Every year, I do something that feels counterintuitive: I act as if I was just hired into my current role.

I do everything a new hire would do. I go on a listening tour with my stakeholders. I rebuild relationships I already have. I look at our processes, tools, and priorities with fresh eyes. I ask questions I have not asked in months, questions I stopped asking because I thought I already knew the answers.

The reason is simple. The longer you stay in a role, the more assumptions accumulate.

You stop seeing things that a newcomer would notice immediately. You stop hearing feedback that people gave up sharing because nothing changed the first three times.

Your relationships with stakeholders shift from active partnerships into passive routines where you meet regularly but rarely challenge each other.

A new hire does not have these problems. A new hire has no assumptions. Every observation is fresh. Every relationship is being built for the first time, which means both sides are investing energy into making it work.

The Listening Tour

When I started as CTO at The New York Times, I spent my first weeks in listening mode. I met with editors, reporters, designers, business leads, and engineers. I asked what was working, what was broken, and what they wished someone would fix. The same when I joined The Wall Street Journal. The same at Hearst.

Every time, the listening tour was the most valuable thing I did. Not because the answers were surprising (sometimes they were), but because the act of asking rebuilt trust. People felt heard. They shared things they had stopped mentioning to my predecessor because nothing had changed.

The insight is that you should do this even when you are not new. Especially when you are not new. I wrote a 90 day plan for a CTO starting a new job years ago. The annual restart is the same playbook applied to a job you already have.

What the Annual Restart Looks Like

Here is what I do, usually in January or whenever I feel the assumptions starting to calcify:

Stakeholder listening tour. I schedule 30-minute conversations with every key stakeholder, same as I would in my first month. I ask three questions: What is working well in how our teams collaborate? What is not working? What do you wish we were doing that we are not? Then I listen. I do not defend or explain. I take notes and follow up within a week on anything actionable.

Relationship audit. I look at my key relationships and ask honestly: which ones have gone stale? Which ones am I maintaining out of routine rather than genuine engagement? A relationship that was strong two years ago may have drifted without either person noticing. The annual restart is when I notice and reinvest.

Fresh-eyes review of processes. I walk through our team’s core workflows as if I were seeing them for the first time. Every process that exists was created to solve a problem. Sometimes the problem no longer exists, but the process persists. A new hire would ask “why do we do it this way?” and sometimes the honest answer is “because we always have.”

Priority reset. I revisit our goals and roadmap and ask whether they still reflect what actually matters. Priorities set six months ago may have been overtaken by changes in the business, the market, or the team. A new hire would not inherit stale priorities. Neither should you.

Check your blind spots. Every tenured leader develops blind spots. Topics you have strong opinions about and stopped questioning. People you trust so completely that you stopped verifying. Assumptions about what the team can and cannot do based on past experience rather than current capability. The restart is when you deliberately look for these.

Why This Works

The annual restart fights three specific problems:

Assumption drift. Small assumptions accumulate over months. Each one is individually reasonable. Collectively, they can lead you far from reality.

Relationship decay. Professional relationships require active maintenance. The ones that seem fine because nobody is complaining may actually be the ones where people have simply stopped engaging. I wrote about how confidence in leaders creates a reinforcing loop, both positive and negative. The annual restart is how you keep that loop positive.

Complacency of expertise. The more experienced you are, the more confident you feel. That confidence can become a liability when it stops you from asking basic questions or considering alternatives.

I have held CTO and CPTO roles at several companies now. The pattern is consistent: the listening tour at the start of each role is always the highest-value activity. I wrote about what makes a technology leader effective and a lot of it comes down to relationships and trust. The annual restart brings that same value without requiring an actual job change.

You do not need a new job to see your current one clearly. You just need to look at it the way you did on day one.