How Microsoft gives its top engineers the judgment of a senior leader, and proves it.

A leadership gap hiding in plain sight

Microsoft's most senior technical people are brilliant at what they do. But the step from expert engineer to strategic leader isn't a technical one, and it doesn't happen on its own. Microsoft wanted a pipeline of future Principals: engineers who could think and decide the way their manager's manager does, without pulling them off the technical track and into people management.

The gap was specific. As Jim Chismar, who runs the program, puts it, individual contributors "don't typically understand the decision-making paths they need to take," and often present ideas "that aren't realistic from a business perspective." Microsoft wanted to close that gap, and to do it at scale.

A program that had to run everywhere at once

The first constraint was logistics. The 60 people Microsoft wanted to develop were spread across 14 countries. It couldn't bring them together for a three-day seminar, and the other options on the table didn't translate to a virtual program. Capsim's did.

The result was Journey to Principal, a virtual, facilitator-led program built on a global business simulation. Two cohorts ran it over three months, meeting every two weeks across seven rounds, with an expert debrief after each session. Teams ran a global company and made the cross-functional calls a senior leader makes.

To make it land, Capsim's facilitator connected the simulation straight to Microsoft's own strategy: he walked the engineers through the decisions Microsoft's leaders had made in recent years, drawn from the company's earnings reports, and showed them they were making the same kinds of calls in the sim.

It's all about teamwork and competition. They have to work as a team, talk through things, make decisions, and live with their decisions.Jim Chismar, Program Lead, Microsoft

Thinking horizontally, not just deeply

For people used to going deep in one domain, the shift was to think horizontally: to see how one decision ripples across R&D, marketing, operations, and finance, and to weigh short-term wishes against long-term strategy. One participant described it as a ton of dominoes to line up before anything moves. And because Microsoft is customer-obsessed, the program kept pulling them back to market and customer needs, the lens a senior leader has to lead with.

Measuring the shift, even when it isn't technical

What makes the program unusual is that Microsoft measures the growth instead of hoping it happened. Every participant takes a leadership assessment at the start and again at the end, a before-and-after read on how their leadership judgment actually changed over the year. The score comes with a map: where each person grew and where to keep pushing, data Microsoft carries into its own development and talent conversations.

That matters most for exactly the skills that are hardest to prove. Technical growth is easy to see. Leadership growth usually isn't. The assessment makes it visible.

The payoff: engineers ready to lead the business

The clearest sign it is working is what these engineers do afterward. They hold more meaningful conversations with their manager's manager, the skip-level discussions where strategy gets set. They come in understanding the problem before they pitch the solution, and they push for ideas that scale. Several participants have since been selected for promotion.

Microsoft treats it as a long-term investment: getting its best technical people out of their silos so better ideas, and better voices, reach the leadership table.