Strategy Archives - Keith Upkes Coaching

Accountability Coaching Execution Strategy

January 13, 2026

The Two Things Every CEO Needs to See Clearly

A great coach is both a mirror and a window.The mirror shows you where you are today: your numbers, your decisions, and the reality of how the business is actually…

Keith Upkes

Accountability Coaching Execution People Strategy Team

January 9, 2026

Why The Right Annual Planning Leaves Your Energized, Not Exhausted

✨ Annual Planning = DONE ✨Yesterday, Keith Upkes Coaching wrapped up our Annual Planning session, and what a day it was.10 hours of deep conversations.Real progress.Fresh ideas.New perspectives.And an even…

Keith Upkes

Coaching Execution Strategy Team

January 7, 2026

Doing Everything Right, Yet Growth Is Flat? The Missing 3-Year Strategy Most Teams Lack

📉 Ever feel like you’re doing everything right… But growth is still flat?I see this a lot with strong leadership teams.They’re smart. They’re working hard.But the strategy beyond “this year”…

Keith Upkes

Coaching Customers People Strategy Team

January 3, 2026

Happy New Year!

Happy New Year! 🎉As we step into 2026, we’re reflecting on the businesses we’ve had the privilege to support, the leaders who trusted us with their growth, and the progress…

Keith Upkes

Accountability Coaching Execution Strategy Team

December 16, 2025

3 Leadership Mistakes That Stop Your Company From Scaling

Most leaders want to scale fast…but end up stuck.In our coaching practice, we see the same three mistakes quietly holding growth hostage:1️⃣ The wrong people in the wrong seats2️⃣ No…

Keith Upkes

Accountability Coaching Execution People Strategy Team

December 11, 2025

Set Your Business Up for a Strong 2026

Set Your Business Up for a Strong 2026As we roll into the holiday season, it’s easy for teams to get distracted and ease off the gas. But the truth is:…

Keith Upkes

Cash CFO Coaching Execution Strategy

November 24, 2025

What is Cowboy Math?

Cowboy Math was born the moment I realized perfect financial accuracy was slowing my company down.As a CFO, accuracy was the job. Large financial wins and losses often hinged on…

Keith Upkes

Coaching Execution People Strategy Team

November 21, 2025

Work Doesn’t Feel Like Work When It’s Fun

Work doesn’t feel like work when it’s fun.Yesterday was video production day at Keith Upkes Coaching, and what could have been a high-stress experience turned into one of the most…

Keith Upkes

Accountability Coaching Strategy

November 19, 2025

Seasoned Veterans Still Learn

Seasoned Veterans Still Learn...Has your business plateaued? Has your team stopped growing? If so… maybe it’s time to look in the mirror.Earlier this month, I spent two days in Scottsdale…

Keith Upkes

Accountability Coaching Customers Execution People Strategy Team

November 14, 2025

How committed are you to your goals?

How committed are you to your goals? In his new book The Science of Scaling, Dr. Benjamin Hardy says, “If you’re not scaling aggressively, you are likely dying slowly.” That…

Keith Upkes