When “Be More Realistic” Is Really About Something Else

We do this exercise in our EOS meetings called Start/Stop. It’s a pretty simple concept: your team takes turns telling each other what they want the person to start doing and what they want them to stop doing. You sit there and you take it, because that’s the whole point.

Someone on my team said they wanted me to start being more realistic, and I’ve been thinking about that.

I know where it comes from because I’m a very optimistic person. I get excited about what’s possible, and when I’m excited, everyone around me can feel it and they get excited about it too. That energy is contagious… until things don’t pan out the way I painted them. Then it stops feeling like just a missed target and more like a personal failure. Not to me, but to them, because I painted a picture that was so vivid that anything short of it feels like a loss.

I think about this the same way I think about the thousand personas we all carry around. There’s a version of me that my team sees when I’m casting vision: optimistic, energized, full of belief in what’s possible. And there’s another version they see when a deadline gets missed and my frustration fills the room. Both of those are me; both of those are real. And the tension between them is where this feedback lives.

Because when things don’t happen on time, I get volatile. I’ll be honest about that. Not because I enjoy being difficult, but because I carry a sense of urgency that not everyone shares. I can see where things are going. That’s not me being a know-it-all, it’s why I’m in the role I’m in. But the gap between my clock and everyone else’s clock is where most of my worst moments as a leader happen.

And I think that’s ultimately what they’re saying when they say “be more realistic.” They’re saying, your reaction to missed deadlines makes us uncomfortable. They’re saying, the way you respond when we fall short feels like punishment.

But I keep coming back to something: we wouldn’t have the iPhone today if Steve Jobs had been “realistic.” The man was famously, almost pathologically unrealistic in his expectations. He pushed people past what they believed they could do.

He was also, by most accounts, brutal to work with. I don’t want to be Steve Jobs. But I also don’t want to be the leader who accepts “it can’t be done” as a final answer just because it makes the room more comfortable.

My sister-in-law Adena taught me something about this years ago. She’s from Romania and grew up under communist rule. When she was staying with us and started talking about launching a magazine, Lora and I and the rest of the family kept telling her to just go for it. Just do it.

She’d look at us and say, “You Americans. You think you can do anything.”

She wasn’t wrong. We do think that. And sometimes that belief is delusional, and sometimes it’s the only thing standing between an idea and a reality. Whether you think you can or think you can’t, you’re right. That’s not just a motivational quote. I’ve lived it, on both sides.

The question isn’t whether my expectations are too high or too low, it’s whether we’ve created a culture where commitments actually mean something.

In our EOS process, people set their own deadlines so they have ownership over the project timelines, but I realized that we haven’t built real consequences for missing those commitments. We talk about being a great place to work, and we are. But the best workplaces I’ve seen aren’t just comfortable. They have clear boundaries. They have standards that aren’t just discussed in quarterly meetings—they’re upheld, consistently, with love and accountability.

That’s what I’m wrestling with.

Would I even need to be “more realistic” if we had hard boundaries and clear consequences for missing self-imposed deadlines? Would the feedback change if accountability wasn’t just a value we talk about but a structure we enforce? Or is the real issue that my volatility—that specific persona of mine—is doing damage that no amount of process can fix?

I think the answer is probably both.

I think we need better structures. And I think I need to hold my vision with more grace, not less conviction. I’m not willing to shrink what I believe is possible just to make the room more comfortable, but I am willing to show more grace in how I respond when reality doesn’t match the picture in my head.

My goal was never to make people feel like failures or to shame them, because a failure is just a learning opportunity. The goal was always to help them see what I see: that they’re capable of more than they think they are. That’s faith, not just in a business sense, but in the deepest sense.

God doesn’t look at us and see who we are right now and say, “Well, I guess that’s realistic.” He sees the fullness of who He created us to be, and He holds that vision even when we can’t.