Working Conversations Episode 233:
Timing is Everything: How to Make Big Changes Stick

Have you ever tried to launch a big change—whether at work or in your personal life—only to watch it fizzle out before it ever really got started? The problem might not be the idea itself. It might be the timing.
In this episode of Working Conversations, I explore the hidden power of timing when it comes to making change stick. Drawing on recent research about CEO transitions, I reveal why aligning change with natural cycles—like the start of a new year, quarter, or even a new project phase—creates momentum and dramatically increases the odds of success.
Change introduced at the wrong time, however, often feels disruptive, exhausting, and harder for people to embrace.
Bringing in principles from user experience (UX) design, I show how leaders can better match initiatives to the rhythms and mental calendars of the people they impact. From organizational rollouts to personal habit changes, it’s not just about what you’re changing—it’s about when.
I also share real-world examples and actionable strategies you can use to reduce resistance and boost adoption. You’ll discover how to spot the right windows for change, structure rollouts that feel natural instead of forced, and create conditions where people are more energized to embrace something new.
Whether you’re leading a team through a major transformation, launching a new policy, or working on personal growth, this episode offers practical advice to help you make your next change easier to adopt and far more likely to succeed.
Tune in now on your favorite podcast platform—or watch the replay on YouTube at JanelAndersonPhD.
If you enjoyed this conversation, don’t forget to subscribe, rate, and leave a review. And share it with a colleague or friend who’s preparing for a big change of their own—because sometimes, timing really is everything.
EPISODE TRANSCRIPT
Want to up your chances at being successful the next time you take on something new? Whether it's a big project at work, a personal goal, or leading a team through change, success isn't just about what you do. It's also about when you do it. Some fascinating new research on CEO transitions shows that leaders who start at the beginning of a new year have a stronger chance at having positive results than those who step in midstream.
Now, why is that the case? Because their timing matches the natural cycles that people already expect. New year, new goals, new direction. And when change aligns with those rhythms, it feels smoother, less disruptive somehow, and easier to accept. In this episode, we'll be using UX thinking to explain how to time your changes and your new initiatives so that they align with the natural rhythms that people already expect, making them again, easier to adopt, less disruptive, and far more likely to succeed. Now, there are certain times for individuals, for teams, and for organizations when it's better to start something new.
And then when you align with that timing, you are going to have more success at starting that new thing. In this episode, you're going to walk away with a practical understanding of how to use timing and alignment with natural cycles that are already occurring in your workplace, in your life and your family to make those changes again, whether at work or in your personal life, and make them more successful and less disruptive. You're going to learn how the heuristic, a match between the system and the real world informs. When you'll be more successful in starting something new, you're going to see how it plays out in real life, like with those CEOs. I'll tell you more about that research and most importantly, you'll get strategies that you can use how to time new projects, new habits, or team changes so that they align with rhythms that people are already expecting, making them easier to adopt and more likely to succeed. So let's get into it. Okay, let me start with the research on those CEOs. So this research appeared in and I have to even just show you here for those of you who are watching on YouTube, the most recent version of the Harvard Business Review published the results of this study.
And again, if you're interested in reading the short summary of the results in it's in the 2025 September October issue print issue of the Harvard Business Review and they summarize a Journal of Management article in which 690 organizations with new CEOs who were just starting in that role were studied. Now, these were all S&P 500 firms. So these are big companies. And the research companies that were studied did not include turnovers that were really unexpected, like if a CEO passed suddenly or if there was a merger or acquisition and the CEO got laid off because of that. What they looked at instead were transitions where there was some control over when the new person started. And they analyzed the firm's performance for three years post new CEO starting to determine the effects of the new leader. Now, those who took the lead in the first 10 days of a new calendar year or a new fiscal year and outperformed those who took the helm at a different time of the year, like mid cycle, mid year. Now the analysis of the researchers I think was spot on and fascinating.
When you choose a start date that aligns with the organization's natural rhythms, say goal setting, planning, new directives happening, that sort of thing. And the, you know, the new CEO of course is going to come in when, with new initiatives, new goals, new directives. But when the new CEO is aligned with the timing, when those things already naturally happen, it's so much less disruptive. So it minimizes that disruption. And the CEO and of course all the folks in the organization who are boots on the ground doing the work and meeting those goals can better achieve those measurable outcomes. Now how do we explain this and more importantly, how can we apply this lesson to, to our own everyday work and life? Because I'm imagining that many of the folks listening to this podcast are not CEOs. Or if you are a CEO, you haven't just recently been appointed or are waiting to be appointed to a new position that will clearly align with the start of the new fiscal year or the start of the new calendar year. Well, this is a great example of how the user experience heuristic or design principle match between the system and the real world and is at play in the real world.
So there's this match of natural rhythms that people are already expecting that was going on when the CEOs were starting again at the beginning of the calendar year or at the beginning of the fiscal year. It just feels like the right time for change. So think about it. If you have ever created your team's goals to align with senior leaders directives, you know, those line of sight objectives that you're asked to follow. I know I did many of those line of sight objectives when I was in corporate roles where my objectives matched with my, you know, senior VPs directives that match with the division's directives and all the way up to the CEO of the Whole organization. Well, if you have carefully crafted those line of sight goals and objectives for yourself and your team to run at for the year, and then all of a sudden mid year, everything switches. Well, that's very disruptive. On the other hand, when the new directive and everything in the organization that flows from it are all in the same alignment, without that switch, mid year, it's just going to feel much more natural and it's going to be less disruptive to your organization.
Now, again, most of us are not new CEOs taking the helm at the beginning of the new calendar year or the fiscal year. So let's talk about how you and I can use this research in our own lives. Again, we don't have to be CEOs to benefit from this research. So whether you're leading a project or starting a personal habit in your own life, or introducing change in your family or in your team, timing matters. That's our biggest takeaway. Timing matters. Now what do we do with that knowledge that timing matters? Well, we match the change that we want to create to the natural rhythms of the people and systems around us and we'll get better buy in less pushback and we'll get more momentum. So we want to start at natural breakpoints.
So whether it's so that, that's your first big tip, start at those natural breakpoints. So whether you're launching a new project or taking on a big goal or leading your team through change, do it or start it at a natural transition point. It could even simply be waiting till Monday at the start of the week. Now maybe it's a little bit a bigger start that you can wait for. Maybe you can wait for the start of the month or the start of the quarter or do it right after a holiday, if there's a holiday coming up. So when you can align the beginning of your change with the natural breakpoints that occur in our world and in our daily and weekly and monthly rhythms, it is much more likely to be more well accepted. This is why we don't see big changes rolling out on a Wednesday afternoon at work. We see the big changes rolling out on a Monday morning or, or if it is a, a layoff or some bad news, we often do see that on a Thursday afternoon or way late in the week because we don't want to disrupt everybody else's work week.
We want to, you know, have a productive work week and then the disruption can happen at the end of the week. Same kind of principle is applying there now. People are already Primed for change during these times. You know, start of a new quarter, start of a new fiscal year, January 1st or the first week of January. I mean, most people are on holiday the January 1st, but the first week of January and we get that fresh start effect. And you know, you see a lot of people doing this in their personal habits, whether it's taking on a new eating plan or starting to go to the gym or whatever it is. Like, I'll start Monday. Now it seems like they're procrastinating until Monday, but there really is some science behind getting that fresh start and the mentality that goes along with it.
You're more likely to be successful and carry through if you're waiting for that fresh start and then garnering that energy and that momentum to be ready for that fresh start. Okay, so that was step number one. Start at natural breakpoints. And step number two is match people's mental calendars. So think about when your colleagues, your employees, or even your family expects shifts to happen. So rolling out new rules for your kiddo in the middle of the week might flop compared to introducing them at the start of the school year or at the very least, introducing them at the beginning of the week. Let's say you want certain quiet hours for homework time for your teenagers or certain times when it's okay for them to be outside of the house and when you need them to be home. You know, whether it's an actual curfew or just home for dinner.
We want to make sure that we're introducing those ideas in a way that's going to match the, you know, again, in this case, your child's mental calendar. But the same goes for your employees and for people across the organization. More widely, even your customers expect new initiatives on a Monday more than they're going to expect new initiatives coming their way on a Thursday. That's why a lot of sales start at the beginning of the week and last through the week. In fact, just yesterday I stopped into my hairdressers to buy some hair product and I found out that they were having a sale. Now yesterday was Monday. I'm recording this on a Tuesday, it was Monday. And I was like, well, what's, what's the occasion for the sale? And they said, we just decided to have a pop up sale to get a, you know, get a little more product moving off the shelves.
Now I didn't even realize that when I stopped in, I just stopped in to buy my product and. But they were doing a Monday, Tuesday, Wednesday sale. So again, the Same with your clients as with your with your staff. Matching people's mental calendars will make a big difference. Okay, and the third big idea here is to minimize disruption. So align change with. When you align change with those familiar rhythms, it avoids creating additional chaos.
I mean, you've heard me talk on this podcast recently about how there's just always so much and the cognitive overload that goes along with. With all of the things that are coming at us all of the time. So instead of feeling like you're adding just one more thing or more likely, yanking the rug out of people midstream, people can anticipate and they can mentally prepare when you are minimizing disruption by aligning the change that you want to have happen with other things that are already happening and other things that are maybe even already changing. All right, let me quickly review these three big ideas for you. The first is start at those natural break points, whether that's a Monday morning, the beginning of the quarter, the beginning of the school year, the beginning of the calendar year, whatever makes sense, or a product cycle, whatever makes sense in your organization. So start at those natural break points. That's number one.
Number two, match people's mental calendars. Because we all have a certain sense of rhythm about when new things start in our life, whether those be on Mondays or the first of the month or the beginning of the quarter. So match people's mental calendars and then do your best to minimize disruption so that, again, you're not springing something on somebody at a time when they're least expecting it. When you compare this with some time that they are going to be expecting it, it is going to flow so much better. All right, my friends, this is a short episode, but hopefully it's packed a lot of punch for you. Key takeaways here in this episode are align change with the calendar or with those natural break points. Now, if you want to start a new habit, whether it's fitness or journaling or budgeting or whatever it is for yourself, tie it to a fresh cycle. Start it on a Monday, start it on the first of the month. Start it at the beginning of, you know, Q4, which is coming up here in just a couple weeks.
So if you want to roll out a new policy or process in your organization, again, start it at the beginning of a project, the beginning of the week, the beginning of the month. At the minimum, beginning on January 1st or the 1st day of a new month isn't arbitrary. It actually helps anchor the change, and we take on that fresh start mentality and that fresh start momentum that goes along with it, especially if you've prepped people that this is coming again. We don't like surprises in organizational life, so if we prep people, hey, there's a new process rolling out. We're going to roll it out in Q4. And so be ready for. We'll announce, you know, we'll be announcing that change prior to Q4, and then we're gonna hit the ground running on the first week of Q4. Okay, so think about one change that you're planning at work or at home, because wherever you practice, you build the muscle.
And then ask yourself, when is the most natural time to introduce this change so that it feels smooth instead of feeling disruptive? Timing it right can make all the difference. And before you roll that thing out, whether it's a big initiative, a project, or a habit, line it up with that natural reset point. The start of a week, start of a month, start of a quarter. You will be amazed at how much easier people, including yourself, will come along for the ride.
All right, my friends, remember that it is not just what you change that matters, it's when you change it. So use the rhythms that people already know to make the change stick. In essence, make a match between the system and the real world, and your change will be much more likely to stick. I would love for this episode to not only stick with you, but to stick with one other person.
So if you wouldn't mind, please do me a favor and share this episode with just one person who could benefit from learning about this. All you have to do right now is just quickly text them and say, hey, catch the next episode of the Working Conversations podcast and. Or, you know, if you're listening to it in an app, you can grab the link right out of that app and toss it right into your text message to them or your email. All right, my friends, be well, and I will catch you next week.