

Code and Capital are the two highest forms of leverage. I use both.

I spent the first half of my career as an Operator: building, scaling, and exiting.

I am spending the second half as an Architect: designing systems that run without me.

Currently building a sovereign ecosystem bridging Private Equity and AI.

The Work:
- Writing: #dhandhekafunda — Deconstructing the algorithms of success.
- Guiding: House of Starts — Funding the next generation of founders.
- Building: Engines of freedom, not just companies.

If you are building at the edge of AI, Finance, or Systems Thinking, follow my linkedin profile. 

Utpal Vaishnav

We often promote people for their Execution (Column 4):

Then we are shocked when they fail because they have zero Self-Mastery (Column 1).

Leadership is not a single skill. It is a "Full Stack" discipline.

If you treat Leadership like an engineering problem, these are the 5 subsystems you need to maintain:

1. Self-Mastery: The Operating System. (EQ, Discipline, Gratitude). If this crashes, the whole server goes down.

2. People & Communication: The Network Layer. (Listening, Feedback, Trust). You cannot lead people you cannot understand.

3. Thinking & Decision Making: The Processor. (Critical Thinking, Problem Solving). The ability to be right when the data is incomplete.

4. Execution & Productivity: The Output. (Delegating, Saying No, Time Management). Vision without execution is hallucination.

5. Growth & Resilience: The Antivirus. (Learning from failure, Combating Imposter Syndrome). How fast do you reboot after a crash?

I mapped out the 50 Essential Skills across these 5 pillars.

Don't try to master all 50 today. Pick one column where you are weak. Focus there for Q1.

Which column is your "bottleneck" right now? (I am doubling down on Column 3 this year.)

~~~
♻️ Repost this #DhandheKaFunda to remind your network that "Soft Skills" are actually the most challenging part.
✔️ Save this Checklist to audit your own performance reviews. 
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Founder & Architect • Systems & Models for Builders, Ventures & Capital

50 Skills of a Great Leader: The Complete Executive Skill Stack (2026 Checklist)

by 

Utpal Vaishnav

#DhandheKaFunda

You think you are a rational decision-maker.
You are actually a rationalizing storyteller.

According to Daniel Kahneman (Nobel Prize winner), our brain has two modes:

• System 1 (The Autopilot): Fast, emotional, intuitive. It runs 95% of your life.
• System 2 (The Pilot): Slow, logical, effortful. It only wakes up when you force it to.

The problem? System 1 is terrible at math and statistics. It relies on shortcuts (Heuristics) that create "Cognitive Illusions."

I mapped out the Thinking Fast & Slow Cheat Sheet to help you debug your own brain:

The Top 3 Traps to Watch For:

1. WYSIATI (What You See Is All There Is):
System 1 builds a story based only on the data in front of it. It never asks: "What data am I missing?" This is why we are so confident in bad decisions.

2. The Planning Fallacy:
We always underestimate time and cost. We imagine the "Best Case Scenario" and treat it as the "Most Likely Scenario." (System 1 is an optimist).

3. Loss Aversion:
The pain of losing $100 is 2x stronger than the joy of finding $100. This makes us play "Not to Lose" rather than "Playing to Win."

How to use this sheet:
Whenever you are making a big decision (Hiring, Investing, Strategy), stop.

Ask yourself: "Is this System 1 jumping to a conclusion? Or has System 2 actually reviewed the data?"

Which of these biases is your personal nemesis? (I suffer from the Planning Fallacy every single week).

~~~
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Thinking Fast & Slow: A Visual Summary of Daniel Kahneman's Framework (System 1 vs. System 2)

Utpal Vaishnav


The biggest mistake new managers make is trying to be “fair”.

They think fairness means treating everyone the same.

It does not.

Treating a junior with low skill the same as a senior with high skill is not fair.

It is negligent.

The junior drowns from lack of guidance.
The senior quits from micromanagement.

Great leadership is situational.
You must diagnose the person before you prescribe the management style.

I use the Skill / Will Matrix to choose the right tool.

1. High Performer (high skill . high will)
Strategy. Delegate and empower.
Trap. Getting in their way. Give them the goal and get out.

2. Contributor (low skill . high will)
Strategy. Guide and support.
Trap. Assuming enthusiasm equals competence. They need training, not just praise.

3. Potential Detractor (high skill . low will)
Strategy. Excite and engage.
Trap. Ignoring them. They are smart enough to undermine the culture if bored or bitter. Find out why their will is low.

4. Low Performer (low skill . low will)
Strategy. Direct or exit.
Trap. Hoping they will change. Give clear expectations. If they do not execute, make the hard call.

Stop looking for one leadership style.
You need four.

Which quadrant is your most difficult team member in right now.

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The Skill / Will Matrix: How to Adjust Your Management Style (Situational Leadership Cheat Sheet)

By Utpal Vaishnav

Excited to lead UCS, the dynamic IT services and consulting division of Upsquare Technologies, as we empower businesses worldwide to achieve their goals through technology.  My focus is on fostering a culture of innovation, driving operational excellence, and delivering exceptional value to our clients.  This includes leveraging my experience in digital transformation, AI/ML, and cloud computing to help organizations:

Unlock data-driven insights: Implementing AI/ML solutions to improve decision-making, automate processes, and personalize customer experiences.

Drive business growth: Developing digital strategies that increase agility, efficiency, and competitive advantage.

Streamline business processes: Implementing and integrating cutting-edge business applications, such as ERP, CRM, and collaboration tools, to enhance efficiency, productivity, and data visibility.

Modernize their IT infrastructure: Migrating to the cloud, optimizing applications, and enhancing cybersecurity.

President and Chief Technology Officer

Upsquare

I lead innovation and technology initiatives at Upsquare.

I work closely with experts and enthusiasts in R&D teams, Delivery Units, Consulting Groups and product companies.

My role excites me to empower everyone, everywhere to co-create a shared future and drives me to lead our mission making an impact on not just businesses but humanity at large.

Upsquare and I share a common value - Curiosity that inspires us to keep an unassuming mindset. 
My child-like curiosity inspires me to observe, and analyze situations from multiple perspectives and co-create.

Chief Innovation Officer

Tata Consultancy Services

I am part of Enterprise Architecture group of my customer. As an enterprise architect, I am responsible for pattern development for deploying workloads in cloud. I own, develop and socialize patterns developed by me across the organizatinon.

This helps my client's organization immensely, by bringing in a standard way of implementing solution in cloud. My work is collaborative, I have to interact with enterprise architects and solution architects across IT domains to build my patterns. I also work with other enterprise architects on an on-going basis in improving the pattern development and governance process.

In my current role, I am working on Microsoft Azure cloud, Well Architected Framework and TOGAF's ADM principles for development of patterns.

Consultant

In my current role, I am working closely with Group CTO as part of his technology office team. Some of the activities I am involved in are Cloud program governance, Portfolio assessment, Guiding teams on target architecture patterns and Architecture review of Applications
I had undertaken 3 key initiatives while on this assignment:
1) To architect and build a data platform on cloud leveraging Microsoft Azure native services
2) Review and recommend performance improvement for microservices based SaaS product deployed on kubernetes on AWS cloud 
3) Application portfolio assessment for more than 10 entities to help them decide on target cloud architecture and define their cloud adoption roadmap

Associate Consultant

Nitor Infotech

Working as an architect for a product. Leading product engineering team. Presales for SharePoint and SharePoint based products

Associate Director

Hexaware Technologies

SharePoint architect working for a leading IT solutions provider. Knowledge in SharePoint 2013 and office 365

Senior Technical Architect

Mondelēz International

I joined Mondelez international as SharePoint support lead.

SharePoint Support Lead

I have joined Hexaware as a SharePoint technical Architect. In my current position I will be working on Client assignments as an Offshore SharePoint technical architect.

SharePoint Technical Architect

MphasiS

I worked as a technical architect in Emerging Technologies group. I was working primarily on SharePoint online based solutions.

Technical Architect

Gateway Technolabs Pvt. Ltd.

Worked as a technical architect for SharePoint Server 2010 projects. Helped implementing a public facing site for a fortune 500 company and helped in presales activity

Cap Gemini Sogeti

Worked as a senior consultant for SharePoint implementations in nordic region.

Senior consultant

I help businesses move from idea to impact: faster, smarter, and with tech that actually works.
 
With 21+ years leading tech at global enterprises, high-growth product firms, and agile Indian IT companies. I now serve as CTO at Upsquare Consulting Services (=UCS).
 
I work closely with founders, product owners, and CXOs to design and scale digital products, platforms, and transformation journeys that are rooted in outcomes, not just code.
 
My focus areas include:
 
• Product Engineering – Co-building digital products from MVP to scale
• Microsoft Tech Stack – Architecting scalable, secure, enterprise-grade solutions
• AI, ML, Web3 & Robotics – Turning hype into usable, efficient systems
• Fractional CTO & Advisory – Translating business needs into strategic tech roadmaps
 
I collaborate with our R&D Lab, delivery units, and innovation partners to bridge cutting-edge technology with execution. I enjoy making complex tech, human; connecting backend architecture to boardroom outcomes.
 
If you’re a startup needing speed, a product firm seeking reliability, or an enterprise planning digital reinvention, we should talk.
 
DM me or reach me at: amish [at] upsquaremail [dot] com

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