This is similar to how software shops would ask a certain amount of apprenticeship from junior engineers before they would get push access or review credentials on a repository. Similarly, before we allow somebody to run loose with the code generating power of an LLM, we should make sure they know how to wield it safely.

Using an LLM for learning and doing research should of course be unlimited. Just that people shouldn’t spend their time trying to one-shot their assignments. That way of working is way too tempting for somebody who doesn’t know better.

Both sides would benefit from this arrangement.

Company

#

It’s obvious that LLMs function as an amplifier. Those who are skilled, can wield them to become better and much more effective. Those who aren’t, will use the tool to paper over their gaps in knowledge and effective delivery.

A company will always demand more of its employees and that all but ensures that the technology will be abused to meet and surpass commitments no matter what externalities that will bring.

Mario Zechner: “All of this compounds into an unrecoverable mess of complexity.” —Thoughts on slowing the fuck down

To utilize the productivity increases of LLMs without having your engineers destroy the coherence of your codebase, some gating will go a long way. Along with the gate, there should be a clear path how to pass it. That would be either through a competency test of some sort or when you hit a predefined career level.

Engineer

#

For the engineer the equation is even more clear cut. Prompting an LLM and doomscrolling while you wait for the output is a direct path to deskill yourself out of the industry.

Mitchell Hashimoto: “This is how you get dumber btw, true even before AI” — https://x.com/mitchellh/status/2031776788532379996

If you’re not continuously adding value in intent, knowledge and nous to the LLM loop, you are just a mindless driver, not that different from a Ralph. As an engineer, you need to be in the code and on top of the LLM. You need to know exactly what is happening, what it’s doing, why and how in many cases the suggested solution is very much deficient.

For a junior this is more or less impossible. Spending your time telling the LLM to “fix lint” until your change passes CI and then hoping somebody else will approve your code to merge, is a losing proposition.

A junior engineer needs to invest to get to a point from where they can use the LLM effectively. This will only happen if they work on their craft diligently and reflectively. The research and learning capabilities of the LLM are perfect for this. Also if there’s no expectation that you will one-shot thousands of lines of code every day, you will get the space to invest in getting better.

A driver’s license for LLMs is not a perfect solution but it could remove a lot of the sharp edges of the usage we are seeing right now. At the very least it should make clear that not all LLM usage is equal.

I noticed this on my watch through and thought it would be good to go back and capture it.

This phrase is it:

“It’s a good for nothing battle, that’s true. But even so, there’s no point in losing.”

Here’s the complete sequence from season 1 episode 21:

　司令官のヤン・ウェンリー

　間も無く戦いが始まる 　碌でもない戦いだが

　それだけに勝たなくては意味がない

　勝つための算段はしてあるから、無理せず気楽にやってくれ

　かかっているのは、たかだか国家の存亡だ

　個人の自由と権利に比べれば、大した価値のあるものじゃあない。

　それではみんな。 　そろそろ始めるとしようか？

We’ll say nothing when we should speak up. We’ll quarrel when we should inquire. We’ll remain reticent when we should be resolved. We’ll be closed-minded and critical when we should be open-minded and curious.

On the one hand, a “little voice” in the back of his brain urged him to raise his concern; on the other hand, he didn’t want to be labeled a troublemaker, a non–team player, or a “high-maintenance” flight operations officer.

Put simply, conversational capacity is the ability to have open, balanced, nondefensive dialogue about tough subjects and in challenging circumstances.

But this collegiality came at a cost: their nice culture created a bad business. While the team members enjoyed pleasant meetings and warm relationships, they sacrificed the candor needed for rigorous problem solving and decision making in order to maintain the amiable environment.

The National Transportation Safety Board, the entity responsible for investigating civil aviation accidents in the United States, estimates that 25 percent of aviation accidents occur because someone doesn’t speak up when a mistake is being made.

“To be honest, it makes me mad. I went out of my way to hire the best and the brightest people I could find, but I’m not getting access to all the intellectual firepower I’m paying for.”

A person with high conversational capacity can do just that. He’s able to remain open-minded, nonreactive, and fully engaged in tough circumstances that send his less disciplined colleagues into a highly reactive state of mind. Balancing candor and curiosity, he converses with his teammates in a way that actually increases the conversational capacity of the entire group.

On the one hand, you feel compelled to speak up, but on the other hand, you don’t want to cause trouble, be labeled a troublemaker or non–team player, tarnish your reputation within the team, or damage relationships.

When we minimize, it’s not that we don’t have an agenda, it’s that our agenda is subverted by a strong need to keep things comfortable, to avoid conflict, to keep things calm.

Any issue can set off our need to win, but especially those ideas that contradict our current ways of thinking, our notions of what is acceptable, proper, or right. When we snap into win mode, we circle our cognitive wagons and load our conversational guns, ready to defend our current map of reality from all foes. We become dogmatic and close down when we should get curious and open up.

If they’re not speaking up, they’re being paid for something they’re not providing. But the harsh reality is that our own management behavior may be stifling their abilities to contribute. By failing to compensate for the minimizing effect our authority has on our people, and, even more egregiously, when we trigger into win behavior, we encourage our people to minimize, guaranteeing we won’t get full access to their knowledge, expertise, ideas, and suggestions.

Under what circumstances in life do I find myself minimizing at the expense of my effectiveness?

But awareness is not the same as skill. A drowning man may know he’s drowning, but his awareness is no substitute for the ability to swim.

When we’re making an acquisition, initiating a major change process, or wrestling with a tough decision, we want access to as much information and as many perspectives as possible to expand our options for effectively tackling the challenge. We want to reduce the number of blind spots in our view of the situation we’re facing.

When we’re truly dedicated to expanding our thinking and making informed choices, difference is our greatest ally.

Because our level of internal commitment directly correlates with how much energy we put into enacting the decision.

When we’re dedicated to informed and effective choices, we pull people into decision-making or problem-solving processes because they’re useful in two ways. First, involving key players leads to better information and more robust decisions because we have access to their thinking. Second, those same people feel more connected to the decisions that do get made. It’s a double win; we get better decisions that are more effectively implemented.

Contrast this unilateral approach with the more learning-focused joint control, where we proactively make our goals and concerns explicit and ask others to help us manage them. This is a far more effective way to make informed and effective decisions because we’re involving others in the important decisions for how to best achieve the desired objectives.

The managers who asked, “What do you need more or less of from me so I can help you do your job more effectively?” were in positions to make better choices about how to manage their people, but the conversations that helped them make those choices weren’t always an ego massage.

requires the mindful use of four distinct skills that are extremely difficult to balance under pressure: Stating our clear position Explaining the underlying thinking that informs our position Testing our perspective Inquiring into the perspectives of others

Like a topic sentence in good paragraph construction, a position statement is clear, candid, and concise. It lets others know where we stand on an issue, the specific point we’re putting forward.

To that end, let’s look at more vigorous tests to employ in situations where it may be more difficult for others to push back, or when we’re putting forward a particularly strong perspective: That’s how I see the problem. What does the problem look like from your perspective? Right now I feel like my idea makes perfect sense, and that makes me nervous. Are you seeing something I’m missing? I am more interested in making an informed decision than in winning or being right, so I’d like to hear your point of view—especially if it differs from my own. If I’ve got a blind spot about this issue, please help me to see it. I’ve shared what I think and why I think it. I’m curious to hear how other people are thinking about this problem—especially those who have a different take on it than I do. To help me improve how I’m looking at this decision, I’d really like to hear from someone who has a perspective that challenges mine. I’d like someone to expand my view of this situation. Who has a different way of looking at it? I know I may be wrong about this—what do you think? If you disagree with me, please let me know. I’d really like to hear your point of view. Push back on me here—especially if you think I am being unfair. What would our worst critic say about this decision?

Randy’s handling of this conversation is impressive. Neither accepting the accusation at face value nor dismissing it, he defused the explosive situation by getting curious. By inquiring into the underlying reasoning behind the assertion, he brought the conversation back to a more balanced, data-based dialogue, pulling a tense and divisive parent-teacher conference right back to the sweet spot.

What are you seeing that leads you to that view? I have to admit that I see the issue very differently, but before I jump to conclusions, please tell me what you have seen or heard that leads you to see it the way you do. Tell me more about how you’re looking at this issue. Obviously, you’re looking at this differently. Help me see this through your lens. How are you making sense of X? What does this look like from your (marketing/finance/engineering) perspective? Help me expand my thinking on this. Tell me how you see X. What have you seen or heard that leads you to think X? Can you provide a couple of examples that illustrate your position? Clearly, we don’t agree. Let’s see what our different perspectives can teach us about this issue. Explain in more detail how you’re seeing the situation. I’m intrigued by the way you’re framing this issue. Can you give an additional example or two so I can better understand your thinking? Can you give me an example of X? Can you illustrate why you see this so differently than I do? When team members haven’t even shared their positions, much less their thinking, and we want to invite their perspectives into the conversation, we might say: We’ve been bouncing this idea around for quite some time, and we haven’t heard from you yet. As you’ve been listening to the pros and cons of this decision, what’s your take on the best choice?

Are you seeing anything that the rest of us may have missed? I’d be interested in hearing your views on this problem. Do you have a different perspective than those that have already been shared?

Imagine a team full of such people. Now imagine an organization full of such teams.

Any dolt can shut down or argue when he or she is being challenged, but it requires real strength to remain open to learning, squarely focused on informed choice, even when we’re feeling stressed and vulnerable. Our capacity to rein in our derailing tendencies in circumstances where other people cannot is a sign that we’re in disciplined control of our behavior and not a piteous slave to our emotional reactions.

For a really challenging conversation—a 10/10 (rated 10 on the difficulty scale and 10 on importance)—there is no substitute for practicing with a partner. By having a colleague play the person with whom we need to have the conversation, we can more realistically assess and improve our ability to maintain conversational discipline.

As we build our discipline for working in the sweet spot, we’re seeking the yin and yang of dialogue by being bold, authentic, and direct and, simultaneously, open-minded, unpretentious, and inquisitive.

When a consensus decision is the best option, a more balanced approach helps to level the playing field. It’s far harder for the team member with the strong win tendency to run away with the decision if the team has the capacity to work in the sweet spot

Trust isn’t a prerequisite for effective conversations; it’s the product of effective conversations.

When it comes to building our competence, the workplace is our dojo—an ideal practice space for building and refining our skills.

As these men explore the city, their unique cultural, educational, experiential backgrounds lead them to filter the available sensory input in very different ways.

The key is to lean our ladder into difference. We don’t learn much by engaging people who agree with our views, we learn the most by engaging people who don’t. This dramatically increases our ability to detect and correct errors in how we’re looking at a situation and to generate a far more accurate mental map. With this in mind, we treat anyone who disagrees with us as the most valuable person in the room.

When we double-loop learn we hop off our hamster wheel of thought and question the way we’ve made sense of the problem in the first place.

described to his fellow workshop participants the loud and combative arguments he and his team had in meetings. They were, as he put it, “very intense.”

Like a group of skilled jazz musicians, a team that can deliberately double-loop learn is more nimble and adaptable in the face of unusual, shifting, complex circumstances because team members can better adjust their thinking to fit the new challenge.

Our minds, in other words, have a self-serving, single-loop tendency to resist information that threatens our current view of reality, so they filter the world around us so we see what we want to see.

When people, teams, and organizations react defensively to an idea, what is it they’re defending? Their current idea and the assumptions, beliefs, and mental models on which it stands—the very things they need to question and adjust in order to double-loop learn.

Because conflict is the primary catalyst for double-loop learning, only teams with reliably high conversational capacity can deliberately orchestrate it.

Their research demonstrates that as people consistently practice the replacement behaviors, they actually change the physical structure of their brains, because, just like a muscle, the neural circuits for any activity grow where they’re being used and atrophy where they’re being neglected.

With regular practice, we produce a flywheel effect, where the more we use the skills, the more our skills grow, and the more our skills grow, the more we use the skills. Is it hard work? Sure it is. Any skill worth learning takes effort.

Use every meeting, problem, decision, conflict, or change as an opportunity to build your skills. There should be no such thing as a boring meeting because you’re practicing as you participate, facilitate, or both.

Your naturally self-serving tendency to look outward, in other words, is a defensive routine: You avoid looking at your own behavior by placing all your attention on the behavior of others.

What are my tendencies, and how are they displayed?

When it comes to disciplined dialogue, you do this by listening to what’s being played, and then playing what’s missing.

Acknowledge and reward people who are making a genuine effort, and do it both publicly and privately. “I tested a view earlier, and Jane took me up on it and pushed back. I know that wasn’t easy, and I’m grateful you did it. I’m hoping to see more of that kind of behavior from everyone around the table as time goes on.”

When someone puts out a naked position, they inquire into it. When someone forgets to test, they jump in and test for that person. When they put forward their own perspective they shore up the conversational capacity of the team by intentionally balancing their push and their pull.

One is a routine problem,1 which can be difficult and bothersome, but for which we have ready experts and proven solutions on which we can depend for a fix. In other words, a routine problem is routine not because it happens regularly but because we have a routine for dealing with it.

Far from routine, an adaptive challenge is a problem for which there are no easy answers,2 no proven routines for dealing with the issue, no expert who can ride in and save the day.

They treated the implementation process like a routine checklist, and failed to address its more adaptive aspects—their corporate culture, their old habits, and their instinctively defensive reactions to change.

It makes no sense to march our team into a challenging predicament it’s ill equipped to handle.

They needed the skills to climb out of their dysfunction, but they were too overwhelmed by their dysfunction to acquire the skills.

Adaptive leadership13 is not about coming up with an idea or solution and then convincing the group to adopt it. It’s about orchestrating a process of learning that gets people with different views and agendas learning from each other as they tackle an adaptive challenge.

But when we liberate leadership from authority we empower anyone who wants to foment productive change because we realize that while authority is assigned to us by the organization, leadership is an activity we choose. Seen this way, leadership can be exercised from any point in the system.

Leadership is not about the roles we’re formally assigned; it’s about the roles we choose to perform.

Tina also spent untold hours behind the scenes listening to concerns, smoothing ruffled feathers, and keeping people engaged in the learning. This trio worked together to do the requisite adaptive work—rebuilding relationships, earning back trust, improving how they interacted with each other, and resolving festering conflicts.

“With or without authority, exercising leadership is risky and difficult,” says Heifetz. “Instead of providing answers as a means of direction, sometimes the best you can do is provide questions, or face people with the hard facts, instead of protecting people from change.”

A person with an inflated ego and a strong opinion says, “I know exactly what to do,” and a flock of people passively minimize by going along with the unadulterated bullshit he’s slinging—even when they know, deep down inside, it’s not going to work.

Whenever we choose to head down one of these daring paths we’d better have our demons in check.

We can seek out and enroll partners, colleagues, friends, or teammates as fellow learners—people eager to head up and out of their own sheltered, self-limiting village by acquiring the mindset, learning the skills, and using both to tackle increasingly difficult issues and situations.

At its core most of my Obsidian time is spent in the Daily Note which is also where most of my actual work happens. I tried to get to a similar setup in my previous note taking tool Foam (see my PR) but there were too many limitations for it to work well.

The Github Gist of the entire setup is here: https://gist.github.com/alper/2bbf8f3cb60466b55026deb47f8e15e6

The main way I use this is I create a new Daily Note for a day and this template seeds that note with all the scaffolding and information I need to be successful that day. It automates and structures what would otherwise be a relatively miserable sequence of manual steps and copy-paste-ing.

The plugins that I use for this are:

• Calendar
• Tasks
• Templater

Let’s go through the template file from the top:

# {{date:dddd, MMMM Do, YYYY}}

This sets the title of the note to the date that we are creating the note for. Nothing very special here but note that with Calendar we can create a daily note for any date (it doesn’t have to be today) and that date is passed in as a parameter to the template.

Tasks

#

Then comes the tasks section:

### Due Today

```tasks
[^1] AND NOT done
```

### Scheduled Today

```tasks
[^2] AND NOT done
```

### Done Today

```tasks
done on <% tp.file.title %>
```

This is a triple that lists all my tasks that are due on that day (or were before), all my tasks that are scheduled for that day (or were before) and if I finish anything, it will list those tasks under the third section as my work log.

The hack here is that the ISO date is passed in to the templates as ` file.title and can then be used to query Tasks. It took me a bit to get this to escape right and figure out how to write the complex boolean condition.

I moved away from Things when I discovered the Obsidian Tasks plugin. Tasks allows me to close over all the tasks that are in my notes and is incredibly flexible and powerful. Being able to do arbitrary queries on tasks in any markdown file in my workspace is nothing short of amazing. I’m still waiting for Notion and other tools to offer something similar.

I always felt the split between taking notes and capturing tasks was incredibly broken and created lots of unnecessary friction. For instance this nonsense with bear:// protocol links in Things that is delusionally claiming that “Bear & Things 3 Work Really Well Together”. These two things should be in the same environment.

Calendar

#

Then the second part is a section that creates a scaffold with all the appointments I have for that day formatted as markdown stubs.

It works using this relatively obscure and somewhat finicky tool ical-buddy. In the template I call a Templater user function days_events:

<% tp.user.days_events({CURRENT_DATE: tp.file.title}) %>

which inserts the result of the following command in-place:

icalBuddy -ec "FE0B6DAB-E598-4DE1-9F2B-7DE06A236647,4242177B-7D2B-4A20-AE23-A99DD51D5B80" -eep '*' eventsFrom:$CURRENT_DATE to:$CURRENT_DATE | sd '•' '##' | sd '\(alper@example.com\)' '' | sd '\n' '\n\n* \n\n'

This call to icalBuddy excludes a bunch of calendars I’m not interested in, queries the calendar for events within the specified day and then does a bunch of replace actions that turn it into markdown.

I don’t use Calendar.app (preferring Cron at the moment) but I have my Google Calendar setup in macOS System Settings and leave Calendar open for it to always have up to date data.

Result

#

Putting everything together, when I double-click on a day, I get a document that looks a bit like this:

The fact that it’s fully automated and that with a single action I can get a relatively complete informational dashboard for what I should be doing that day has been an immense load off. It allows me to hit the ground running and immediately start sifting tasks, go through my meetings and create a plan for the day.

When I know a day is coming up that’s going to be particularly intense, I create the daily note for it ahead of time and start lining up information and talking points for each appointment in the scaffold. Reducing the effort it takes to start that prep and storing it in a standardised format makes it much more likely that I’ll do it and use it. With that preparation ready-to-go in Obsidian it takes out all the stress and I can run my day in a pure flow state.

What you need on day one is to ratchet up expectations, energy, urgency, and intensity.

You can engulf your organization with energy, step up the tempo, and start executing the basic blocking and tackling with a lot more focus and higher expectations. It will feel like busting a log jam. All of a sudden, everything is moving and shaking.

Don’t let malaise set in. Bust it up. Raising the bar is energizing by itself.

MBO causes employees to act as if they are running their own show. Because they get compensated on their personal metrics, it’s next to impossible to pull them off projects. They will start negotiating with you for relief. That’s not alignment, that’s every man for himself.

The questions you should ask constantly: What are we not going to do? What are the consequences of not doing something? Get in the habit of constantly prioritizing and reprioritizing.

I always operated as if I owned everything, whether I did or not. That didn’t always sit well with peers or superiors. I have since always tried to increase our people’s sense of ownership so they will act as owners. That mentality needs to be nurtured.

We coped in ways I have used ever since: hire people ahead of their own curve. Hire more for aptitude than experience and give people the career opportunity of a lifetime.

We still say, “Architecture matters”at Snowflake; all of our successes at the three companies where I’ve been CEO trace back to superior architecture.

Underperforming tech assets seemed to follow me around like a bad habit.

I had to explain that there is no such thing as an override for CEOs. I said, “You can go to the board and see if they’d like to fire me and give you your old job back. In the meantime, we are doing as I outlined.”

There are times you need to check your own views at the door and bet on the conviction of others.

Today I am less driven by career ambition than by a hunger for sport, action, excitement, teamwork, and a never‐ending pursuit of self‐improvement.

When you take over a company with a wide range of issues, you have to start solving the more straightforward problems as fast as possible so you can narrow the focus on the harder ones. Bringing in some proven performers was a no‐brainer.

As I got more experience, I realized that I was often just wasting everybody’s time. If we knew that something or someone wasn’t working, why wait? As the saying goes, when there is doubt, there is no doubt.

For a more recent example, remember that when the Coronavirus pandemic first hit the US, lockdowns were described as a short‐term strategy to stop the contagion from overwhelming our healthcare system. But before long, lockdowns became the designated method to control the pandemic indefinitely, dragging on in many states for well over a year. Pandemic responses began to seem like a “make it up as we go along”approach to policy, completely untethered from any clear mission.

Not that there’s anything wrong with financial metrics or showing progress to investors or shareholders. I take those targets very seriously, but they are never our mission.

Investors and executives take huge risks on start‐ups that need to be rewarded when a company is successful.

Urgency is a mindset that can be learned if it doesn’t come to you naturally. You can embrace the discomfort that comes with moving faster instead of avoiding it.

Only the government can print money; the rest of us have to take it from somebody else.

The more high‐achieving people who desert their current employers to join us, the more we are winning.

As long as there are no new challengers with new ideas, you can do fine with an incremental approach. But in free markets, somebody is always thinking about dramatic changes. You’re much better off doing so yourself rather than hoping it won’t happen.

Folks prefer narratives that make them feel safe, however removed from reality those narratives might be. Intellectual honesty is a frequent casualty in business.

If you don’t know how to execute, every strategy will fail, even the most promising ones.

One of my favorite observations is that “good judgment comes from bad judgment.”Experience may be overrated by some, but it’s hard to find a substitute for it.

When we promote inexperienced managers to senior roles, chaos ensues. It becomes the blind leading the blind. Organizations cannot scale and mature around inexperienced management staff.

We sometimes use the expression “that dog won’t hunt”—not in reference to a person but to a strategic approach that just isn’t working, no matter what we do. It’s hard to say that if you’re irrationally attached to a strategy.

A strong product will generate escape velocity and find its market, even with a mediocre sales team. But even a great sales team cannot fix or compensate for product problems.

You should resist this temptation by remembering an old joke: “Consultants are people who borrow your watch, tell you what time it is, and then keep the watch.”

The bottom line is that great execution can make a moderately successful strategy go a long way, but poor execution will fail even the most brilliant strategy.

Hire Drivers, Not Passengers, and Get the Wrong People off the Bus

Passengers are largely dead weight and can be an insidious threat to your culture and performance. They inadvertently undermine the mojo of the organization. They sap the animal instinct and spirits you need in business to thrive.

“How do I know if I’m a driver or a passenger?”My flippant answer was that he’d better figure it out before I did.

Don’t surrender to the temptation to go into wait‐and‐see mode, hoping that time will reveal everyone’s true value. You need to make things happen, not wait around and hope for the best. You have to practice sizing up people and situations with limited and imperfect information—because that is all you are ever going to get.

If you don’t act quickly to get the wrong people off the bus, you have no prayer of changing the overall trajectory. We often believe, naively, that we can coach struggling teammates to a better place. And sometimes we can, but those cases are rarer than we imagine. At a struggling company, you need to change things fast, which can only happen by switching out the people whose skills no longer fit the mission or perhaps never really did in the first place.

those standards, that’s fine too. I know this philosophy may come across as harsh. But what’s even harsher is not doing the job you were hired to do as a leader. If you can’t find the backbone to make necessary changes, you are holding everyone else back from reaching their full potential.

Then I started moving faster to replace people who were badly suited for their roles. And often not even catastrophically bad, just worse than the caliber of people we knew we could hire to replace them. This process of systematically upgrading the talent at each key role is called “topgrading,”a strategy developed by hiring expert Brad Smart.

You can’t wait till you have an acute need; that is a reactive posture. If you wait for a vacancy to open, you can only tap the then‐current supply, which may be quite suboptimal. So create a vetted, prioritized list of possible candidates for each critical role you are responsible for.

The problem is that people don’t learn from posters. Like children and pets, they learn from consequences and the lack thereof. If you want to drive a more consistent set of behaviors, norms, and values, you have to focus on consistent and clearly defined consequences, day in and day out.

Accountability is uncomfortable because we all live with the anxiety of not being good enough and the anxiety of telling others they aren’t good enough. But if you want a great company, you can’t give out free passes for mediocrity. Good enough is never good enough.

Culture doesn’t just happen because of a CEO’s declaration or because senior management exhibits the willingness to act on core values. It happens when most of the organization is willing to defend and promote those values and call out deviations on a day‐to‐day basis.

The paradox is that any business that’s large enough to have functional silos must pull together as if these organizational delineations barely exist.

My role as CEO is to facilitate their initiative and encourage them to reach creative solutions, not simply to tell them what to do. Everyone gets a seat at the table as we hash out challenging issues.

I am generally not a fan of just trying things, throwing ideas against the wall to see if they stick. We lose time and waste resources that way. Let’s try a rifle shot instead of a scatter gun.

Customer grievances are best solved by establishing proper ownership, reducing internal complexity, and removing bureaucratic intermediaries.

Good sales managers are constantly hiring and firing, which helps them develop a clear sense of which candidates are likely to become gunslingers.

Never simply throw them into stone‐cold territories without a viable plan or support. That’s setting them up for failure, which will lead not only to their own failures but to your reputation as a leader who breeds failure.

I have often distinguished between actual profitability and what we call “inherent profitability.”

The question is what would profitability look like if we substantially stopped investing for future periods altogether? Inherent profitability is driven by unit economics, or the gross margin line in the profit and loss statement. If things cost more than what we sell them for, the business will obviously never become profitable. The next question is how operating efficiency will benefit from increased scale. Those answers help us understand what the inherent profitability of the business really is.

So they play it safe. But trying to hang on to a modest business doesn’t mean you have a viable business.

How can I possibly answer those questions for someone else’s business? The answers are relative and situational.

If possible, always own your distribution rather than delegate it to a third party. Nobody cares about selling your product more than you.

It takes intellectual honesty and humility to admit how big a confluence of factors gave rise to your original success. Just because you struck gold once doesn’t mean you know how to do it at will.

I know I said earlier that growth should be prioritized over profitability, but when it costs much more than a dollar to generate a dollar, you don’t really have a business.

I cannot emphasize enough how important it is to have strong financial oversight and discipline on sales compensation. You may be tempted at some point to make your comp plans more generous to recruit and retain top sales talent, but abandoning financial rigor can be a fatal mistake—not just during the planning stages of each year but every day, literally from one sales deal to the next.

But the most valuable leaders are those who can combine the scrappiness of a start‐up leader with the organizational and diplomatic discipline needed in a big company. Those who can scale up or scale down as required. Those who can set aside their experience when necessary, apply first principles, and think through situations in their elementary form.

When a truly new market does appear, it’s usually due to a confluence of industry‐wide factors and circumstances, not the innovations of just one company.

The issues we faced in scope, expansion, and runway now preoccupy my thinking. As a leader, you need to make time to assess these issues from day one; don’t wait for the crush of urgent business to calm down.

Having a bunch of roles on your resume without clear success at each one can become a strike against you. You start to look like a passenger, not a driver.

Start‐ups typically need hard drivers, passionate leaders, goal‐oriented and achievement‐focused personalities—the kind of people who are easily frustrated in larger, more rigid, slower to evolve enterprises. We often liked people with a chip on their shoulder, who had a lot to prove to themselves and others. But it is easy to see how others would be less enamored by such personalities.

The longest‐serving employees tend to be the most prone to nostalgia, constantly reliving the romance of the early days. Those days always seem better in retrospect than they did at the time.

Dan Warmenhoven, the highly successful CEO of NetApp, once remarked that every great CEO has a large ego because you simply could not do this kind of work any other way—but if you can’t keep that ego in check, you’ll be insufferable and therefore ineffective. That’s an uneasy balance.

Even so, continue to share credit as much as possible with the founders. Never lose sight of the fact that success takes a village, and the founders are still honorary members of the village.

Conceding the board’s authority for every major decision isn’t playing it safe. In fact, in the long run it’s much riskier than asserting your own authority and legitimacy and taking responsibility for your own decisions.

You’re not there to make friends or get a gold star for obeying orders; you are there to win.

Apply those experiences, and the insights we’ve discussed in previous chapters, to become a truer, more honed, more effective version of who you already are. Finding your own path, however long it takes, will unlock your personal power.

At the end of the day, great leaders at any level have great outcomes. You can be the most empathetic, charismatic, and popular leader ever, but none of that will matter if your business falls short. And when it does, there will be nowhere for you to hide. No one will care about your legitimate explanations, let alone your excuses. No one will care about the unlucky breaks that were completely beyond your control. Is that fair? Of course not! But it’s the world we live in, the world we have to accept as leaders.

You need to use your time differently. You need to rise above the work. You need to figure out how to make yourself less busy with your current workload to make room to do higher-value work. No one will do this for you.

She was trying to teach her team this lesson: you can’t work yourself to death and succeed over the long term. It was a hard cultural challenge, because her team believed that this overwork was not only highly valued by the company, but demanded.

You don’t win the game for running up and down the court; it’s the points on the board that count.

But if they are successful, the other thing that you will notice is that they have a ruthless focus on the things they care about. It may seem that they are not doing a good job—but maybe that is just on the part that you are looking at. You need to understand: what else are they doing?

Welcome to being a leader. This is your job. Your job is not to deliver work when everything lines up to support you. Your job is to get the most important stuff done despite everything that lines up to kill you.

I know that what I wanted from my staff was for them to catch all the work, analyze it, make judgments about business priorities, and come back to me and negotiate. I wanted them to debate with me about what is most important and why and suggest how to rework the plan to do the most important things first.

This is how you keep your boss from continuing to pile things on. Get him on the hook for the same critical business outcomes—your Ruthless Priorities.

Yes, you need to find a way to succeed if your boss is being stupid, but if your plan requires you to win against your boss, you will lose, even if you are right.

If you’re tempted to work on everything because it feels less risky, just realize that you will remain unremarkable because you have not given yourself the opportunity to really excel on something that has a big impact on the business.

Only when you are mind-numbingly bored with talking about your Ruthless Priorities will your organization really know you are serious and feel confident about acting on them.

Getting big things done is so powerful that you will get smarter as you do it. Getting things done helps you see around corners. You learn, because you can actually test the reality of the impact of what you got done.

But you must focus. If you don’t, you will work very hard but fail to deliver significant business outcomes. So you will fail. This is one of those lonely leadership moments. All leaders face this. The most successful ones get on top of it. They rise above the work.

It’s critical to recognize that your job as a leader is to collect and respond to all of the requests that come from above, but not to try to actually do them all. You are expected to tune the workload, to change the game, to figure out better ways to do things.

If your executive management could figure out which of the things, in all of this work they assign to you, were truly critical to the business, they wouldn’t need you. That’s your job.

It is a core trait of the most successful people to rise above being overbusy. If there are any secrets to what really successful people do, this is one of them. They make more time.

When communications are not clear, the number of questions and individual conversations rises exponentially. Be really clear about decisions, priorities, and issues, and find a communication mechanism to distribute the information. You will increase the capacity of your team greatly if you simply communicate better.

If you are good at fixing things or just can’t stand unanswered questions, open loops, or disorganize data, get over it. You can’t fix everything, and most of it doesn’t matter anyway.

Make three lists on one sheet of paper, in three columns.

In the first column, list the things on your to-do list that you are actually getting done.

In the second column, list things that you have committed to get done to your boss or your customers or your peers or your team—but are not getting done.

In the third column, list the things that you know are really important, but that you have no chance in hell of being able to do because of the existence of the first two lists.

Having more energy multiplies your time. You don’t just work faster; you take on things you wouldn’t otherwise. You solve bigger problems and pursue bigger challenges. You have more to give to others. You help your team and your peers more. You have more confidence and make better decisions.

Do things on purpose that help you recover your energy, but don’t give yourself too hard a time for being in a slump along the way. If you keep moving forward in your life and your work, even if you are not at your most brilliant, the slump will eventually pass.

Once you realize that your job is both your job description and dealing with all the crap that gets in the way of your doing your job description, and that what you are actually getting paid for is dealing with the crap, not the enjoyable parts, it all makes more sense.

The first and biggest hazard of taking your strengths for granted is that you waste too much time trying to fix your weaknesses. As humans we tend to focus on the things we are not good at. I don’t believe in investing in fixing weaknesses. It is a waste of time and energy, especially compared to building on strengths.

They decided it was important to thrive. They redefined the terms under which they were willing to work. They stopped trying to do their job as it was defined for them, focused on what they were really good at, and worked with other people to cover the areas they were not good at.

Leaders emerge because they are seen to get the work done through their leadership, not by their personal effort.

When you are a workhorse, people value you for your work output; they don’t value you. They don’t care how hard you work; they only care that the work gets done. Your company can absorb an unlimited amount of work from you.

It’s about figuring out how to do things better when the world and budgets are set against you

If you don’t enable and allow your team to make you bigger, you shouldn’t have a team.

if, as a leader, you are not sure what to do, talk to everybody.

Build a plan to drive the overall strategy for your team and its contribution to the business. Look for game-changing opportunities.

Clarify Ruthless Priorities. Tune everyone’s workload to ensure that they deliver on the most important things.

Ensure that there is strategic alignment of your team, peers, and boss with priorities and values.

Assess your organization’s fitness for what it needs to do, and make changes, train, and/or upgrade talent where necessary.

Create systems and frameworks to execute, track, and measure the work so you can feel comfortable that you know what is getting done without diving into the details. See also chapter 7, Delegate or Die.

Create a specific learning agenda for your team, such as understanding the financial realities of the business, getting closer to customers, or competitive awareness and positioning.

Develop talent. Help your team become better leaders and support them. Focus on the development of their top talent.

Improve communication inside and outside your organization.

Find ways to steadily reduce the cost of things you do every year to make room for new things. See also chapter 8, Better with Less.

Continually make connections outside your direct organization to create positive visibility for your team and create a broader base of support.

You need to be prepared emotionally for not being the expert any more and for finding your value elsewhere. You need to earn your team’s respect with your leadership skills, not by trying to stay as smart as they are on the detail.

Don’t think of delegating as just giving work to other people; think about it as making sure the highest-value work gets done at the right levels.

Let some important stuff go undone, or get done poorly, so you make it clear that you really need the hire.

Always think of delegating as a teaching opportunity. Remember, delegating is about taking responsibility to ensure that the highest-value work gets done at the right levels. It is about pulling your people up and making them more capable.

You may be more comfortable with the deliverables, but you are completely cutting off the possibility that, with your encouragement and support, they could become even better at it than you. In fact, you are limiting them to never being any better at it than you.

If you overmanage people, they will not be motivated to excel; they will just be motivated to get you off their back.

As a leader it is your job to cut the cost of doing the same stuff year over year—full stop.

Dealing with shrinking budgets and increased responsibility is a way of life. As a leader you can’t let that prevent you from raising the bar and driving higher-value business outcomes each year. No one will help you with this. Your team will get annoyed that they have less money to do the same stuff. It’s up to you to lead.

A high-trust environment is a fast, competitive environment. A low-trust environment is a slow, dysfunctional environment.

If you try to avoid all negative discussion or always put a positive spin on everything, you will be seen as clueless by your people who are experiencing the reality. That will destroy trust. If you acknowledge difficult issues, then get your team focused on what they can do during times of uncertainty, you will build trust.

You must get comfortable with differentiating. Treating everyone equally is not fair to your high performers.

Do this now. With each of your reports, say the following: “As your manager I am going to worry about what matters to you. When I worry about you, what should I worry about?”

But it is imperative that you have a “What happened? This is unacceptable. What are you going to do about it?”conversation.

Although these are not fun, comfortable conversations, if you avoid them, you are degrading trust.

Good work does not stand on its own. Delivering results alone does not ensure you will get recognized and rewarded. It’s sad but true. You need to take it upon yourself to make your work visible and make it count.

You need to show that you can think like a general manager about the whole business and put the business first, at the center of your thinking and discussions.

Doing your job well, as defined, keeps you from getting fired. What makes you stand out is finding additional ways to add value to the business over and above what is in your job description. Otherwise, you are just one more person doing what is expected of them.

Bringing the external voice of the real world back into your business sets you up as highly credible because most people don’t bother.

Being inconsistently good just pisses people off. It creates a high expectation and then a big letdown.

When you observe me at work or life, what is always true? What do you always see?

What is my manner of communicating?

What do I “look like”when I am delivering?

What am I expert in?

How do I relate to others at work: What do I give? What do I expect?

How do my personality and values affect what I offer?

What outcomes do you associate with my being involved in something?

By focusing on her brand, she gave herself the opportunity to sell her strengths without hesitation.

If you operate in your own department most of the time and don’t have personal relationships or functional reasons to talk to your boss’s boss, your boss’s peers, and leaders of other organizations, you can consider yourself invisible. And you can consider yourself stuck.

When the executives talk about who is the best, the people whose names are known (even if nothing else is known about them) come out way ahead of the more-talented people whose names are not known.

You can be doing a fantastic job, but if some of your key stakeholders either don’t know about it or have an incorrect, not-that-impressed perception of your work, it can be a huge block to your success and your ability to get promotions and resources for your team members or approval for projects you care about.

If you are remote, it is up to you to not disappear.

Are you being clear, succinct, and compelling?

Have you tuned the presentation to be highly relevant to each audience?

Do you get to the point? Are you sure you are not boring?

Have you made sure you won’t be tempted to go on and on about details?

Do you show strong personal presence?

Do you show confidence rather than defensiveness?

Can you deal with disagreements and attacks and not get drawn off track?

Can you field questions succinctly and not get nervous?

Can you continue to be succinct and not babble on and on when you get drawn off topic?

Can you regain control of the conversation?

For example, don’t talk about needing data on something. Ask questions like, “What decisions will you be making based on this data?”or “What action do you need this data to inform?”

You first need to get yourself there. Once you are there, learn really fast, do the job, and get more comfortable and confident as you go. Then leap again.

The world is not waiting for you to check all the boxes; they are merely watching to see if you’ll step up.

The ones who step up and go for things are the ones who get them. The ones who are fearless get there faster.

Any executive is much stronger after having spent significant time with customers where the business really happens. Spending time in sales changes your perspective forever, for the better.

This is one of the reasons it is so important to make more time, as we talked about in chapter 3. If you are completely consumed by your current job, you will not have any time or energy to do the things you need to do to get a better or bigger one.

You are already committed to your day job. Your extra work that you volunteer for should serve your personal purpose to get ahead.

A key test of executive presence is to look like you are doing your job with ease and grace. Even if behind the scenes it is chaos, what people should see is you being calm and in control.

The bigger the role, the broader your influence needs to be. As a top executive your impact needs to be on a much broader and more external stage. You need to prove that you know how to impact business growth and transformation internally and externally in a big way, if you want a big job.

However, building your career and letting your life go to hell does not work either. The trick is, if you want to do better at either work or life, you need to get better at both.

Your company wants you to have a good life that you enjoy. They know they will get more out of you at work if you are happy outside of work.

Anything north of half a million a year is the hazard pay for the company acting like it owns you, letting you know your time is not your own, and finding seemingly laser-targeted ways to torture you.

If you have a toxic or useless boss who is damaging you and your career, you need to get out. It’s not worth your time, your health, or the money that lured you into this in the first place.

Bluffing is just another example of why being an executive takes a fair amount of guts, and you need to be OK with the fact that from time to time you are going to be scared and way out of your comfort zone. That is a requirement of the job—get comfortable with it.

As long as you demand rigorous accountability to the business and measure and manage performance accordingly, you can be nice to people.

Along these lines, I often get asked whether you can or should be friends with a boss or employee.

Yes, you can be friends, as long as the friendship does not keep you from being tough on accountability and results in the business.

If you are the kind of person who can keep those separate, friends at work are fine. But if you end up holding your friends less accountable, or not imposing consequences because they are friends, and this makes you uncomfortable, then don’t make friends with employees.

If you don’t seriously manage performance with employees who are friends, everyone will see that you are letting your friend get away with things. You will squander huge amounts of trust. People will accept your friendships as long as they see you being fair.

I am a firm believer that growing businesses come from growing people, and to be highly successful, you need to make the people supporting you successful too.