leadership pitfalls

leadership training

"The adjustment to leadership is challenging. Preparation prevents failure."

Introduction

Stepping into a leadership role can feel exhilarating, but it comes with unique challenges. New leaders often stumble not because they lack potential, but because they’re unprepared for the hidden traps that come with the transition to leadership.

At Your 3rd Spot, we believe in empowering our leaders by shining a light on these common pitfalls, and preparing them to avoid the mistakes that could hinder their growth and the team’s success.

Each pitfall below includes lessons, parables, and actionable advice to guide youas you transition into leadership.

Growth begins with self-awareness—let’s start the journey.
Click on a Pitfall below for resources and advice
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The People Pleasing Politician

the lesson

Leaders often fall into the trap of wanting to be liked. While building positive relationships is essential, prioritizing popularity over principle leads to shallow leadership. People-pleasing leaders avoid hard conversations, make decisions to earn favor, and compromise their integrity, which eventually erodes respect.

Authentic leadership requires making tough calls aligned with values, not popularity. Respect grows when a leader is consistent, transparent, and willing to have candid conversations.

Psychological Connection

This theory explains our tendency to compare ourselves to others for validation. For leaders, it’s crucial to break free from seeking external approval and anchor decisions in core values.

Social Comparison Theory

parable

A wise emperor appointed a prime minister to manage rewards and punishments. The minister gained the people's obedience by maintaining order, while the emperor sought favor. When the emperor reclaimed punishment, his harshness led to discontent, resulting in the people replacing him with the respected prime minister, who balanced fairness and firmness.

The Emperor and The Prime Minister

Lesson

Leadership isn’t about being liked; it’s about earning trust by standing firm in your values, even when it’s unpopular.

"Decisions based on values build trust. Popularity is temporary and fades."

resources + advice

resources

the emperor's New clothes

HANS CHRISTIAN ANDERSEN

Radical Candor — The Surprising Secret to Being a Good Boss

KIM SCOTT | 21:20

The Blacksmith and the forge

Actionable Advice

  • Reflect on whether your decisions align with company values or seek approval.
  • Have at least one candid conversation this week that addresses a tough issue.
  • Celebrate respect over popularity—lasting impact comes from consistent integrity.

“If you want to make everyone happy, don't be a leader. Sell ice cream.”

- Steve Jobs

The illusion of knowledge

the lesson

New leaders often believe they need to have all the answers to maintain authority and gain respect. But pretending to know when you don’t creates a fragile foundation of trust. Once your team realizes you weren’t truthful, credibility is lost, and respect erodes. True leadership lies in vulnerability and curiosity. Admitting, “I don’t know, but let’s find out together,” not only builds trust but also fosters a culture of collaboration and growth. It sets the tone for your team to value integrity over ego, and learning over pretending.

Leadership isn’t about knowing everything—it’s about knowing how to guide others toward the best solutions.The more you guess, the more you risk believing your own missteps, and the more your team will eventually see through it.

Psychological Connection

The Dunning-Kruger Effect explains why those with limited knowledge tend to overestimate their expertise, while those with more knowledge are often aware of their limitations. By understanding this bias, leaders can embrace humility and seek out opportunities to grow instead of hiding behind the illusion of knowledge.

The Dunning-Kruger Effect

parable

A new restaurant manager, eager to prove his expertise, found himself hosting a wine tasting for an influential group of guests. Midway through the event, a guest asked him a detailed question about the history of one of the wines. Rather than admitting he wasn’t sure, the manager confidently made up a story that sounded believable. The guests seemed satisfied, and the evening continued. However, one guest quietly looked up the story on their phone and discovered it was completely false. Word spread among the group, and what began as an impressive evening unraveled into whispers of mistrust.

The next day, the manager confided in the head sommelier, admitting what had happened. The sommelier said, “You’re not expected to know everything about wine, but you are expected to be honest. A simple,‘That’s a great question! Let me look that up for you,’ would have left your credibility intact. Now you’ve not only lost their trust but risked the reputation of this restaurant.” From that moment on, the manager adopted a new approach: admitting what he didn’t know and inviting his team or guests to explore the answer together. Over time, his willingness to learn became a hallmark of his leadership, and trust was restored.

The Wine Expert's Mistake

Lesson

Leaders must protect their time like the lighthouse keeper protects his beacon. If you spend all day solving everyone else’s problems, you’ll neglect the responsibilities that define your role.Learn to say no. Set clear priorities. The most important tasks—the ones that keep your team moving forward—must come first.

"Admit what you don’t know so you can grow."

resources + advice

resources

How to speak up for yourself

Adam Galinsky  |  14:59

How you can use impostor syndrome to your benefit

Mike Cannon-Brookes | 13:43

The power of vulnerability

Actionable Advice

  • Write down one area where you need to grow and create a plan to address it.
  • Practice saying, “I don’t know, but let’s figure it out together,” at least once a week.
  • Share a recent moment of learning with your team to model humility and continuous improvement.

“Being ignorant is not so much a shame as being unwilling to learn.”

- Benjamin Franklin

Brené Brown  |  20:49

firefighting vs. preventing fires

the lesson

The thrill of solving crises often tempts new leaders into a firefighting mindset. While resolving issues can feel rewarding, the true mark of leadership lies in preventing them. Leaders must shift from reactive to proactive by analyzing root causes, building systems, and fostering a culture of prevention. Remember, the goal isn’t to be a hero—it’s to create stability and efficiency for the team.

Effective leaders don’t just solve problems—they create environments where problems rarely occur.

Psychological Connection

This bias makes people feel they must “do something” immediately when faced with a problem. Leaders must resist this impulse and focus on creating systems that prevent long-term problems.

Action Bias

parable

In a small village, fires broke out every summer. Leaders celebrated their bravery in putting out the flames, but the fires always returned. One leader, instead of joining the firefighting effort, invested in clearing brush, educating villagers, and building firebreaks. Over time, the fires stopped. The villagers learned that preventing problems earned greater respect than heroically solving them.

The Town and the Forest Fires

Lesson

Effective leaders don’t just solve problems—they create environments where problems rarely occur.

"Stop reacting. Start preventing."

resources + advice

resources

Are We Celebrating the Wrong Leaders?

Martin gutmann  |  15:55

Do you prefer a firefighter or an invisible superhero?

Got a wicked problem? First, tell me how you make toast

Actionable Advice

  • After resolving a crisis, identify and address its root cause.
  • Develop one preventive system (e.g., checklists or training) to help avoid recurrences.
  • Recognize team members who take steps to prevent issues.

“An ounce of prevention is worth a pound of cure.”

- Benjamin Franklin

TOM WUJEC  |  9:05

time management

the lesson

New leaders often mistake movement for progress. They race through their days answering questions, attending meetings, and reacting to every issue, believing their packed schedules are proof of productivity. But leadership isn’t about being busy—it’s about being effective. The real work of a leader isn’t just doing tasks but deciding which tasks truly move the team forward. Time is a leader’s most valuable currency, and without discipline, it’s easy to waste it on low-impact work. Leaders must take control of their schedules, ensuring that their energy is spent on the things that create lasting results. This means prioritizing, setting boundaries, and understanding that not every problem requires their solution.

Psychological Connection

Parkinson’s Law states that work expands to fill the time allotted for its completion. If you give yourself all day to complete a task, it will take all day. If you set strict time constraints, you’ll work with more focus and urgency. Leaders must recognize this tendency and create structured time blocks to maximize efficiency instead of allowing work to consume them.

Parkinson's Law

parable

There was once a lighthouse keeper responsible for keeping the beacon lit to guide ships safely to shore. Every day, he diligently cleaned the glass, refilled the oil, and ensured the light shone brightly. One evening, a fisherman came to him in distress. His boat needed repairs, and he begged for help. The lighthouse keeper, being a kind man, agreed to assist. Then another villager arrived, asking him to help mend a torn fishing net. Again, he obliged. More people followed, each requesting small favors. He worked tirelessly through the night, solving everyone’s problems—except his own.

As dawn approached, the keeper realized he had been so busy helping others that he had forgotten to refill the oil. The beacon flickered out, and without its guiding light, a ship crashed against the rocks. The villagers rushed to the shore in horror. The lighthouse keeper, devastated, turned to them and said, “I thought I was helping by saying yes to everything, but in doing so, I failed my true responsibility.” From that day on, he set strict priorities: first, the beacon. Only after it was shining brightdid he offer his time to others.

The Lighthouse Keeper’s Dilemma

Lesson

Leaders must protect their time like the lighthouse keeper protects his beacon. If you spend all day solving everyone else’s problems, you’ll neglect the responsibilities that define your role.Learn to say no. Set clear priorities. The most important tasks—the ones that keep your team moving forward—must come first.

"You are the programmer, not the machine."

resources + advice

resources

How to gain control of your free time

Laura Vanderkam  |  11:54

Swallow the Frog

Inside the Mind of a Master Procrastinator 

Actionable Advice

  • Schedule two blocks of uninterrupted time each week to focus on high-priority tasks.
  • Audit your week: What tasks advanced the team’s goals? What was wasted effort?
  • Learn to delegate: If a task doesn’t require your expertise, trust someone else to handle it.

“Don’t be so busy managing the small fires that you let the lighthouse go dark.”

- Unknown

Tim Urban  |  14:03

what got you here, won't get you there

the lesson

A leader's greatest challenge is recognizing that what made them successful before will not make them successful now. Many struggle with this transition, clinging to the skills, habits, and control that earned them their promotion instead of developing the mindset required for their new role. Leadership is not about proving you are the best at the work. It is about ensuring the team is set up for success. A great leader steps back from being the star performer, releases the grip that feels safe, and becomes the person who builds others instead of the person who does it all.

Psychological Connection

People are promoted based on previous success, often until they reach a role they are not yet equipped for. The trap is not in being promoted. The trap is staying who you were instead of growing into who the role requires. Loss Aversion compounds this — leaders hold onto control because letting go feels like losing something, even when holding on is what is actually costing them.

The Peter Principle

parables

There was once a gifted apprentice who worked under a master carpenter.For years, he studied every detail of the craft—chiseling, sanding, measuring—until he became the best in the workshop. His precision was unmatched, his designs flawless. One day, the master told him, “You are ready. From now on, you will lead this workshop.” The apprentice was thrilled. Now, he could build even more magnificent furniture than before. But something strange happened. As he buried himself in his own work, the shop fell into chaos. His team struggled, unsure of their tasks. Deadlines slipped. Clients complained. Frustrated, the new master carpenter worked harder, convinced that if he just built faster and better, everything would improve.

One evening, the old master returned to check on the shop. Seeing the frustration in his former apprentice’s eyes, he said,“You are still working as if you are an apprentice. But your job is no longer to build furniture—it’s to build craftsmen. The success of this shop isn’t measured by what you can make with your own hands, but by what your team can create under your guidance.” The words struck deep. The next morning, the master carpenter put down his tools and began teaching his team. He shared techniques, corrected mistakes, and gave his workers the confidence to succeed on their own. Within months, the workshop flourished—not because he was the best carpenter, but because he had become the best leader. 

The Apprentice and Master Carpenter

Lesson

Leadership requires a shift in mindset. It’s not about being the best at the job—it’s about making others better at theirs. The leader’s role isn’t to do more but to develop more—more skills, more leaders, more success for the entire team.

"Adapt to the role you have, not the one you had."

resources + advice

The Monkey and the Bucket

In the jungle, hunters would trap monkeys by placing treats in a bucket with a narrow opening. The monkey’s hand fit inside, but once it grabbed the treat, it couldn’t remove its fist. Refusing to let go, the monkey became trapped. Freedom required releasing the treat—but the monkey couldn’t let go.

resources

Actionable Advice

  • Identify one task you excel at and delegate it to a team member, guiding them through the learning process.
  • Spend time mentoring someone on their development goals, focusing on their growth instead of your own contributions.
  • Acknowledge and celebrate team successes over personal achievements.

“Your job as a leader is to make yourself less necessary, not more.”

- Unknown

Who moved my cheese?

Strategic Quitting

Paul Rulkens  |  11:42

Elizabeth Gilbert   |  19:28

Your Elusive Creative Genius

someone else will do it

the lesson

Leaders often assume someone else will address an issue, but this passivity undermines accountability. Leaders must act with a bias for action, stepping in when necessary and empowering others to do the same. Every unaddressed issue becomes a tacit endorsement.

Psychological Connection

This phenomenon occurs when individuals assume others will take responsibility in a group setting.Leaders must combat this by fostering ownership and accountability.

The Bystander Effect
The Diffusion of Responsibility

parable

A group of villagers were walking along a path. Suddenly, one of them slips and falls into a deep ditch on the side oft he path. Each villager stops and looks in on the fallen villager, but none reach down to help, assuming the next villager will. Leaving the injured villager in the ditch while the group continues walking.

Villagers and the Ditch

Lesson

Leadership requires stepping in when others hesitate—your action sets the standard.

"What you permit, you promote."

resources + advice

resources

Everyday leadership

Drew Dudley  |  6:14

The Science of Taking Action

Teamwork: When a Mousetrap isn't about the mouse

Actionable Advice

  • Identify one neglected issue and take ownership of resolving it this week.
  • Empower your team to take initiative by modeling decisive action.
  • Reflect on one instance where inaction led to a missed opportunity.

“Leadership is taking responsibility while others make excuses.”

- John C. Maxwell

Steve Garguilo   |  9:47

there's no such thing as a dragon

Holding the ball instead of creating clarity

the lesson

This pitfall exists because one of the hardest leadership transitions is learning how to start when the work is unclear. When a leader is asked to take on a project, it usually means they are being trusted with more than execution. They are being trusted to think, organize, clarify, and move the team forward.

That is the opportunity. The leader is being asked to move from machine to programmer. The machine executes the current script. The programmer helps write the next one.
A first project will rarely be beautiful. That is not the point. The point is to build the muscle. We are not trying to judge a young leader by their first project. We are trying to help them become the kind of leader who can own the 20th project, the 40th project, and the bigger opportunities they cannot see yet.

Psychological Connection

High performers are especially vulnerable to this pitfall because they are used to being good at things. They were promoted because they were reliable, hardworking, and strong in their previous role. Their confidence came from knowing what good looked like.

Then leadership changes the game.

Now the work is less clean. The answers are less obvious. The project has moving pieces, unclear ownership, shifting deadlines, and people waiting on them.

That is when fear shows up.

Fear rarely announces itself as fear. It usually shows up as overthinking, delaying, preparing a little longer, waiting for the right moment, or convincing yourself you will start tomorrow.

Delay gives temporary relief. For a little while, nobody can criticize the work because nobody has seen it.

But that relief is expensive. The project gets later. Trust erodes. The leader has to be chased. The final version becomes rushed. The exact mistake they were trying to avoid becomes more likely.

This is how overachievers accidentally become avoiders. They care about the work. They care about their reputation. They care about being seen as capable. They care so much that they stop moving.

This is also where impostor feelings show up. A leader starts asking, “Am I actually qualified for this?” The honest answer is that none of us are fully qualified for the next level before we grow into it. That is why the opportunity matters.

The work is not to prove you already know everything. The work is to show that you can move, learn, adjust, and improve.

That is leadership.

“The cave you fear to enter holds the treasure you seek.” Joseph Campbell

the pitfall

A leader is asked to take on a project. They understand the ask. They care about doing it well. They may even agree that it matters.

Then nothing happens.

No first draft. No questions. No outline. No update. No ugly version. No visible progress.

Just silence.

Most of the time, this is not laziness. It is avoidance dressed up as confusion.

The leader wants to do it right, but they do not know where to begin. So they wait. They tell themselves they are thinking, gathering information, or waiting for the picture to get clearer.

The problem is that clarity usually comes after movement.
A project rarely becomes clear while it sits in your head. It becomes clear when you write down what you know, name what you do not know, ask the next question, and let the first version expose the gaps.

A blank page feels safe because no one can judge it. But in leadership, silence creates a different kind of judgment.

No update is an update. No progress is a signal. No first draft means the project is already behind.

The Clarity Problem

Often, the thing stopping the leader is not the work itself. It is the lack of clarity.

They do not know the real goal. They do not know what success looks like. They do not know who needs to be involved. They do not know what is fixed, what is flexible, or when the first draft is expected.

Instead of seeking clarity, they hold the ball.

That is the mistake.

When someone tosses you the ball, do not disappear with it. Toss it back with better questions. That does not mean rejecting the project. It means showing ownership by clarifying the target.

Clarity is not something you wait for. Clarity is something you pursue.

If you are unclear, your first job is to get clear enough to take the next step.

The First Version Has a Job

The first post was not supposed to be perfect. It was supposed to be posted.

The first draft is not supposed to be perfect. It is supposed to exist.

The first plan is not supposed to answer every question. It is supposed to reveal the next question.

Perfection is the enemy of done. Remember this always.

A blank page protects your ego for a moment. A rough draft protects the outcome.

That is the trade.

The Project Is the Stretch

The project is rarely just the project.

The assignment on paper may be a post, a checklist, a training document, a menu rollout, or a room plan. The deeper lesson is ownership, confidence, follow through, and the willingness to step into unfamiliar work.

A leader often receives a project because someone sees more in them than they currently see in themselves. They are being given a chance to step outside the comfort zone where they already know how to win.

That stretch can feel uncomfortable because it threatens the identity they have built. A new project asks them to be a beginner again.

That is where growth happens.

A rubber band only serves its purpose when it is stretched. The stretching is the point.

read parable

tools + applications

parable

The banquet captain sat at the manager desk with a blank prep list open in front of her. Her first large event was four days away. The guest count was high. The client was important. The menu was close, but not final. The room layout had changed twice.

Her leader had asked her to build the plan.
She opened the document and froze.

She did not know the final menu. She did not know if speeches were before dinner or after dinner. She did not know if the bar needed two wells or three. She did not know how many bussers would be enough.

Every question created another question.
So she waited.

The first day passed. Then the second. Each time her leader asked how the plan was coming, she said, “I’m working on it.”

In her mind, she was telling the truth. She thought about it while she walked the room. She thought about it while she watched service. She thought about it on the drive home.

But nothing was written down. No one had been asked for input. No timeline had been started. No staffing gaps had been flagged. The project was alive in her head and invisible to everyone else.

On the third day, the chef walked by the desk and saw the blank prep list.

He asked, “Where is the plan?”
She said, “I do not have enough information yet.”
The chef looked at the empty document and said, “That is the only plan we cannot fix.”
Then he pulled up a chair.
“Write what you know. Write what you do not know. Write what could go wrong. Then ask the next question.”
She said, “It is going to be rough.”
He nodded. “Good. Rough means we can start.”

So she started. She wrote the event date, guest count, confirmed menu items, missing decisions, departments involved, open questions, potential risks, and next three actions.

The list looked unfinished because it was unfinished. But now the gaps could be seen.
The chef answered two menu questions. The beverage manager caught a staffing issue. The events manager clarified the timeline. Facilities caught a room flow problem before it became a guest problem.

By the end of the day, the rough draft had become a working plan.
The event went well. The captain learned something bigger than how to build a banquet prep list.

She learned that the work did not begin when she understood everything. She began to understand because she started the work.

The Banquet Captain and the Empty Prep List

Leadership Lesson

Leaders do not wait for the full picture before they move. They create the first version. They expose the gaps. They ask better questions. They let the team improve the plan.
A first draft is not supposed to be impressive. It is supposed to be useful.

It gives people something to coach. It gives the team something to challenge. It gives the project a shape.

The Clarity Loop

Use this loop any time a project feels unclear.
  1. Catch the ball. Acknowledge the ask and confirm that you understand why it matters.
  2. Name the target. Say what you believe the outcome should be.
  3. Name the fog. Identify the specific pieces that are unclear.
  4. Toss it back. Ask the few questions that are actually blocking progress.
  5. Move on what is known. Start the parts that do not require more information.
  6. Set the next check in. Tell your leader when they will see the first draft or next update.

The Five Questions That Create Clarity

  1. What does success look like?
  2. What is fixed, and what is flexible?
  3. Who needs to weigh in or make the final decision?
  4. What would make this fail?
  5. When do you want to see the first draft?

If you can answer those five questions, you can usually begin.

The 24 Hour Project Start Template

Within 24 hours of receiving a project, send this update.

“I wanted to send a quick project start update so you know where this stands.
  • Here is what I understand the goal to be:Here is what I know so far:
  • Here is what is unclear:
  • Here are the questions I need answered:
  • Here are my next three actions:
  • You will see my first draft or next update by:
Please correct anything I am misunderstanding so I can make sure I am aiming at the right target."

What Good Looks Like

A leader who is handling this well does not wait to feel fully ready.
  • They acknowledge the project quickly.
  • They clarify the goal.
  • They ask a small number of specific questions.
  • They create a rough first draft.
  • They identify risks early.
  • They communicate progress before being chased.
  • They use feedback without getting defensive.
  • They keep improving the plan until it can be executed.

The Standard for Getting Started

You will not always know where to begin. That is normal.

Doing nothing because you do not know where to begin is the pitfall.

Start with what you know.
Name what you do not know.
Ask the next question.
Build the first draft.
Make it better.
Your first draft is your worst draft. That is not a problem. That is the process.
Mistakes are expected. Disappearing is not.
Do not overthink this.
Just start.

resources

What I learned from 100 days of rejection

Jia Jiang  |  15:31

Inside the mind of a master procrastinator

Tim Urban  |  13:54

the Science of Taking Action

Steve Garguilo |  9:47

eat that frog

Brian Tracy

The power of vulnerability

Brené Brown |  20:02

What is First Principles Thinking?

Shane Parrish

Inversion and The Power of Avoiding Stupidity

Shane Parrish