Designing Design Leadership

I don’t have a formal design background. I had to learn everything the hard way through the usual methods. Diving into, or letting myself get thrown into, the deep end of the pool. Working hard to learn as much as I could whenever I could. Asking lots of questions. Admitting what I don’t know to myself and others. And just plain trying again. And then again.

This is true for the work I do as a leader as well. It’s probably true for everyone who’s put into that position. At some point all you have are hard problems to solve. There are no easy answers and some days it can even feel like you’re picking from a pile of only wrong answers. “Which wrong answer will be the best right one today?” There’s only one way to learn there and it’s always and only the hard way.

That could mean things are twice as hard if you’re a design leader in that position. “I have two things I’m always learning the hard way all the time. Great.” I don’t think that’s true though. There’s only overlap. I think it’s common to say as a design manager or leader, “Well, I’m designing a team that designs now.” And that is how I think of it.

And that means I can apply what I know from design to leading.

For example, I often find myself thinking of the different elements of art and visual design and how can I use them as a leader in communication.

Here’s a few examples …


Repeat, repeat, repeat — and then repeat some more. Communication is always hard. Everyone has their own definition terms and jargon. Everyone interprets everything differently. The only sure way to make sure important messages, direction, and goals are understood is to just keep repeating the message. With different metaphors, with different terms, and even in different mediums. Repeat, repeat, repeat.


My mnemonic for, “could you add some more color here?” to an idea you’re trying to get across. Also known as “adding why?” I find it’s often too easy to communicate a “what” without a “why”. As in “why the heck are we doing this?” or “why the heck is this thing important?” Add that color and make it clear where the value is in a decision, task, or project.


I’ll repeat myself from the section on repetition. One, remember to repeat yourself and two, consider the medium or form of that repetition. Should you be communicating in text? Where? In Slack? A longer text document? A voice call? Video? A video in a text document? Everything? It’s probably going to be everything. But think about the message you’re making and how it fits in that form.


What kind of texture does your communication have. Are you direct and terse? Earnest and hopeful? Dispassionate? Exuberant? Funny? Serious? The answer is, “the appropriate one” or “the appropriate mix.” You won’t be one thing all the time and you’ll want to bring the appropriate texture to your communication.


This is the big one for me. Both in leadership and in design. I want to make sure I know where everyone is looking. And where I’m leading people to look. I don’t even have to make the metaphor explicit there. It works both ways. You have to know where you’re going, make it clear to others, and lead them there.

Just like I can use these elements to create visual harmony and an effective design or piece of art I can use these same elements to be a better leader in design.

The featured image in this post is Thirty by Wassily Kandinski.

By Ian Stewart