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

Swipe my growth resume template: https://docs.google.com/document/d/1FR6Bbdwg80Hu-6TSz-8aGe4GgIBDukUzYXTdbr4pd0I/edit?tab=t.0

New role? Get my 90-day Growth Leader onboarding plan here: https://deliveringvalue.co/90

In this solo Field Notes episode, I break down a simple but powerful career reframing I’ve been sharing with clients who feel stuck, burned out, or misaligned in their current roles: the idea of treating your next job as a one-year deal.

Borrowing from how professional athletes think about their careers, I go over why looking for a great one-year fit instead of a perfect long-term home can lead to better decisions, less pressure, and more momentum, especially once you’re well into your career.

In this episode, you’ll hear:

• Why long-term “forever job” thinking often backfires in fast-changing companies

• How the one-year deal mindset helps you maximize fit, impact, and optionality

• When this approach makes sense and when it’s better to stay put and build depth

Things to listen for:

(00:00) Intro to the “One Year Deal” concept

(00:29) Example and parallels in an athletic career

(01:33) The One Year Deal in a professional context

(02:39) Practical application of the One Year Deal

(04:30) How to take this further

Resources:

Connect with me:

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

Substack: https://media.deliveringvalue.co

Apply for coaching: https://deliveringvalue.co/coaching

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

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

In this episode, Jay Desai, Growth Lead at Navattic, shares his approach to stepping into an early-stage growth role with clarity and purpose. He reflects on how his first 90 days were spent gaining product knowledge, ramping up without burnout, and aligning cross-functional teams around a unified vision of growth.

Jay talks about the ambiguity of growth roles and how the early days are about building relationships, learning, and strategic prioritization. He explains how he uses frameworks like “task-relevant maturity” and sprint systems to manage expectations while delivering early wins.

Now leading growth at Navattic, Jay discusses his role in designing operating systems, building trust, reducing capacity confusion, and creating a repeatable model for experimentation to drive long-term success.

In this conversation, you’ll learn:

• How to architect your first 90 days for impact across product learning, trust-building, and operating system design
• A practical framework for capacity planning, effort scoring, and balancing quick wins with long-term bets
• The most common misalignments growth leaders face and how to proactively prevent them

Things to listen for:

(00:00) Intro

(01:52) Jay’s role and scope at Navattic

(03:20) How Navattic defines “growth”

(06:03) What feels new vs. familiar in the role

(08:37) Why the first 90 days set the tone

(17:46) Learning the product and meeting the team

(32:42) Capacity limits and prioritizing work

(34:16) Tools Jay uses to run growth

(38:22) Applying engineering workflows to marketing

(49:11) Quick wins vs. long-term initiatives

(54:04) When to share the first strategy draft

(57:09) Pitfalls that derail growth roles

A huge thanks to this episode’s sponsor:

Navattic: Interactive Product Demo Software - https://navattic.com/value

Resources:

Connect with Jay:

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

Navattic: https://navattic.com/value

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