Squirrel Squadron Substack

The Squirrel Squadron Substack blends insights on technology, leadership, and management, targeting tech and non-tech executives. It emphasizes collaboration between humans and AI, encourages questioning norms, and seeks to enhance team dynamics and innovation through strategic experimentation, intelligent disobedience, and understanding the business value in tech initiatives.

Technology and Innovation Leadership and Management Team Dynamics and Culture Strategic Planning and Execution Artificial Intelligence and Human Collaboration Software Development and Engineering Practices Product Management Business Strategy and Value

The hottest Substack posts of Squirrel Squadron Substack

And their main takeaways

Centaurs and the Future of AI

1 HN point • 01 Jun 23

Computers and humans work best together, not separately.
When using AI, consider the computer as a 'method actor' in conversations.
Incorporate humans in the loop with AI for better results, especially in operational processes.

Secret Supercharger for Engineers - Squadron Weekly Email

0 implied HN points • 08 Dec 23

Engineers can build and release software faster if they believe it's possible.
Tools like Stable Diffusion demonstrate the power of breaking mental boundaries.
Giving engineers freedom from limits can lead to innovative and rapid development.

Ignorance Is Criminal - Squadron Weekly Email

0 implied HN points • 11 Dec 23

💼 Business Ethics Technology Finance Management Security

Keep your tech team informed about business strategy and technical decisions.
Ensure multiple engineers review every code change and understand the business implications.
Obscurity and lack of knowledge can lead to dangerous modifications in software.

Ready, Fire, Fire, Fire, Aim, Fire, Fire, Aim, Fire… - Squadron Weekly Email

0 implied HN points • 11 Dec 23

💼 Business Management Innovation Entrepreneurship

Certainty and over-preparation can hinder your product and team.
Failing in public and correcting mistakes is important for progress.
Running experiments, making mistakes, and iterating quickly is key to success.

Flying Blind: Your Tech Instrument Panel - Squadron Weekly Email

0 implied HN points • 11 Dec 23

🕹 Technology

Having the right instruments in your tech projects is crucial for staying on course.
Key instruments to track progress include radar system, glidepath indicator, stall warning, ground proximity warning system, and cabin CCTV.
Many teams and projects are not monitoring all these key indicators, leading to potential issues.

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Confidently Strolling Off The Cliff - Squadron Weekly Email

0 implied HN points • 10 Dec 23

🕹 Technology Software Complex Systems

Lack of doubt can be a dangerous sign, not a positive one.
Having unwavering confidence doesn't guarantee success.
Teams that are about to crash often appear confident, not uncertain.

Chekhov’s Gun - Squadron Weekly Email

0 implied HN points • 10 Dec 23

💼 Business Tech Management Analytics Productivity

In business, always focus on demonstrating the "business value" of your tech initiatives.
Encourage your team to measure and be accountable for the business results of their work, not just activity metrics.
Consider failures in achieving targets as successful experiments that provide valuable learnings.

Poisonous Rewards - Squadron Weekly Email

0 implied HN points • 10 Dec 23

💼 Business Management Collaboration Rewards Incentives

Rewarding individual success can undermine collaboration and morale in a team.
Individual reward systems create competition and resentment, hindering collaboration in crucial projects.
Consider recognizing and rewarding collective team efforts to encourage overall success.

If They Don’t Jump, Push - Squadron Weekly Email

0 implied HN points • 11 Dec 23

💼 Business Innovation Professional development

A 100% retention rate on your tech team isn't good.
Stagnant tech teams may lack new challenges and ideas.
Healthy conflict and new ideas help developers grow.

What If You Owned The Company? - Squadron Weekly Email

0 implied HN points • 08 Dec 23

💼 Business Leadership Strategy Innovation

Stop waiting for someone above you to set strategy, invent your own.
Imagine having complete control of your organization to unlock new ideas.
Trying different strategic plans is okay as long as you stay unstuck and keep moving forward.

Ask Experts Dumb Questions - Squadron Weekly Email

0 implied HN points • 08 Dec 23

💼 Business Management Communication Innovation Strategy Productivity

Don't be afraid to ask experts dumb questions; it can lead to valuable insights.
Preparing basic questions and practicing effective interruptions can keep the conversation on track.
Asking 'dumb' questions can help overcome fear of looking ignorant and lead to important discoveries.

Stone Soup - Squadron Weekly Email

0 implied HN points • 08 Dec 23

💼 Business Leadership Management Technology

Effective leadership in a technical team doesn't require deep technical knowledge.
Shift work to expert employees to manage better.
Encourage collaboration and visibility in project planning and execution.

Agile Fantasy - Squadron Weekly Email

0 implied HN points • 27 Nov 23

💼 Business Management Meetings Team Dynamics Process Improvement

More process and meetings won't solve business problems.
Don't cater to engineers craving certainty in an 'agile' environment.
Focus on business results over excessive processes.

Stop Improving Your Product - Squadron Weekly Email

0 implied HN points • 27 Nov 23

💼 Business Product Development

Stop the belief that you know what changes are obvious for your product without customer validation.
Don't focus on improving aspects like speed without confirming its value to customers.
Validate every product decision with at least one passionate customer supporter.

No One At the Wheel! - Squadron Weekly Email

0 implied HN points • 27 Nov 23

💼 Business Product Management Software Development Workplace dynamics

Tech teams need a clear product direction to avoid feeling lost.
Having a busy product manager doesn't necessarily mean work is being done effectively.
Implementing a solid product process is crucial to prevent software teams from making guesses and facing negative outcomes.

Fire Your Programmers - Squadron Weekly Email

0 implied HN points • 26 Nov 23

💼 Business Technology Management

You don't always need engineers to build complex software systems.
Consider using off-the-shelf tools and simple methods in place of custom software.
Evaluate if engineering skills are truly required in all roles within your organization.

Blow Up “Good” Relationships - Squadron Weekly Email

0 implied HN points • 26 Nov 23

💼 Business Relationships Workplace dynamics Conflict resolution

Low-conflict relationships at work might not be as good as they seem.
Conflict can lead to progress and uncover underlying issues.
Creating productive conflict in relationships can be beneficial.

Intelligent Disobedience - Squadron Weekly Email

0 implied HN points • 26 Nov 23

💼 Business Leadership Teamwork Innovation

Not following orders can be a sign of health in a team.
Encourage intelligent disobedience in your teams.
Praise your teams when they challenge orders that may be harmful.

The Santa Claus Promotion Method - Squadron Weekly Email

0 implied HN points • 11 Dec 23

💼 Business Management Leadership Product Development Employee Development Risk management

Promoting someone uncertain? Test them in a low-risk scenario first.
Encourage team experimentation for learning and improvement.
Use gradual exposure to prepare for potential changes or challenges.

Down With Betterism! - Squadron Weekly Email

0 implied HN points • 11 Dec 23

💼 Business Tech Innovation Customer Relations

Don't assume improvement is always necessary.
Tech teams can focus on the wrong problems.
Avoid the trap of chasing 'better' instead of addressing real needs.

Don’t Build a Jack-In-The-Box - Squadron Weekly Email

0 implied HN points • 10 Dec 23

🕹 Technology Software Development

Avoid surprises by slicing tech work thinly to get real value daily.
Don't let engineers take the 'jack-in-the-box' approach to projects.
Insist on 'elephant carpaccio' to show valuable progress frequently.

Napkin Strategy - Squadron Weekly Email

0 implied HN points • 10 Dec 23

💼 Business Strategy Management Coaching Leadership

Summarizing ideas into brief forms helps understanding
Use simple language to communicate strategies effectively
Define what you won't do to create a clear picture of the future

Electrified Engineers - Squadron Weekly Email

0 implied HN points • 08 Dec 23

💼 Business Strategy Leadership Management Teamwork Productivity

Setting goals quarterly can be a nightmare for many.
A short, surprising message can shift thinking and lead to immediate action.
You can define a message for your team even if you're not in charge of the strategy setting process.

Do More Nothing - Squadron Weekly Email

0 implied HN points • 08 Dec 23

💼 Business Leadership Productivity Efficiency

Feeling bored and useless as a new executive is normal- it shows you're doing impactful simple tasks.
Stop equating being busy with being productive in your work.
Create empty space in your calendar to achieve the feeling you want.

You’re Losing The Strategy Race - Squadron Weekly Email

0 implied HN points • 08 Dec 23

💼 Business Strategy Product Leadership Decision-making

Successful competitors take quick action on strategy without waiting for meetings or approvals
Keep strategy discussions lively, with productive conflict, and focused on actionable decisions
Take charge of leading strategic conversations and ensure accountability within your team

Aim While Firing - Squadron Weekly Email

0 implied HN points • 08 Dec 23

💼 Business Management Productivity Leadership

Setting quarterly objectives should focus on completion rather than perfection.
It's better to have imperfect objectives than to wait for a perfect message from the top.
Start moving forward with messy objectives and adjust as needed.

Having Fun: The Key To Tech Team Profit

0 implied HN points • 25 Oct 23

🕹 Technology Software Engineering Creativity Culture Business

Software engineering teams should bring excitement and fun to the workplace to motivate developers and increase creativity and profitability.
In complex systems like software, relaxation and fun can lead to better problem-solving and creativity.
Encouraging experimentation and taking appropriate risks can lead to innovative solutions and success in technology teams.

Creating A Tech Money Machine

0 implied HN points • 25 Oct 23

💼 Business Technology Engineering Supply Chain Innovation

An engineering organization is like a profit-maker's dream with adjustable products and low delivery costs.
Technology offers a gold mine of opportunities, but there are traps to watch out for.
Join the Squirrel Squadron for access to live events, weekly emails, and an executive forum.

Exponential Product Growth - Squadron Weekly Email

0 implied HN points • 11 Dec 23

💼 Business Marketing Strategy Revenue Partnerships

Consider effective accelerants for software products to speed up adoption, market breadth, and profit.
Look for simple strategies that can significantly increase users, revenue, and profit.
Explore opportunities like marketing through channel partners, broadening markets, and repackaging data to grow efficiently.

Yelling is Healthy - Squadron Weekly Email

0 implied HN points • 27 Nov 23

💼 Business Team Dynamics Productivity Communication

Yelling from your tech team can be a sign of healthy disagreement and progress.
Productive shouting is not a problem and can lead to better outcomes.
Respectful discord that leads to advancement is similar to muscle pain during exercise.

Engineers Who Sweep The Floor - Squadron Weekly Email

0 implied HN points • 26 Nov 23

🕹 Technology Software Development

Team members should be willing to contribute outside their expertise.
Software teams benefit from 'T-shaped people' with deep skills in one area.
Success in tech teams is shown by members making contributions beyond their roles.

Inaccuracy Is Your Friend - Squadron Weekly Email

0 implied HN points • 26 Nov 23

💼 Business Data Decisions Truth Information

Don't focus on having perfectly accurate data; multiple sources of truth are beneficial.
Even with noisy and conflicting data, successful outcomes are possible, as seen with the Apollo 11 landing.
Embrace inconsistent information and make decisions based on the bigger picture, like looking out the window, rather than getting bogged down in details.