32 leadership areas.
Seven days each.
Pick the area where you are stuck. Work it for seven days. Watch what moves. Built on 15 years of research across 80+ technology organisations. Free.
Not sure where to start? Read the 32 learning area guides first →
One complete series
Every area where CTOs and heads of engineering get stuck, fall behind, or stay reactive. Mapped across four domains. Seven days each. Each one free.
Browse All 32 ChallengesYou already know what you should be doing. That is not the problem.
The problem is that knowing and doing are separated by a gap that feels impossible to close while you are in the middle of it. You are in back-to-back meetings. Putting out fires. Delivering for the business. There is no time to step back and work on the leadership stuff.
So the trust issues stay. The performance conversations get deferred. The metrics still do not tell a story. The stakeholders still do not see you as strategic. And the gap between the leader you are and the leader you need to be quietly widens.
Most leadership development makes this worse. Courses you do not have time to finish. Frameworks that do not connect to Monday morning. Books that sit on your desk half read. Good intentions, zero traction.
Seven days. One area. Three tasks a day. A reflection question designed to make you sit with the uncomfortable truth. Small enough to actually do. Specific enough to actually change something.
Simple by design.
Seven days. Three tasks per day. One reflection. Designed so you can do it while leading a real team under real pressure.
Pick your area
Choose from 32 leadership areas across People, Process, Product, and Profit. Start where the pain is, or where the CEO keeps asking questions you do not have great answers to.
Do the seven days
Day 1 is honest self-assessment. Days 2 to 5 build the skill through action. Day 6 uses AI to surface what you already know but have not acted on. Day 7 is one specific commitment.
Move to the next one
Seven days per challenge. String a few together and the cumulative effect is significant. This is how real leadership development works in practice, not in theory.
More than tasks. A methodology in action.
Every challenge is built from the ground up on 15 years of research across 80+ technology organisations.
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A Day 1 diagnostic that tells you where you actually are
Not where you think you are. Four questions designed to make you honest with yourself before you start building. This is where most leadership development skips the hard part.
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Days 2 to 5 built from the area's own actions
Each task is specific enough that you know exactly what to do. No reading lists. No theory. Doing the work that actually moves the needle in this specific area.
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A Day 6 AI prompt built specifically for this area
Not a generic prompt. Built for this challenge. Paste it into Claude or ChatGPT. It will surface the thing you already know but have not acted on. This is the day most people get the most from.
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Reflection questions that a trusted peer would ask
Not HR-safe softballs. The kind of question you would pay a good executive coach to ask. Designed to make you sit with something uncomfortable long enough that something actually shifts.
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A Day 7 commitment that makes it real
Every challenge ends with one specific, observable change and the instruction to tell someone. Accountability is not built into most free resources. It is built into every one of these.
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4 emails across the week written for this challenge specifically
Not generic nudges. Written for each area. Day 3 for Delegation is different to Day 3 for Budget Planning because the stuck point is different. Timed to keep you moving when it gets hard.
Four domains. Every dimension of strategic leadership.
Click any area to go to your challenge. Start where the pain is.
Real results from technology leaders.
From heads of engineering to first-time CTOs. Built for the people doing the hardest job in the building.
"The diagnostic on Day 1 of the Trust Building challenge was the most uncomfortable 10 minutes I had in a long time. I realised I had not actually kept three promises I thought I had. That alone was worth it."
"I have done expensive leadership courses that gave me less than Day 6 of the Delegation challenge. The AI prompt surfaced something I had been avoiding for six months. I had the conversation the next morning."
"The format is the thing. Three tasks I can actually do. One question that sits with me all day. Nothing has created as much change per hour invested as these challenges."
32
Challenges across 4 domains
7
Days per challenge
15
Years of research behind this
80+
Technology organisations studied
Sometimes you need a human in the room.
The challenges are designed to move things. But some things are stuck for a reason that a PDF cannot reach.
The Unblocking Call. Show up. Talk it through. Leave knowing what to do.
You have done the challenge. You have run the AI prompt on Day 6. You know what the issue is. It is still not moving. That is when you book this call.
No prep required. No notes to write up beforehand. No follow-up deliverables after. You show up, talk through what is stuck, and leave the call with clarity on exactly what to do next.
Timothy J. Hitchens. 6x CTO. 15 years of research across 80+ technology organisations. 7 years at Amazon across Asia Pacific. He has seen your problem before. He knows what shifts it.
Limited spots each month. If the booking link is live, there is availability.
Leave Unblocked.
- ✓ 60 minute call with Timothy J. Hitchens
- ✓ Bring the problem. No preparation needed.
- ✓ Direct conversation. Not a coaching program.
- ✓ 15 years of pattern recognition across 80+ orgs.
- ✓ You leave the call knowing your next move.