This post comes from a separate, smaller Build-in-Public session, rather than the Lunch & Learn call that produced the earlier posts in this series. Somebody in the Build in Public session asked me the question I’d been half expecting for a while. We were a few people in a room, and the person asking had been at Improving for under three years. They pointed out that someone like me, who had been here for ten, has a kind of context they simply cannot have yet: I have watched how Improving has addressed gaps before, tried to improve itself, and I have seen which efforts stuck and which faded. So they asked, what do you think are the highest priority gaps, or the easiest gaps, that we have not addressed yet?
It is a fair question, and a useful one. When you love the place you work, the temptation is to answer with everything you love about it. But a place that has been around long enough to celebrate a decade of anyone’s tenure has room to be honest. So here is my honest answer, in the spirit of one colleague talking to another.
The overwhelming part of a wonderful problem
I want to start with the easiest thing to name, because it is the one I have the clearest picture of, and because it touches every newcomer who walks in the door. Improving has built an enormous amount of programming over the years: trust pods, the Involvement Program, Come Together, The Learning Circle, ImprovingU classes, Delivery Excellence, PATH coaching. I am grateful for all of it. But I am also aware that when I talk about it all at once, it sounds like a lot.
We may overwhelm newcomers. Someone joins and hears about all of the things we offer, and it is genuinely amazing that we have all of it. But amazing is not the same as navigable. There is a difference between having a rich set of opportunities and having a clear way for a new person to know what to do with them in their first month, their first quarter, their first year.
I have written before about the idea that the important thing is not to know everything, and that idea applies here almost too literally. I remember feeling, at various points over the years, that a new person needs a deliberate path through all of this, the way you would give someone a map of a city they just moved to rather than a list of every street.
The question is whether we are making the richness of the place feel like an invitation rather than a pile.
The highest priority gap: leveling questions and the growth checklist
The question in the room pushed me to rank things, and I resisted at first, because I honestly did not know how deep some of these issues go. But when I thought about it, the thing that has been a gap for years, across many of our programs, is the question of leveling: how we know, with clarity, where someone is in their growth and what we should be asking them next.
This is the work behind the PATH program, which has been around for years in one form or another. We have looked at different models and tried different things, and a lot of it has been hit and miss. The most recent iteration is the growth checklist. What excites me about it is that it changes the conversation from a rating to a set of questions. Instead of someone saying they are a two at this and a three at that, the growth checklist asks: at this level, have we done this thing? Yes. Have we done this thing? Yes. Have we done this thing? No. Out of a bucket of ten, you have done eight. Now the last two are known, named, and much easier to get our minds around.
I find this genuinely promising, and I have some history with it. The questions behind the growth checklist came, in part, from work I was directly involved with on our interviewing process. We were trying to level new hires properly: are they really principals, or are they more like strong seniors? We did not have clarity on that, so we built a better framework around interviewing, and the growth checklist is feeding off those same questions to give us better clarity on the other side.
That is why I call this the highest priority gap rather than low-hanging fruit. It is not a quick fix. It touches how we understand careers, how we coach people, how we set expectations, and how PATH conversations actually land. It has been a gap for a long time. But it is the gap I am most excited about us closing, because I can see the shape of the answer.
The low-hanging fruit: a clear path for the things we build
Now for the easier one, and I think this one is genuinely easy. We are in an age where anyone with an idea can quickly build an internal tool. Someone sees a problem, has an idea for a better way, and puts together a working prototype in an afternoon. The blocker is rarely the building anymore. The blocker is what comes after: there is no documented, clear way to put an internal app behind our internal infrastructure so that others can actually use it.
We ran into this on a recent project, and the interesting part was that it had nothing to do with the technology of the tool itself. The real blocker was that nobody had written down the path. Several people have this same problem, and each of us was rediscovering it on our own. That is the definition of low-hanging fruit. We have the tools. We have people with ideas. What we need is a clear, written path for turning “I threw together a working prototype this afternoon” into “my team can log in and use it.”
There is a second part to this that I care about as much as the first: the culture of actually showing the thing. When someone has an idea, I want them to build it and then present it to a wider audience, so the rest of us can say, oh, that is what you were thinking. We already have forums like Build in Public and Learning Circles where this can happen. The encouragement to build and share is there. The missing piece is a paved road from idea to deployed, and that road is very buildable.
The one thing I would change
Someone else in the room asked what one thing I would change about Improving, and my answer did not really involve changing anything we have. It was more about continuing and strengthening what we are already doing: finding more and more reasons to encourage people to be in the office. Not because presence is the point in itself, but because the in-person moments are where the culture comes alive. The in-person Come Together events, the shared lunches, the conversations that happen because people happened to be in the same room. I would like more of those reasons, not fewer.
I have written about the timeless habits of effective remote teams, and I believe remote work can be done well. But for me, a decade in, the things that keep me here are largely the people and the programs, and the programs feel most real when we are together. So my one change would not be a program at all. It would be a gentle push, over and over, toward the moments we already know are worth having.
Honesty about a place you love does not have to feel like criticism. It can feel like care. Naming the gaps, especially in a company that has spent a decade building good things, is how good things keep getting better. The onboarding overwhelm, the leveling questions, the missing path for internal apps: none of these diminish what Improving is. They are just the next set of problems, the kind you only get to have because you solved a lot of earlier ones. And the fact that we can have this conversation openly, in front of each other, is itself a sign of the culture I keep writing about.
Leave a Reply