Leadership Journaling Techniques

The simple practice that has improved my decision making Shane Parrish from Farnam Street introduced me to decision journaling in 2019. What started as a simple concept has become one of my most valuable leadership tools. After years of making big decisions and wondering why some worked out better than others, I started doing something that felt almost too simple: writing them down. Not just the decision itself, but the assumptions behind it. For every major decision such as product launches, key hires and more, I document three things: 1. What decision we're making and why 2. What key assumptions are driving this decision 3. What outcomes we expect and by when Then, six months later, I revisit the journal. Not to judge past decisions, but to understand which assumptions were wrong and why. Where This Gets Really Powerful: Hiring I apply this to every senior hire. During interviews, I document what we think this person will excel at and what outcomes we expect. Six months later, during performance reviews, I compare the interview notes to reality. "We thought Sam would spike on innovation. She scored high in interviews. But looking at her first six months, where are the innovative ideas?" This isn't about being right or wrong—it's about calibrating my assessment skills. I've done this for every promotion and attrition too. When someone leaves, I go back to their original interview notes and ask: What did we think they'd be great at? What actually happened? The Compound Effect After two years of decision journaling, I can see my own blind spots clearly. I tend to underestimate implementation complexity. I overvalue certain interview signals. These insights don't just improve future decisions—they help me know when to seek different perspectives. The practice takes a few minutes per decision and has fundamentally changed how I think about leadership accountability. What systems do you use to improve your decision-making over time?

You've just received feedback from your team, but something doesn't sit right. Their words clash with your self-image, leaving you feeling defensive and confused. Self-reflection isn't just introspection. It's the key to unlocking your leadership potential and fostering genuine connections. Let's explore why reflection matters and how to master this critical skill: Many leaders struggle with meaningful self-reflection because: • They're too busy "doing" to pause and process experiences. • They fear confronting personal weaknesses or mistakes. • They lack structured methods for effective reflection. This reflection deficit leads to: → Repeated mistakes and missed growth opportunities. → Disconnection from team members and their needs. → Stagnation in leadership development and effectiveness. Most people confuse a 5-minute journaling session with true reflection. I’m not saying short, sporadic attempts at journaling lack their merit, but they do lack the depth and consistency needed for real insight and change. So here are 3 Solutions to enhance reflective practice: 1. Implement a structured reflection routine: ↳ Set aside dedicated time daily or weekly for guided self-reflection exercises focused on recent experiences and interactions. 2. Utilize the "Consultant" perspective: ↳ Practice mentally stepping outside situations to observe yourself objectively, as if you were an external consultant. 3. Engage in reflective conversations: ↳ Regularly discuss your thoughts, actions, and their impacts with a trusted mentor or coach who can provide additional perspective. Mastering reflection is an ongoing process that transforms reactive leaders into thoughtful, adaptable visionaries. By committing to these practices, you'll develop deeper self-awareness, make more intentional decisions, and cultivate stronger connections with your team. Remember: The most profound leadership insights come from within. What’s stoping you from looking deeper? — P.S. Unlock 20 years' worth of leadership lessons sent straight to your inbox. Every Wednesday, I share exclusive insights and actionable tips on my newsletter. (Link in my bio to sign up). Remember, leaders succeed together.

Listening to an inspiring podcast this morning (shout out to Emily Abbate and her awesome Hurdle podcast), I was struck by a question posed to Nikki Ogunnaike: What does leadership feel like for her? It's a thought-provoking inquiry because, indeed, the answer likely fluctuates based on various daily factors. For me, today, leadership feels playful, energizing, and a bit cozy (And no, I don't normally sit around all day with my slippers propped on my desk but felt called to on this rainy So Cal day 😉 ). This got me thinking – how do other leaders in my community feel daily? How does leadership manifest in their emotions, attitudes, and actions on a day-to-day basis? Tracking our daily leadership vibe can offer valuable insights into our leadership style, effectiveness, and overall well-being. It's not just about how we lead others but also how we lead ourselves through the highs and lows of each day. Here are a few simple actions to help monitor and reflect on your daily leadership vibes: ⭐ Morning Check-In: Start your day with a brief reflection on how you're feeling about your leadership role. Are you excited, anxious, or somewhere in between? ⭐ Daily Journaling: Take a few minutes at the end of each day to jot down your leadership highlights, challenges, and overall mood. Look for recurring themes or shifts in your emotions. ⭐ Feedback Loop: Engage with your team or peers and ask for their observations on your leadership style. Their insights can provide valuable perspectives. ⭐ Adjust as Needed: Based on your reflections, make adjustments to your leadership approach as necessary. Whether it's practicing more empathy or embracing spontaneity, small tweaks can make a big difference. I'd love to know ~What does leadership feel like for you today? Let's spark a dialogue and learn from each other's experiences. Together, we can cultivate more mindful and impactful leadership journeys. Share your thoughts in the comments below!