Articles

My Popular Articles
How to Scale Your Company in Founder Mode

Founders

How to Scale Your Company in Founder Mode

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.
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.

animated GIF of a conversation between two bobbleheads. First bobblehead says,

Founders, Leadership

10 Worst Pieces of Startup Advice
(And What to Do Instead)

Tired of bad startup advice? This article debunks 10 common — and terrible — pieces of advice given to startup founders, like "fail fast" and "never do business with friends." Learn what to do instead.

Culture, Founders

How to Create a Company Vision People Want to Follow

Want authentic company values your team will actually embrace? This article provides a seven-step guide to crafting company values that resonate, starting with personal reflection and involving your core team. Learn to define actionable values, avoid corporate jargon, and create a culture that embodies your company's beliefs.

Recent Articles
7 costly pitfalls of OKRs by Scot Chisholm

February 27, 2025

OKRs: 7 costly pitfalls (and how to fix them)

Who created OKRs 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...

7 rules to crush your 1 on 1 meetings.

Leadership, Management, Ops | February 13, 2025

Crush Your 1 on 1 Meeting: A guide for both manager & individual

Tired of unproductive meetings? This article provides a comprehensive guide to transforming your one-on-one meetings from dreaded obligations into powerful tools for boosting team performance and unlocking individual potential. [1, 2] Learn practical rules and pro tips for both managers and team members to maximize these essential check-ins.

Adam Aarons

January 17, 2025

3 powerful lessons from a world-class Chief Revenue Officer (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.

How to make a financial plan for your business

Ops | January 4, 2025

How to make a financial plan for your 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 with Hiten Shah

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.

Scale your team.
Unlock your dreams.

👆 Subscribe free to get all future articles.

The ideal Compansation Package
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

5 essential rules of giving feedback the right way

Culture, Management | August 30, 2024

5 Essential Rules of Giving Feedback (The Right Way)

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.

How to run the perfect executive meeting

Leadership, Management | August 16, 2024

How to Run the Perfect Executive Meeting

Tired of unproductive executive meetings? This article provides a clear framework for running efficient and effective executive meetings. It covers the ideal meeting length, frequency, and participants, and offers a detailed agenda focused on goal review and actionable outcomes.

July 12, 2024

7 Imaginary Rules Holding You Back as a Leader

Are you a leader tired of self-sabotage? This article identifies seven common misconceptions about leadership that may be holding you back. It provides practical tips for becoming a more effective leader, including prioritizing tasks, communicating clearly, and taking calculated risks

Leadership, Management | June 28, 2024

The Annual Performance Review Is Dead – Do This Instead

Ditch the annual performance review! This article explores a continuous performance management system that favors ongoing coaching and feedback. It provides a step-by-step guide to implementing this system, including setting clear goals, leveraging 1-on-1 meetings, conducting quarterly check-ins, and fostering personal growth.

5 steps to $100M in revenue

Founders, Ops | June 7, 2024

5 Steps to Scale to $100M & Beyond

Whether you're just starting out, or you're a seasoned CEO, this masterclass will give you the framework you need to break free from the operational grind and elevate yourself as a true leader. 

Thank you for subscribing!

I'd love to learn more about you to better customize the tips I send, ensuring they are as relevant and helpful as possible.

Skip

 Arrow

Sign up free below! 

Every week I tackle management, operations & startup topics that are helping 20,000+ people become better leaders.

No thanks  Arrow