Make It Easy to Draw the Elephant
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Ever played a game of telephone inside a startup? It starts with someone whispering, "We need to focus on user growth," and by the time it reaches the last person, it's somehow turned into, "We're pivoting to enterprise AI."
If you're leading a growing company, you’ve probably felt this pain: people are working hard but are misaligned, projects that should have been simple turn into messes, and teams waste time fixing misunderstandings instead of building momentum. It all comes down to communication—or, more specifically, bad communication.
The Elephant Problem: Why Communication Falls Apart
Remember these “connect the dots” puzzles from when we were kids? You were given a picture like the one below and told to connect the dots. Once you did, it revealed an animal or a person or something fun.
One way to think about running a company is to imagine that you are giving different teams at your company a picture like this one. By doing things like communicating a vision, setting goals, and reiterating priorities, you’re asking them to own and fill in separate parts of a dot-grid picture. You’re giving Marketing 1-20, Sales is assigned to 21-35, Engineering gets 36-45, and so on.
Your job is to give them the outline; their job is to connect the dots.
But as anyone who played this game will remember, there are very different versions of these dot drawings — some are easy and some are more challenging. Here are three examples of an elephant:
These are three very different companies that are communicating in very different ways. Imagine you’re the team that owns dots 10 through 20 in each of these pictures. In the one on the right, your job is easy, honestly. In the picture on the left, there’s a huge amount left up to the interpretation of the individual and their team. One team ends up with a giraffe neck. Another thinks it’s a horse, so they draw horse legs. Someone in Sales is convinced it’s a duck, so suddenly you’ve got a beak. What you should have is an elephant, but instead, you get a Frankenstein mess of conflicting interpretations.
The farther apart the dots are, the more room there is for interpretation. Wherever you’ve left ambiguity — or white space — each team will guess at what they’re supposed to be drawing. When people don’t have enough context, they will fill in the blanks themselves.
Great communication is simple if you think about it as “connect the dots”. It isn’t about talking more—it’s about creating clarity and alignment.
Your job as a leader is to make it as easy as possible for each team—and ultimately each person—to draw their part of the elephant.
But that’s not a one-time memo or an inspirational All Hands. It’s a habit. A discipline. And it requires three things (well, there’s a longer post over here, but here’s the 3 to focus on first):
1. Context before content.
Most leaders make the same mistake: they start in the middle of the sentence. They assume that because they know the history — the meetings, the pivots, the executive debates — everyone else does too. They don’t. What feels repetitive or obvious to you is often brand new to the person on the receiving end. If you want alignment, start with the "why." Bring people on the journey. Show them the terrain before you hand them a task. If you skip that step, they’ll fill in the blanks with their own assumptions, and you end up with a team drawing a duck when you meant an elephant.
2. Clear signal.
Once your company passes a certain number of employees (cough cough 50 cough cough), it can be hard for the average person to tell what’s important. When there’s no hierarchy of communication—when every Slack message, every email thread, every comment in a doc carries equal weight—people eventually tune out. Or worse, they tune in to the wrong things. One of the most important things you need to do as a leader is design for signal. Create known channels—your weekly CEO email, a single announcements Slack channel, a monthly All Hands FULL of important info and announcements (and light on birthday celebrations and skippable content). Make it crystal clear: this is where clarity lives. If you don’t, the elephant becomes a whisper, and teams start guessing what matters.
3. Repetition.
Say it once, and it disappears. Say it twice, and maybe one person hears it. Say it a dozen times, and it starts to stick. Great communication cultures don’t treat repetition as redundancy; they treat it as reinforcement. If it matters, say it again. And again. In every format: live, written, informal, formal. Especially if it’s a new behavior or a big shift.
So if your team is drawing a duck when you meant an elephant, don’t blame the team. Zoom out. Ask yourself: Did I make it easy to connect the dots? Did I give them enough information and context to see the whole picture? Or did I just toss some dots over and hope for the best?
Great leaders don't just see the elephant. They teach everyone else to see it too.