Importance of Regular Check-Ins

I made a surprising discovery after coaching 47 teams in OKRs And almost every team gets it wrong. Here's the truth: Succeeding with OKR has zero to do with: • The most ambitious moonshot goals. • The most inspirational Objective • The perfectly-written Key Results • Automating your data collection It all comes down to one single thing: 𝗖𝗵𝗲𝗰𝗸-𝗶𝗻 𝗳𝗿𝗲𝗾𝘂𝗲𝗻𝗰𝘆. Here's what I learned the hard way: • Weekly check-ins = OKR success • Bi-weekly check-ins = Mixed results • Monthly check-ins or less frequently = Almost guaranteed failure But here's the game-changing insight I owe to Christina Wodtke: • Stop measuring progress. • Start measuring 𝗰𝗼𝗻𝗳𝗶𝗱𝗲𝗻𝗰𝗲. The single most important question in every check-in should be: "How confident are we that our current strategy is still helping us achieve our Key Results?" This simple shift transforms OKRs from a project management tool Into an engine that turbocharges your strategy execution. Low confidence? Could be an early warning signal to pivot. High confidence? Double down on what's working. 🔑 The secret: Run regular 15-minute weekly confidence check-ins instead of hour-long progress meetings and you'll see real traction. Want to transform how your team uses OKRs? Reply "✅" if you'd like my exact OKR check-in template [Follow me for more simple strategy frameworks and insights that drive results]

Leadership isn't just about making big decisions. That’s obviously really important. It's about the small, consistent actions that build trust and empower teams to do their best work. A recent comment from a former team member reminded me of this: they noted how I tried not to move or cancel our 1:1 meetings, regardless of how hectic things got. I can’t take full credit for this compliment. I’ve been incredibly lucky to work under some thoughtful and masterful leaders who paved the way for me and informed how I lead. But the seemingly ‘small’ things like 1:1s matter. Here’s why: 1. Consistency breeds trust When you consistently show up, you demonstrate reliability. This builds a foundation of trust that's essential for high-performing teams. 2. Open communication matters Regular 1:1s create a space for open dialogue. They allow team members to voice concerns, share ideas, and feel heard. 3. It allows your team to be proactive Regular check-ins enable you to address issues before they escalate. It's about prevention, not just reaction. 4. You understand your team as people  By prioritizing these meetings, you show you value everyone’s time and input. We’re all people with lives who are just trying to do a good job. 5. How to lead by example When you prioritize these meetings, it sets a standard for the entire organization. It shows that open communication and engagement is not just encouraged, but expected. 6. It helps you face crises as a team In times of crisis or change, 1:1’s are so often quickly pushed aside. That’s the opposite of what you should do when stability and clarity are needed most. Transparent leadership isn't about grand gestures (although those have their place as well). It's about consistent, intentional actions that create an environment of trust and open communication.  It's about showing up, even when - or, especially when - things get busy. Special thanks to Lily Russell for your kind words. And shoutout to Eric Sprunk, Mike Brewer, Hannah Jones, Nick Athanasakos, Gerry Rogers, Patty Ross, Mark Allen, Ernie Rose and Andrew Campion for shaping me into the leader I am and strive to be.

I’m a firm believer that regular check-ins are the key to project success. Are you checking in enough? Ever been part of a project that suddenly veered off track without warning? You’re not alone. The truth is, projects rarely fail because of one big mistake; they fail because of small issues that go unnoticed until it's too late. That’s where regular check-ins come in. When I was managing projects with multiple suppliers, we established a game-changing routine: monthly supplier progress review meetings. Each supplier would submit reports highlighting all open items, supported by a three-month rolling KPI for each. This simple process was a game changer for four key reasons: 1️⃣ Proactive Problem-Solving: Instead of scrambling to fix issues at the last minute, we could see which items were stalling and tackle them head-on before they became bigger problems. It wasn’t just about reacting; it was about staying ahead. 2️⃣ Accountability & Transparency: Regular check-ins meant everyone knew their performance was being monitored. Suppliers had a clear platform to raise concerns, and we could address them collaboratively. It drove accountability and created a culture of transparency. 3️⃣ Stronger Partnerships: Communication isn’t just about managing; it’s about connecting. These monthly sessions allowed us to build trust and work together as true partners, not just client and supplier. Problems were solved faster, and relationships grew stronger. 4️⃣ Continuous Improvement: With regular data and feedback, we could spot patterns and make adjustments. We weren’t just tracking progress; we were optimizing it. Over time, this approach led to significant improvements and fewer roadblocks. Consistent communication, like these check-ins, can be the lifeline of any project. It keeps everyone aligned, proactive, and focused on solutions. So, whether you’re managing suppliers, a team, or an entire organization, don’t underestimate the power of regular, open dialogue. How do you keep projects on track? Drop your thoughts below, and follow me for more insights on leadership, contract management, and strategic collaboration. #Leadership #ProjectManagement #TeamCollaboration #SupplierManagement #ContinuousImprovement #CommunicationMatters

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.

Regular feedback stops minor issues from snowballing into avalanches. One or two degrees off course might seem small at first, but over time? It’s a problem. That’s why creating space for frequent feedback is essential in leadership. As I've matured as a leader, I’ve learned that the best way to avoid future roadblocks is by making feedback a regular part of how my managers and I operate as a team. I’m always intentional about creating space for constructive feedback from my managers. I want them to feel comfortable offering honest input so we can course-correct early and avoid small issues turning into bigger ones. I make a habit of setting up consistent check-ins where I’m able to ask my managers direct questions like: 🔎 Where should I focus in the coming year? 🔙 Are there areas where I should step back? ⌚ Am I spending my time in ways that deliver the results we need? It’s those kinds of questions that open up space for honest conversations. And honest conversations are the key to helping us all improve. When you make feedback a consistent practice, you can pivot quickly before things go off course. And by keeping the conversation open, you set both yourself and your team up for success. The clearer your sense of direction, the sooner you and your team can start making progress. #LeadershipDevelopment #ConstructiveFeedback #TeamSuccess

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!

Annual Review season is here... AND I hope that many organizations are embracing "Regular Check-ins!" vs just waiting until the annual cycle to roll around. The significance of ongoing performance conversations cannot be overstated. If your organization solely relies on once-a-year reviews, you might be missing out on a golden opportunity to foster real impact within your teams. Why Regular Check-ins? Annual reviews, while valuable, often fall short in capturing the nuances of an employee's journey. Regular check-ins provide a continuous feedback loop, allowing for agile adjustments, acknowledgment of achievements, and addressing challenges promptly. It's about steering the ship together rather than waiting for a yearly course correction. Prioritize regular Check-ins and don't leave the follow skills behind... Active Listening: Understanding your team members requires active listening. Hear their thoughts, concerns, and aspirations. Listening fosters a sense of being valued and promotes a culture of openness. Empathy Matters: Empathy forms the bedrock of meaningful connections. Put yourself in their shoes, acknowledge their experiences, and demonstrate that you genuinely care. It's the emotional glue that binds our teams together. Supportive Inquiry: A simple "How can I support you?" can go a long way. Check in on their workload, challenges, and overall well-being. By offering assistance, you show that their success and well-being are critical to the team's success. Impact on Team Dynamics: Regular check-ins not only enhance individual performance but also contribute to a healthier team dynamic. They build trust, encourage open communication, and empower individuals to bring their authentic selves to the workplace. The era of annual reviews as the sole performance conversation is evolving. Embrace regular check-ins as a powerful tool to drive growth, engagement, and collaboration within your teams. Remember, it's not just about the destination; it's about the journey we embark on together. #PerformanceConversations #Leadership #TeamEngagement #ContinuousFeedback

This may sound counterintuitive from a tech executive, but change can also happen comparatively slowly in this industry—just like in the rest of life. That means regular check-ups can prevent or minimize disasters, as well as spur progress. When you go in for a physical, the doctor orders a baseline blood panel and then compares your results over the years. Yes, sometimes emergencies happen. But when we make incremental assessments compared to that initial benchmark and accept necessary adjustments when small problems arise, we’re often able to avoid catastrophic damage down the line. And we may glean information that helps us to improve our overall health. The same goes for technology companies. To thrive—and avoid sudden shocks—a business requires regular check-ups, too. Here are a few questions to ask: - Where is my industry headed?  - What are the incoming threats?  - Is our structure still effective? If the answers to these indicate there may be a need for change, chances are you won’t have to make a dramatic, instantaneous shift. You’ve got time: Collect more data. Start a pilot project. Survey your people. Reassess. Then, if a larger change eventually becomes warranted, it won’t feel like such a leap. Those assessments and corresponding small tweaks have provided fair warning that a larger course correction may be in sight—and likely helped to prevent an emergent situation. Question for others here: What are some additional “business check-up” questions worth asking?

It's that time again. The dreaded annual performance review. Annual performance reviews are undeniably ineffective. (Yes, I’m an “HR person” putting a nail in the coffin of an activity that’s been our swan-song for eons….)    Survey after notable survey have reported that nearly every manager AND employee questioned believe that annual performance reviews weren’t effective or useful.    My friends, the traditional process is flawed.    Why?    First, the traditional review process focuses on the past rather than the future. This backward-looking conversation has shown to demotivate employees. (And, who really remembers what they did 11 months ago!? Raise your hand if you’ve reviewed your calendar from the past 12-months to remember what you did and accomplished? 🙋♀️)    So, how do you hold staff accountable while avoiding a cumbersome (and demoralizing) conversation?    Here’s the deal -    Employees prefer consistent, timely feedback to address roadblocks, receive recognition, and build a foundation of trust with their leaders. That’s why a less formal, more consistent approach to performance management benefits employee, team, and business success.    So, what should the process be?     1. 𝗠𝗼𝗻𝘁𝗵𝗹𝘆 𝗢𝗻𝗲-𝗼𝗻-𝗼𝗻𝗲𝘀  These informal meetings serve as an opportunity to recognize employees for their hard work, assess roadblocks, and coach performance. Regular one-on-ones help managers evaluate results as they come, not months later. That way, you can correct ineffective processes before they become a habit.    2. 𝗤𝘂𝗮𝗿𝘁𝗲𝗿𝗹𝘆 𝗰𝗵𝗲𝗰𝗸-𝗶𝗻𝘀  Quarterly checks are a great supplement to your one-on-one opportunities. These can be more formal.    3. 𝗖𝗼𝗻𝘁𝗶𝗻𝘂𝗼𝘂𝘀, 𝘁𝘄𝗼-𝘄𝗮𝘆 𝗳𝗲𝗲𝗱𝗯𝗮𝗰𝗸  This enables both employees and managers to ask for feedback. Not only does this make employees feel like their opinions matter, but it gives managers the insight they need to improve the employee experience and grow as a leader. In addition, your employees will be more likely to accept feedback without hesitation when it goes both ways.    4. 𝗖𝗮𝗿𝗲𝗲𝗿 𝗱𝗲𝘃𝗲𝗹𝗼𝗽𝗺𝗲𝗻𝘁 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻𝘀  Career development conversations help employees and managers align on the future. These conversations allow managers to recognize employee talent. When you show an employee that they are valued, you’ll be able to bring out their full potential.    The war for talent is real. It’s critical for leaders to establish a routine where expectations are clear, direct feedback is delivered real-time, and career development is actively supported.    How do you review your employees? And as an employee, how would you like to be reviewed?