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The Pragmatic Engineer published an interview with Imprint CTO Will Larson about how expectations for engineering managers have changed since the 2010s. Larson argues that managers may need to return to hands-on technical work as AI reshapes engineering and technical decisions move closer to leadership; the interview presents these as his views, not settled outcomes.
The Pragmatic Engineer has published an interview with Will Larson, CTO of Imprint, about how engineering management has changed since the 2010s and how artificial intelligence may alter leadership roles. Larson argues that some middle managers should return to line management and rebuild hands-on technical skills, a view that matters to engineers weighing management careers as companies reconsider how software teams work.
Larson, who has held engineering leadership roles at Carta, Calm, Stripe and Uber, discusses a shift from management practices formed during the long period of low interest rates and abundant technology investment to a more demanding environment. The interview describes changing expectations for both managers and engineers, though it does not provide industry-wide data measuring how widespread those changes are.
One central argument is that middle management may be a less secure career path than it appeared in earlier years. Larson recommends that some managers return to line management and reskill, including by engaging more directly with technical work. The discussion also considers whether some leaders might choose retirement rather than adapt; it does not suggest that this is the right choice for every manager.
The episode connects those career questions to AI and engineering decision-making. Its description says AI is changing engineering roles and bringing technical decisions back toward leadership. It also notes that Larson is hiring engineering managers at Imprint to use agents in rethinking software teams. The source does not specify the roles, hiring timetable or results of that work.
Management Careers Face New Pressures
The interview speaks to a practical concern for engineering professionals: management may no longer be a one-way move away from technical work. If organizations expect managers to understand tools, systems and AI-enabled workflows closely, some leaders may need to refresh skills they have not used regularly. That could affect career planning, promotion expectations and how companies support experienced managers.
Larson’s position is a perspective from an experienced technology executive, not a measured forecast that middle-management jobs will disappear. Still, the question has consequences beyond individual careers. Companies deciding how to organize teams around AI tools must determine which responsibilities belong with managers, senior engineers and executives—and how accountability for technical choices should be shared.
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Lessons From Earlier Tech Roles
The interview uses Larson’s past experience to explain how management norms and incentives can shape engineering organizations. At Yahoo, where he worked from 2008 to 2010, he recalled having only two one-on-one meetings with his manager: one about another employee’s performance and another after he gave notice. The anecdote contrasts with the more regular manager-employee contact common in many workplaces today, though it is one person’s account rather than a survey of the period.
Larson also recounts working at Digg during its v4 rewrite in 2010. The report says the launch brought performance and reliability problems and alienated users. Larson attributed technical problems to Python memory leaks introduced by developers unfamiliar with the language. He does not believe the rewrite alone caused Digg’s decline: he said the company was already losing ground to Facebook and Reddit, while a Google algorithm change had cut traffic by 60% to 70%, according to the account.
These stories provide background for the interview’s broader point: management choices operate within business constraints, and changing a system or process cannot by itself reverse every underlying problem. The episode also revisits Larson’s route to becoming a CTO and his view that career ladders remain useful.
“I only have suffering to offer, but this suffering is what’s going to make the business succeed.”
— Will Larson, as quoted in The Pragmatic Engineer interview
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How Broad Is the Shift?
The source is an interview and does not establish how many companies are changing management structures, whether middle-management roles are shrinking overall, or how quickly AI is altering day-to-day engineering work. Larson’s recommendation reflects his experience and judgment; the material does not present comparative employment data or a forecast of job losses.
Details about Imprint’s agent-focused team work are also limited. The source says Larson is hiring for several engineering-manager roles, but gives no job descriptions, start dates or evidence about the results. The Digg traffic loss and technical diagnosis are reported as part of Larson’s account, and the source does not independently document them in this material.
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Testing New Team Models
The immediate next step is for readers and employers to watch how organizations translate these ideas into practice: whether managers take on more hands-on technical responsibilities, how teams use AI agents, and which decisions remain with engineering leadership. No industry-wide milestone or timeline is identified in the interview.
Larson’s work at Imprint offers one place to follow the discussion, as the company hires engineering managers to rethink team practices with agents. The source does not report a launch date or outcomes. Further reporting would be needed to determine whether such approaches change staffing, productivity or management career paths beyond individual companies.
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Key Questions
What is the news about Will Larson?
The Pragmatic Engineer published an interview with Larson on changing engineering-management expectations, career paths and AI’s influence on technical leadership.
What does Larson recommend to middle managers?
He recommends that some managers return to line management and rebuild hands-on technical skills. The interview presents this as his advice, not a rule for every manager.
Does the interview say AI will eliminate engineering managers?
No. It discusses how AI may change engineering roles and bring technical decisions closer to leadership, but does not claim that AI will eliminate management jobs or quantify its employment effects.
What does Larson say about Digg’s 2010 rewrite?
He recounts that the v4 launch had performance and reliability problems and alienated users. He also says the rewrite was not the sole cause of Digg’s decline, which was already facing competition and a substantial traffic loss.
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