Imagine developing a set of skills that enables you to get a management job, only to find you have to throw away the entire toolkit that made you successful. This is the jarring reality for many new managers, a career change that is less of a step up and more of a step over into a completely different profession. This week in episode 334, John White flies solo to share a candid teardown of his first two and a half years as a first-time manager. He unpacks the great “unspoken skill swap” required to transition from a top individual contributor to an effective leader. Drawing from his own journey and advice from past guests, John offers a realistic preview of a manager’s daily reality, covering the jarring shifts in responsibility from doing the work to setting the context, from having the answers to finding the resources, and from individual achievement to enabling the success of others.

Original Recording Date: 06-29-2025

Imagine the skills that you had to develop in order to stand out as an individual contributor.

Imagine that the managerial job that you get as a result uses almost none of those skills in your day to day

Join John on a reflective journey on the realities of becoming a first-time manager.

The first jarring skill swap is moving from being the best individual doer to someone who communicates strategy and ensures operational smoothness for the team.

John recounts his initial instinct as a new manager to immediately re-engineer his team’s reporting process.

He recognized this as the wrong move, an attempt to act as the head practitioner rather than the manager.

He advises new managers to adopt an “Imitation before Variation before Innovation” framework.

Your first job is not to innovate but to create clarity and stability. You must first crawl by understanding why things are done the current way, then walk by making small tweaks, and only run with a major overhaul once you have a deep understanding of the context and have built trust.

As a manager, your value no longer comes from having all the technical answers yourself, but from ensuring your team has the tools and connections they need.

John shares his experience of becoming a manager at a new company for a product he had never been a sales engineer for.

He knew he would never be the top technical expert on the team.

His instinct was to dive deep into the technology and certifications, but he realized his true job was to unblock his team.

The key shift in mindset is asking “Who knows the answer?” instead of “What’s the answer?”

A new manager must learn to tap into the team’s collective knowledge, relying on tenured members and peers to draw organizational maps that reveal where to go for help and how to solve problems.

A skill that is often celebrated in an individual contributor—fearlessly asking challenging questions to find the best idea—can be detrimental for a manager.

The new job requires managing up and sideways to protect the team and secure resources, which involves navigating a complex political ecosystem.

John learned this lesson the hard way, realizing that asking pointed questions in a leadership meeting could be seen as confrontational or critical rather than constructive.

The new skill is understanding influence, timing, and venue. You must learn to have tough conversations privately, build consensus before a big meeting, and strategically navigate the chain of command to get your questions answered effectively without undercutting others.

The metric for a “good day” changes entirely. As an IC, satisfaction comes from completing tasks and making tangible progress. * As a manager, you can end a day full of back-to-back meetings feeling like you accomplished nothing.

The new job is to measure your success through the output and growth of others.

John emphasizes that your most powerful tool is the one-on-one meeting, and the most important question you can ask is, “How can I help?”

“A good day is when you leave your team members more clear, capable, and confident than you found them.”

Your job shifts from being a do-er to an un-blocker, and your long-term success is the sum of your team’s successes.

Transitioning to management often means moving from occasionally helping with interviews to owning the entire, complex hiring process.

This responsibility extends from crafting the job description to ensuring the new hire is successfully onboarded.

A manager must coordinate with recruiters, budget approvers, and a cross-functional interview panel, all while ensuring consistency and fairness for every candidate.

This involves evaluating not just skills, but also understanding a candidate’s weaknesses and gaps, what training would be required, and how they compare to the team’s needs, turning it into a highly complex project management challenge.

So, how do you develop these new managerial skills, perhaps even before you have the title? John provides actionable advice for aspiring managers.

Start by observing your current manager like an anthropologist—decode the “why” behind their actions. *

Become an interviewer by taking other managers out for coffee to ask about the unseen parts of their job, such as handling performance conversations or advocating for budget.

Finally, find low-stakes opportunities to practice influence without authority by volunteering to lead small cross-functional projects or mentoring junior employees.

Call to action: perform a “micro experiment” in your next team meeting by holding back an answer and instead guiding the team to their own solution with questions. This feeling of guiding, not doing, is the core sensation of being a manager.

The hosts of Nerd Journey are John White and Nick Korte.

E-mail: [email protected]

DM us on Twitter/X @NerdJourney

Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman

Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_

Leave a Comment on Your Favorite Episode on YoutTube

If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.