You’re Asking The Wrong Questions When You’re Building That Engineering Team

A few months ago, I was on a call with a Head of Data at a major financial services firm. She walked me through her roadmap. She needed a data cleanup and a new risk model. Her board had also requested a dashboard backlog. 

When she finished, she took a breath and asked the question every engineering or data leader eventually asks: “So … how many engineers do you think we need to make all this happen?”

It’s a totally natural question. And it’s also the wrong question.

It’s the question leaders across hedge funds, fintechs, and data-heavy organizations ask most often. The problem is framing. If you start with the wrong question, you end up with the wrong structure, the wrong resourcing plan, and the wrong team.

Stop Asking: “How Many People Do We Need?”

Start Asking: “What Combination of Expertise Gives Us the Best Outcomes?”

Headcount is the least useful variable when you’re trying to build a high-performing team. Yet it’s the variable leaders worry about the most because it’s tangible, measurable, and easy to justify to finance.

But the companies that consistently outperform don’t think in terms of bodies, they think in terms of capability.

Research is crystal clear on this: a meta-analysis from Oxford shows that top engineers are 5–15x more productive than average contributors. McKinsey has found similar ranges, especially in complex or regulated environments.

You don’t need more people; you need the right people doing the right work in the right structure.

Stop Asking: “Do We Need More Flexibility?”

Start Asking: “Does This Solve Our Actual Budget Reality?”

Staffing vendors love to sell “ultimate flexibility.” Month-to-month or even six-month contracts sound like a dream—if you’re a seed-stage startup pivoting every 8–10 weeks.

But most established companies operate on annual budget cycles, not ever changing runway.. By the first quarter, most leaders already know:

• their biggest initiatives 
• their deadlines 
• their regulatory commitments 
• their hiring limitations 

The real challenge is delivering everything inside a fixed budget envelope. Gartner’s 2024 CIO Survey found that 77% of tech leaders have rising expectations without rising budgets, which means flexibility alone doesn’t solve the problem. Strategic talent composition does.

It’s not about the ability to scale up and down. It’s about whether your team structure makes financial sense across the entire year.

Stop Asking: “Can’t Any Strong Engineer Figure This Out?”

Start Asking: “Who Already Knows This Domain?”

One of the biggest performance multipliers in financial, data, and compliance-driven environments is domain expertise. But it’s also the most overlooked.

People who have worked in your world—regulatory systems, high-frequency pipelines, risk modeling, multi-step approvals—navigate your roadmap differently. They anticipate edge cases instead of discovering them. They avoid the rabbit holes that waste months. They catch the architectural decisions that turn into six-figure rewrites.

Accenture research shows domain-experienced teams shorten timelines by 30–50%, not because they code faster but because they avoid preventable mistakes.

Stop Asking: “Who Can We Afford Full-Time?”

Start Asking: “What Should Be Full-Time vs. Strategic External Talent?”

Many companies still treat staffing as a binary: full-time employees or contractors. But the teams that perform best think in terms of strategic allocation.

Some roles must be internal because they shape your architecture, security posture, or core product logic. Others shouldn’t be full-time hires at all, they’re specialized, niche, or variable in workload.

The smartest organizations build hybrid models where senior external experts support internal teams in highly targeted ways:

• internal talent for core, long-term, deeply integrated work 
• external specialists for niche, high-skill, or variable workloads 

This blends budget efficiency with quality—without forcing you to choose between them.

The Question That Actually Builds a High-Performing Team

When leaders shift from headcount to capability, from flexibility to fit, from generalists to domain experts, their teams get faster, more accurate, and far more cost-effective.

The strength of your engineering team isn’t determined by how many people you can hire. It’s determined by whether you’re asking the right questions when you build it.

If you’d like help strategically building a capable engineering team, let’s chat.