Wherever You’re At, we’ve got some tools to help you
get there.
These are not summaries of the book. They are standalone tools — built for the leader who is in the middle of something right now and needs a practical resource, not another thing to read.
Most leadership content asks you to sit with an idea. These ask you to do something with it. Each one is a short, focused exercise — something you can work through in ten minutes or less that will tell you something honest about how you are leading right now. Not how you think you are leading. How you actually are.
Each tool is drawn from the same framework that drives The Waypoint Leader — the idea that leading people well is a skill you can actually develop, and that most leaders improve fastest when they have something concrete in front of them. A question worth sitting with. A mirror worth looking into. A checklist that makes you a little uncomfortable in exactly the right way.
Use them on your own. Use them with your team. Pass them to a leader you know who is stuck and doesn't know why. No email required. No subscription gate. Free, the way tools should be.
If something here connects and you want to go deeper, the book picks up where these leave off. And if you want to see these principles applied to real leadership situations, the case studies on Substack are built for exactly that.
A gut-check for every person on your team. Thriving. Coasting. Struggling. Ready for more. Ready to move on. Most leaders don't do this scan until someone resigns. This prompts it before that.
Three scenarios. Three response prompts each. Fill it out when things are calm so it's ready when they're not. Based on the First 15 Minutes protocol from Chapter 8 of The Waypoint Leader.
A simple three-part structure for 1:1s that have gone flat or transactional. Check in on the person. Check in on the work. Close with a forward question. One page. Ready to use today.
Five questions for the end of any workday. Not a journal — just a gut-check. Did I lead with open hands today? Did anyone feel more known because of something I did? Based on the Pillow Standard from The Waypoint Leader.
A posture check before a difficult conversation. Not a script — a set of honest questions about who the conversation is really for and what you're tempted to avoid saying. For more, see Chapter 6 of The Waypoint Leader.
Two columns. Metrics-focused decisions in the last 30 days. People-focused decisions in the last 30 days. Just name them. The list is the mirror. No scoring, no scale — just the honest look.
25 questions for your next 1:1 — organized from surface to meaningful. Not performance questions. Person questions. For new hires, inherited teams, or any leader who wants to know the people they lead a little better.
Before you ask your team about their story, you need to know your own. This worksheet helps you identify the 5–7 mile markers in your own leadership journey. Start here. For more, see Chapter 1 in The Waypoint Leader.
8 questions that help you diagnose whether you're operating in scarcity with a specific team member. Quick. Honest. Uncomfortable in the right way. For more on this, see Chapter 2 of The Waypoint Leader.
Six questions to ask yourself before delivering corrective feedback. Is this timely? Is this clear? Am I saying this for them or for me? Based on the Attribution Test and Clarity Is Kindness framework from the book.