Implementing Regular Check-Ins for Sales Staff

At Stone Road, one practice I introduced immediately when I joined the team was implementing weekly 1:1 check-in calls. I firmly believe in the power of structured communication, regardless of team size – even in our tiny, two-person team, these calls have proven invaluable. They provide dedicated time each week to discuss ongoing projects and strategize for the week ahead, ensuring alignment and accelerating goal achievement. Our approach to these 1:1 meetings involves using a Google Sheet that we fill out before the meeting and alternate who leads each week. This allows both of us to openly share perspectives, ideas, and talking points, ensuring a collaborative and productive discussion. During these check-ins, we cover several key topics: 1. Last Meeting Follow-Up: We review highlights from our previous check-in to assess progress and identify outstanding tasks. 2. New Discussion Topics: We identify and discuss new topics for the week which are then followed up on in our next meeting, ensuring continuity and forward momentum. 3. Wins of the Week: Recognizing and celebrating both small and significant victories is essential, especially in our dynamic industry. Even in the most challenging weeks, we can identify at least 10 bullet points of wins we’ve had that week. 4. Action Items: We outline specific tasks to be completed before the next check-in, ensuring accountability and progress. 5. Weekly Deals: We assess our inventory and strategize on which SKUs to push and tailor our weekly deals around those specific SKUs. Do you conduct weekly 1:1 meetings with your team? I’d love to hear about the topics you find valuable to cover. Share your insights below! 👇

Annual reviews feel stale and out of touch. Real impact comes from continuous growth conversations—quick, meaningful check-ins that drive engagement, performance, and results. 𝚆̲𝚑̲𝚢̲ ̲𝙸̲𝚝̲ ̲𝚆̲𝚘̲𝚛̲𝚔̲𝚜̲ 𝟭. 𝗥𝗲𝗮𝗹-𝗧𝗶𝗺𝗲 𝗙𝗲𝗲𝗱𝗯𝗮𝗰𝗸 𝗥𝗼𝗰𝗸𝘀 No more waiting a year to course-correct. Immediate feedback means employees can improve now, not later. 𝟮. 𝗘𝗻𝗴𝗮𝗴𝗲𝗺𝗲𝗻𝘁 𝗦𝗼𝗮𝗿𝘀 Frequent chats show employees they’re valued and supported. Engaged people = better work. 𝟯. 𝗚𝗼𝗮𝗹𝘀 𝗦𝘁𝗮𝘆 𝗥𝗲𝗹𝗲𝘃𝗮𝗻𝘁 Ongoing updates keep goals aligned with shifting business priorities. No more outdated plans. 𝙷̲𝚘̲𝚠̲ ̲𝚝̲𝚘̲ ̲𝚂̲𝚝̲𝚊̲𝚛̲𝚝̲ 𝟭. 𝗤𝘂𝗶𝗰𝗸, 𝗥𝗲𝗴𝘂𝗹𝗮𝗿 𝗖𝗵𝗲𝗰𝗸-𝗜𝗻𝘀 Weekly or biweekly. Keep it short but impactful. 𝘌𝘹𝘢𝘮𝘱𝘭𝘦: “What’s one thing that’s going well? What’s one challenge I can help with?” 𝟮. 𝗙𝗼𝗰𝘂𝘀 𝗼𝗻 𝗚𝗿𝗼𝘄𝘁𝗵 Balance tasks with career development. Help employees level up. 𝘌𝘹𝘢𝘮𝘱𝘭𝘦: Suggest a new project to build leadership skills. 𝟯. 𝗖𝗲𝗹𝗲𝗯𝗿𝗮𝘁𝗲 𝗪𝗶𝗻𝘀 Catch someone doing great work? Call it out right away. 𝘌𝘹𝘢𝘮𝘱𝘭𝘦: “I loved how you handled that client issue—great thinking!” Small Moves, Big Payoffs 𝟭. 𝗕𝗲𝘁𝘁𝗲𝗿 𝗧𝗲𝗮𝗺 𝗗𝘆𝗻𝗮𝗺𝗶𝗰𝘀 More trust, less drama. 𝘌𝘹𝘢𝘮𝘱𝘭𝘦: Weekly chats reveal overlapping tasks. Fixing it clears confusion. 𝟮. 𝗕𝗼𝗼𝘀𝘁𝗲𝗱 𝗣𝗿𝗼𝗱𝘂𝗰𝘁𝗶𝘃𝗶𝘁𝘆 Fast feedback keeps work on point. 𝘌𝘹𝘢𝘮𝘱𝘭𝘦: Early tweaks to a project saves hours of rework later. 𝟯. 𝗦𝘁𝗿𝗼𝗻𝗴𝗲𝗿 𝗕𝗼𝘁𝘁𝗼𝗺 𝗟𝗶𝗻𝗲 Happy employees stick around. Fewer replacements = big savings. 𝘌𝘹𝘢𝘮𝘱𝘭𝘦: Regular check-ins drop turnover by 15%, keeping star players in the game. 𝗧𝗵𝗲 𝗕𝗼𝘁𝘁𝗼𝗺 𝗟𝗶𝗻𝗲 Frequent conversations aren’t just nicer—they’re smarter. Start with a 10-minute check-in this week. Watch how small changes spark big results—for your team and your business.

Ever wondered the difference between good sales leaders, and great ones? (PART 2) The Power of Structured 1:1s in Sales Leadership Too many sales leaders treat 1:1s as casual check-ins or status updates. Great leaders do it differently. They run structured, intentional meetings that drive real results. A well-run 1:1 isn’t just about “How’s it going?” It’s a dedicated time to align on goals, remove roadblocks, and develop skills. Done right, it builds accountability, trust, and long-term success. Here’s what a structured 1:1 should include: -> Pipeline Review – Not just deal updates. A structured review focuses on whether opportunities are qualified, advancing, and moving at the right pace. It’s about coaching strategy, not just reporting numbers. -> Deal Strategy Discussion – Where are deals getting stuck? What’s the plan to move them forward? Great leaders help their team think through next steps, uncover blind spots, and anticipate challenges. -> Skill Development – Every 1:1 should include coaching. Role-playing, objection handling, or reinforcing key behaviors. Sales is a skill, and development should be ongoing—not just when numbers dip. -> Accountability Check-In – Goals were set last time. Were they met? If not, why? Great leaders don’t let things slide. They create a culture where commitments matter and follow-through is expected. -> Personal and Professional Growth – Salespeople are more than their quota. Great leaders take the time to understand career goals, challenges, and motivators. They help their team see the bigger picture beyond just this quarter. A 1:1 without structure is a missed opportunity. A structured 1:1 is a leadership tool that drives performance, engagement, and growth. How do you structure your 1:1s? For the love of sales, 💗 TMH

Management Tip 5/13: One-on-One Meetings. Have Them. Here's a story I've lived too many times: A manager calls, frustrated. "I need to do something about Jamie. Nothing's working." "Tell me more," I say, settling in for what I expect will be a revealing conversation. He describes a talented hire who started strong but is now missing deadlines and producing mediocre work. A client has complained, and he sees no choice but to begin managing Jamie out. "That sounds frustrating," I acknowledge. Then ask, "How often do you two connect one-on-one?" Pause. "We meet when there are issues to discuss." "So no regular weekly—or even monthly—check-ins?" "We're all so busy... honestly, none of my team has needed regular check-ins." I ask him to commit to four consecutive weekly meetings with Jamie before taking any action. Three weeks later, he calls back: "I owe you lunch. We just delivered our most challenging project ahead of schedule—and Jamie was a key contributor." What changed? Through consistent weekly meetings, issues were discovered: unclear expectations, competing priorities, and missing resources. Most importantly, Jamie had space to ask for help. I've seen this pattern throughout my career. Without regular touchpoints: • Small issues balloon into crises • Feedback comes too late to be actionable • Trust deteriorates • What appears as poor performance is actually disconnection This isn't about being friendly—it's about being effective. When managers tell me someone isn't performing, my first question is always about the consistency of their communication. Attached is the HUDL framework I developed (more details in the comments): • Health check (5 min) • Updates on goals (5 min) • Discussion and feedback (15 min) • List next steps (5 min) Every team's one-on-ones will differ, but this simple structure offers a place to start. Has a regular check-in practice transformed your leadership? Share your experience!

Sales leaders: Are your one-on-one meetings driving real impact or just routine checkboxes? 🤔 The quality of these interactions can make or break your sales team’s performance. Done right, they’re not just meetings but catalysts for growth, strategic alignment, and future leadership development. When done wrong, they are simply backslapping events that are done for repetition without impacting your business (or your ability to drive revenue). 🔑 The key lies in how you approach them:   ✅ Consistency: Regular, structured meetings (weekly or bi-weekly) with clear expectations.   ✅ Preparation: Sales managers AND reps should dive deep into the CRM beforehand to cut the noise and focus on strategy.   ✅ Ownership: Encourage salespeople to lead discussions, spotlight challenges, and analyze their pipeline—this builds analytical and problem-solving skills. Hint: If the salesperson is just answering your questions, then you are doing these things wrong! ✅ Mentorship, not micromanagement: Guide, don’t steer. Your goal is to foster independence, not dependency.  Empowering your team through these pivotal one-on-ones doesn’t just improve numbers—it sharpens your sales culture. It builds resilient teams ready for tomorrow’s challenges. Are you transforming your “check-ins” into gamechangers? Let’s discuss.👇