“My annual review exposed my biggest blind spot.” (Dan Wolchonok)

Download my customizable 90 Day Plan here: https://deliveringvalue.co/90

High performers don’t get stuck because they lack talent. They get stuck because the habits that made them successful as individual contributors quietly stop working once they’re leading others. In this episode of Growing Forward, I sit down with Dan Wolchonok, founder of Work Coach, to unpack what happens when a strong operator runs into the “player-coach” trap. Dan reflects on a painful 360 review from his time at Reforge that forced him to confront how jumping in to do the work himself was unintentionally holding his team back.

We talk through a defining moment in Dan’s journey: presenting a company-wide growth model to the executive team after weeks of preparation, only to be met with silence. No questions. No debate. Just a hollow reaction that left him gutted. Dan shares what that experience taught him about leadership at higher levels, including the importance of bringing a clear point of view, strong next steps, and enough conviction to spark real discussion and action.

Dan also walks us through how he responded to tough feedback without spiraling, using executive coaching, systems, and intentional changes to rebuild trust and momentum. We explore why remote work and flatter orgs make career guidance harder to access, and how Work Coach was born from the desire to give people a reliable sounding board as they navigate growth, feedback, and leadership transitions.

In this conversation, you’ll learn:

• How the “best doer” instincts can create a manager death spiral, and how to break it
• Why a presentation can flop even if the work is strong, and how to lead with a clear take + next steps
• How to respond to brutal feedback with maturity, momentum, and “next play” energy

Things to listen for:

(00:00) Intro

(02:20) Dan’s early building roots in tech

(05:12) The messy side of success

(07:04) Thank you to our sponsor, Hire Overseas

(08:45) Why talking about failure matters

(09:57) What setbacks can reveal

(10:45) Trying to scale with the company

(15:15) Pitching a growth model to execs

(17:46) When the feedback hits hard

(23:11) Resetting after a missed swing

(25:12) Turning feedback into momentum

(26:28) Shifting from doer to leader

(27:19) Reading painful 360 feedback aloud

(40:14) Why Dan built Work Coach

A huge thanks to this episode’s sponsor:

Hire Overseas: Exceptional Talent for Less - https://www.hireoverseas.com

Resources:

Connect with Dan:

LinkedIn: https://www.linkedin.com/in/danielwolchonok/

X: https://x.com/danwolch

Learn more about Work Coach: https://work.coach/

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching

Join Growth OS: https://deliveringvalue.co/growth-operating-system