Week 5 Day 4: The Three Questions: What Is Blocking You? What Do You Need? What Should I Stop Doing?

Ask your team these three questions regularly: What is blocking you right now? What do you need that you do not have? What am I doing that is making your job harder? The first two are comfortable -- most leaders ask some version of them already. The third one is where the real information lives. Because sometimes the obstacle your team is fighting is you.

The third question -- 'What am I doing that is making your job harder?' -- is the one that changed how I lead. The first time I asked it, there was a long silence. People do not expect their boss to ask them that. Then a senior engineer said, 'You change priorities mid-sprint. It happens every other week. By the time we context-switch, we have lost a day, and then the old priority comes back.' She was right. I had been doing it for months. I thought I was being responsive to the business. What I was actually doing was thrashing my team. Another person said, 'Your Slack messages at 10 PM make me feel like I should be working at 10 PM.' I had no idea. I was just jotting down thoughts before bed. But the team experienced it as pressure. Neither of these were things I would have discovered on my own. The data only came because I asked a specific, uncomfortable question and then sat in the silence until someone answered. You cannot fix what you cannot see, and you cannot see what nobody tells you.

The three-question framework draws from multiple research traditions. 'What is blocking you?' aligns with agile's daily standup protocol but is more effective in private one-on-ones where psychological safety is higher. 'What do you need?' maps to Hackman's conditions for team effectiveness -- the leader's role is to ensure the team has adequate resources, clear direction, and a supportive context. 'What should I stop doing?' is a direct application of Marshall Goldsmith's feedforward methodology, which emphasizes asking for specific behavioral change suggestions rather than general performance assessments. Research by London and Smither (2002) on feedback-seeking behavior shows that leaders who actively solicit negative feedback are rated as more effective by their teams, not less -- the act of asking signals self-awareness and genuine interest in improvement. The critical implementation detail is frequency: these questions lose their power if asked only during annual reviews. Leaders who ask them monthly create a continuous feedback loop that catches problems while they are still small and fixable.