When Good Intentions Meet Bad Systems

How are those New Year resolutions going? You know the ones. Get more done. Stay calmer. Be more strategic. Less reactive. Maybe you even blocked time in your calendar for deep work. Maybe you committed to checking email less frequently. Maybe you told yourself this would be the year you finally got ahead of the chaos. And then you came back to work. By Tuesday, the inbox was exploding. By Wednesday, you were in back-to-back meetings. By Friday, you were wondering where the week went and why nothing on your actual priority list got done. Here's what I've learned from working with leaders across multiple organizations: Your good intentions don't stand a chance against bad systems. The 30-Day Delete A few weeks ago, the CEO of a company I'm working with messaged me. One of his department leaders, someone I've been coaching, had shared some of the practices we'd been implementing together. The CEO decided to try one himself. He deleted every email in his inbox older than 30 days. All of it. Gone. Let that sink in for a moment. If you're like most leaders I work with, that idea makes your stomach drop. What if there's something important in there? What if someone follows up and you can't find the thread? What if you need to reference something and it's gone? But here's what he discovered: The psychological weight of carrying hundreds (or thousands) of old emails is exhausting. It's like walking around with a dozen suitcases you're afraid to set down. You might even call it digital hoarding. And the truth? Most of what's buried in those old emails will never matter again. And if it does? People will follow up. I applaud his boldness. Not because deleting old email is the right answer for everyone, but because he took ACTION instead of continuing to dread opening his inbox every morning. When Email Becomes a Graveyard The company I'm working with has new leadership pushing for efficiency and effectiveness. It's a welcome cultural shift, but change is hard. And one of the biggest challenges they're facing is a deeply ingrained habit: using email as a primary communication system across departments. Email trails with 5, 10, sometimes 15 people on the To and CC lines. Conversations stretching back months. Requests buried in paragraph 7 of the 23rd reply. Accountability diffused across so many people that no one actually owns the outcome. Sound familiar? Working with one of their leaders, I created summaries of over 50 email threads using a complex AI prompt. I organized them into a table with these columns: - Date - Name - Background and Explanation of Issue - People Tasked - Solutions Contributed - Outstanding Tasks or Responses - Notable Patterns The emails were arranged from newest to oldest, tracking who said what, when, and what was still unresolved. When my client saw these threads visualized in chart form, something shifted. He could suddenly SEE: - Where the ball was dropped - Who was being thrown under the bus - Clients asking for updates repeatedly, becoming more agitated with each round - Accountability evaporating into a cloud of CCs He was embarrassed, not because he didn't know it was happening, but because he'd normalized it. It seemed acceptable because it was so common. But email is not a communication system. It's not designed for collaborative problem-solving. It's not built for accountability. And it's terrible for tracking complex issues over time. Once he saw the pattern clearly, he knew what he had to do. He instructed his team to move internal communication to Microsoft Teams, where conversations are threaded, searchable, and accountable. He couldn't change the entire company's behavior overnight, but he could change his team's. Two System Changes That Matter These two examples, the CEO's bold email deletion and the leader's shift away from email threads, illustrate something crucial: Productivity isn't about trying harder. It's about better systems. When you're drowning in email, the problem isn't your discipline. It's that you don't have a system for: - Triaging what's actually urgent - Processing messages efficiently - Deciding what belongs in email versus other tools - Protecting yourself from digital hoarding When accountability is diffused across endless email threads, the problem isn't your team's competence. It's that you're using the wrong tool for the job. Systems That Fit Your Reality Here's the part that matters: Not every system works for every person. The CEO's 30-day delete might feel too risky for you. The shift to Teams might not fit your organization's culture. And that's okay. The goal isn't to copy someone else's system. The goal is to design systems that work for YOUR work style, YOUR team, and YOUR situation. That's exactly why I created the 4-Week Productivity Sprint as a one-to-one program. Because the leaders who succeed aren't the ones who adopt generic productivity hacks. They're the ones who build customized systems that address their specific challenges: - How the