Miles Goldstein: Let’s Build Something

Welcome! This is the first in our series of Escalations: sharing stories of some amazing careers that started in Customer Support. While many of these will be compiled into a book, I will also be regularly sharing stories here, too. If you like this content, please consider subscribing or sharing. 

The Starting Point

Walking into a computer room on April 1, 1980, simply looking for a way to earn a paycheck, Miles Goldstein stepped into what would become a decades-long career in technical support and operations. As he puts it:

He began by soldering cables and installing phone lines—tasks that eased him into the daily reality of technology. Over the next four years, he grew into an expert on the prime operating system (Primos), then made the leap to a frontline support position for Prime Computer in Southern California. That’s when he realized tech support was no longer just a day job—it was a genuine career choice.

A pivotal moment in Miles’s youth shaped his leadership style even before he had a formal role. As a shy high-schooler entering college, he made a choice to, as people were walking past his dorm lounge, invite them in to hang out with him instead of going wherever they were on their way to. Folks took him up on his offer, and soon he was hosting full-blown parties—something that past-Miles would never have imagined. This slight spontaneous shift of “putting himself out there” changed his self-image and laid the foundation for the confidence he would need in his support career.

The Growth Path

Miles describes himself as a “support lifer,” although he’s tried stepping away more than once. He’s held roles in tech operations, implementation, and release engineering. Yet every time, support called him back:

Central to that calling is solving puzzles, both technical and interpersonal. He loves seeing immediate, concrete outcomes for customers, rather than working on a single project for a year only to see it scrapped, as sometimes happens in the engineering field.

Still, he acknowledges that not everyone has to stay in support forever. For those who do want to transition into product, sales, or marketing, Miles recommends leveraging the unique customer viewpoint that support professionals possess:

In his view, the best transitions occur when you can demonstrate tangible value to your new team. That might mean sitting in on product planning meetings and explaining how a small fix could save hours of frontline work or showing marketing why specific support interactions illuminate a key competitive differentiator.

Implementing This in Your Career

• Map Your Skills: List out the customer-facing insights and problem-solving skills you already have. Whenever you consider a new role or lateral move, show how your support experience directly addresses that team’s challenges.

• Partner Up: Offer to be the “support representative” in product or engineering meetings. Use your firsthand knowledge of customer pain points to propose quick wins. This builds trust and shows you can speak the new team’s language.

• Set Clear Goals: If you want to transition, let your manager know. Ask for small projects that stretch your skill set—Miles calls these “slight push” projects—to help you grow toward your target role.

Breaking Through: Lessons & Key Decisions

1. Solve the Real Problem, Not Just the Question

Miles credits one lesson, learned early in his career, for shaping much of his approach to customers: you need to actually solve the problem, not just give them an answer.:

By probing deeper, you avoid superficial fixes and gain a real understanding of the customer’s underlying need. This approach also transfers seamlessly to managing teams: instead of simply answering questions from your direct reports, you help solve the root problems that hold them back.

How You Can Apply It:

• Use Clarifying Questions: Before jumping into a technical fix, spend an extra minute asking, “What does success look like for you?” or “What would solve this completely?”

• Look for Patterns: If you notice the same question appearing often, the real problem might be documentation gaps or a product flaw. Flag these patterns and suggest changes that fix the cause, not just the symptoms.

2. Embrace Continuous Learning & Toastmasters

When Miles first became a manager, he joined Toastmasters, a public speaking training program, to conquer the fear of public speaking. He also took advantage of company-sponsored management development programs that taught him how to coach others and handle conflict constructively.

How You Can Apply It:

• Seek Formal Training: If your company doesn’t offer management programs, look for external courses (like Toastmasters or online leadership workshops).

• Adopt a Beginner’s Mindset: Technology and customer expectations evolve quickly. Even seasoned pros can benefit from re-examining “basic” skills in a new context (e.g., how to manage remote teams or create data-driven roadmaps).

3. Self-Advocacy & “Baring Your Teeth”

Miles learned an important lesson about self-advocacy from a boss who advised him to be more assertive. At first, he hesitated but then realized it was part of a broader skill: pushing for what your team needs so they can serve customers effectively.

While not everything needs to be so aggressive, there is value in being willing to stand up for yourself, your team and your customers.

How You Can Apply It:

• Set Boundaries & Standards: If you find yourself constantly asking other teams for help, shift to a partnership mindset. Show them how solving your request creates value for everyone.

• Practice Diplomatic Assertiveness: Being direct doesn’t mean being confrontational. Come prepared with data that illustrates the mutual benefits—whether it’s improved customer satisfaction or reduced backlog.

4. Building Strong Cross-Functional Relationships

One of Miles’s favorite real-life examples is persuading engineering to add a missing date filter to a reporting tool. Doing so freed support staff from repetitive manual reporting, ultimately saving both teams time: “I showed them we’d free up a lot of frontline capacity, which reduced the burden on engineering in the long run. It was a clear win-win.”

Not everything is a favor—most of the things that we ask for in support have whole-company benefit.

How You Can Apply It:

• Frame Issues as Opportunities: Present problems in a way that highlights ROI for other teams. For instance, “If we fix X, we’ll save Y hours, which can be reinvested in a new product feature.”

• Prioritize Relationship-Building: Have regular check-ins with adjacent teams—CS, product, engineering—to stay informed on what they need and how support can help.

5. Cultivating a Team Mindset

Miles often sees how one or two star individuals get all the opportunities, while quieter contributors go unnoticed. He makes a point to assign “slight push” projects to those who are less vocal but equally capable:

How You Can Apply It:

• Request a Project or Initiative: If you’re that quieter contributor, volunteer for a small project that showcases your strengths.

• Give Others the Spotlight: If you’re already a lead or manager, rotate special assignments among your team. Make it clear that initiative is welcomed and rewarded.

Actionable Takeaways

1. Solve the Underlying Problem

   • Use clarifying questions to identify real needs.

   • Document recurring issues to drive product or process changes.

2. Continuously Upskill

   • Seek out classes, webinars, or professional groups where you can build new skills or refresh old ones.

   • Challenge yourself to learn something outside of your typical area—like Miles did when managing tech ops.

3. Practice Self-Advocacy

   • Learn to articulate the business value of your requests.

   • Don’t wait for permission to share your opinions—“have an opinion, speak it with confidence, then sit down and listen.”

4. Build Partnerships, Not Hierarchies

   • Treat engineering, product, or marketing as collaborators. Show how meeting your need will also serve their goals.

   • In cross-team meetings, volunteer to represent the support viewpoint. Offer data and stories that demonstrate the impact on customers.

5. Give—and Seek—Stretch Assignments

   • If you’re a manager, look for “slight push” projects that let quieter team members shine.

   • If you’re an individual contributor, ask for responsibilities that build your leadership or subject-matter expertise.

Where They Are Now

Today, Miles continues to write monthly articles and consult on support leadership. Whether running a small specialized team or a global 24/7 organization, his enthusiasm is fueled by a desire to “build something”—and it doesn’t stop at the office. He brings the same mindset to constructing theater sets for a local children’s program.

“I like to build teams, build processes, see how it all comes together. …Taking a concept, turning it into reality, that’s what attracts me.”

He offers one last reminder for anyone pursuing a similar path in support:

From shy college freshman to serial builder of support organizations, Miles’s career proves that the right combination of curiosity, assertiveness, and empathy can turn what starts as “just a job” into a lifelong vocation. Whether you stay in support or eventually move on, the lessons of solving real problems, partnering with others, and continuously learning will serve you well at every stage of your career.

Do you have a story to tell or insights to share? Consider having a conversation with me so I can share something like this about you!