2026-08-16 08:00:00
As companies get larger, scheduling a decision starts to take longer than making it. Decisions that used to get alignment in an hour now “can only happen three weeks from now, once Michael and Melissa are both back.”
The problem goes deeper than big decisions. Daily operational decisions on things like on-call can become impossible to make at all. Teams that need rapid alignment end up in Slack threads that linger and die before end of day, right before the same incident happens again overnight.
The answer is blindingly simple: book recurring time that exists only for as-needed, cross-functional meetings.
I’ve seen this exact setup take an organization from Slack-thread purgatory to crystal-clear daily alignment on operational next steps.
While the meeting format is simple, keeping it alive takes skill. The necessary conditions are:
It’s often the only slot your most senior people all hold at the same time. On canceled days, it becomes prime real estate for ad-hoc 1:1s.
The irony in many cases is that people often have “Do not book” private blocks on their calendars, they’re just at separate times. This allows people to just sync up a portion of those for collaboration.
2026-08-12 08:00:00
Imagine that you’re in a board room, locked in an intense negotiation. Maybe you’re selling your company, maybe you’re signing an NFL contract, maybe you’re fighting a legal case. During a negotiation, there’s a lot of meaning to what side of the table you’re on. Most significantly, everyone on the same side of the table is on the same team – we might not like each other, we might not always disagree, but we’ll close ranks and look out for one another if needed because we’re representing our shared goal more than ourselves.
The cardinal rule of meetings with your direct reports is that you are always on the same side of the table. From the moment you walk in to the moment you leave, every single thing that your team does is a reflection and extension of you:
(The only exceptions are for cases that are truly insane, like your direct report assaulting someone or getting naked on a table. In that case you’re of course permitted to physically defend yourself; you don’t need to get naked and assault people alongside them)
Your team isn’t going to be perfect. If you have a large enough team, from time to time they will mess up while you’re in the room. But when this happens you can either handle it well, or poorly.
Here are examples of what to do when someone on your team is messing up. These approaches avoid over-defending your team, which would shield them from autonomy and consequences, but also avoid turning on them as part of the angry mob:
Finally, you should commit to your team that you will always be on their side of the table in the meeting. A simple statement like “if this gets heated, I will help to navigate the conversation” sends the type of unambiguous signal of support that people often need to hear.
For a real-world practical example, I once had some mid-level team-members (Senior PMs / Engineering Managers) who were asked to present their product to a very sharp, incisive, but (potentially) intimidating board member. A few steps that I took:
Sports teams have not forgotten the ancient rules of teamwork even as the corporate world has totally abandoned it. Watch a press conference after a team loses and it was obviously one guy’s fault: teams will go well out of their way to avoid blaming their teammate, no matter how obvious their failure was, because they know that blaming your teammate doesn’t absolve you. And that’s in spite of the fact that professional sports teams are famously savage about managing performance, reliably cutting or trading players without warning.
There are practical reasons to close ranks. Blaming people both eliminates any hope of them redeeming themselves, and more importantly instills a culture of fear that impacts future performance. It’s the curse that keeps on taking.
It’s also simply a matter of honor. People leave their team’s side of the table out of a misguided grasp at self-preservation. But people aren’t that dumb. If someone messes up, that reflects directly on their manager too. By staying on your team’s side of the table, even if it’s uncomfortable, you’re showing that you have honor. And in the long run, the best people only want to work with other honorable people, because they’re honorable themselves.
2026-08-05 08:00:00
Everyone knows that lying to your team is bad. Only a complete sociopath would argue that lying to your team is a positive, happy activity. But there’s a particular form of lying that many of the most experienced, compassionate, and honorable managers indulge in all the time: overpromising, and in particular overpromising career rewards. When managers are under pressure, and especially when they’re under pressure to retain a high performer, overpromising is one of the most common tools to reach for. The industry is rife with promises that someone will get a promotion, a new role, a large bonus, 5 more days of vacation, or any number of goodies, large or small.
Overpromising carries a terrible risk/reward tradeoff. Here’s how it goes down:
At this point, you have a very serious personnel problem on your hands that is almost certainly much worse than whatever you had at the start.
How overpromising actually goes
Decent managers routinely overpromise because if you’re an optimist with a can-do attitude, overpromising doesn’t feel like lying at all. You tell someone “I’m going to get you that promotion,” and you really do want them to get promoted. And you’ll be extra tempted to utter a promise that you can’t quite guarantee because you’re in one of the most stressful situations that a manager can face: a high performer on your team is distressed and upset, and you want to give them the confidence to stay engaged on your team. So you say the words.
But the words are a lie. You often can’t guarantee that you’ll get them promoted. Perhaps you are a department head, and you control all of the budgets and promotion decisions within your group, so you feel confident promising Jeff the promotion to Director. But what if:
All of these things can and do happen.
Even though overpromising doesn’t feel like lying, it will absolutely be interpreted as lying by your team. Contrast it with a much more mild form of deception: omitting the whole truth, for example by failing to mention that you’re fielding acquisition offers. Despite the fact that this comes from a more deceptive place (you technically really are intending to deceive your team in order to change behavior), people are generally much, much more understanding of merely unrevealed plans. But any untrue statement leaving your mouth, no matter how well-intentioned, runs the potential of causing a huge problem.
The solution is simple: Never, ever overpromise. Never let happy promises leave your lips until you are absolutely, 100% certain that you will be able to follow through on them beyond a reasonable doubt.
Of course, you don’t need to run your team like some sort of psychological experiment where you never share anything positive about the future. The way to navigate the landscape feels weird at first, but you should caveat any forward-looking career promises like you’re a paranoid lawyer and/or running down the list of scary-sounding disclosures on a pharmaceutical advertisement. I have literally said “I’m gonna try really hard to do X, but I need to add a disclaimer because I don’t ever want to make a hard promise I can’t keep.”
Here are some common fixes to lines that feel totally normal to say, but run a very real danger of overpromising:
Avoiding overpromising doesn’t mean that you can’t be sincere with your team. If you feel an emotion, like the fact that someone is really great and you hope they get promoted, it’s usually okay to show it within reason. Emotions that you really feel are authentic by definition, so they don’t run the risk of letting a lie leave your lips.
Your word as a manager is your bond. And if you want to be a good manager you can never break your word, especially to people you manage.
Management is an asymmetric relationship where you hold the power to enable someone to put food on the table, so your word is sacred. It’s better to be honest and painfully disclaim future looking statements than to risk being an optimistic, confident liar. And in the long run your team and your blood pressure will thank you for it.
2026-07-27 08:00:00
In the course of conversations with startups that I’ve invested in, that I advise, or that I simply encounter, it’s very common to get into discussions about prioritization.
Some common situations that I hear about all the time:
The advice that I give in almost every case – the best way to prioritize is to not prioritize.
Prioritization sucks for a few reasons.
First off, frameworks are BS. People have written breathless blog posts about product prioritization frameworks like RICE or the Kano model which are designed to generate imposter syndrome about your decision-making and encourage you to buy some online course. These frameworks are often largely vibes, or rooted in such completely abstract concepts or unknown assumptions that you might as well just ask ChatGPT what to do. Like what’s the meaning of “Reach” (the “R” in “RICE”) when we’re in a market that’s growing 50% YoY, or when we’re a startup with 10 customers? How do we calculate “Effort” (E) when AI coding is going exponential?
And just as importantly, the quality of your prioritization skills is unprovable. You’re only going to set your team on a single path, and proving that it was optimal retrospectively will be a purely philosophical exercise. Your business is going to thrive or it’s not, and it probably isn’t going to hinge 100% on this decision anyway. So while we can debate various merits going into prioritization, you’ll never even really know if you were right; you’ll just know whether the business overall worked or you got fired. As a side effect, this sort of unprovable philosophical argument is also a recipe to make people furious (“I told you that we shouldn’t have done that!”).
And of course reprioritization also takes a lot of cognitive effort. It’s wild how many planning meetings, summits, planning spreadsheets, and program managers can get rallied to answer the question “what do we do next week.” If your startup has less than 50 people and you see a Gantt chart, you should pull the fire alarm, throw out your employee badge, and run.
So there’s basically two alternatives to prioritization that work well.
The first is to just build faster. If you can only build one thing, what you choose to work on matters enormously. If you can build 10 things, you only need to have a vague sense of what a good idea looks like, and a sensible way of determining whether it’s actually working once it’s done.
The better you are at moving fast the worse you can be at prioritization. Prioritizing well requires being very clever. Building fast is great because you don’t need to be clever at all.
And I don’t mean this in some facetious, philosophical trick-question kind of way, I mean literally cut time spent on prioritization and refocus it on being faster. Instead of a week-long planning onsite with 2 travel days, have a half-day planning session and then spend an abbreviated offsite streamlining the build process, making sure teams are well-resourced, helping teams get into a better operating rhythm, and actually hanging out so that people are motivated to build faster. And then just do actual work for the rest of the week.
Speed pays dividends in basically every scenario and it’s empirically proven to work. There are many winning companies that make dumb prioritization decisions that they have to unwind all the time. There are no winning companies that move slowly. Also, shipping faster teaches you more about good prioritization than reading blog posts about backlog grooming. You’re unironically probably better off building 3x faster and going down your list of product roadmap candidates in alphabetical order.
The next strategy is to take cross-goal prioritization off the table entirely.
Team A is working on increasing sales for our new product, but what if they helped reduce support on our core product instead? Which is a higher priority? I dunno. What if we just literally didn’t ask that question, and teams stayed in their lanes forever?
Enforcing that teams always focus in one area takes a huge amount of total prioritization effort off of your plate. All of your decision-making turns into apples-to-apples comparisons within a fixed domain – for example, do I want my core product:
These are vastly simpler questions than the apples vs. oranges comparisons like new product vs. old product. You can just ask customers or your CFO what they need, and all the variables are simpler. Also, your business would be stronger if you did all of these things (bringing us back to the prioritization point above).
Keeping teams together through thick and thin turns your prioritization problems (hard, difficult to prove correctness, cause significant context-switching) into resourcing problems (easier to reckon with, faster overall). Resourcing problems are far better because they’re less contentious and force you to transact in the world of facts – how fast is this team actually moving, how much actually needs to get done to ship. The fact that you solve resourcing problems by hiring, downsizing, or reorging teams is also an advantage because those activities take longer, which means that you’ll move slower on the decision, which causes less thrash, which gives more focus, which drives higher velocity (see above).
Teams that stick together are also a better match for certain types of problems. For example, if you’re running a high-upside experiment on a new product area, you could pare off a varying amount of resourcing every month to try to breathe life into it. Or you could just have 1-2 engineers spend 3 months seeing if they can go 0-1 on their own. The 2 engineer model is significantly more likely to work (simulates an early stage startup) and it doesn’t require any ongoing logistics. If the product takes off, add more resources. If it doesn’t, spin it down to 0.
This strategy is almost unfair in how well it works compared to constantly reprioritizing work. Stakeholder management also becomes dramatically easier. “When is that new product shipping?” is much simpler to answer if you don’t need to jump through the mental hoops of whether or not you could prioritize some other team’s project, and what that would do to other promises that you’d made. Even if that time is technically longer than pulling everyone onto the key project, the certainty and confidence that you can project typically make customers and internal partner teams happier overall.
Prioritization is a trap. It wastes time, wastes effort, and delivers worse results than just executing faster. Instead of spending your time prioritizing:
2026-07-16 08:00:00
A lot of people simply don’t understand the degree to which competition matters in B2B software, and what competing effectively feels like. Competition is simply the art of increasing your win-rate when you and a competitor vie for the same customer’s business, and this is what I would tell my team if I had to motivate them to compete hard and win:
***
If our market has any value at all, we’re going to have competitors. Many of them will be formidable, because the thermodynamics of capitalism dictate that competition always eventually appears. If it didn’t, it would mean that we were doing something useless.
If our market is as large as we think it is, competitors will continue to spring up and get funded until there’s no longer positive expected value in trying to own it. VCs need to make money, and they will pay an endless train of Stanford dropouts to try to kick our ass. Our goal is to instead kick their asses so quickly, decisively, and publicly that people stop signing up to take shots at us.
You’re gonna read stuff written by rich people who tell you that competition doesn’t matter. They’re going to not-so-subtly imply that even thinking about the competition is some kind of weak behavior. These people are wrong, and they were typically late joiners at dominant consumer monopolies like Google. Assume that we are not Google. Once you’re at scale (i.e. not a tiny startup), competition matters and there is no shame in recognizing it; the fact that you have competitors who deserve respect doesn’t make you somehow lesser.
They will sagely make pronouncements like “Startups die from suicide not homicide,” but I will tell you now that I have seen startup homicide with my own eyes. They’ll write that competing is some kind of beta loser move, because they’re standing so high up on the shoulders of giants that they don’t even know how they got there. We aren’t standing on the shoulders of giants yet, we are the giants, and if we do our job well, then one day we can explain to some kids that we, too, needed to compete like maniacs years before.
Even if you don’t personally feel like conflict, it will still be brought to our door. We cannot unilaterally declare a stalemate and have competitors disappear. They are coming whether we like it or not, so we can live in only one of two worlds. In the first:
The odds of us getting fired at Step 4, 6, or 7 are high. In contrast, there’s Scenario #2:
The competition wants to force us into Scenario #1. They want us to go out of business. They want to put you at your kitchen table at 9pm explaining to your wife that you’re going to need to cancel that vacation or trade in the car for something cheaper. Perhaps they’re not envisioning that actual scene, but every day they wake up and take actions that can literally lead to that conversation. I don’t want that for my kids, and I don’t want it for yours.
To really move win-rates we need to be far better than competing offerings – half as expensive, 10x faster, 3x better results, etc. 10% improvements won’t cut it because it’s so annoying for our customers to change or do literally anything. Even finding their credit card and verifying their email for some $29/month PLG product is enough hassle that most won’t do it.
So we aren’t going to get higher win-rates with incremental feature improvements. It’s great that some 5% product improvement that you want to prioritize is a good idea, but it’s probably not going to move the needle and put us in a stronger market position unless it’s part of a story where we fix literally everything. So if you’re looking at a modestly good idea, you either need to build it really fast or not at all. We are looking for knockout blows rather than love taps.
This is going to take a long time. In B2B you win deals one at a time, so it’s house-to-house fighting. You’re hearing us talk about beating the competition right now; you’re going to hear about it for years. Software companies, particularly enterprise ones, are like bugs that can survive a nuclear blast and live off of discarded Kind bar wrappers and half-empty Mountain Dew cans for decades. We’re going to have to track down every last bug in the landfill.
But luckily, focus and hard work are the two easiest things to control. So if we actually focus and do the right things, we won’t be the ones that need to cancel Christmas.
2026-06-22 08:00:00
Technology businesses are heavily influenced by waves of technology change, like the rise of the internet or AI. Knowing how to adjust strategy for these changes is one of the most important skills to develop.
As technology has advanced, technology waves have become larger, more frequent, and more sudden. In just the last 30 years (less than a full career, literally less than the time between graduation and your first 401k payout) we’ve seen:
This has happened for thousands of years. I’m sure there was some Bronze Age metalsmith in 3000 BC who had to explain to his pissed-off wife that he lost his job because some asshole figured out you could make a better sword out of iron. Disruption from technology waves has been happening for thousands of years and will continue for the indefinite future.
I’ve been around long enough to watch multiple technology waves swell and break on the shore. There are a few super simple questions below that I ask as early as possible in a technology wave that I’ve found invaluable for orientation. The key is to ask them, in order, every time:
These questions are not hard to answer. They do not require a deep math background or Machiavellian cleverness. If this is a road trip, you’re not trying to find a shortcut through backroads, you’re just trying to figure out if the bridge you’re about to drive over has collapsed. But it is essential that you actually take the time to ask them, which is surprisingly hard because…
Whenever a new technology wave comes along (like the internet, mobile, or AI), a huge number of businesses simply ignore it because change is annoying. Maybe if we ignore these dumb phones they’ll go away. This GPT thing can’t count how many Rs are in the word “strawberry,” it’s useless.
(Worth noting that the tendency to ignore new technology waves seems to have gone down over time. There were many, many more internet skeptics than AI skeptics)
Ignoring new technology waves feels good because most technology waves do sputter out. The few big businesses built on crypto have (so far) been mainly related to speculating or buying drugs. VR games never got mainstream adoption. Only weirdos and tinkerers have 3D printers in their homes. Being lazy pays off pretty often. It also lets you talk down to others, which many people unfortunately enjoy.
Additionally, just assuming that nothing is happening is a somewhat self-correcting problem. You can ignore iPhones for a long time, but eventually literally everyone you’ve ever met has one, and you can just shamefully pretend that you never said they were pointless. As a result, being lazy is often less dangerous than the other trap…
A lot of senior leaders, even “leaders” at tech companies, are fundamentally insecure about technology. They’re either not technical by training or so out of practice that they don’t know how their products work. This is especially true in fields where projecting confidence is a key part of the job: Sales, Marketing, Human Resources, and arguably even Security are all examples.
So in order to instill confidence in their teams, or to win whatever political battle is being fought this week, whenever a tech wave appears on the horizon many execs feel compelled to project wisdom and understanding.
Critically, these execs don’t actually understand what’s going on – they haven’t followed the steps outlined above, and they often also fall into the trap of being lazy. So instead they follow the hype: This is popular on X (or worse, LinkedIn), all our competitors are leaning in, or “Gartner said this is the next big thing.” It’s classic herd behavior. Once the hype is loud enough, these leaders’ next step is to declare that the new technology is the birth of a new machine god, and that they will be its prophet.
Going all-in on something you don’t understand can work out fine if you capture something like the iPhone moment and build a mobile empire. But it’s deeply damaging if it causes you to mortgage your business’ future on some Web3 technology with 0 actual users. Or if you cancel your entire roadmap to put a hat that says “I ♥️ AI” on top of your product, when your customers actually wanted you to add better approval flows.
Blind over-rotation is the default strategic mistake in times of major change. To avoid it, you need to make sure that you and your team aren’t falling into the trap of avoiding embarrassment by leaning in on whatever is hot.
New technology waves can make or break your business, but only some of the bumps in the water actually matter.
Follow the steps of thoughtfully asking whether the technology is impactful, researching how it functions, establishing the facts on what it makes possible, and considering whether it impacts your business. Beyond that, don’t assume it’s just nothing, and don’t let embarrassment drive you to go all-in just because everyone else is.
Most importantly: The greatest sin of technology waves is missing an obvious wave and pretending it wasn’t real because of your ego. If you miss a wave, the single most important step is to swallow your pride and immediately take strides to catch up:
The silver lining of technology waves is that when they matter they’re big, and when they’re big they’re eventually obvious. Missing them, more than anything else, is truly business-killing, but luckily you don’t need to be that clever to detect a wave that matters.
