Helping a Dev Manager Focus on ACTION—Not Fear

1:15:32

You don’t have to keep running on the same treadmill just because it’s familiar.

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What Is Tech Career Coaching Really Like? A Live Coaching Session

The Realities of Tech Career Coaching

Ever watched one of my YouTube videos and wondered: What’s this tech career coaching thing Jayme keeps talking about? Is it some kind of fluff, or is it actually helpful? Well, today, you’re going to get a behind-the-scenes look at what I do. I recorded a real coaching session with Ben, a client I’ve been working with for over a year.

Ben’s had a great career—he’s been an engineering manager, an agile coach, and a technical individual contributor. But now, he’s at a crossroads, considering stepping into working for himself. This session dives into his fears, uncertainties, and how he can take control of his career trajectory. As you read, try putting yourself in Ben’s shoes. You might just walk away with insights into your own career path.

A Comfortable Job, But an Uncomfortable Future

Ben landed a great job back in October, one that’s provided him with stability, good colleagues, and work he enjoys. In many ways, it’s an ideal position—he’s leading a team while staying hands-on with engineering. Yet, despite all of this, he still feels a looming fear.

Even in a strong company with a solid culture, he realizes that his financial future and career direction still aren’t truly in his hands. He’s still managing perceptions, still playing the corporate game, and still answering to someone else. This leads to a deep feeling of instability. The economy, the rise of AI, and market uncertainty only add to this fear. He’s wondering: Is this sustainable? Will I ever be able to retire?

The Fear Factor: Is It Justified?

Fear is a major driver for many people in the tech industry right now. The fear of layoffs. The fear of obsolescence. The fear of not keeping up. Ben is no exception—he worries about the rapid pace of change in the industry, particularly around AI. He’s found himself consuming a lot of industry news, LinkedIn posts, and YouTube videos, all warning about the need to constantly level up.

But here’s the reality: you can’t win the infinite game of keeping up with everything. If you put your peace in the hands of industry news and influencers, you’re bound to feel anxious and overwhelmed. Instead of chasing every new trend, the better question to ask is: What kind of work energizes me?

Choosing Work That Fuels You

When I lost my last corporate job and had to start over, I had two choices:

1. Get another high-paying job and grind away until retirement.
2. Build something that aligns with my passions and allows me to work in a way that gives me energy instead of draining it.

Ben is in a similar spot. He enjoys leadership and team-building more than individual coding, but he’s spent years sharpening his technical skills out of necessity. Letting go of that identity is tough, but it may be the key to moving forward in a way that actually excites him.

The Path to Leadership Coaching

Through our conversation, it became clear that Ben wants to help mid-career engineers step into leadership roles. Many technical professionals want to move into management, but they lack the skills, experience, and confidence to do so.

Companies often look for leadership traits like communication, presence, and polish—qualities that aren’t always natural for introverted engineers. Ben understands this firsthand. He knows what it takes to transition from being an individual contributor, to leading teams. The challenge is figuring out how to take this knowledge and turn it into a business.

The First Steps to Coaching Others

One of Ben’s concerns is whether people will be willing to invest in themselves. He doesn’t want to attract people who just want to vent about their frustrations—he wants to work with individuals who are truly ready to grow.

The best way to validate this? Offer free coaching sessions to a few people and see if the demand is there. I suggested he find engineers who are looking to step into leadership and work with them for a set number of sessions. In return, he can ask for testimonials or case studies. This allows him to refine his approach without overcommitting to a rigid program before he knows what works.

Building Without Overbuilding

Ben wondered if he needed a structured program before starting. My advice? Don’t over-engineer it.

A coaching program isn’t a piece of software. You don’t need to design every module in advance. Instead, start by identifying the key themes you want to focus on—building confidence, owning projects, learning to communicate as a leader—and then tailor the approach based on what people actually need.

The Fear of Letting Go

One of Ben’s biggest blockers is the idea of “wasting” all the work he put into sharpening his engineering skills. He spent years retooling himself to stay employable, so the thought of stepping away from hands-on coding again is scary.

But just because you can do something doesn’t mean you should.

If leadership excites him more than technical problem-solving, that’s where he should put his energy. The reality is, he’ll never be fully in control of his career if he stays in the cycle of constantly proving his technical worth to employers.

Selling the Right Service to the Right People

Ben originally thought about offering his services to companies, but the reality is, most companies don’t want better leadership—they want things done cheaper. Instead, individuals who want to grow their careers and earn more will likely be the better audience.

However, not all engineers will be the right fit. People drowning in burnout may not be in the right mindset to invest in coaching. Instead, Ben should look for individuals who are stable but stuck. Those who want more responsibility but don’t know how to position themselves for it.

Long-Term Vision: Beyond One-on-One Coaching

Ben’s ultimate goal isn’t just one-on-one coaching. He wants to build something scalable—possibly a combination of an online course and a community-driven coaching program. This makes sense. While courses alone often don’t work, blending them with real interaction and accountability could be incredibly valuable.

That’s where starting with individual coaching makes sense. By working closely with a few people first, he’ll learn exactly what problems they face and what solutions actually help. That experience will guide him in creating something bigger later on.

The Next Steps

Ben left our conversation with a few clear action steps:

• Find a handful of mid-career engineers who want to grow into leadership and offer them coaching in exchange for testimonials.
• Focus on working with people before trying to build a full-fledged program.
• Start thinking about the long-term vision, but don’t overcomplicate it before knowing what truly works.

Conclusion

Tech career coaching isn’t about magic formulas or generic advice. It’s about real conversations, deep insights, and actionable strategies. Whether you’re considering coaching yourself or just figuring out your next career move, the key takeaway is this:

You don’t have to keep running on the same treadmill just because it’s familiar.

If you’re feeling stuck, ask yourself: What kind of work actually energizes me? The answer to that question might just be the key to your next big move.

About the THRIVING TECHNOLOGIST show

On YouTube and all major podcast networks, Jayme shares teamwork and leadership strategies, guidelines for healthy company culture, and stories about real projects so you can have a sustainable career in the software industry.

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YOUR HOST

Jayme Edwards

A family man and veteran of nearly 40 software projects, Jayme experienced many wins and losses over his career as an architect and consultant.

Now he's coaching software developers, managers, and business owners to overcome challenges in the IT industry - so they keep growing.