Fit Happens: The Executive Search Podcast

Jason Baumgarten 00:00
I'm Jason Baumgarten and you're listening to Fit Happens, the podcast where top leaders, investors and board directors share the stories, surprises and hard earned lessons behind finding the right fit. Let's get into it.
Jason Baumgarten 00:17
Here's a question for you. When a new CEO walks in the door, how long do you think it takes before their decisions actually show up in share price? 90 days? 100? Try 19 months.
Jason Baumgarten 00:32
19 months. And yet somewhere right now, a board is sitting down with a brand new CEO and asking the same question that boards have been asking for decades. What's your hundred day plan? Today I want to make a case that this question, maybe one of the most common questions in all of leadership interviews, is built on a foundational lie. Not a small exaggeration, not a harmless shorthand, a genuinely damaging idea that distorts how we behave as leaders and how boards and CEOs judge us and how organizations design the entire transition.
Jason Baumgarten 01:06
I'm Jason Baumgarten and this is Fit Happens, the show about why talented people fail in the wrong roles and thrive in the right ones. Let's get into it. So first of all, where does the hundred days actually come from? It doesn't come from leadership research. It doesn't come from a study of executive transitions.
Jason Baumgarten 01:23
It comes from politics. Franklin D. Roosevelt, 1933, referring to a hundred day session of Congress during the Depression. It was a description of a legislative sprint, and a rhetorical one at that. And somewhere along the way, that political example migrated into the corporate world and hardened into doctrine. Books got written, even by friends of mine, and coaching frameworks got built, search firms and consulting firms, and I say this as part of this organizational group, that a new leader has 100 days to hit the ground running to prove themselves, and it's a critical window and that we should all be onboarded.
Jason Baumgarten 02:06
Now, why did this idea stick? Well, a couple reasons, and most of them don't really matter whether it's true. So first, it reduces ambiguity. Leadership transitions are one of the most uncertain, politically charged moments in an organizational's life, no matter how big it is. Boards want clarity, investors want signs of momentum, employees want clarity, and new leaders want a script.
Jason Baumgarten 02:30
So 100 days gives everyone a shared calendar, and shared calendars are comforting. Second, it flatters a very specific image of leadership. Think about what looks leaderly in the first hundred days: announcing priorities, reshuffling the team, communicating forcefully, visibly, decisively. A leader who spends a lot of time listening, learning, building relationships can be perceived as slow, even though in many cases that's exactly the right behavior. And third, it's pretty marketable.
Jason Baumgarten 03:03
We wrote a book on this. Some other folks have written books on this, and it's a bounded promise. And the more accurate version, something like The First Two Years of Context Sensitive Adaptation, is a terrible book title, but it's probably a lot closer to the truth. And the same goes true with onboarding. So the hundred days survives because it's convenient, it's flattering, and it sells.
Jason Baumgarten 03:26
But what it isn't is particularly supported by the evidence. So let's talk about the research, because that's where the story gets a little bit wobbly. My old employer, McKinsey, looked at this question and their conclusion is very specific. In the first hundred or ninety days, there is no data that supports that leaders must be fully productive, and that new leaders, especially external hires and specifically CEOs, take far longer than that to reach any kind of meaningful impact. Now, this is useful, because often a CEO's first six to 12 months is largely credited to them, when in fact one could argue it's largely exogenous.
Jason Baumgarten 04:06
And here's the part that I find useful, because when you ask shareholders how long a CEO realistically gets, they'll give you numbers. Nine months to develop a strategic vision. 14 months to build the right team. 19 months before their impact shows up in the share price, not 100 days. These horizons are much longer, and they're focused on whether the work this leader is doing lands. One consulting firm which studied CEO transitions in the nonprofit world reached a very striking conclusion.
Jason Baumgarten 04:37
Their recommendation: think of a thousand days, roughly three years, because that's how long the real work of a transition, the socialization, the change agenda, the process of actually becoming an insider, is real. In fact, they found that many leaders only begin to feel like they really know what they're doing through a full cycle of the organization's events and rhythms. And that's often around year two. And we're talking about the first hundred days. And then there's a third body of work, a lot of the research coming out of Harvard Business School, that shows that transition outcomes can't be separated from context.
Jason Baumgarten 05:13
Was the predecessor pushed out or did they leave on their own terms? Is the successor an insider or outsider? What condition is the organization actually in? And those factors materially shape what a new leader can achieve and in how much time. So universally timeboxing everyone into some generic 90 or 100 day sprint was really never going to work in the first place.
Jason Baumgarten 05:36
So it's not that actions in the first hundred days don't matter. They do enormously. It's that this hype and doctrine make some specific errors. One, it's pretty arbitrary. Two, it's falsely precise.
Jason Baumgarten 05:51
Three, it confuses things: signaling, learning, coalition building, team design, business impact, strategy. Some of those start on day one and get wrapped up quickly. Some take years. And then finally, the most important, is it changes behaviors, and often for the worse. So let's talk about a different mental model.
Jason Baumgarten 06:12
A leadership transition doesn't run on one calendar. It runs on a different set of clocks, all ticking at once, but all on different speeds. So the first is the strategic clock. A new leader has to diagnose the business and the industry position, test assumptions, understand the organization's real appetite for change, and build a credible direction of travel and make sure they can communicate it in a way that's clear. And most shareholders say that this takes about nine months for a CEO.
Jason Baumgarten 06:42
It's not something you jot down for your first meeting or first all hands, because it's about sense making and political grounding of what's capable, what your organization will adapt to. The second is the socialization clock, the roles, the norms, the rules of engagement. And this is usually a full cycle or two, two years in, that that socialization clock starts to normalize. Three is the team clock.
Jason Baumgarten 07:09
Building teams requires a lot of assessment of trust, of design choices, and then often selective replacement. And typically it takes 12 to 16 months. Some changes can wait until strategic direction is clear, some need quick action. But a dramatic hundred day reshuffling is often more performative than it is substantive. Clock four is the cultural clock.
Jason Baumgarten 07:34
You have to really understand a culture before you shift it. Even if you're an insider, your experience, your lived experience might actually give you the biggest blind spot to what the culture really is. You might have worked in one country when the country operates in 20. You might have worked in one type of organization functionally when you now oversee all of them. The norms to respect, the traditions to preserve, what needs challenging.
Jason Baumgarten 07:58
This is not something you get started in in 100 days. And finally, and perhaps most importantly, is the performance clock. Results lag actions. And this is hard, because we all want to see the share price pop the minute we put a new leader in the role. Our own research has suggested that that's a very poor indicator of long term success.
Jason Baumgarten 08:18
That real disciplined operating performance reflects cumulative processes. And judging a leader on the first hundred days is often confusing activity with effort. So these clocks are not in synchronous behavior. And that hundred day doctrine takes all five and smushes them together. So is it hurting anyone?
Jason Baumgarten 08:39
Isn't a little urgency healthy? So here's the problem. It doesn't just misdescribe these transitions, it makes them worse by changing how people behave. Think about what happens to a leader who believes that they have 100 days to validate their own appointment. They over-index on visible action.
Jason Baumgarten 08:55
They compress diagnoses. They rush personnel and leadership decisions. They start managing the impressions of their leadership as opposed to really understanding the levers of systems change they need to embrace. And that pressure produces the failure modes that you'd predict: theatrical reorganizations, premature commitment to strategy, bold cultural reset announcements before they really even understand where the bathroom is.
Jason Baumgarten 09:23
And boards making judgments early can get it wrong the other way. False positives: action oriented, fast paced leaders can really just be early acting momentum. And false negatives: the diagnostic leader who's really trying to figure out the deep work gets labeled as slow. It doesn't really help either side. And there's a psychological cost as well.
Jason Baumgarten 09:45
Top leadership is deeply isolating. It's hard to even get leaders to talk about how hard a transition into leadership is. And so when they're being measured on a hundred day script, it's even worse, because it's like a solo pressure cooker. Leaders become afraid to admit uncertainty, afraid to slow down or ask for help, because it doesn't fit the script of where they're supposed to be three and four months into the role. So exactly when a leader most needs the support of their board is the moment they're least likely to ask for it.
Jason Baumgarten 10:18
And I want to talk about onboarding, because it's so intertwined in this notion. Onboarding is a word from the human resources playbook. It was built for helping employees assimilate into an existing system: orientation, training, learning how things are done. And that's fine for many roles.
Jason Baumgarten 10:35
But think about what it applies when you apply it to a leader or a CEO. It casts the executive as somebody who needs to be absorbed into the organization as it stands. And that if I just know the standard operating procedure or the rules of engagement, that I'll be successful. But that's not the job. A CEO in particular is not integrating into a system.
Jason Baumgarten 10:57
The system is being reoriented around a new mode of authority. The board, the top team, the whole organization has to adapt to the leader as the leader must adapt to them. It's a reciprocal exchange and it's political. The real work of clarifying a mandate, establishing authority, mapping coalitions, deciding what to preserve and what to change, none of that is captured by a better orientation packet and a schedule of introductory meetings.
Jason Baumgarten 11:24
And the onboarding frame can pathologize exactly the wrong behavior. The CEO who doesn't quickly absorb the inherited assumptions gets labeled as slow to integrate. But sometimes we don't want assimilation. That's not the point, particularly when the prior strategy or power structure is part of the problem.
Jason Baumgarten 11:44
At a lower level of employment, fast assimilation is usually a virtue. You want people to kind of get with the program and figure out their jobs. But at the top, assimilating too fast means you've been captured by the existing system. You've adopted the way of working before you've questioned whether it's the way to work. So if the transition is onboarding and the integration is a 90 or 100 day plan, the vocabulary props up this myth and perpetuates these bad behaviors.
Jason Baumgarten 12:15
So what's the truth? A replacement model. Think of it as architecture. Milestones, sequences, not deadlines. Phases, not an endpoint.
Jason Baumgarten 12:27
And the phases matter a little bit more than the exact dates. Phase one is about entry and clarity of role, ensuring the mandate's clear, that you understand the stakeholder landscape, that you've negotiated the contours of the role. This is not about proving yourself, it's about understanding the conditions of success and the contours of your part in it. The second phase is diagnosis and relational embedding. This is the listening tours, the learning, the cultural, the team assessments, the trust building.
Jason Baumgarten 12:58
This is often formalized. It's not something that's rushed and put on your calendar in 30 days. And it's often where you need deeper trust based relationships, whether you're an insider or an outsider. And only after that diagnosis do you hit the next phase, where you really start to lock into the strategic decision and make durable commitments. Remember, nine months for a vision, so you need to lock in.
Jason Baumgarten 13:26
And then your next phase is really redesigning the team and the systems and the alignment. That 12 to 14 month clock where interpretation turns into a redistribution of power, supply systems, money, budgeting, et cetera. This is critical. And then the final phase is when you start to calcify or institutionalize that design and alignment, and you start to measure the success you hope will show up, often a year and a half to two years in. So if a CEO had a spectacular first year, thank their predecessor. If they had a spectacular second and third year, it's more likely on them.
Jason Baumgarten 14:04
And you know from our research on the life cycle of a CEO, that's often not the pattern we see. The second year is the hardest, because really the 90 days is more like two years. Now let me break this down in a practical way for a couple of audiences. So if you're on a board, separate diagnostic milestones from impact milestones. You want to diagnose early, you want strategic clarity early, and you want strategic and team clarity to follow.
Jason Baumgarten 14:32
And you want the performance later than that. And you want to evaluate those not against a predetermined calendar, but against the phases of the work to be done. Most boards skip this, which means we create urgency for new leaders without creating the support. So the questions to ask are not how to manage impressions and perceptions, but are you actually getting through the right diagnostic work with the organization. If you're the leader, replace your sense of urgency with deep thinking on your sequences.
Jason Baumgarten 15:07
The order matters a lot more than the raw speed. You need to get the steps right. Announcing leadership before you're clear on strategy, bad move. Announcing strategy before you've finished your diagnosis, bad move. Making bold commitments before you really understand your stakeholder support, bad move. Treat listening as leadership, not as a delay.
Jason Baumgarten 15:30
It's a core mechanism of effective entry. Those early wins for learning value and coalition value, not just visibility, are critical. Build yourself a kitchen cabinet. Understand different layers of the organization and what's really going on. And negotiate your time horizons explicitly with the board up front.
Jason Baumgarten 15:50
Get aligned on what's realistic at 6 months, 9 months, 14 months, 2 years. Take away this notion of onboarding and 100 day plan. It's at least a year before you have your sea legs.
Jason Baumgarten 16:03
Take your time and move carefully now. Do you need some boldness in your first year? Absolutely. But you want that boldness to be calculated in the spectrum of all of the changes you're hoping to make. Now, in a genuine crisis or a turnaround, these clocks all compress and some decisions can't wait. But then it's still not what should I be doing in three months or on day 100.
Jason Baumgarten 16:29
It's what decisions require immediate action, and what required immediate diagnoses. Crisis does compress the clocks, but not all of them. So I come back to the first hundred days is a lie. Not because it doesn't matter, but because it takes one useful idea that's kind of cute and moves everything around it. It stretches into kind of a universal rule or yardstick.
Jason Baumgarten 16:54
And you know, the reality is we all need to think about those different clocks over the first three years. The CEO needs the most help when they least expect it. And the myth says a lot about how we think leadership works. It assumes that leadership is mostly about visible decisiveness, some heroic individual imprinting everyone in a 100 day sprint. And the evidence says something much more interesting: that effective entry is built on disciplined learning, coalition building, sense making, and thoughtful timing of systems change.
Jason Baumgarten 17:28
We don't enter blank slates as leaders. These are living systems with histories and predecessors and political constraints, unseen information and third rails. The system has to adapt to you, and you need to adapt to it. So the next time somebody asks you what's your hundred day plan, I'd love for you to think instead about the question: what do I need to learn before I make an irreversible decision?
Jason Baumgarten 17:52
And what are the irreversible decisions? Throw out the simplification. Start digging deep. Thanks for listening to Fit Happens. If this episode changed how you feel about transitions, share it with somebody who's about to step into a new role, or the board about to judge one.
Jason Baumgarten 18:09
Until next time, this is Jason Baumgarten.