🎙️ Pod Shots

Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised a $200M round at a $13.4B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple. In this wide-reaching 1st Round Review podcast he covers lessons on culture, org-design and product, characteristics of great CEOs, how to be a better executive leader, leading with kindness and impatience and how to fight entropy.

As ever it’s packed with great practical insights to help you become a better leader.

⚒️ How To Be Effective Up and Down the Org Chart

🎙️ Listen to the full episode here

📆 Published: July 11th, 2024

🕒 Estimated Reading Time: 3 minutes. Time saved: 72 minutes🔥

🚀 Understanding the Unique Role of a CEO

Every CEO's journey is unique. The role is inherently idiosyncratic, shaped by the market, the team, and the specific moment in the company's lifecycle. Successful CEOs leverage their strengths unapologetically, focusing on what they do best and letting their teams handle the rest. As Matt points out, "successful CEOs act with impunity, allowing their subordinates to manage the fallout of their strengths."

The key takeaway for founders is to embrace your natural abilities and instincts while ensuring your leadership team complements your style.

Key Advice:

• Play to Your Strengths: Don’t be overly concerned with the downsides of your strengths. Use them to drive the company forward.

• Build a Complementary Team: Ensure your team can balance your strengths and mitigate any potential downsides.

🏢 Designing Organisational Culture and Structure

When it comes to culture and organisational design, it's crucial to maintain a high velocity and fight against entropy. Matt emphasises that "velocity is a competitive advantage," and slowing down can be detrimental to a company’s success. Entropy, or the natural tendency for processes to slow down over time, is a constant battle for executives.

Key Advice:

• Prioritise Velocity: Encourage rapid experimentation to maximise the number of opportunities before resources run out.

• Combat Entropy: Stay vigilant in maintaining pace and ensuring that the team remains focused on the highest priorities.

👩‍💼 Characteristics of Great CEOs

Great CEOs share common traits: impatience, a relentless focus on results, and a deep understanding of their unique strengths. They do not get bogged down by self-doubt or the fear of how they are perceived. Instead, they focus on "what it takes to win."

Key Advice:

• Be Impatient with Progress: Push for faster timelines and challenge the team to think about how tasks can be accomplished more quickly.

• Embrace Your Uniqueness: Understand that your distinct approach is what will lead your company to success.

🌱 Becoming a Better Executive Leader

Executive leadership requires a balance of decisiveness, accountability, and the ability to manage uncertainty. Matt explains that "executives should act with velocity over perfection because perfection is often unavailable."

Key Advice:

• Focus on First Principles Thinking: Break problems down into their fundamental components and build solutions from there.

• Act with Confidence: Make decisions swiftly and learn from the outcomes, rather than striving for perfection.

💗 Leading with Kindness and Impatience

Leading with kindness does not mean lowering standards. On the contrary, it's about respecting the people who choose to work with you and holding them to high standards. Kindness is about ensuring that everyone is aligned and feels valued while driving towards ambitious goals.

Key Advice:

• Hold People Accountable: Maintain high expectations while providing the support needed to meet those expectations.

• Balance Empathy and Drive: Lead with compassion but also with a clear focus on achieving results.

🔄 Fighting Entropy in Your Organisation

Entropy is the silent enemy of progress. As companies grow, there is a natural tendency for processes to become sluggish and for the pace to slow down. Matt underscores that "everything in a business is about fighting entropy."

Key Advice:

• Maintain High Standards: Regularly review processes to ensure they are efficient and effective.

• Encourage a Sense of Urgency: Foster a culture where quick decision-making and action are the norms.

🎯 Focusing on Output and Impact

The concept of output and impact is crucial for managing teams effectively. Matt uses the analogy of corporate finance to illustrate this point: "Corporate finance distills an entire company down to a single number, which is free cash flow." Similarly, teams should focus on clear, measurable outputs.

Key Advice:

• Define Clear Metrics: Ensure that every team understands the key outputs they are responsible for.

• Align Activities with Outcomes: Regularly inspect inputs to ensure they are contributing to desired outputs.

🌟 Cultivating a Culture of Clear and First Principles Thinkers

Clear thinkers and first principles thinkers bring different strengths to an organisation. Clear thinkers have a comprehensive understanding of their area, while first principles thinkers can break down problems and create novel solutions.

Key Advice:

• Hire for Thinking Styles: Identify roles that require clear thinking versus first principles thinking, and hire accordingly.

• Encourage Diverse Perspectives: Foster an environment where different types of thinkers can collaborate effectively.

📚 The Importance of Relevant Experience Over Advice

When seeking input, focus on gathering relevant experiences rather than generic advice. Matt highlights that "relevant experience allows you to integrate insights into your context," which is more valuable than following advice that may not be applicable.

Key Advice:

• Seek Experience, Not Advice: Look for people who have faced similar challenges and learn from their experiences.

• Apply Insights Contextually: Use the insights gained to inform your decisions based on your specific situation.

🌍 Leading with a Sense of Purpose

Ultimately, leading a company is about more than just achieving business success. It involves understanding your own motivations and finding fulfilment in the process. Matt shares that being true to oneself and operating without self-doubt is key to both personal and professional success.

Key Advice:

• Embrace Your Journey: Be authentic and pursue your vision with confidence.

• Find Fulfilment in the Process: Enjoy the challenges and triumphs that come with leading a company.

Want to know more quickly? Just ask the episode below [web only]👇️🤯
or if you prefer, 🎙️ Listen to the full episode here

📅Timestamps:

• (00:00) Introduction

• (02:14) Great CEOs don’t worry about their weaknesses

• (06:31) The third-time founder mindset

• (08:09) Why every great CEO is impatient

• (11:54) How executives fight entropy

• (19:11) Experience ≠ wisdom

• (21:26) Managing workplace politics

• (24:02) Why all businesses should dogfood

• (26:20) Overseeing employee expenses

• (27:43) The best CEOs don’t need coaching

• (29:55) The hidden cost of advice

• (40:40) Why execs are “tortured but happy”

• (44:16) Clear versus first principles thinking

• (51:09) Finding first principles thinkers

• (53:13) Why people overcomplicate culture

• (55:53) Don’t make this mistake when interviewing

• (59:26) The importance of anti-patterns

• (61:27) Important business values

• (63:28) How Matt thinks about output

• (66:33) Rippling’s key leadership principle

• (71:02) Why kindness matters

• (72:03) Freeing yourself from self-doubt