The First 100 Days as CEO: What Separates the Leaders Who Last from the Ones Who Don’t

I’m Glenn Gow, and I ask every new CEO I coach the same question in week one: what’s on fire right now? Nathan Louer, CEO of Magnolia Bakery, took over a company with more than 50 locations and answered it the way an ER doctor would. He triaged. He treated the worst cases first. That is the only 100-day plan that survives contact with a real company.

Quick Answer

New CEOs who succeed in their first 90 days do three things. They rank inherited problems by size of prize instead of trying to fix everything at once. They protect the parts of the company that already work instead of tearing them down to prove they’re in charge. And they make decisions on 80% of the information instead of waiting for certainty that never comes. I’m Glenn Gow, and after interviewing over 150 CEOs on my podcast, I’ve watched the ones who last do this and the ones who don’t do the opposite.

Why the First 90 Days Work Like an Emergency Room

Nathan Louer runs his first 90 days the way an ER doctor runs a shift: triage first, treat the worst cases first, work down the list. “I don’t know what being an ER doctor is like, but I assume you get patients in, you triage, and then you take care of the worst cases first and you go on down the line,” he told me.

Not every CEO inherits the same kind of mess. Jeff Cates, CEO of ContactMonkey, stepped into the role in March 2026 right after the company closed a $55 million Series A round. His triage list looked different from Louer’s. “The technology hadn’t been invested in, certainly like the infrastructure for a long time,” Jeff told me. “We were on like probably one of NetSuite’s first 20 customers from 2012. So that was kind of duct tape and twine.” Jeff’s first 90 days went into rebuilding operating systems most employees never see. Louer’s went into deciding which business units needed him and which didn’t.

Both approaches count as triage. The difference is what they measured as the biggest patient in the room. I ask every CEO I coach to name their size-of-prize list in writing before the end of week two, because a list you can point to holds up better under pressure than a list you’re carrying in your head.

I use a simple filter with clients: score every inherited problem on two axes, dollar impact and time to fix. The problems that score high on both go first. Everything else waits, even if it’s loud.

I also ask what happens if the CEO does nothing on a given problem for 90 days. If the honest answer is nothing bad, that problem waits. If the honest answer is real damage, it jumps to the top no matter how small it looks today.

Two Ways to Start: Set the Agenda or Listen First

New CEOs split hard on this question, and I’ve seen both approaches work. Some leaders believe you must set direction immediately or the organization drifts. Others believe you must listen before you speak or you’ll optimize for the wrong problem.

Travis Hedge, CEO of Vouch, spent his first month running a listening tour across more than 100 employees before making a single structural call. Compare that to a CEO who walks in with a fully built 90-day plan and starts executing on day one. Here’s how the two paths tend to play out for a new CEO:

ApproachWhat It Produces in Month OneRisk If Overdone
Day-One MandateFast clarity, immediate execution, measurable early winsTeam feels steamrolled before trust exists
Listening Tour FirstDeep buy-in, accurate read on real problems, loyaltySlow start, organization reads hesitation as drift

Jeff Helfgott, CEO of Boardroom Salon for Men, splits the difference. He told me new leaders face “the flirting stage before the deal is done,” where everything feels aligned, and then a shift once the work actually starts. His fix is a stated boundary: “for the first 90 days, we’re going to be focused on the run the business stuff.”

I tell CEOs to pick a lane in writing before day one, not during day one. Announcing a listening tour after you’ve already made three changes reads as backpedaling, not humility. Announcing ninety days of run-the-business focus after you’ve already reorganized two departments reads the same way.

The Ego You Have to Kill in Week One

The most common mistake I see new CEOs make has nothing to do with strategy. It’s ego. Steven Monterroso, CEO of ShareVault, came up through sales, where hustle solves most problems. “You can’t outwork bad processes, bad systems,” he told me. “It’s more hours equals more sales, right? But you can’t run a business that way.”

Dan Turner, CEO of Xperigo, took the CEO seat as COVID hit and had no playbook to fall back on. “I took over as the CEO just as COVID was hitting,” he said. “Throwing the toolbox out the window because we’re going to have to reinvent this as we go into this new way of running a business.” Dan also does something most new leaders won’t: he extends trust before anyone earns it. “A lot of people tend to wait for somebody to show that they can be trusted before they will trust those individuals,” he told me. “I’ve taken an opposite approach now, which is I will trust everybody until they give me a reason not to.”

I watch for a related pattern constantly: the new CEO who answers every question in the first meeting because silence feels like weakness. It isn’t. A CEO who says “I don’t know yet, give me two weeks” earns more credibility than one who invents an answer on the spot.

Louer applies the same humility to himself. Being self-aware of his own blind spots, he said, is what makes the difference: “It humanizes you. It allows you to tear down walls so that you can build back stronger quicker.” I ask every new CEO I coach to make that same admission to their team in week one, out loud, before anyone has a chance to ask.

Every Move You Make Is Being Watched

New CEOs underestimate how closely they’re being observed. Colby Durnin, CEO of CREDE, put it bluntly: “You’re on a Zoom call with a team and you raise your left eyebrow and everybody goes crazy because Colby’s upset about that issue.” Ask the right questions about your own behavior before you ask them about the business, because your team is already asking those questions about you.

I tell new CEOs to write down, in one sentence, what they want their calendar, their tone in meetings, and their first three decisions to communicate. Then check that sentence weekly. If your actions don’t match it by week four, your team already noticed before you did.

This cuts both ways. The same magnification that turns a raised eyebrow into a rumor also turns a genuine thank-you into a story that spreads through the whole building by the next morning. Use the spotlight instead of just surviving it.

Respect the Foundation, Don’t Blow It Up

Keith Zubchevich and Devon Macdonald give new CEOs opposite advice about what to do with what they inherit. Keith Zubchevich, CEO of Conviva, calls inheriting a predecessor’s operating model the single biggest mistake a new CEO can make. “They come in and then they inherit someone’s management framework, their operating plan, and they try and continue down that road,” he said, “when in fact it’s like running in someone else’s shoes.”

Devon Macdonald, CEO of Cairns Oneil, argues the opposite. “It is not time to throw everything out,” he told me. “It is not time to blow things up.”

I ask new CEOs one question before they touch anything: was this company underperforming or outperforming the year before you arrived? The answer tells you more about which side of this table you’re standing on than any org chart will.

Both are right, depending on what you inherit. Here’s the split I coach CEOs through:

StrategyWhat It Produces for the CompanyBest Fit
Build a Bespoke FrameworkA system matched to the new CEO’s actual strengths, faster ownership of resultsCompany had no clear operating rhythm before you arrived
Protect the Existing FoundationPreserved institutional knowledge, avoided disruption to what’s already profitableCompany was performing well under the prior structure

Keith and Devon are both right, depending on what you inherit. The mistake is picking one without checking which situation you’re actually in.

Make the Call at 80%

Tom Ragen, CEO of Color Communications, told me the CEOs who stall in their first 90 days are usually chasing data they’ll never fully get. “Having 80% of the information is enough to make a decision,” he said. “Roughly 80% is enough to make the call and you’re going to adapt. Stop trying to postpone perfection and just get after and make things better each day.”

Travis Hedge learned a version of this the hard way at Vouch. He came in assuming he needed to do 80% of things differently from industry standard practice. He now believes that ratio was backwards. “It might be more like eighty percent: let’s do the best practices that have been proven to work, and really pick the twenty percent of spots that we want to go innovate in,” he said.

The CEOs who wait for 100% aren’t being careful. They’re avoiding the discomfort of being wrong in public. I’d rather coach a CEO through one bad call made on time than watch them protect their record by making no call at all.

I coach CEOs to write their decision down with a date next to it. If new information changes the picture, they can revise it. What they can’t do is leave it open indefinitely and call that diligence.

Set the Pace Your Organization Can Absorb

Jason Baumgarten, CEO of Spencer Stuart, spends his career advising boards on CEO transitions. He calls the timing question a “metronome of change.” Turn it up too fast, and you break the culture no matter how good your strategy is. Turn it up too slow, and the board starts asking why nothing’s happening. Getting that pace right, he told me, matters more than getting the strategy right.

Baumgarten sees a related pattern derail transitions before pace even becomes the issue: “I think the thing most people get lost in is their desire to be a CEO or the desire to be a leader with is this the right moment in time, the right context for them.” Getting the pace right assumes you got the timing of taking the job right in the first place.

That’s the piece most new-CEO advice skips. I’ve watched a 100-day plan that worked at one company wreck a different one because nobody checked the organization’s stomach for change first. The size of the problem matters. So does the size of the organization’s stomach for solving it, and that number is different at every company you’ll ever lead.

FAQ

What should I do in my first 100 days as a leader?

Rank every inherited problem by size of prize, the way Nathan does at Magnolia Bakery. Premal Shah, CEO of MyOme, describes the shift new leaders have to make in the same window: stop asking “how do I solve this?” and start asking “how do I build the conditions for others to solve this without me in the room?” Glenn Gow tells every new CEO client the same thing: your first 100-day plan is a triage list, not a to-do list.

What is the biggest common mistake new CEOs make?

According to Keith, CEO of Conviva, it’s inheriting a predecessor’s management framework instead of building one that fits how you actually operate. He describes his own turning point this way: “The epiphany moment I had when I took over as CEO was the phrase every problem is now my problem, owning from not just the strategy and the vision, but all the way back through to final execution, all the way through finance and reconciling every quarter’s books.” Glenn Gow sees this mistake more than any other in the CEOs he coaches.

Should a new CEO make changes right away or wait?

It depends on what you’re walking into. Travis at Vouch spent his first month on a listening tour across more than 100 employees before changing anything. Tom Ragen takes the opposite approach: lay out the vision on day one with measurements that are clear and results based, what he calls SMART goals, then tell the team “okay, I need your help.” Glenn Gow recommends the stated boundary Jeff Helfgott uses, run the business for 90 days first, because it buys time without looking like drift.

Should a new CEO replace people on the leadership team right away?

Not by default. Devon Macdonald’s rule against blowing things up in the first 90 days applies to people as much as it applies to process. Jeff Helfgott’s stated 90-day boundary, run the business first, keeps the existing team in place long enough for a new CEO to see who’s actually producing results versus who’s just been there the longest. Glenn Gow tells clients to make their first personnel change only after they can name the specific business outcome it fixes, not before.

What should a 30-60-90 day plan for a new CEO include?

Days 1 to 30 should mirror Nathan Louer’s triage model: identify the two or three problems with the largest size of prize and leave the rest alone. Days 30 to 60 should follow Jeff Cates’s approach at ContactMonkey: fix the operating infrastructure underneath whatever you triaged first, even if it’s unglamorous work like systems and reporting. Days 60 to 90 should follow Jason Baumgarten’s metronome principle: introduce your first structural change at a pace the organization can actually absorb. Glenn Gow builds this exact 30-60-90 sequence with every new CEO he coaches.

Who has more power, a CEO or a founder?

A CEO holds operational authority once appointed, but a founder often retains outsized influence through culture, relationships, and board trust, especially in the first year after a transition. Colby Durnin, CEO of CREDE, told me the hardest part of any founder-to-CEO handoff is culture integration: “You can’t do it with money, you can’t do it with structure. It really comes down to finding the right folks.” Glenn Gow has seen this play out repeatedly in founder-to-CEO handoffs.

What is the first rule of being a leader?

Admit what you don’t know. Nathan says pretending to have every answer is the fastest way to lose a team’s trust. Dan Turner, CEO of Xperigo, got the same advice from his own executive coach: “Dan, be yourself. Instead of trying to invent who this new CEO guy is and try and come up with it kind of on the fly in real time, be yourself.” Glenn Gow calls this the real test of leadership humility, and most new CEOs fail it in their first month.

How do I build trust with my team as a new CEO?

Dan extends trust before it’s earned instead of making employees prove themselves first. Steven Monterroso, CEO of ShareVault, builds trust a different way, by handing off control: “Can my team get us 80%, 90% of the way? And can I live with the other 10% miss? By thinking that way, what happens is you end up unlocking your departments, and executing quicker is a lot more important than being bottlenecked by a CEO.” Glenn Gow has watched both approaches shorten team integration by weeks.

What should a CEO do in the first 90 days after taking over during a crisis?

Dan Turner took the CEO seat at Xperigo as COVID hit, with no existing playbook to follow. His approach was to abandon the old toolbox entirely and rebuild leadership habits in real time rather than force a pre-COVID plan onto a changed business. Glenn Gow’s advice to CEOs in a live crisis: solve for the next 30 days, not the next 300.

How much data do I need before making a big decision as a new CEO?

Tom Ragen puts the threshold at 80%. Eric Edelson, CEO of Fire Clay Tile, was living this out in real time 13 weeks into a new acquisition when he told me, “I’m figuring it out. The challenge is how do we bring order to that, how do we get as much sorted upfront?” Glenn Gow tells clients that waiting for the last 20% of information is usually fear disguised as diligence.

Should a new CEO keep or replace the existing management framework?

There’s no universal answer. Keith argues you should build your own framework because inherited ones don’t fit. Devon Macdonald argues the opposite: protect what’s already working before you touch it. Glenn Gow’s rule for clients: check whether the company was underperforming or outperforming before you inherited it, and let that answer decide.

How fast should a new CEO change company culture?

As fast as the organization can absorb it, according to Jason Baumgarten, who calls this pace the metronome of change. Devon adds a caution worth pairing with that idea: “The most important part is the starting point, and that is to understand that when you come into a company as a leader, there is a lot of good things that have happened in the past.” Glenn Gow coaches new CEOs to measure organizational pace before setting any 100-day cultural targets.

What should a new CEO focus on if the company has 50+ locations or a large existing footprint?

Nathan’s approach at Magnolia Bakery, a chain with more than 50 locations, is to leave high-performing legacy units alone and focus his personal time on the units causing the most damage. Jeff Cates took the opposite focus at ContactMonkey following a $55 million Series A round, spending his early months professionalizing infrastructure rather than triaging individual business units. Glenn Gow tells clients the right focus depends on where the actual financial risk sits, not on which units are loudest.

What You Do Next

If you’re a CEO in your first 90 days and you’re not sure whether you’re fixing the right problems, that uncertainty is the actual problem. I’ve walked more than 150 CEOs through exactly this transition on my podcast, and the ones who get it right build a triage list before they build a strategy deck. If you want help building yours, book a time to talk it through with Glenn Gow and we’ll map out what your first 90 days should actually look like.

Glenn Gow
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