A few weeks ago, I heard Daniel Coyle talk about his latest book, Flourish. During the conversation, he mentioned that the idea that readers have most frequently connected with is the concept of “yellow doors” that appears in the epilogue.1

The idea is that while we normally go through life alert to clear, unmistakable signals—that is, green doors that are open and red doors that are closed—life deepens when we become aware of the yellow doors, the ones we glimpse out of the corner of our eye.

I was initially surprised (and a little embarrassed) by this. When I read the book, I highlighted a number of passages. The section on yellow doors wasn’t among them.

But it makes sense that it would resonate with a wide range of readers. The idea is easy to understand and, more importantly, it has a strong emotional component. For some, yellow doors are the choices they dared to make that changed their lives. For others, they’re the missed opportunities and what ifs they still think about to this day.

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As I listened to Coyle talk, I began to reflect on my own experiences. My career has had its fair share of yellow door moments. Each time, I agonized over the decision before ultimately saying yes and stepping into a new and uncertain reality.

Eventually those decisions proved beneficial, creating lasting relationships and pushing me to grow in ways I wouldn’t have otherwise. But there was always a lag between the decision and the payoff. Because, for me, the hard part has never been stepping through the door. It’s been embracing the choice once I made it.

Yellow doors often lead to new experiences. And new experiences — while exciting and ultimately worthwhile — put us back in the unwanted position of being a novice again. Even the most self-assured people can find themselves embarrassed, frustrated, and afraid of what others will think of them when they’re forced to start something new.

The irony is that the best way through the novice phase is to lean into the uncomfortable feelings — to channel our child-like qualities, and let curiosity and experimentation guide us.

Far more often, pride gets in the way and we do the opposite. We hold back questions, avoid situations where we might fail, and give up too soon. We’re so concerned with perception that we don’t allow ourselves to learn and get better.

That’s been my experience in every new role I’ve taken. In my last job, I spent the first six months trying to prove myself in another equally destructive way: by mimicking my previous boss. Turns out, I’m not him, and while he was great in his role, I was never going to succeed in the same way. It wasn’t until I realized what I was doing that I could drop my ego and finally start doing the job.

Most people don’t struggle to find, or even take, opportunities. The struggle comes after walking through the door. We get in our own way, letting fear and hubris keep us from really giving the opportunity a chance.

It’s often said that fortune favors the bold. But it’s important to understand what it means to be bold. Bold people aren’t fearless. They’re as scared as the rest of us, but they acknowledge their fear and act in spite of it.

The takeaway isn’t to blindly take every yellow door that appears — they’re yellow for a reason, after all.2 But when you do decide to walk through a door, do more than merely say yes. Walk through with your eyes wide, your mind open, and your pride tucked safely away. Accept that things will be messy and enjoy the ride. Otherwise, you might as well not walk through the door at all.

It’s starting up again. Over the last week, the Red Sox and Phillies fired veteran managers Alex Cora and Rob Thomson.

When a manager is dismissed in-season — at least in recent memory — it’s safe to assume what the general manager is going to say.1 They’ll acknowledge that responsibility for the roster and the success of the organization falls on them, praise the outgoing manager for their professionalism, and explain the move with the need for a new voice.

If you don’t look too closely, the statements sound good, even if they are a bit repetitive. They paint the picture of a leader taking ownership and acting decisively for the good of the franchise. But on closer inspection, the sense of accountability doesn’t hold up.

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In the same breath, the GM suggests they’re to blame for the team’s underperformance and as a result…someone else is being fired.

It’s almost as if they want to signal responsibility without taking the more difficult steps to enact real change.

And that’s what separates accountability from something that’s merely symbolic. It’s not enough to claim ownership; actions need to follow.

GMs — while ultimately responsible for the rosters — aren’t very well going to fire themselves when things are going poorly (even if some fans would prefer that). But that isn’t the only way to be accountable for underperformance.

When outcomes fall short, it’s worth asking why. A good place to start is with an honest assessment of the processes and decisions behind those results. There are likely ways the organization can improve or continue to evolve.

Evaluating inputs and then taking action based on those findings to promote change — that sounds more like accountability.

And there will be cases where that work points to a change in leadership. Managers should be fired at times.

But two things are usually true:

1. Far more often, the more accountable move is supporting that manager rather than replacing them.

2. If a change is necessary, it warrants a more complete explanation than the need for “a new voice.”

Finding a good manager is hard. The role demands so many things — leadership, communication, in-game decision-making, media relations — that it’s unrealistic to think anyone will excel at all of them.

That makes it even harder to believe that a new manager will be better, unless something fundamental has broken.

In many recent cases, the manager still commands respect, upholds the organization’s values, and makes daily effort to improve. Removing them — especially as the only form of action — might feign accountability, but it’s unlikely to do much.

A more accountable response would be to publicly support the manager and outline organizational changes in pursuit of better results.

It’s probably not a coincidence that the best organizations have the most continuity in leadership. Some would say their success allows for that stability, but those teams still have down seasons and fall short of expectations from time to time.

And yet, clubs like the Tampa Bay Rays, Cleveland Guardians, and Milwaukee Brewers rarely fire leaders, and often promote from within when they do. The same is true for big market teams like the New York Yankees and Los Angeles Dodgers. Despite impossible expectations — where anything short of a World Series title is viewed as a failure — they maintain similar standards and patience, sticking behind their people when things don’t go as planned.

Giants’ President of Baseball Operations Buster Posey offered a clear version of accountability last July when the organization decided to pick up manager Bob Melvin’s option:

“I still believe in (our) group of players, but it boils down to them needing to play better baseball. If anybody deserves blame from the top, it should be on me. It shouldn’t be on our manager or our coaching staff. I’m the one who sets the roster.”

A few months later, after the season ended, Posey fired Melvin. Explaining the decision to the media, he said:

“When seasons don’t go the way you want, it’s never one person’s fault, it’s never one group’s fault. But when they don’t go the way you want them. You can’t, in my opinion, can’t sit there and say we’re gonna come back and do the same thing for the next year. Having said that, that’s partly why we landed where we landed.”

That’s a stark change in tone.2 The first statement takes responsibility, backs the manager, and reinforces that everyone is in it together. The second one says something altogether different.

And the message is a critical part of tough decisions.

Most people in an organization form their impressions of leadership through public comments. They don’t have personal relationships with or consistent access to senior leaders like the general manager. For every Slack message or video call they see, there are five to ten times as many media appearances that shape their opinions. What’s said publicly becomes a narrative about how decisions are made and what’s valued in that culture.

Even when expected, firing a manager is rarely easy or popular. Making tough choices is part of leadership. But doing so and offering a vague explanation — or worse, no explanation at all — misses an opportunity to build trust and it forces others to fill in the blanks themselves.

One of the common refrains when a manager is fired is that someone had to be held accountable. The turnover and accompanying statements don’t phase us anymore, because we’ve been conditioned to believe that’s what accountability looks like.

Only it’s not. Accountability isn’t about a single decision, or someone falling on the sword when things go wrong. It’s about ownership, understanding, commitment, and, at times, meaningful change.

And just as importantly, it’s about why those choices are made and how they’re explained. Accountable leaders don’t hide their thinking. They trust the people around them to understand their actions — even when they disagree with the decision.3

I’ve been thinking about Jeremiyah Love a lot this week.

Love is the uber-talented running back from Notre Dame likely to be selected within the top 5-10 picks of tonight’s NFL draft. He’s projected to be a top pick despite consistent evidence that investing in running backs early is not a good strategy.

Every public draft analyst knows that research and has still ranked Love as one of the top players available. The argument is that he’s different from other running backs and the type of player that negates concerns over positional value.

It’s exactly the kind of situation where an outside view helps.

I was first introduced to inside and outside views from Shane Parrish at Farnam Street.1 An inside view looks at situations strictly through the task at hand, using specific details and circumstances to make decisions based on a narrow band of information that’s easily accessible. Outside views take the opposite approach, zooming out to look for similar situations that can help inform how to operate in the current context.

The inside view itself isn’t a problem; the problem comes when we only focus on the inside view. Humans are naturally biased to overemphasize unimportant details, construct narratives not supported by evidence, and overestimate the likelihood of good outcomes. We’re inherently flawed decision-makers.

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And yet almost everyone defaults to the inside view. The challenge or decision is right in front of us, and everything about the situation feels unique. We immerse ourselves to understand what’s going on and select the best path(s) forward. It’s easy to miss the bias when everything looks right.

That’s where the outside view comes in. Outside views force us to think about problems as anything but unique, and find people in comparable situations to examine and learn from what they did.

We know what good decision-making looks like. It’s using the past to inform predictions, relying on large samples, incorporating a variety of perspectives, and learning as we go. These ideas are all about moving beyond specifics to consider the big picture. That’s the logic — and the benefit — of outside views.

More importantly, outside views inject a healthy dose of humility into decisions. Intentional or not, inside views are teeming with ego. It’s arrogant to think that we know better than anyone else or we can succeed where others have failed. But we all do it. We convince ourselves our situation is different.

Outside views help curb those instincts. Armed with success rates from similar situations, we can shift from arrogance to confidence — a subtle but important distinction. We’re still making decisions with conviction, only now the conviction is grounded.

If the benefits are so obvious, why doesn’t everyone use outside views? Like many things, what’s simple in theory is more challenging in practice. Stepping back means fighting human nature and biases that aren’t always noticeable. It also requires slowing things down to add time and effort.

Still, with intention, outside views can be applied in nearly any situation.

It begins with a reference class of similar situations or decisions to examine. Ideally, a group that is large enough to carry weight and specific enough to match the dynamics at play. Getting this right takes critical thinking and creativity, but with a little practice, we can assemble useful comparables to learn from. And once we get more comfortable, we can layer multiple outside views to look at problems from every angle.

Which brings us back to Jeremiyah Love. By all accounts, teams should consider Love with an early pick. He was an incredibly productive college player. He is an elite athlete that could potentially excel at multiple positions on the field. And for all the praise for his talent, people speak even more highly of his character. The information is all overwhelmingly positive.

But everything I mentioned focuses exclusively on Love. It’s specific to him and the details of his profile. It’s the inside view.

To really grapple with selecting Love, we need to go beyond those details and ask a different set of questions:

• How have first-round running backs (especially those taken in the top 10) performed?

• How have teams that spend top-10 picks on running backs fared?

• Where do winning teams typically get their running production?

Those questions aren’t about Love. They’re about base rates, the factors surrounding the pick, and what’s happened in previous situations. And in this case, the answers tell a different story.

First round running backs have fared fine individually, but the teams that have selected them have struggled to build winning rosters around them.2 Similarly, the more successful teams of the last decade have rarely invested premium draft capital into running backs. That might not be enough to move Love down the board, but it at least warrants consideration.

Outside views don’t make decisions for us. They won’t tell us what we should or shouldn’t do. But they will provide more information and better context.

Often, that additional context improves decisions. Understanding how similar situations have played out leads to better predictions. It’s easier to give someone else advice than to follow it ourselves. Outside views allow us to step back and approach decisions from the same objective lens.

I’m not suggesting it’s wrong to take Jeremiyah Love with an early pick. I wouldn’t do it, but I understand someone coming to a different conclusion. As long as that conclusion accounts for what’s happened before.

There’s too much to learn from the past to treat any decision as unique. It may feel different. In reality, it usually isn’t.

This wasn’t the plan.

With the NFL draft around the corner, I intended to build a simple model and write about my projections for this year’s crop of quarterbacks. But after fiddling with inputs for a few days, my results remained no better than simply using draft position.

Fortunately, not all was lost. In my attempts to improve performance, one variable continually showed signal: age at the time of the draft.1 And that’s a more interesting subject to talk about.

At this point, most, if not all, professional organizations use a model to help inform draft decisions. The type of model, and the degree to which it’s relied upon may vary, but they have something that aggregates information to predict how good players will be.

And if my experience is at all representative, the inclusion of age in those models elicits strong feelings.2 That’s because 1) it clearly adds predictive value above and beyond scouting reports and performance and 2) where that value comes from is misunderstood.

When most people hear that age is important for draft picks, they assume it means:

• Younger players have more time remaining for physical development

• Younger players have played less and therefore their skills will develop quicker with professional instruction

• Younger players are more athletic with higher upsides

Despite being plausible, none of these reasons explain why age matters. Or maybe they do. Because we don’t know, with any real certainty, why age shows signal. All we know is that the combination of scouts and statistics alone under-project young players and over-project old players. Anything beyond that is conjecture.

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That’s a hard truth to accept. Uncertainty is far less comforting than an understood narrative.

And if it stopped at narrative, it wouldn’t be a problem. Unfortunately, it rarely stops at the rationale; that rationale is then weaponized to dismiss age when the story doesn’t fit. Anyone who’s been in draft meetings can attest. The young player who is physically mature moves down the board, or the older player who only recently began playing their sport rises.

It could be correct to discount age in those cases, but it’s not based on evidence. The objective information says that predictions improve when they account for age.

That leads to the important question: how should teams incorporate age into their models?

Because, like most things, it’s not as simple as taking the output at face value.

Draft models are built on history. A good training set — something recent enough to be useful but with enough time to understand outcomes — will consist mostly of data that’s 10 or more years old.3

But things have changed dramatically, for any organization, over ten years. Many of the scouts who wrote the old reports have moved on to new teams. Player development has modernized with new technologies and added emphasis on training, nutrition, and recovery. And maybe most importantly, teams understand far better that age matters.

Since Rany Jazayerli’s groundbreaking article 15 years ago, scouts have slowly acknowledged that young players tend to perform better.4

If evaluators are aware that age matters, and that awareness influences their reports, including a model adjustment for age runs the risk of overcorrecting. Then again, there’s plenty of research to suggest that awareness of bias isn’t enough to overcome bias. Even if scouts are factoring in age more than they did previously, the signal may be as strong as ever.

Teams use models because they’re better than humans at combining and weighing information, which is really what decisions in the draft are all about. But there’s a reason the most well-known quote about models tells us that only some of them are useful. Models don’t (perfectly) reflect reality and they require a great deal of choice and understanding to use effectively.

You could convince me that nearly any magnitude of adjustment for age makes sense; you just won’t be able to prove it.

The inclusion of age boils down to belief. Based on everything — history, environment, people — what do we believe is appropriate? What bet are we comfortable making?

Fernando Mendoza, the presumptive top pick in next Thursday’s NFL draft, is 22.5 years old. That’s slightly younger than the average quarterback drafted this century. How much that matters is a question that every NFL team has to answer for themselves.

We tend to think about reading in terms of usefulness.

In school, we’re asked to write reports and take tests to prove comprehension. As adults, we usually follow one of two paths: we stop reading altogether, or we select books based on their utility.

That framing is too narrow. It’s the wrong lesson. The point of reading isn’t to change what you know. It’s to change how you think.

Reading for utility sounds reasonable. Correct, even. That’s the rub.

The irony is that reading to acquire knowledge can actually work against learning.

When acquisition is the driver, you read quickly, skimming pages for surface level insights. You can get through more content, but you don’t truly engage with or contemplate ideas.

Without realizing it, you focus on memorizing facts, confusing retention with understanding. We’ve all crammed for a test that way, only to find that the material is out of our brain faster than it entered. Memorization feels like learning, but it’s not the same.

You also limit what you read. The majority of works are off the table immediately, leaving only a handful of books in related subjects. Even if you expand the filter, you’re likely to select things that are safe and easy to consume. There’s no room for new ideas that challenge or expand your thinking.

And again, learning, in the conventional sense, isn’t the purpose.

I used to exclusively read books about sports front offices.1 Eventually, I broadened my criteria to include adjacent topics like decision-making and communication — as long as the books covered something that could reasonably apply to my professional life.

Where that standard came from, I couldn’t tell you.

I know I didn’t enjoy reading in school. It was mandatory. Teachers selected the books.2 And I felt forced to adopt consensus views rather than come up with my own thoughts.

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When I got older, I found reading to be more enjoyable, but it was still homework in many ways.

It wasn’t until a few years ago that I redefined my own purpose. For me, it began with reading more fiction. I had always treated fiction as taboo because I couldn’t see how it would enhance my career. What I didn’t realize — obvious as it now seems — is that my thinking wasn’t only wrong, but it also didn’t matter. Novels transport you to different worlds. They take you inside the minds of other people. They ignore conventional rules and push the boundaries of what is possible.

At first, it felt strange reading things that weren’t directly useful. I may have even felt guilty. Slowly, I began to see that there might be a different way to approach reading.

I could tell you that shifting purpose comes with a host of benefits related to learning and growth. It allows for slower, more reflective reading and sparks connections that didn’t previously exist.

But — and I can’t stress this enough — that isn’t the point.

Instead, I’ll tell you that when you let go of the need to take something away from everything you read, something cool happens.

Sometimes you’ll read something and learn.

Other times you’ll read something and feel a certain way, a certain emotion.

Occasionally, you’ll read something and find it’s not for you.

In every instance, you’ll be different when you finish reading than when you started. Not necessarily noticeably different (which would be exhausting for you and everyone around you), but in small, almost imperceptible ways. Your thinking will evolve because you opened yourself up to something new, regardless of what exactly happened as a result.

Think about it. The best books you’ve ever read, are they really the ones you remember perfectly? That you can quote line for line?

We love books that expand the way we think, for a variety of different reasons. That’s enough.

The other great thing about redefining purpose — it doesn’t actually have to change what you read. Every book you could possibly select when reading for utility remains available when you shift your mindset.

I still read a lot of books about decision-making, learning, and communication. I also read memoirs, novels, and oral histories of emo’s mainstream explosion. Everything is on the table.

Reading is often seen as a sign of intelligence, drive, and status.

I realize now that I was reading for me, but I was also doing it to support my identity. To offer opinions where I hadn’t yet formed my own thoughts. To not be excluded from conversations.

I was reading out of obligation, acting based on what I should do, not what I wanted to do. And that obligation was entirely self-inflicted, which is the worst kind of obligation.

Once I realized what I was doing, I made a tiny reframe. A reframe that changed how I think about reading. Maybe it will do the same for you.

Everyone seems to be talking about AI. You can’t open a browser, turn on a television, or venture out in public without hearing debate about how the job market will shift.

For some companies, the time to act is now. In a recent move, Block laid off 40% of its workforce, citing AI’s capabilities to automate and eliminate work.

In a vacuum, organizations that move with speed and clarity are often rewarded for their decisiveness. Block may be no different. The theoretical benefits of AI adoption are easy to see. Automation increases efficiency, saves money, and diverts resources toward higher-value tasks. But as others follow Block’s lead, I can’t help but ask a few questions. What are the costs of replacing workers? And are leaders moving too quickly without considering second-order effects?

One concern is the effect on learning, development, and leadership pipelines.

If the work being replaced helps prepare employees for more impactful roles, that loss of development could negate any efficiency gains.

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Many professionals spend the early parts of their careers performing menial work. In sports, that includes data entry, video tagging, report writing, article summaries, research, sales calls, and wearing a mascot costume.

Someone has to do these things. But even beyond that, these seemingly meaningless tasks often provide context, teach skills, and allow for the kind of failure necessary to succeed in the future. The work blends an immediate component with a development tail. Apprenticeships have existed in some form for thousands of years, built on the idea that learning drives skill acquisition. There is a gap between apprentice and master, and automating work without that in mind threatens our ability to close that gap.

The concern isn’t limited to entry-level positions, either. Anthropic’s labor market impact study suggests that AI may have significant capability in many management tasks as well.

A well-intentioned company might look at that data and decide to automate the majority of its performance feedback processes.1 AI can design rubrics, generate templates, and organize notes. Eliminating that work allows managers to spend more time delivering feedback. Win-win. But what if creating supporting materials is an integral part of learning to give good feedback?

Writing the rubric helps the manager give clear and explicit expectations. Organizing notes develops empathy and forces more intentional word choice. And the effort expended — while low impact on the surface — shows genuine care, increasing the likelihood that feedback is received and internalized.

If that’s the case, automating those elements doesn’t help the business. It removes an important part of how managers develop the ability to give good feedback.

My hope is that the organizations adopting AI at scale are considering these ramifications. But I’m skeptical. Just the other day, a friend told me about a conversation at his consulting firm. His boss suggested that AI will allow them to eliminate junior analysts across the company, relying solely on technology and senior analysts. When my friend asked the obvious question — where their future senior analysts will come from — his boss didn’t seem to have an answer.

That response is disappointing. It’s also surprising given the similar discourse happening in education. Educators and parents are afraid that students who use AI in the classroom are not going to develop writing, research, or critical thinking skills. Even if students have access to these tools in the future, they won’t be able to use them effectively without first building foundational knowledge and skills.

It makes sense. Using AI to replace tasks largely increases efficiency. Learning, on the other hand, is many things — but it isn’t efficient.

To combat the issue in education, two camps have emerged. One champions AI regulation. The other wants to redesign education to incorporate AI in ways that prepare students for the future. At the core of both approaches is the importance of ensuring learning and development aren’t lost as the landscape shifts.

Organizations are often rewarded for decisive action. That’s especially true when decisions are reversible.

But replacing work — especially if it comes at the expense of development — isn’t clearly reversible. It’s less experiment and more choice. Once a company eliminates roles or processes, it’s hard to put the genie back in the bottle.

Major League Baseball’s implementation of the Automated Ball-Strike Challenge System offers an example of how technology can be adopted without sacrificing skill development. Human umpires will call balls and strikes, with the ABS system running in the background and teams permitted two challenges per game.2

MLB could have allowed ABS to call every pitch of every game. If the goal is to get all of the calls correct,3 there’s a strong argument that’s what they should have done. But if fans don’t like the challenge system, or the technology fails, there is still a need for humans who can identify whether a 99 mph fastball on the edge is a ball or a strike. The challenge system is a hybrid that improves accuracy while preserving the skill development of umpires.

These things can coexist. Mass AI adoption and robust people development programs are not mutually exclusive.

In the performance feedback example, providing context and prompting AI agents might be enough to develop the underlying skills that managers need. If not, organizations can keep those workflows or find other ways to build the same capabilities. The outcomes hinge on the choices they make.

Every emerging technology creates opportunity. AI is no different. But as work changes, it’s worth considering what will remain the same. And it’s hard to imagine a future that doesn’t continue to reward learning, development, and growth.

Early March has always been my favorite part of Spring Training. Young players getting meaningful playing time in Major League games with backfield games starting up — how can you not be romantic about baseball?

Alas, the spring isn’t without frustrations. Because as much as I enjoy this time of year, it’s also a striking example of how inertia and misaligned incentives enable obviously incorrect practices to persist.

What am I referring to? That the days during Spring Training start way too early.

Before we get too far, it’s worth admitting that I’m the diametric opposite of a morning person. If it was up to me, sleeping in would be more normalized across society.

But the thing about Spring Training start times is that no one thinks they should be as early as they are. More often than not, there is emphatic agreement that something needs to change.

Professional baseball is a highly competitive environment mixing elite athletics with high-pressure decisions. It’s well understood that sleep, rest, and recovery have huge impacts on performance, injury prevention, and critical thinking. Some might quibble on the magnitude of the effect, but directionally, there is no argument, evidenced by the large investments teams make in specialists and technology to track, evaluate, and improve sleep. Expecting young athletes — and in the minor leagues we’re often talking about teenagers — to get 7-8 hours of sleep before an early morning training session is unrealistic.

And yet every year, camps across Florida and Arizona still hold workouts that require players and staff to arrive before the sun comes up.

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If you ask someone why that is, they’ll try to provide some sort of explanation. I’ve heard them all. The most convincing is probably that the games begin around 1:00 pm, necessitating early start times so players and staff can finish their work beforehand. But that rationale falls apart on inspection because teams set their own game times during Spring Training1, and the workouts don’t begin any later before games start.

I’ve even witnessed a General Manager ask why the days start so early, as if he wasn’t the person most empowered to change things.

Now, I bring all of this up not to be critical of any one person or organization. The people that work in sports are bright, creative, and driven. But the simple reality is that this is an all-too-familiar situation where something is likely wrong, easily fixable, and yet stays the same.

It’s puzzling and frustrating to think about. In an industry seemingly obsessed with efficiency and competitive advantage, how do teams justify this type of behavior?

Inertia and peer pressure — while both poor reasons — are big factors. Things have been done a certain way in baseball for a long time. Change is uncomfortable for coaches and players, particularly veteran players who have grown accustomed to routine.

If we dig a little deeper, the more powerful force is that the incentive structure facing leaders in the sports industry doesn’t encourage change when the benefits are hard to prove.

Let’s say that the General Manager I referenced decides he’s had enough and he shifts the team’s Spring Training schedule so that games, workouts, and meetings begin later. He explains to players and staff that this is to prioritize rest, recovery, and well-being, and he truly believes this is going to help the organization perform better in the upcoming season.

In the best case scenario, the team stays healthy and outperforms their expectations. Is that because of the later start times in Spring Training? How much did the extra rest and recovery help the team? What would have happened if they didn’t adjust the times?

These questions cannot be answered. There is no control group2, making attribution impossible. The team may succeed, but there’s no clear way to credit the change.

That’s the best case scenario. There’s also a full spectrum of outcomes where the team plays poorly or has a rash of injuries.

In those scenarios, attribution isn’t any more feasible, but that probably wouldn’t stop a narrative from developing. An article would be written that the clubhouse was too relaxed, a veteran would complain publicly, or unnamed sources in the organization would talk about how serious teams get to work early in the day.

Leaders aren’t going to risk that type of visible downside, particularly in an industry where job security is hard to come by atop organizations. Better to stick with the status quo, even if that doesn’t live up to the standard of sound decision-making they hope to uphold in other spaces.

Changing something as benign as Spring Training start times wouldn’t actually be difficult. It is research-backed, requires no dedicated budget, and is supported by many people throughout organizations. The ease is the most frustrating part.

What makes the move challenging is accepting that any benefits likely come without proof.

Even with small changes, someone has to take responsibility for outcomes they can’t control or predict. In environments where leaders feel trusted and empowered, that isn’t a problem. Unfortunately, those don’t always exist in professional sports. Leaving players, coaches, and staffers with early morning wake-up calls, spring after spring.

Most organizations want to keep their best employees.

Few leaders would suggest that retention is unimportant. Even those that aren’t especially people-first understand there are costs to hiring and training new people.

Despite near-unanimous agreement that it matters, strategies to address retention are typically nonexistent or optimized for the wrong thing.

Ironically, organizations that do attempt solutions for retention often make things worse. They implement and emphasize wellness and lifestyle perks, team-building events, flexible policies, and recognition awards that don’t address core issues. Why is that worse than doing nothing? Because they’re visible — and visibility can create the illusion of progress while also signaling what an organization prioritizes. Well-intentioned policies may signal an effort to make work more comfortable, rather than making the work itself clear, developmental, or meaningful.

The issue is that retention should not be a stand alone target. It needs to be a by-product of a healthy culture where employees are engaged — which is not the same as happy or comfortable.

Focusing on anything else largely wastes time, effort, and money. And if the new policies don’t address the underlying causes of disengagement — or if they don’t align with established cultural norms — they may end up pushing more employees out the door who feel less connected to the organization than ever.

Now, like what’s often the case, just because this sounds simple doesn’t mean it is easy. Creating a culture where people are engaged takes effort and intention. That starts with paying people fair wages and benefits, but it goes well beyond that.1

In engaging environments, employees have managers who invest in their development. They are given clear expectations and feedback that helps them grow. Experimentation is encouraged and failure is framed as learning. And decisions can be understood, because the organization’s values are consistently applied.

That’s what people want. They want to feel challenged, supported, valued, and included. It’s those feelings that drive engagement and connection. And when employees are engaged, retention largely takes care of itself.

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The other sneaky secret about retention is that healthy organizations have meaningful turnover.

Strong, engaged cultures develop people that are ready to take the next step in their career, sometimes without an opportunity in the organization. As employees grow, their needs and aspirations change. Some will seek challenges that don’t exist internally. Others may realize the organization’s values or direction are no longer aligned with their own.

Organizational decisions and strategies require an infinite mindset. But employee-employer relationships? They almost always have expiration dates. The goal is not to extend tenure at any cost, but to maximize contribution while employees are there and to build systems that can withstand their eventual departure. When treated as a natural part of development, that movement can prevent stagnation and create space for new perspectives.

Leaders who treat retention like an outcome are trying to do the right thing; unfortunately, their focus is on the effect rather than the cause.

They fail to ask a critical question: what actually makes employees stay?

The challenge isn’t to prevent movement. It’s to create an environment where people are engaged — and to wish them well when they move on to new opportunities.

A colleague of mine once remarked that my notes and to-do lists are an absolute disaster. As much as I’d like to disagree, he’s not wrong. Things are frequently scribbled on scraps of paper in short, incomplete thoughts that are impossible for others to understand.

And yet, my to-do lists and the feelings around them are probably not much different than anyone else. They’re long, never finished, and most days I add more than I cross off. Instead of feeling organized, I’m left with a nagging sense that I should be doing more than I am.

That’s why an idea in Oliver Burkeman’s Meditations for Mortals was so intriguing to me. Rather than keeping a to-do list, Burkeman suggests starting a done list:

My favorite way of combating the feeling of productivity debt in everyday life is to keep a ‘done list,’ which you use to create a record not of the tasks you plan to carry out, but of the ones you’ve completed so far today — which makes it the rare kind of list that’s actually supposed to get longer as the days go on.

As Marie Curie understood, our default stance is to measure our actual accomplishments against all the things we could, in principle, still do. But that’s a yardstick against which we’re doomed to find ourselves perpetually wanting. By contrast, what makes a done list so motivating and encouraging is that it implicitly invites you to compare your output to the hypothetical situation in which you stayed in bed and did nothing at all. And what makes that comparison any less legitimate than the other one?

What a wonderfully simple reframing. A list that showcases what you’ve accomplished rather than what you haven’t. It takes a self-imposed standard — everything you could have done — and replaces it with a better one: what you actually did.

Practically speaking, there’s still a need for a list or another system to keep track of the things to be worked on, but making a done list has the potential to be transformative.

In addition to the psychological benefits, moving away from accomplishment-based thinking allows for clarity about what’s important. To-do lists can distract from action, especially on the biggest or hardest things. They reward completion, biasing us toward what’s easy to finish instead of what matters. I know I’ve spent plenty of time on low-impact tasks just for the feeling of crossing something off. Moving to a system that isn’t defined by obligation makes it much easier to decide what actually deserves your time.

The shift isn’t easy. It’s hard to shake the feeling that there’s always more you could do if you only had the time. A done list won’t magically clear your inbox or eliminate deadlines. But it might lessen the guilt that comes from asking yourself why didn’t I do more? And let you ask a better question: what did I actually do with the time I had?

One of my favorite shows of all-time is Silicon Valley, the HBO series that follows Richard Hendricks and a group of engineers as they try to build their company, Pied Piper. I’ve watched the series several times, and it never stops being funny.

Beneath the satire is a surprisingly sharp look at how organizations actually work. The jokes hit on things many of us have experienced at work — and in the process make complicated dynamics feel more relatable and easier to understand.

More surprisingly, it’s one of the most honest and insightful looks at leadership I’ve seen. Here are a few moments from the show that changed how I think about leadership.

Show people what you believe

In the pilot episode of the series, Richard turns down $10 million for his compression algorithm from Hooli (the show’s version of Google). Richard instead opts to take a much more modest total of $200,000 in exchange for 5% equity and the chance to build his own company.

The next episode begins with Jared Dunn, a VP from Hooli, congratulating Richard on the funding. We quickly realize that Jared isn’t only interested in giving kudos; he’s also looking to join the newly formed company. He tells Richard, “Watching you say no to ten million dollars to build your own thing. There’s just something very exciting about that. I would love to be a part of this.”

While we don’t know Jared’s exact title or compensation, it’s safe to say he’s giving up a significant salary and stock options at an industry leader to join a startup with a high likelihood of failure. He doesn’t do that because he’s passionate about compression — he does it because Richard’s decision gives him something to believe in.

Leaders often assume that candidates are drawn to compensation, titles, or perks. Joining a company is much more than a financial calculation. It often comes down to tradeoffs — stability, resources, and prestige vs meaning and identity.

It’s easy to think this dynamic only applies in startups, where cash is tight and risk is a given. But the underlying tradeoff shows up anytime a team is trying to build something new or difficult.

Richard doesn’t recruit Jared with a job posting or a vision speech. He recruits him based on action. By turning down the money, Richard signals his values — namely a willingness to trade short-term security for infinite possibility — and that signal naturally attracts someone who values the same things.

There is more than one way to lead

As Season 5 opens, Pied Piper absorbs two smaller companies and their full engineering teams. Jared schedules a multi-day orientation with carve-outs for Richard, as CEO, to address the groups. He implores Richard that he needs to lead and unify the team.

Richard responds that “he’s a coder” and he “can’t do inspiration.” After a failed speech attempt, he cancels the orientation and offers severance to any employees that don’t want to be a part of Pied Piper. Minutes later, he turns around to find that nearly everyone has taken him up on it.

Rather than chasing after them, Richard grabs a post-it from the company’s to-do list and gets to work. He works for 24 hours straight, clearing a backlog that was supposed to take the entire team four days to complete. His work not only puts Pied Piper ahead of schedule, it also draws the engineering teams back to work.

The contrast between those two moments — the failed speech and the coding sprint — says something about leadership. Richard’s breakthrough isn’t that he suddenly becomes more charismatic. It’s that he stops trying to lead in a way that doesn’t match how he actually creates value.

Jared was right that the groups needed leadership. But he was pushing a version that was never going to work for Richard. By focusing on the work itself, Richard finds a more authentic way to lead — through technical credibility, visible contribution, and obsession for the product.

Communication isn’t optional

In a show full of questionable characters, Hoolie CEO Gavin Belson manages to separate himself as a shining example of how not to act as a leader.

A prime example is the way he communicates casually, without much thought. Right before leaving for Jackson Hole for a few days “off the grid”, Gavin is asked if there’s anything that needs to be taken care of. He responds:

The bear is sticky with honey.

What ensues is one of the funniest — and uncomfortably real — portrayals of how communication works when authority is involved. The company’s senior leaders spend the next few days trying to decipher the meaning behind “the bear is sticky with honey”, organizing white board sessions and debating courses of action.

When Gavin returns, he’s confused to hear that major changes have been made to a presentation he thought was already fine — and that the literal bear-shaped honey container in the break room is still sticky.

The joke works so well because it exaggerates truth. Leaders don’t only pass along information when they speak. In organizations, perception quickly becomes reality. People assume meaning, urgency, and intent even when it doesn’t exist.

Gavin isn’t being malicious; he’s simply talking without intention. But once you’re in a leadership position, there’s no such thing as an offhand comment anymore.

I like this example because it highlights how easy this is to get wrong. I like it so much that I may or may not have unsuccessfully used it in a job interview a few years back1. Once you’re a leader, people tend to stop hearing what you say and instead respond to what they think you mean.

What makes Silicon Valley such a great study in leadership is that it doesn’t only focus on big decisions or dramatic turning points. Most of the time, it lingers on the smaller, everyday actions that shape teams and culture.

When I think about the throughline from the moments above, it comes back to belief, authenticity, and intention. Richard and Gavin’s actions influenced the people around them — whether they intended to or not.

Next week, Major League Baseball will begin arbitration hearings to determine salaries for the remaining players who have not yet agreed to contracts.

The arbitration system is one of the more distinct and misunderstood oddities of baseball’s economic system. Most players never step foot inside a hearing room, agreeing to settlements beforehand. If you’re interested in learning more about what it is and how it works, ESPN’s Jeff Passan wrote a great primer earlier this month.

For nearly a decade, I worked on arbitration on the Club side, negotiating more than twenty cases and advising on dozens more. It’s a strange environment. The rules are rigid and outdated. The arguments don’t exist elsewhere. Emotions run high and logic takes a back seat.

Arbitration strips negotiation down to basics. After years inside the system, I came away with a handful of lessons that apply beyond baseball. They’re about what works in the moment — and what matters once you stop thinking about any single negotiation in isolation.

Stick to your best points

Negotiation is a process where less is almost always more.

Early on, I wanted to debate and win every point. If the agent on the other side raised something, I was ready with a response. When it was my turn, I launched into long soliloquies about why I was right. The phone calls were often long and boundless.

It wasn’t until later that I realized that I wasn’t just wasting energy — I was actively obscuring and hurting my case.

Every time I engaged with an argument that wasn’t central, I gave it credence. The harder I fought something, the more I validated that it mattered. And my insistence on engagement made it much more likely that I would contradict myself somewhere along the way.

The better strategy was to identify one or two key points and stick to them. It is far simpler and much more effective to introduce the most important thing and repeat it until a deal gets done.

Imagine you want to ask your boss for a raise. Which approach sounds more persuasive: listing every reason you think you’re underpaid, or anchoring the conversation around the single thing you do better than anyone else and how costly it would be to replace you?

Sticking to your point doesn’t mean ignoring the other side. That would be rather rude, and being rude is not a good strategy. Instead, you have several response options:

• Acknowledge and dismiss the point. Saying something like “I hear you, but that doesn’t really drive this market” respectfully acknowledges and allows you to redirect the conversation to what matters.

• Concede the point. You don’t have to win every point. In fact, it’s okay to lose some, too. “You’re right” can be as devastating as landing a punch of your own.

• Let them talk. Sometimes the best response is no response. Listen, let them make their point, then calmly move on or change the subject.

You don’t have to engage with everything. In most negotiations, doing so only dilutes what actually matters.

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Make arguments you believe in

The corollary to “stick to your best points” is “focus on arguments you actually believe.” Sounds obvious, but I’m amazed how many people ignore this.

This typically manifests when negotiators want to anchor artificially high or low to create room to “show progress” later. To justify the position, they reach for arguments that technically support it — even if they don’t believe them.

I did this early in my career. I used to throw out comparable players well below what I thought was a reasonable starting place, then dig in to defend them. I rationalized it as strategy: I could move later, and in the meantime I was laying groundwork for future concessions.

That’s not what happened.

At best, all I accomplished was delaying the real work from starting. In other cases, I actively hurt the negotiation. The artificial start damaged my credibility, detracted from my strongest points, and turned things immediately antagonistic.

As I gained experience, I scrapped the disingenuous arguments and focused on the ones I believed. They were more convincing — not because they were better, but because I didn’t have to sell them. And while I won’t pretend I frequently changed someone’s mind1, the credibility alone helped move deals toward a resolution.

No is a powerful word

Once you’ve narrowed your scope and committed to arguments you believe in, the next question becomes how hard to hold the line. That often comes down to whether you’re willing to say no.

Saying no can be powerful in a number of situations. Negotiation is no different.

In fact, I’ve closed more than one negotiation simply by saying no consistently until the person on the other side came around.

There’s a natural urge to respond to an offer with rationale and maybe a new alternative. That feels more collaborative and complete, especially compared to saying no.

Saying no isn’t creative, but that’s sort of what makes it so effective.

When you say no, you limit the options forward. You show that you are willing to walk away rather than accept a bad deal.

It helps if you are actually willing to walk away, but you don’t have to be to use no to your advantage. If you’ve stuck to your best points and used arguments you believe in, drawing a firm line won’t surprise anyone.

And if holding the line doesn’t move them, you can still choose to accept the offer — knowing you tested the boundary before doing so.

Relationships matter

I mentioned that early on I tried to win every point. Truthfully, I didn’t just want to win, I wanted to crush the opposition. I would interrupt their arguments and overwhelm them with facts and figures. No matter how circular or heated talks became, I had the persistence to stick things out.

Over time, I shifted the way I operated. I moved to a calmer, more measured style, identifying one or two points I believed in and sticking to them. I heard the other side out. I focused on what I could control — often saying that “we might see it differently.” When I reached my line, I used the word no to try to close the deal.

I can’t say with certainty that strategy was better. Neither the results nor the sample size allow for that kind of conclusion2. But the calls were shorter and less contentious, momentum rarely stalled, and regardless of outcome, I heard a lot more gratitude and appreciation for the way I worked with my counterpart.

When I oversaw new staff members working on arbitration, one of the first things I told them was: you need to decide what kind of negotiator you want to be. I know I’m not the best arbitration negotiator. My approach is predictable, I cut off upside, and I’m extremely averse to going to hearings.

I’m okay with that. I decided I wanted to negotiate in a way that felt true to me, and that my relationships with agents — and players — mattered more than squeezing out slightly better settlements. I was going to have to work with these people again, not only in arbitration but in higher leverage negotiations like free agency.

Relationships don’t just create goodwill; they underscore everything that enables negotiation. They affect how information flows, how disagreement is resolved, and how much trust exists.

Choosing to emphasize relationships meant negotiating with more than the current conversation in mind. I no longer saw winning in terms of points or arguments, but how productively we could work together to reach a deal.

Salary arbitration is a strange, imperfect system. That doesn’t mean these lessons are unique to baseball. Most of us negotiate far more often than we realize — with managers, colleagues, partners, and ourselves.

The focus is usually on tactics and outcomes. Those things matter. But over time, how you negotiate tends to matter more. The approach you take leaves a lasting mark on your relationships, your reputation, and the way future conversations will unfold. That’s worth thinking about before you start your next negotiation.

January has a way of inviting reflection. For me, that means setting and revisiting goals.

I’ve set some form of New Year’s resolutions every year since 2018, hitting some and missing others. Along the way, my thinking about goal-setting has changed considerably — shaped by what I’ve read and the real world lessons I’ve learned.

Today, I’m going to walk through my current views on goal-setting and how it shapes behavior.

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Goals often aren’t the best way to accomplish what you want

Goals can be useful. But often they’re not the best way to get to where you want to go.

My thinking here was challenged by James Clear’s Atomic Habits, particularly the distinction between goals and systems.

Take a Major League Baseball team that sets a goal to win the World Series. Every team begins the season wanting that very thing. The goal doesn’t differentiate in any way, nor does it offer guidance on how to get there. Winning a championship is an outcome, not a strategy.

The goal also flattens progress. Twenty-nine teams fall short each year, regardless of whether they outperform expectations, overcome adversity, or lay groundwork for the future. The team that wins experiences a brief moment of satisfaction, then immediately turns forward with the same questions and challenges. The goal is binary and finite, even though the work is continuous.

Now, instead of goals, I mainly emphasize habits and values. That directs my energy more towards who I want to be and the small, consistent actions I need to take to become that version of myself.

Small and consistent are intentional words. What habits capture better than goals is the power of compounding effects — actions that feel insignificant on their own but become meaningful over time.

Saving a single dollar won’t prepare me for the future. It probably won’t cause any visible or tangible differences in my life. But stack enough singular savings, and I will see and feel real benefits.

Values are even more clarifying in that having a clear picture of my values — the things that are most important to me — informs choices I make about how I spend my time and how I interact with others. Once I know my values, I can design habits to complement those and essentially negate the need to set goals. I’m more agile and more aligned.

Identity has a big effect on goals and habits

Identity plays a large role in behavior.

I started this newsletter just a few months ago. As such, it would be reasonable for me to set goals related to writing for 2026. Maybe I want to publish 50 articles or I want to hit 1,000 subscribers this year.

While targets may help, the better strategy is to begin thinking of and referring to myself as a writer. If I’m a writer, I’m going to make different choices — namely to write — than someone who simply writes once in a while. It’s easier to build habits and prioritize work when it’s an identity instead of a hobby.

The inverse has proven true for me when it comes to learning the guitar. For years, I’ve set a goal of learning to play a single song. But practicing never took priority over other projects. I’ve never acted like a guitar player.

You can hold multiple identities for yourself that align with and inform what you do. I can be a writer, a healthy person, a chef, a good husband, a reader, and a lifelong learner at the same time.

Now, identity isn’t a silver bullet. The same thing that makes it powerful also makes it dangerous. When identity hardens, it narrows how we interpret information and make decisions. That’s why Julia Galef’s advice to “hold identity lightly” is important to keep in mind.

Eliminate should and embrace joy

Should. Ought. Want. Try.

I’ve learned that these words have no place in goal setting. I used to use them all the time. “I want to volunteer more this year.” “I’m going to try to run 10 miles a week.” They seemed like perfectly acceptable goals, but they didn’t seem to change my behavior.

Those words evoke feelings of obligation, not commitment. Don’t set a goal because you feel like you have to do something or you should do something. You almost certainly don’t have to — and framing it that way makes it far less likely you’ll do it well, or do it at all.

Even goal-setting can feel like something you have to or should do, right? It did for me for a long time, but that’s not true either.

I’ve shifted away from what I should do to find the things that light me up. I’ve realized I’m much more likely to follow through on things I genuinely enjoy, find interesting, or am curious about.

There’s research behind this. It’s proven that people learn more and progress faster when they’re engaged. While much is made about deliberate practice, Adam Grant points out that what often drives significant improvement is deliberate play.

If you really can’t get past the idea of should — or you have no choice in a matter — finding ways to increase engagement can help. That might be changing the activity or environment, or finding another way to address the behavior altogether.

But in most cases, the move is simple: choose pursuits you actually want to show up for.

The most important thing might be saying no

Some lessons have to be learned firsthand. Others may try to teach them, but it usually takes experience for them to click.

One of those for me has been that saying no is at least as important to achievement as deciding what to pursue.

I used to set tons of goals and say yes to every idea, project, and request that came my way. Why would I limit myself?

Wrong, wrong, wrong. Taking on more rarely equates to doing more. It merely results in scattered focus, underwhelming outcomes, and unfinished work.

When you take on too many things, you become your own blocker. You distract yourself and limit the amount of time you can spend on the things that matter the most and bring you the most joy.

If you do set goals, keeping the list small — and saying no to almost everything else — is how you protect them.

It’s also okay to reshape a goal once you start working on it, or to walk away altogether. You can change your mind or realize that you don’t enjoy something. You don’t have to stick with it just because you set a goal. Persistence isn’t always a virtue.

I like to read. For a long time, if I started a book, I felt compelled to finish it no matter how much I enjoyed it. That wasn’t discipline — it was counterproductive. I read less because I avoided picking the book back up. Now, if I’m not enjoying a book, I put it down and find something else.

Don’t go it alone

Resolutions and goals are individual. Sure, in certain settings you might set collective goals, but what we’re talking about here pertains to a single person.

Don’t let that lead you to ignore the effect that others can have on goals, habits, identities, and values. Their influence is hard to overstate.

The environment you operate in — and the people in that environment — impact what you do and who you become. The sentiment that “you’re the average of the five people you spend the most time with” is true, making it incredibly important to choose those people wisely.

Others can inspire confidence as well. Some of the things you want to do will be hard. Having others that believe in you — especially if you’re struggling to believe in yourself — can lift you up. Their expectations can become self-fulfilling.

Beyond influence and inspiration, others can provide something equally important: accountability. I’ve already made the case that you don’t have to do anything, but letting a small number of trusted people know what you’re working on can make it harder to drift when things get uncomfortable.

I’ve shared my resolutions with one or two close friends1 most years. While they’re not responsible for anything, the act of telling them makes me more likely to follow through.

Do things

It’s worth asking what the goal of setting goals actually is. For most, the answer is some version of accomplishing something, inspiring change, or learning. In other words, the goal of the goal is action.

Too often I’ve found that setting goals actually discourages action. It could be that the goal is too ambitious and daunting, so you hesitate to try. Maybe it’s designed poorly and moves you further away from your desired outcome. At times, even defining a goal becomes a distraction.

The most important thing I’ve learned about goals is the value of a simple skill: the willingness to do something without waiting for the right circumstances. When planning becomes a barrier to action, it’s no longer helping.

There are many things that look like action, but aren’t. Whatever system you adopt, the point isn’t the plan — it’s the doing.

If I believe all of this, why do I still set some version of New Year’s resolutions? I’ve come to think of resolutions the same way I think about performance reviews. The most meaningful feedback happens in real time — through habits, decisions, and iterations — not a single, formal moment. But setting aside time for deliberate reflection can still be useful, especially if the daily work isn’t perfect.

There isn’t a single right way to approach goals. What’s worked for me has changed over time, and I’d expect it will continue to evolve.

For now, I care less about what I write down and more about what I actually make time for — because that’s what shapes the person I become.

In a Season 6 episode of The Office, newly promoted co-manager Jim Halpert is tasked with delivering bad news about annual raises to the Dunder Mifflin staff. Jim spends most of the episode failing to communicate effectively or find a fair solution. By the close, he’s come to a hard realization: new responsibilities aren’t the only thing challenging about a promotion.

Two people can walk into the same office on the same morning, shake the same hands, and inherit the same job – and still be stepping into completely different realities. Where they came from matters. An internal candidate is going to experience distinct advantages, expectations, and challenges from an outsider joining the team.

Most of the writing I’ve seen on the topic focuses on the organization’s decision when faced with the choice to promote or bring in an external hire. There doesn’t seem to be quite as much content on what it means for the person assuming the role. Today we’re going to look at the practical realities that exist under both sets of circumstances.

Internal Promotions

Earning a promotion in your organization is exciting. It feels good to be recognized for your work and to take on new challenges with people that know and care about you. Your reputation and relationships can position you to succeed. But your standing can also create real obstacles.

The biggest – and often unspoken – challenge for an internal promotion is that people tend to see and treat you the same way they did in your previous role. That can undermine authority and make succeeding in a new role harder than it already is. I observed this early on in my career in sports. We had two Assistant General Managers – one who began as an intern and another hired directly into that role from the outside. The internal AGM’s opinion was never taken as seriously by some of our senior leaders because they still remembered him as “the kid that used to get coffee and lunch.”

That same problem is heightened if a promotion leads to managing people that were previously peers or superiors. It might be hard for some to take direction or feedback from someone who was an equal not long ago. Even in situations with deep connections already in place, the relationships have to shift for things to work. A reporting relationship introduces a hire/fire dynamic that coworkers simply don’t have. The dynamic inherently exists for external hires; internal promotions have to actively establish it with care and respect.

On the other hand, internal candidates step into jobs with meaningful advantages. They have the benefit of knowing the organization. They know the people, the culture, the strengths, and the politics. Unless it’s a newly created role, they’ve seen someone succeed and fail doing the exact role within the organization. And if it is a new role, they have an understanding of why the position was created. That allows them to operate with context immediately.

In total, the realities facing internal promotions are:

• People may view them as the version of themselves who held an old role.

• They have people in their corner who already know their character and work product.

• They have existing relationships – but they might have to adapt to fit changing circumstances.

• They can operate with immediate understanding of how the organization functions.

Internal promotions must do two jobs at once – step into a new role while reshaping their reputation and relationships with people who think they already know them.

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External Candidates

Other than moving from an intern to a full-time employee, my experience with promotions has always been as an external candidate.

When I joined a new organization, one of the first things I noticed was that I was often treated with a certain amount of respect immediately. Save team members closest to me and direct reports – which we’ll get to – people in the organization generally assumed credibility based on my job title. Because they didn’t have history with me, it was enough that someone else had vetted me and decided I was the right person for the job.

But that credibility is more fragile than it looks. Maybe people give the benefit of the doubt initially, but it doesn’t take much for the opinion to shift. After all, it isn’t based on much. That made it harder to fully be myself, to take risks, to shine light on failures, or even to ask simple questions that would help me learn faster. I found myself focused more on being perceived as doing a good job than on actually doing one. That is a common trap for external hires.

External hires also have to build relationships and institutional knowledge from scratch. They don’t yet know the people, the roles, or the culture of their new organization. There’s nothing to stop them from walking into landmines they don’t know about. Learning those dynamics and a job simultaneously is hard. Relationships take time and intention; there aren’t shortcuts.

A sneaky advantage – and one that I didn’t utilize enough – is the fresh perspective outsiders bring. External hires have no attachment to decisions made in the past. They can question assumptions that others have taken for granted. In many cases, outside hires are made because change is needed. They should lean into that sentiment to question things and push boundaries.

The realities facing external promotions are:

• They are granted immediate legitimacy based on title alone.

• That credibility is fragile – respect is given, trust is not.

• They bring an outside perspective and often have early support for change.

• They start from scratch in terms of relationships and institutional knowledge.

External hires must build trust, credibility, and understanding quickly – often before they feel ready.

Realities in either situation

Internal and external transitions look different, but both share a core truth: stepping into a new role is not a continuation of the job you were doing before. It is fundamentally a new job with new responsibilities and expectations. The things that made you successful before are not always the things that will make you successful moving forward.

One shared challenge is that someone, somewhere will feel they deserved the promotion more than you did. In some cases, you might find yourself overseeing that person. That creates a tricky relationship. The worst-case scenario is that the person will actively undermine your authority and try to make you look bad. More commonly, their skepticism shows up quietly. They’ll hesitate in meetings, resist buy-in, and question everything you do or say. External hires won’t be afforded the immediate credibility we suggested earlier. Working with these individuals will require confidence, kindness, and proactive outreach.

You might question if you deserve the promotion as well. Or you may feel like you’re not ready. Imposter syndrome doesn’t care whether someone is hired externally or promoted from within; it affects everyone all the same. It took me more than six months to feel comfortable in my last role doing the job my way. I was so worried about proving I deserved the role that I tried to emulate others instead of leaning into my own unique strengths.

There is also the need to shift mindset. The Peter Principle gets a lot of publicity in these spaces. It’s the idea that people are promoted until they rise to “a level of respective incompetence.” While that absolutely exists, I’ve seen something different in many cases. The real struggle is that people don’t evolve quickly enough into what their new role requires. They cling to what worked for them previously instead of embracing new skills and competencies.

Another shared reality is that change is hard – especially early on, when every move is scrutinized and overinterpreted. Whether you’re hired from the outside or promoted internally, people watch closely for signs of what your leadership will look like. Change is uncomfortable and requires action when inaction is the default. That creates difficulty for anyone.

Lastly, regardless of how someone comes to a promotion, the drivers of success are the same. Build trusting relationships. Communicate clearly. Stay open to learning and willing to change your mind. Create an environment where people can contribute ideas and execute with clarity. And get support from those around you. No one succeeds in isolation.

Title changes always represent transitions, but not the same transition for everyone. Internal promotions must overcome history to establish a new identity. External hires face immediate expectations while navigating a foreign landscape. Excitement and uncertainty fuel the early days in either situation.

Eventually, the work converges. No matter how you got the job, you’ll need to build rapport, understand the systems and constraints around you, and communicate effectively. Promotions aren’t rewards for past accomplishments; they’re invitations into new work. Successful promotions require a person to grow into a new version of themselves. Those who recognize that – and embrace the shift – give themselves the best chance regardless of where they came from.