Writing and Communication¶

How to Lead AI Engineering Teams

Have you ever wondered why some teams seem to effortlessly deliver value while others stay busy but make no real progress?

I recently had a conversation that completely changed how I think about leading teams. While discussing team performance with a VP of Engineering who was frustrated with their team's slow progress, I suggested focusing on better standups and more experiments.

That's when Skylar Payne dropped a truth bomb that made me completely rethink everything:

"Leaders are living and breathing the business strategy through their meetings and context, but the people on the ground don't have any fucking clue what that is. They're kind of trying to read the tea leaves to understand what it is."

That moment was a wake-up call.

I had been so focused on the mechanics of execution that I'd missed something fundamental: The best processes in the world won't help if your team doesn't understand how their work drives real value.

In less than an hour, I learned more about effective leadership than I had in the past year. Let me share what I discovered.

The Process Trap

For years, I believed the answer to team performance was better processes. More standups, better ticket tracking, clearer KPIs.

I was dead wrong.

Here's the truth that surprised me: The most effective teams have very little process. What they do have is: - Crystal clear alignment on what matters - A shared understanding of how the business works - The ability to make independent decisions - A systematic way to learn and improve

Let me break down how to build this kind of team.

The "North Star" Framework

Instead of more process, teams need a clear way to connect their daily work to real business value. This is where the North Star Framework comes in.

Here's how it works:

1. Define One Key Metric: Choose a single metric that summarizes the value you deliver to customers. For example, Amplitude uses "insights shared and read by at least three people."

2. Break It Down: Identify the key drivers that teams can actually impact. These become your focus areas.

3. Create a Rhythm:

4. Weekly: Review input metrics
5. Quarterly: Check relationships between inputs and your North Star

6. Yearly: Validate that your North Star predicts revenue

7. Make It Visible: Run weekly business reviews where leadership shares these metrics with everyone. Start manual before building dashboards - trustworthy data matters more than automation.

This framework does something powerful: it helps every team member understand how their work drives real value.

The Weekly Business Review

One of the most powerful tools in this framework is the weekly business review. But this isn't your typical metrics meeting.

Here's how to make it work: - Make it a leadership-level meeting that ICs can attend - Focus on building business intuition, not just sharing numbers - Take notes on anomalies and patterns - Share readouts with the entire team - Use it to develop a shared mental model of how the business works

Rethinking Team Structure

Here's another counterintuitive insight: how you organize your teams might be creating unnecessary friction.

Instead of dividing responsibilities by project, try dividing them by metrics. Here's why: - Project-based teams require precise communication boundaries - Metric-based teams can work more fluidly - It reduces communication overhead - Teams naturally align around outcomes instead of outputs

Think about it: When teams own metrics instead of projects, they have the freedom to find the best way to move those metrics.

Early Stage? Even More Important

I know what you're thinking: "This sounds great for big companies, but we're too early for this."

That's what I thought too. But here's what I learned: Being early stage isn't an excuse for throwing spaghetti at the wall.

You can still be systematic, just differently:

1. Start Qualitative:
2. Draft clear goals and hypotheses
3. Generate specific questions to validate them
4. Talk to customers systematically

5. Document and learn methodically

6. Focus on Learning:

7. Treat tickets as experiments, not features
8. Make outcomes about learning, not just shipping
9. Accept that progress is nonlinear

10. Build systematic ways to capture insights

11. Build Foundations:

12. Document your strategy clearly
13. Make metrics and goals transparent
14. Share regular updates on progress
15. Create systems for capturing and sharing learnings

The Experiment Mindset

One crucial shift is thinking about work differently: - The ticket is not the feature - The ticket is the experiment - The outcome is learning

This mindset change helps teams focus on value and learning rather than just shipping features.

Put It Into Practice

Here are five things you can do today to start implementing these ideas:

1. Define Your North Star: What's the one metric that best captures the value you deliver to customers?

2. Start Weekly Business Reviews: Schedule a weekly meeting to review key metrics with your entire team. Start simple - even a manual spreadsheet is fine.

3. Audit Your Process: Look at every process you have. Ask: "Is this helping people make better decisions?" If not, consider dropping it.

4. Document Your Strategy: Write down how you think the business works. Share it widely and iterate based on feedback.

5. Shift to Experiments: Start treating work as experiments to test hypotheses rather than features to ship.

The Real Test

The real test of whether this is working isn't in your processes or even your metrics. It's in whether every team member can confidently answer these questions:

• "What should I be spending my time on today?"
• "How does my work drive value for our business?"
• "What am I learning that could change our direction?"

When your team can answer these without hesitation, you've built something special.

Remember: Your team members are smart, capable people. They don't need more process - they need context and clarity to make good decisions.

Give them that, and you'll be amazed at what they can achieve.

P.S. What would you say is your team's biggest obstacle to working this way? Leave a comment below.

SWE vs AI Engineering Standups

When I talk to engineering leaders struggling with their AI teams, I often hear the same frustration: "Why is everything taking so long? Why can't we just ship features like our other teams?"

This frustration stems from a fundamental misunderstanding: AI development isn't just engineering - it's applied research. And this changes everything about how we need to think about progress, goals, and team management. In a previous article I wrote about communication for AI teams. Today I want to talk about standups specifically.

The ticket is not the feature, the ticket is the experiment, the outcome is learning.

The right way to do AI engineering updates

Helping software engineers enhance their AI engineering processes through rigorous and insightful updates.

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In the dynamic realm of AI engineering, effective communication is crucial for project success. Consider two scenarios:

Scenario A: "We made some improvements to the model. It seems better now."

Scenario B: "Our hypothesis was that fine-tuning on domain-specific data would improve accuracy. We implemented this change and observed a 15% increase in F1 score, from 0.72 to 0.83, on our test set. However, inference time increased by 20ms on average."

Scenario B clearly provides more value and allows for informed decision-making. After collaborating with numerous startups on their AI initiatives, I've witnessed the transformative power of precise, data-driven communication. It's not just about relaying information; it's about enabling action, fostering alignment, and driving progress.

Content Creation Mastery: From Tweets to Long-Form

Look, creating content that matters is hard. Here's how to craft impactful content without the bullshit.

Content Creation Mastery: 9 Strategies to 10x Your Impact

Look, creating content that actually matters is hard. Here's how to do it without the bullshit:

1. Titles That Demand Attention: Your title is the gatekeeper. Make it count or no one will read your shit.

2. Hook with a Powerful Intro: You've got 15 seconds. Don't waste them.

3. Use Evidence, Not Adjectives: "Our platform is blazing fast" means nothing. "3ms average response time" does.

4. Foreshadow Value: Tell them exactly what they'll get. No vague promises.

5. Structure for Scanners: People skim. Deal with it. Use headers, bullet points, and short paragraphs.

6. Make It About Them, Not You: No one cares about your journey. They care about their problems.

7. Be an Oracle: Predict future challenges. Be right more often than not.

8. One Clear Call-to-Action: What do you want them to do? Ask for it. Once.

9. Iterate Based on Data: If it's not working, change it. Ego has no place here.

1. Craft Titles That Demand Attention

Your title is make-or-break. Here's how to not fuck it up:

• Evoke emotion: "The Writing Hack That Tripled My Audience Overnight"
• Address pain points: "End 'Writer's Block' Forever: A Foolproof 3-Step System"
• Offer clear value: "5 Persuasion Techniques That Boosted Our Sales by 287%"
• Use numbers: "7 Unconventional Marketing Tactics Used by Top Brands"
• Create urgency: "Limited Time: Learn the SEO Secret That's Transforming Businesses"
• Ask intriguing questions: "Is Your Content Strategy Secretly Sabotaging Your Growth?"

A/B test your titles. Use tools for keyword research. Keep it under 60 characters for search engines.

2. Hook with a Powerful Intro

You've got their click. Now keep them. Here's how:

1. Validate their challenge
2. Hint at your solution
3. Establish why they should listen to you

Example: "Struggling to stand out? You're not alone. After helping 100+ creators grow their audiences by 500%+, I've cracked the code. Here's how to turn readers into raving fans."

Use shocking stats, the PAS formula, or a relatable story. Keep it under 5 sentences.

3. Use Evidence, Not Adjectives

Vague claims are worthless. Be specific:

❌ "Our platform is blazing fast" ✅ "Our platform delivers 3ms average response time with 99.99% uptime last quarter"

Use: - Data and statistics - Case studies - Expert quotes - Before and after comparisons - Social proof

Always cite sources. Use visuals to make data digestible.

4. Foreshadow Value

Tell them exactly what they'll get:

"By the end of this guide, you'll know how to: - Boost email open rates by 203% - Craft headlines that convert 43% better than average - Create 10 high-engaging pieces from a single idea - Cut content creation time in half while doubling output - Land features in Forbes, Entrepreneur, and TechCrunch"

Be specific. Align with their pain points.

5. Structure for Scanners

People skim. Make it easy for them:

• Short paragraphs (2-3 sentences max)
• Bullet points and numbered lists
• Descriptive subheadings
• Bold key phrases
• Use white space
• Include relevant images
• Pull quotes for emphasis
• Table of contents for longer pieces

Use the inverted pyramid: Most important info first.

6. Make It About Them, Not You

No one cares about your journey. They care about their problems. Focus on that:

❌ "I increased conversions by 50% using this method" ✅ "You can boost your conversions by 50% with this proven method"

• Use "you" language
• Address reader benefits directly
• Ask questions
• Use relatable scenarios
• Provide actionable takeaways
• Anticipate and address objections

Always ask: "So what? How does this benefit my reader?"

7. Be an Oracle: Predict Future Challenges

Show them you're ahead of the curve:

1. Analyze industry trends
2. Predict audience evolution
3. Look for cross-industry insights

Example: "While everyone's mastering short-form video, prepare for immersive, interactive content. By 2026, 30% of content will have an AR/VR component. Here's how to get ahead."

Back predictions with data. Offer actionable steps for each prediction.

8. One Clear, Compelling Call-to-Action

Tell them exactly what to do next. Once.

• Make it stand out visually
• Use action-oriented language
• Clearly state the benefit
• Create urgency when appropriate
• Ensure it's relevant to the content

Example: "Join 50,000+ content pros getting weekly insider tips. Sign up now!"

A/B test your CTAs. Optimize for mobile.

9. Iterate and Improve Based on Data

If it's not working, change it. Track:

• Engagement metrics (time on page, scroll depth, shares, comments)
• Conversion metrics (sign-ups, downloads, purchases)
• SEO metrics (organic traffic, keyword rankings, backlinks)
• Content-specific metrics (video watch time, podcast listen-through rate)

Analyze top performers. A/B test everything. Update high-performing older content.

Remember: Content creation is both art and science. Creativity matters, but data drives results.

Now go create something worth reading.

How I want you to write

I'm gonna write something technical.

It's often less about the nitty-gritty details of the tech stuff and more about learning something new or getting a solution handed to me on a silver platter.

Look, when I read, I want something out of it. So when I write, I gotta remember that my readers want something too. This whole piece? It's about cluing in anyone who writes for me, or wants me to write for them, on how I see this whole writing product thing.

I'm gonna lay out a checklist of stuff I'd like to have. It'll make the whole writing gig a bit smoother, you know?

Crafting Compelling Titles

I often come across titles like "How to do X with Y,Z technology." These don't excite me because X or Y are usually unfamiliar unless they're already well-known. Its rarely the dream to use X unless X is the dream.

My dream isn’t to use instructor, its to do something valueble with the data it extracts

An effective title should:

• Evoke an emotional response
• Highlight someone's goal
• Offer a dream or aspiration
• Challenge or comment on a belief
• Address someone's problems

I believe it's more impactful to write about specific problems. If this approach works, you can replicate it across various scenarios rather than staying too general.

• Time management for everyone can be a 15$ ebook
• Time management for executives is a 2000$ workshop

Aim for titles that answer questions you think everyone is asking, or address thoughts people have but can't quite articulate.

Instead of "How I do something" or "How to do something," frame it from the reader's perspective with "How you can do something." This makes the title more engaging. Just make sure the difference is advisory if the content is subjective. “How I made a million dollars” might be more reasonable than “How to make a million dollars” since you are the subject and the goal might be to share your story in hopes of helping others.

This approach ultimately trains the reader to have a stronger emotional connection to your content.

• "How I do X"
• "How You Can do X"

Between these two titles, it's obvious which one resonates more emotionally.

You can take it further by adding specific conditions. For instance, you could target a particular audience or set a timeframe:

• How to set up Braintrust
• How to set up Braintrust in 5 minutes

NO adjectiives

I want you to almost always avoid adjectives and try to use evidence instead. Instead of saying "production ready," you can write something like "scaling this to 100 servers or 1 million documents per second." Numbers like that will tell you exactly what the specificity of your product is. If you have to use adjectives rather than evidence, you are probably making something up.

There's no reason to say something like "blazingly fast" unless those things are already known phrases.

Instead, say "200 times faster" or "30% faster." A 30% improvement in recommendation system speed is insane.

There's a 200 times performance improvement because we went from one programming language to another. It's just something that's a little bit more expected and understandable.

Another test that I really like using recently is tracking whether or not the statements you make can be:

• Visualized
• Proven false
• Said only by you

If you can nail all three, the claim you make will be more likely to resonate with an audience because only you can say it.

Earlier this year, I had an example where I embedded all of Wikipedia in 17 minutes with 20 bucks, and it got half a million views. All we posted was a video of me kicking off the job, and then you can see all the log lines go through. You see the number of containers go from 1 out of 50 to 50 out of 50.

It was easy to visualize and could have been proven false by being unreproducible. Lastly, Modal is the only company that could do that in such an effortless way, which made it unique.

Strong Introduction

So, if you end up doing any kind of sales, you'll realize that.

What you actually need to understand is not what you have to offer as the product, but the size of the pain that the prospect is going through.

• There are going to be readers that are just kind of curious and bored. They're not really going to be the ones that care about the product itself unless you can contextualize the pain for them.
• It's really important to have an introduction that contextualizes the pain and foreshadows the solution.

If we can build that trust and I can correctly describe the pain that you are going through, then you will believe me when I am predicting the pain that you may also go through in the future. Ultimately, that is how you become a leader in the space—by demonstrating your ability to be right consistently.

The next time you publish or write something, they will believe it, and they will believe that they get value from it.

Strong Hooks

In the same sense that a title should often try to change the "how I" to a "how you" by eliciting an emotional response, the introduction can also help select the reader into a group that is feeling the pain.

This is the same reason why a plumber will have an introduction that says, "Do you have a leaky faucet? Call 1-800-PLUMBERS." That's a much more selective hook than just "I'm the best plumber in town." You can say that to everybody, whereas if someone answers the question of whether they have a leaky faucet, it automatically selects them to be a part of their readership.

I truly believe if you try to build a product too soon for everybody, you're gonna end up in a bad place.

Foreshadow Content

Once you hook them, you still have to first retain them. You can do that by foreshadowing the content you'll cover and even hinting at the reward.

For example, an introduction could look like the following:

• If you're making $10,000 a month consulting right now, my goal at the end of this blog post is to help you increase your prices by:
  • Asking the right questions so you understand the value of the solution you're offering.
  • Providing tips on writing proposals and offering different options you can let your customer pay you more.
  • Lastly, sharing some anecdotes with you on how I became more comfortable with charging two or three times more than I did when I started

Here, I've pre-qualified the reader for a certain range and told them what their goal is by the end of the post.

Two things are just the tips and the questions I'm going to suggest, and then the final reward is something a little bit more personal. Ideally, they read the first two knowing that my personal stories are coming after. That intro itself outlines the entire post.

Use Lists

Once you've hooked your audience, you have to retain them and reward them.

You'll also see that as part of the foreshadowing content, I've listed three items that I want them to take away. I can also be specific with the number of questions and the number of tips I'm providing.

By using lists and counting things, I can give them a notion of progress towards the final conclusion. If I'm on the second part, I know where I am in the story. The list itself allows us to break down the body and give the reader a sense of position. Since they know where they are, they know where they're going to be.

Demonstrate being an Oracle

One thing that's also really valuable to call out is the fact that you want to be seen as a leader or an oracle to this audience.

For example, if we go back to this charging more case, it's one thing to demonstrate that you understand that the reader's dream is to be able to charge more. It's useful that you're giving them a couple of tips and stories. But what can be even more powerful is to simultaneously:

• Demonstrate your knowledge of the current problem.
• Predict future problems as they come.
• Foreshadow or reference those future issues in later content.

For example, the things you do to go from $10,000 to $30,000 a month are very different from what you would need to do to get to $200,000 a month. They require things like hiring, prioritizing your services, and improving distribution. If you can foreshadow that and call that out, when your audience gets to those levels, there's a chance they will remember what you said.

They'll think, "Wow, Jason was not only right about where I was but also where I was going." This brings a tremendous sense of trust and value.

It's not just this idea of future work or future considerations of the current work, but actually being able to predict the problems they're going to have in the future and suggesting that you are also the solution to those problems. You can foreshadow that as part of a series or whatever, but the general idea remains.

Have a Strong CTA

You also have to think about what the reward for yourself is. Ultimately, you should be writing this because you think the message is important and that you believe your audience should and deserves to get this message. The content of this post delivers the reward to those who stay and finish the article.

But at the end, you also have to get something in return. You should ask your user to do something. If it's a tweet, a simple one could be a repost, a like, or a share. It could even be a follow. It could be entering some GitHub link and giving the repost a star, etc.

What I realized to be very important was to make sure you only ask for one thing and don't split the attention. If you do that, you can have solid metrics on how you phrase CTAs and how that converts to certain content. For example:

• How many people from the tweet go to the blog post?
• How many go from the blog post to a subscription to a newsletter?

The more I think about it, the more I believe that most people should be capturing information into a newsletter rather than just Twitter. A direct email is so much more powerful.

No matter what it is, make sure you only ask for one thing. Sometimes it's to sign up, sometimes it's to try a one-click deploy. But if there's no action that your users can take, you've definitely made a mistake.

It's also good to call out that taking the action should have some kind of outcome as well.

• If you want to see more of this content, follow me because I post twice a week.
• That would be an example that I can qualify as a user and set expectations on what the outcome is.
• If you like it, then subscribe. You'll get two posts a week.

I also think in many situations we should have tiers of qualified CTUs.

If you want to split your traffic, you should have an obvious condition as to which one someone should take. For example, on Indexify:

• If you're dealing with terabyte-scale datasets, contact us.
• If you want to try the Open Source library

It sets a prequalifier.

The terabyte-scale dataset is an evidence-based pre-filter. It could have said "in production," but something so specific like a terabyte or a terabyte a day really qualifies who should contact indexify

Anatomy of a Tweet

The goal of this post is basically to share what I have learned about writing a tweet, how to think about writing a hook, and a few comments on how the body and the cta needs to retain and reward the user. Its not much, I've only been on twitter for about 6 month.