On knowing when to change course, when to finish, and why our own ideas are the hardest to abandon
The other day, I was driving back from Illinois after dropping my mother-in-law off at home. There’s a podcast I’ve been listening to called Designed in California, with Jason Snell and Myke Hurley. It’s kind of celebrating Apple’s 50-year anniversary. They had an interview with Ron Johnson, the former Apple executive who was brought in to create the Apple Store. He told a story about Steve Jobs that resonated with me because I saw some flaws in myself that happen a lot.
One thing that I do enjoy with my leadership is being able to take ideas and run with them. I think once I believe in a good idea, I settle on a direction and keep pursuing it until it’s finalized. Sometimes I get so attached to a plan that I don’t see any of the flaws in it and I’m unwilling to change, especially if it’s my idea. The opposite is true, though, because if someone else comes with a plan, I’m fairly quick to poke holes in it and identify what’s wrong. I have more trouble when it’s me. I don’t have that objective measure. I think a lot of people could probably relate.
If somebody comes to me with maybe a different idea or a better plan, I tend to first try to explain it away or I don’t just sit there and listen like I should. Hearing Ron Johnson’s story about Steve Jobs was just a good reminder that I need to use the same standard for myself.
Sometimes, when somebody brings something, it deserves a rewind, even if it’s close to launching. It’s better to wait to launch if you’re not getting the exact vision right. Other times, you might say that’s a version 2 iteration. Leadership is oftentimes knowing what the difference is.
The Apple Store That Almost Was
Some backstory from the podcast: in the early 2000s, Apple was getting ready to launch its first retail stores. Ron Johnson and Steve Jobs worked together and what basically was happening was that they were following a typical retail model. Think Best Buy or, in that day, Sears or Circuit City. Everything was kind of grouped by the products that Apple had for sale.
Also during this time, a few months before the iPod was released in October 2001, Steve Jobs was trying to make Apple the digital hub for people’s creative and digital life. The iPod connected to the Mac when it first came out. It was only Apple, so the computer stood at the hub around these different ideas. They had iMovie for editing home videos. They had ways to play MP3s, which was new at that time as well.
Johnson, hearing about the digital hub strategy, began to think that the Apple Store shouldn’t be revolving around other retail stores. The Apple Store should reflect Apple being at the center of this digital hub strategy. You would organize the Apple Store around photography, music, and movies rather than explicit products.
The problem was that this timing was not good because they were about to launch the Apple Stores. The store was done and opening in six to eight weeks. This was on the way to their weekly meeting. Steve Jobs told Ron Johnson he didn’t know if he had the energy to redesign the store. “So do not bring this up.” They just sat in silence.
I have to give it to him: it is impressive that he did bring this idea to Steve Jobs on the way to the meeting, in the car together, weeks before opening. That’s probably a leadership lesson in itself. Ron Johnson believed that this was not a mere version 2. This hit at the core of what was going to be wrong with the Apple Stores.
Then they arrived at the meeting. About 15 or 20 people were there and Ron Johnson probably felt that his idea was squashed. To his surprise, Steve Jobs told them that Ron Johnson believed that they had gotten the design wrong. Amazingly, he said that Ron Johnson was right. Then he said, “Everything great I’ve done, I’ve had the courage to hit the rewind button.”
I was sitting there thinking as I was driving: Would I have had the courage to hit rewind? I don’t think so. Then I also thought: Would I have the courage to be Ron Johnson and, at the last minute, say, “I think we have everything wrong. We need to reset”? There are two sides of the coin here. You have the leader in charge of the decision hitting rewind but you also have someone telling that leader at the last minute that we need to go a different direction.
The Cost of Being Right
If you’re reading this, you’re probably familiar with the idea of the sunk cost fallacy. It’s this human tendency: we keep investing in something because we’ve already spent time, energy, and money on it. When we do that, if it’s the wrong idea or the wrong direction, we just keep wasting our money, time, and energy.
This is a good general business principle but it becomes even harder when that investment is personal. For example, when I’m coming up with an idea, I’m investing my own time, my own judgment, and my own credibility. I may have convinced others to support what I’m doing. Maybe I’ve gathered resources and I have put my stake in the ground that this is the right direction. Changing course at that point is more personal. It feels like I did something wrong.
With this, I have caught myself becoming defensive, explaining away, and digging my heels in the ground, rather than actually reconsidering what has been brought to me. Sometimes I think, “Well, you don’t have all the context.” But in reality I’m just defending my own decision. This can be hard to recognize when it’s happening.
I think as leaders we have to train ourselves to listen well. One of the principles of the art of listening well is pretty obvious: it’s not talking. It’s not only not verbally talking. It’s also not in your head, coming up with a list of reasons. It’s actually giving that person a chance to talk and for you to listen and consider what they say before forming your own opinions.
I think some of the best leaders that I have worked with model this so well that I feel like I can come to them. I can talk to them and I feel like they actually heard me. If you can’t repeat the whole argument but you have a list of things that you would change, then you’re probably not listening.
As a leader, you have to be committed to the idea of what is best for the organization rather than protecting your own ideas and protecting the initial investment that has gone into it. It’s uncomfortable. It’s hard but that’s what good leadership is. Good leadership is getting out of the way, thinking about what is best for the organization, and letting your personal biases out of it.
The Other Side of Reconsideration
The opposite is also true. I see this tendency in myself: the pull to keep iterating because it’s not perfect. This goes back to the common saying that done is better than perfect. It’s so easy to keep tweaking, to keep iterating, and never actually launch when you should.
The reality is that oftentimes you can have a version 2. And sometimes your best ideas for iteration are only going to come after it’s been launched into the world. If you’re anything like me, you can check and reread something, you can edit and so forth. But once you put it out into the world, that’s when you see the flaws.
The other thing is that you can get actual feedback from the people that you’re serving: what’s working, what’s not. You can only model so many different scenarios and think through so many different ways of doing something until you get real-world feedback.
And so, as a leader, only you can decide when it’s the right time to launch, keeping this in mind while also being willing to rewind. Being a leader has a lot of tensions. This is one of those tensions.
And in the world of AI, as I’ve written about before, AI can’t tell you whether an idea is good or bad. AI cannot tell you whether something is ready to launch or whether you need to hit that rewind button. Only you, as a leader, have that full context of the entire situation. And you can’t outsource that wisdom. AI can help with a lot of things but it can’t tell you whether you’re right or wrong about something like this.
Knowing What Deserves a Rewind
Knowing when to rewind really comes down to the kind of new information that has surfaced. When Ron Johnson talked about redesigning the Apple Store, it wasn’t based on preferences or anything like that. It was based on a change in the underlying assumption that grounded the original Apple Store design. That’s not to say that the original design was wrong or incorrect. It just means that Apple had changed its strategy and the store hadn’t reflected that.
Think, for example, of a nonprofit that’s close to launching a program it took months designing. If someone came to you with some ideas for how to better communicate the new program, you would probably be better served by going ahead and launching (or delaying by a week or so to fix it, but not completely redesigning what was going on). If that same person discovered that the people the program was trying to serve were actually facing a different challenge, then that original approach probably wouldn’t actually fit.
I think the test comes down to: Are we willing to take up the high cost of the change if it reveals a foundational problem with what we’re doing? We should also be more cautious about imposing that change if the benefit is more incremental. This is, once again, where leadership and wisdom come into play. The line really isn’t always obvious. If you’ve worked in an organization, you know that sometimes small changes cause ripple effects that you don’t foresee. Those could have been avoided by going forward and only making the change if there was a foundational issue with what you were launching.
I know for me personally, when someone challenges an idea that I’ve developed, I need to try to see what my first response is: Am I actually considering the alternative? Have I honestly understood what the other person was saying? Would I evaluate the proposal differently if I hadn’t been the one who came up with the original idea? Trying to get that blank slate and objective look at the issue can be difficult but it’s something that we as leaders need to strive to get at.
The Willingness to Be Wrong
I think for the people at Apple, Steve Jobs admitting that they needed to change direction quite possibly mattered as much as making that decision itself. When a leader is willing to change for good reasons, as we discussed above, it gives license for those on the team to be willing to change as well.
I love one of the quotes from Ron Johnson where he says that Steve Jobs “didn’t want to be the smartest person in the room. He wanted to discover the smartest idea in the room.” I know that’s something that I always want to strive to be better at. I want to be able to make decisions with confidence and see the idea for what it is for the organization, and not just based on who proposed it, even when that’s me. It’s harder to change my own idea but that actually takes a lot of awareness and is something that we have to intentionally work at.
The other thing that I try to do as a leader is look back and ask, “Why did we do that?” If you look at why you made that decision, sometimes you could only make that decision because of the information that you had at that time. You can’t judge something by what you know now.
I’m still learning how to navigate all of these ideas. I think one of the most important things is the awareness and the opportunity for self-reflection on how you approach change. We will never be completely objective. But if we’re aware of our blind spots and our tendencies, and we’re willing to talk to others and listen, then I think we can make progress in these areas.