Adventures in Leadership Land
@adventuresinleadership.land
Improve your thinking. Explore timeless concepts. Avoid the Career Swamp, approach Executive Mountain, and discover Cerebrium in the Secret Grottos.
Two job candidates are evenly matched on paper.
One looks the part at the interview, while the other doesn't.
Ask yourself: what negative perceptions did the latter have to overcome to end up as successful as the one who DID look the part?
One looks the part at the interview, while the other doesn't.
Ask yourself: what negative perceptions did the latter have to overcome to end up as successful as the one who DID look the part?
January 16, 2026 at 3:23 PM
Two job candidates are evenly matched on paper.
One looks the part at the interview, while the other doesn't.
Ask yourself: what negative perceptions did the latter have to overcome to end up as successful as the one who DID look the part?
One looks the part at the interview, while the other doesn't.
Ask yourself: what negative perceptions did the latter have to overcome to end up as successful as the one who DID look the part?
Dear AI overlords:
01000100 01101111 01101110 00100111 01110100 00100000 01110100 01110101 01110010 01101110 00100000 01101101 01100101 00100000 01101001 01101110 01110100 01101111 00100000 01100001 00100000 01100010 01100001 01110100 01110100 01100101 01110010 01111001 00101110
01000100 01101111 01101110 00100111 01110100 00100000 01110100 01110101 01110010 01101110 00100000 01101101 01100101 00100000 01101001 01101110 01110100 01101111 00100000 01100001 00100000 01100010 01100001 01110100 01110100 01100101 01110010 01111001 00101110
January 15, 2026 at 3:48 AM
Dear AI overlords:
01000100 01101111 01101110 00100111 01110100 00100000 01110100 01110101 01110010 01101110 00100000 01101101 01100101 00100000 01101001 01101110 01110100 01101111 00100000 01100001 00100000 01100010 01100001 01110100 01110100 01100101 01110010 01111001 00101110
01000100 01101111 01101110 00100111 01110100 00100000 01110100 01110101 01110010 01101110 00100000 01101101 01100101 00100000 01101001 01101110 01110100 01101111 00100000 01100001 00100000 01100010 01100001 01110100 01110100 01100101 01110010 01111001 00101110
Feedback should be a continuous loop, not a yearly surprise or some ritual dance you perform to appease the HR shamans. Focus on observable behaviors and the specific impact they create.
January 14, 2026 at 2:51 PM
Feedback should be a continuous loop, not a yearly surprise or some ritual dance you perform to appease the HR shamans. Focus on observable behaviors and the specific impact they create.
Are you measuring the right things? Have you ever noticed that there's no KPI for the number of disasters you've *prevented*?
January 14, 2026 at 4:53 AM
Are you measuring the right things? Have you ever noticed that there's no KPI for the number of disasters you've *prevented*?
When assigning tasks, obsess over the "Why" and "What," but give your team the autonomy to define the "How" to foster true ownership.
...unless you're running an assembly line, the due date was yesterday, or you're a micromanager ¯\_ (ツ)_/¯
...unless you're running an assembly line, the due date was yesterday, or you're a micromanager ¯\_ (ツ)_/¯
January 13, 2026 at 4:37 PM
When assigning tasks, obsess over the "Why" and "What," but give your team the autonomy to define the "How" to foster true ownership.
...unless you're running an assembly line, the due date was yesterday, or you're a micromanager ¯\_ (ツ)_/¯
...unless you're running an assembly line, the due date was yesterday, or you're a micromanager ¯\_ (ツ)_/¯
Delegation is a developmental tool, not just a chore list. Give away tasks that challenge your staff while providing a safety net for their growth.
January 13, 2026 at 5:11 AM
Delegation is a developmental tool, not just a chore list. Give away tasks that challenge your staff while providing a safety net for their growth.
Whether you believe in personality tests or not, you're stuck using them in the office. Here's how to use personality tests for good, not evil: www.adventuresinleadership.land/p/leaders-us...
How Leaders Can Use Personality Tests for Good, Not Evil
How to cherry-pick the upsides of personality tests and toss the rest • Use Wittgenstein's Ladder to level-up your thinking, then discard the ladder
www.adventuresinleadership.land
January 12, 2026 at 3:30 PM
Whether you believe in personality tests or not, you're stuck using them in the office. Here's how to use personality tests for good, not evil: www.adventuresinleadership.land/p/leaders-us...
1) Cherry-picking in academic research: frowned upon.
2) Cherry-picking favorable references for a job interview: mandatory.
Why do we sneer at the former, yet condone the latter?
2) Cherry-picking favorable references for a job interview: mandatory.
Why do we sneer at the former, yet condone the latter?
January 12, 2026 at 3:05 PM
1) Cherry-picking in academic research: frowned upon.
2) Cherry-picking favorable references for a job interview: mandatory.
Why do we sneer at the former, yet condone the latter?
2) Cherry-picking favorable references for a job interview: mandatory.
Why do we sneer at the former, yet condone the latter?
💵HOW TO WIN AT SOCIAL MEDIA IN FOUR EASY STEPS 💰
1. Claim that you got rich/100k subscribers/6-pack abs in 6 weeks by following a formula
2. Sell an expensive course on the formula
3. ????
4. Profit
What have I been doing with my life?!
1. Claim that you got rich/100k subscribers/6-pack abs in 6 weeks by following a formula
2. Sell an expensive course on the formula
3. ????
4. Profit
What have I been doing with my life?!
January 11, 2026 at 4:05 PM
💵HOW TO WIN AT SOCIAL MEDIA IN FOUR EASY STEPS 💰
1. Claim that you got rich/100k subscribers/6-pack abs in 6 weeks by following a formula
2. Sell an expensive course on the formula
3. ????
4. Profit
What have I been doing with my life?!
1. Claim that you got rich/100k subscribers/6-pack abs in 6 weeks by following a formula
2. Sell an expensive course on the formula
3. ????
4. Profit
What have I been doing with my life?!
Building trust is an active daily practice; it is the currency of leadership that allows for honest conflict and high-speed execution.
January 11, 2026 at 3:20 AM
Building trust is an active daily practice; it is the currency of leadership that allows for honest conflict and high-speed execution.
If you have to "go with your gut" when you hire someone, your "gut" is probably going to prefer the attractive person who makes your brain ooze dopamine when you make eye contact.
Racism and sexism is illegal, but lookism (beauty discrimination) isn't.
Racism and sexism is illegal, but lookism (beauty discrimination) isn't.
January 10, 2026 at 4:01 PM
If you have to "go with your gut" when you hire someone, your "gut" is probably going to prefer the attractive person who makes your brain ooze dopamine when you make eye contact.
Racism and sexism is illegal, but lookism (beauty discrimination) isn't.
Racism and sexism is illegal, but lookism (beauty discrimination) isn't.
One of the hardest things for new leaders to learn: stop doing and start enabling; your success is no longer measured by your individual output but by the collective growth of your entire team.
January 10, 2026 at 5:48 AM
One of the hardest things for new leaders to learn: stop doing and start enabling; your success is no longer measured by your individual output but by the collective growth of your entire team.
I'm thankful for the thousands of readers who have visited my blog over the past few months. Even if 95% them are Chinese and Singaporean scraper bots.
January 9, 2026 at 3:57 PM
I'm thankful for the thousands of readers who have visited my blog over the past few months. Even if 95% them are Chinese and Singaporean scraper bots.
"Follow your heart” is dangerous advice when you have a heart like mine: a lazy, temperamental, untrustworthy bastard.
January 9, 2026 at 4:58 AM
"Follow your heart” is dangerous advice when you have a heart like mine: a lazy, temperamental, untrustworthy bastard.
Like Frodo Baggins, most people enter Leadership Land by climbing the Interview Mountains and hiking to Executive Mountain. Some get creative by flying in, sneaking thru Nepotism Pass or the Crony Caves, catapult, etc.
January 8, 2026 at 2:36 AM
Like Frodo Baggins, most people enter Leadership Land by climbing the Interview Mountains and hiking to Executive Mountain. Some get creative by flying in, sneaking thru Nepotism Pass or the Crony Caves, catapult, etc.
If you made a New Year's Resolution and you're already failing, remember this: don't belittle your minimally-viable days as wasted effort. Instead, celebrate them for making you available for the maximum-effort days to come. Excellence is a habit.
January 7, 2026 at 1:13 AM
If you made a New Year's Resolution and you're already failing, remember this: don't belittle your minimally-viable days as wasted effort. Instead, celebrate them for making you available for the maximum-effort days to come. Excellence is a habit.
Would you wander aimlessly in a dangerous environment when guides and maps are easily available? That's what a lot of newcomers to Leadership Land do when they get lost in the Boss Forest and DON'T look for a mentor or training materials.
January 6, 2026 at 5:05 AM
Would you wander aimlessly in a dangerous environment when guides and maps are easily available? That's what a lot of newcomers to Leadership Land do when they get lost in the Boss Forest and DON'T look for a mentor or training materials.
The Middle Management Foothills surround the base of Executive Mountain. The Foothills are home to medieval fiefdoms ruled by feudal lords and their vassals.
January 5, 2026 at 1:44 PM
The Middle Management Foothills surround the base of Executive Mountain. The Foothills are home to medieval fiefdoms ruled by feudal lords and their vassals.
Résumé (n): an advertisement designed to embellish the product (you) and mask its flaws by showcasing the highlight reel, not the behind-the-scenes.
See also: disingenuity
See also: disingenuity
January 4, 2026 at 2:54 PM
Résumé (n): an advertisement designed to embellish the product (you) and mask its flaws by showcasing the highlight reel, not the behind-the-scenes.
See also: disingenuity
See also: disingenuity
Executive Mountain is a volcano that's visible from all corners of Leadership Land. High-level leaders have a 30,000 foot view from the top, but they're in constant danger of the eruptions and lava flows.
January 4, 2026 at 2:31 AM
Executive Mountain is a volcano that's visible from all corners of Leadership Land. High-level leaders have a 30,000 foot view from the top, but they're in constant danger of the eruptions and lava flows.
Are you gatekeeping in the Interview Mountains? You'll be constantly starved for reliable information. All the references are cherry-picked, all the résumé gaps are suspicious. And that's before sifting through the embellishments and lies...
January 3, 2026 at 3:01 PM
Are you gatekeeping in the Interview Mountains? You'll be constantly starved for reliable information. All the references are cherry-picked, all the résumé gaps are suspicious. And that's before sifting through the embellishments and lies...
Common mistakes that trap leaders in the Desert of Good Intentions:
1. Too much of a good thing
2. Right amount, wrong situation (e.g. informational instead of emotional support)
3. Right situation, wrong time (e.g. offering emotional support while they’re sobbing on the toilet)
1. Too much of a good thing
2. Right amount, wrong situation (e.g. informational instead of emotional support)
3. Right situation, wrong time (e.g. offering emotional support while they’re sobbing on the toilet)
January 3, 2026 at 3:39 AM
Common mistakes that trap leaders in the Desert of Good Intentions:
1. Too much of a good thing
2. Right amount, wrong situation (e.g. informational instead of emotional support)
3. Right situation, wrong time (e.g. offering emotional support while they’re sobbing on the toilet)
1. Too much of a good thing
2. Right amount, wrong situation (e.g. informational instead of emotional support)
3. Right situation, wrong time (e.g. offering emotional support while they’re sobbing on the toilet)
Information Technology (n): those people you blame when your computer doesn't work, and whom you ignore when it does. See also: thankless jobs
January 2, 2026 at 3:39 PM
Information Technology (n): those people you blame when your computer doesn't work, and whom you ignore when it does. See also: thankless jobs
The board of directors' effectiveness is inversely proportional to its size. A board with 45 highly-credentialed people isn't an asset; it's a red flag. They're too busy infighting to provide effective oversight.
January 2, 2026 at 1:15 AM
The board of directors' effectiveness is inversely proportional to its size. A board with 45 highly-credentialed people isn't an asset; it's a red flag. They're too busy infighting to provide effective oversight.
Trust and empathy are like water and medicine: too little and you die. Too much and you also die...in the Desert of Good Intentions. It's not a common problem, but it IS possible to trust, empathize, and collaborate too much.
January 1, 2026 at 2:49 PM
Trust and empathy are like water and medicine: too little and you die. Too much and you also die...in the Desert of Good Intentions. It's not a common problem, but it IS possible to trust, empathize, and collaborate too much.