon them.

The best managers are terrific detectives Imagine this scenario: Two employees, Sam and Sarah, both failed to meet several goals last year. Seems like they're in the same boat, right? Well, not necessarily. Behind the scenes, their reasons for underperformance could be worlds apart. Now, picture yourself as their manager. You want to be fair, but you also need to hold your team members accountable for their performance. So, where do you start? It's important to begin with few questions: ·     Is the employee new to the organization? Or Function? Or Role? ·     How was his / her performance in the past? ·     What has changed in the ecosystem – both internal and external? ·     What’s happening in his / her life outside work? ·     How has his / her relationship been – with me and others in the team?   Underperformance can happen due to several reasons: 1.    Lack Fitment to the role. I remember my first job in key account management, I disliked it and didn’t do too well. The reason was not my lack of knowledge or hard skills, but the personality mismatch. A person may also not fit the culture of the organization or function or the team (every team has a subculture with nuances).   2.    Ambiguity Overload that naturally comes with many roles today, or simply unclear on the expectations and deliverables.   3.    Lack of Capability to deliver the role, be it knowledge, critical cognitive or behavioral skills. While with right mindset and resources, anyone can develop the capability, it is important to identify the mismatch and address it.   4.    External Environment can significantly influence performance of an individual, be it dwindling customer pool, entry of new competition, regulatory pressures, difficult terrain… the list can be endless. Within the same organization, people are likely to face varying external pressure.   5.    Interpersonal Issues either with the manager or rest of the team or peers. Does the person feel valued? Recognized for his / her contributions? Or empowered to deliver results? It’s important to reflect on this as it needs effort from all parties to rectify interpersonal issues.   6.    Personal Battles can be varied: ranging from workplace stress and burnout, boredom with the job, to personal issues at home, poor health, or crisis at home. Sometimes life throws a curve ball and all we can do is keep our head above water.   So, here's the bottom line: The root cause of underperformance isn't always obvious. That's why it's crucial for managers to play detective and get to the heart of the matter. Only then can we strike the delicate balance between accountability and fairness. #performanceappraisal #managers #performance #performanceimprovement

If you're a manager, and your employee is surprised by receiving a PIP / coaching plan, you've failed. Before their poor performance is a problem, you need to give feedback early and often. "I noticed you were late for standup for the second time. I just wanted you to know that it impacts our team's ability to get through standup quickly, and it can be frustrating to us all. Got it?" When the pattern becomes more serious, you need to ensure they understand the feedback is serious. And you need to own it, with "I", not "We" "That's the third time you've missed an important deadline without letting us know ahead of time. I am losing trust in your ability to deliver on your committed work. This is a problem." When serious feedback hasn't made an impact, you need to be extremely clear of where this is going, since many people don't have experience with this process. I find it helpful to make it clear that you're not the enemy. "I have warned you repeatedly that pushing code to production without peer sign-off is unacceptable. If this continues to happen, it will lead to you not working at this company anymore. I like you, and would like you to be successful, but I need to ensure that you understand what's at stake." Only then, after friendly warnings, serious warnings, and extremely clear warnings, should you proceed with PIPs/Coaching. Because only then have you actually given them a chance to improve their performance.

Is your PM underperforming, or are you under-managing? Three PMs were labeled 'underperformers' on my first day. My boss wanted all of them gone. I didn't let go any of them. Not immediately. Instead, I asked: had anyone actually managed them? Turns out no. They'd never received real feedback. No one taught them how to write requirements or connect their work to business outcomes. There were all these expectations of them never communicated explicitly. So I built what should have existed: coaching sessions, templates, peer reviews, 1:1s. One rule: explain the why behind every ticket, not just the what. Two turned it around within weeks. The structure was all they needed. The third didn't make it. Same investment, same tools, but couldn't move from order-taker to problem-solver. Here's what stuck with me: we almost fired three people for a management failure, not a performance failure. Before you label someone an underperformer, ask if you've given them the tools to perform. Most "low performers" are just operating in low-performance systems. The fastest way to improve your team isn't always hiring better. Sometimes it's just managing better.

Do you really think replacing the salesperson will fix occupancy? Outside of legitimate HR issues, swapping out a salesperson because of metrics alone often creates more damage than progress. And no— A PIP is not a strategy. It is usually an admission that leadership missed the real issue. Before you post the job ad, answer this: Where is the pipeline actually breaking? • Is it lead-to-connection? • Tour-to-advance? • Advance-to-decision? • Or the absence of a real next step? Most teams aren’t underperforming because of effort. They are underperforming because the process is vague, unfocused, and poorly coached. Here’s what actually moves occupancy: 1. Dive into the pipeline—not the personality Metrics don’t indict people. They expose skill gaps. 2. Narrow the focus Fix one or two conversion points, not everything at once. 3. Train to the gap Teach how to advance a family, not how to “follow up.” 4. Bake in accountability Coaching without accountability is encouragement. Accountability without coaching is punishment. And let’s stop chasing unicorns. Great salespeople are rarely found fully formed. They are created—through clarity, coaching, repetition, and leadership. One more uncomfortable truth: If occupancy isn’t moving, look upstream. You also need regional leaders who can coach and train, not just: • Send polished emails • Re-state CRM data • Micromanage basic tasks Occupancy doesn’t change because of reports. It changes because someone teaches, observes, corrects, and advances the team. Hope is not a growth strategy. Leadership is. #hiring #teambuilding #greatleaders

I led teams for 10 years. Here are 3 of my favorite frameworks to diagnose most performance issues: (Use them to become a better manager to your team) 1️⃣ The Skill/Will matrix: This tool is useful if you’re: - having trouble finding a way to motivate your employees (they might be low will, time to dig into why) - dealing with team members whose work doesn’t meet your expectations (they might be low skill, time to figure out how to upskill) - feeling like you’re offending your team member by offering help (they might be high skill and don’t need the level of hands on assistance you’re providing them). → Try this: First of all, this friction is normal. Plot your team member on the matrix, reflect on your recent interactions or their recent work, and with this new information come up with an approach that meets them where they’re at. 2️⃣ The Task Relevant Maturity Framework (TRM): If you find yourself constantly saying things like “I don’t know why they just don’t get it. If it were me, I would…” This tension is typically a result of there being a disconnect between your direct report’s skill level and your managerial approach with them. → Try this: Evaluate your direct report on the TRM framework and adjust your approach accordingly. You’ll find that you probably need to: provide more structure, engage in two way communication and mutual reasoning, OR be minimally involved (yay!). 3️⃣ The Learning Curve: If you’ve tasked your direct report with a task or project that you’re confident they can do (or know they have the skills to do) but find that they’re stuck, try evaluating where they’re at on the learning curve. They might be on a low point in the curve and need some assistance to keep going. → Pro tip: Don’t let them linger in this feeling, intervene before they’re tempted to give up. Intervening can look like encouragement and a vote of confidence in their abilities. These frameworks have been a part of my toolkit for longer than I can remember. They’re so reliable that I still use them in my work with clients. What are some management frameworks that you’ve found helpful?

🧠 Not every underperforming B2B seller needs a new technique. Sometimes, they need space. Sometimes, they need clarity. And sometimes, they just need to be coached as a human — not fixed as a number. In high-stakes sales orgs, it’s easy to assume: 📉 Low quota = low skill But here’s what we miss: 👉 Quiet stress 👉 Emotional burnout 👉 Identity collapse 👉 Fake productivity masking real fatigue That’s why I wrote Silent Struggles, Stronger Teams — a playbook for sales leaders who want to coach for performance, not manage the person. Inside, you’ll learn how to: 📘 Spot the silent signs of stress before they hit attrition 📘 Use ego-state coaching (Adult vs. Parent/Child) to regulate emotional reactivity 📘 Apply the GROW model to rebuild clarity and self-worth 📘 Separate who they are from what they produce 📘 Use AI not for inspection, but for insight 📘 Run coaching conversations that unlock belief, not just behaviors 👉 Download the full playbook (PDF): https://lnkd.in/ddx-BbQw More at: https://lnkd.in/dg2-Vac6 Because not every seller who’s stuck needs more tactics. They need more truth. More safety. More space to reset. 🧭 How are you coaching under the number, not just around it?