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What a CEO Actually Does

Founders, Leadership

What a CEO Actually Does

Most CEOs think they’re better than they actually are. Especially founders who inherited the title on day one. But when you ask what a CEO does day-to-day, most can’t give you a clear answer. I...
The perfect bonus plan for any company

Founders, Leadership

The Perfect Bonus Plan for Any Company

Want highly-aligned, motivated employees? This article reveals a simple, transparent, and effective company-wide bonus plan that incentivizes individual and company performance. Learn how to calculate payouts, set goals, and foster a high-performance culture.

one-on-one meetings

Leadership, Management, Ops

How to Crush Your 1-on-1 Meetings

Tired of unproductive 1 on 1 meetings? This article provides a comprehensive guide to transforming your 1 on 1 meetings from dreaded obligations into powerful tools for boosting team performance and unlocking individual potential.

why top performers quit

Leadership, Management

7 Reasons You’re Losing Your Top Performers

Is your team losing its "A-players"? This article explores seven hidden reasons why top performers leave, from bad managers and lack of purpose to low compensation and poor work-life balance. Discover practical strategies for retaining your best employees and creating a thriving workplace.

Recent Articles
Are Leaders made or born

Leadership, Founders | November 23, 2025

Are Leaders Born or Made? Evidence from 20 Years of Leading Teams

Leaders are made, not born. Research proves 70% of leadership effectiveness comes from learned skills, while only 30% traces to genetics. Based on 20 years building teams and coaching 100+ CEOs, this guide reveals the seven teachable skills that create great leaders.

Animated GIF of Scot as an archer that reads How to Set & Achieve Your Business Goals

Management, Ops | November 15, 2025

7 Essential Rules For Setting Business Goals

Want a winning business strategy? This article offers seven key rules for effective business goal setting. Learn to set focused goals, define measurable outcomes, create supportive routines, track progress, and reward your team for success.

Culture, Founders | May 11, 2025

How to Create a Company Vision

Most traditional vision statements fail. This article details how the best companies create a strategic vision, and introduces a tool called the Vision Ladder that you can copy for your own company.

April 5, 2025

The WhyGo Framework: An OKR Alternative

Why we created an alternative to OKRs If you’re having problems with OKRs (objectives & key results), then you’re in the right place. After using this system for years at the company I founded, Classy...

7 costly pitfalls of OKRs by Scot Chisholm

February 27, 2025

OKRs: 7 Costly Pitfalls

OKRs stand for Objectives & Key Results. They are a popular goal-setting framework for organizations, particularly within the startup and tech communities. OKRs were an evolution of MBOs (Management by Objectives), created by Andy Grove in the 1970s, the long-time CEO at Intel. Many decades later, OKRs were popularized again by Google, after venture capitalist John Doerr introduced them to the company.

Adam Aarons

January 17, 2025

3 Powerful Lessons from a World-Class CRO

I recently sat down with sales legend Adam Aarons for a Highland fireside chat, and wow did he bring the heat. As the CRO who helped scale three major tech companies past $100M+, including my own company Classy, Adam shared his most valuable (and non-obvious) lessons from the trenches - from knowing when to walk away from a deal, to balancing mission with performance, to optimizing the critical CEO-CRO relationship.

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How to make a financial plan for your business

Ops | January 4, 2025

How to Build a Financial Plan for a Startup Business

Know thy financial plan, know thy business. If you can’t build a strong financial plan, it’s unlikely you’ll ever build a strong business. But given its importance, I’m always surprised how little attention it gets...

Hiten Shah Blog on Scot Chisholm's

Founders, Ops | December 14, 2024

Three Rules for Early-Stage Startups

A deep dive into three powerful insights from my fireside chat with Hiten Shah, one of Silicon Valley's most underrated founders. From reframing product-market fit as a dial rather than a switch, to building formulas over funnels, to the real talk about raising capital - these are lessons every founder needs to hear right now.

How to lead like a minimalist, Scot Chisholm, Highland

November 22, 2024

How to Lead Like a Minimalist

Complexity is the enemy of success. Here's how to start leading like a minimalist and create simplicity within your company.

5 Rules to Master Delegation, Scot Chisholm, Highland

Founders, Leadership, Management | November 8, 2024

5 Rules to Master Delegation

Master the art of delegation! This article offers five rules to effectively delegate tasks, empowering your team and freeing you to focus on higher-level priorities. Discover how to choose the right projects and people, provide clear guidance, and conduct effective check-ins without micromanaging.

How to scale your company in founder-mode by Scot Chisholm

Founders | October 13, 2024

Founder Mode: What It Actually Means

What does this transition from startup founder to scale up CEO look like? The way I describe it to Highland members is this - you need to transition from working on all the details all the time, to working on the right details at the right time. There is a massive difference here. This means spending your time on two things: guardrails and checkpoints.

5 essential rules of giving feedback the right way

Culture, Management | August 30, 2024

5 Rules of Giving Feedback

Good feedback should empower, not deflate. Yet most managers stumble through the feedback process. Here are 5 essential rules will transform your approach to feedback and elevate your team's performance.

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