How to scale yourself as a creative leader
The key to becoming a successful startup leader is to develop the ability to scale yourself. That doesn’t just mean handling a growing list of demands: it’s about finding the appropriate level of focus, zeroing in on problems that matter, leading through others, and building processes and structures that don’t rely on you.
As Adam Pisoni puts it, “Here’s the real danger: as a leader, you’ll probably feel great about how busy you are. It feels like you’re adding so much value, when it’s just a sign that shit is rolling uphill to you too quickly.”
I worked with a client we’ll call Amy who tried to solve every problem her startup faced. She was a high-achieving leader and was incredibly disciplined — you should have seen her prioritized lists! But she burnt out. She felt like she was failing and constantly letting everyone down.
When we reflected on how she ended up there, it came down to the fact that she was just damn good at problem solving. The company relied on her, so she kept saying “yes” to every challenge. But as the startup grew and the problems stacked up, she couldn’t juggle it all.
New creative leaders like Amy often struggle with the entropy of a startup and feel like they need to prove themselves, so they take on too many projects. Rising leaders try to hold onto things they’re good at, when those are the things we can easily teach others to do. And it’s not just new leaders; experienced ones also go through growth phases that test their existing systems and balance.
To help Amy scale, we started developing strategies that allowed her to be responsible for outcomes but allowed others to deliver the actual solutions. Her primary tool was coaching. She helped her team members grow and navigate their challenges more autonomously with minimal support. There was no longer a need to come up with solutions herself, because she coached people through their thinking.
Approaches like these helped her scale her influence in a rapidly growing organization, while providing her team with growth opportunities.
When I stepped into my design leadership role at Square, a wise peer told me, “This role will take everything you can give it.” It was true: it was always hungry for more. Only I could define what I was going to feed it.
These are the techniques I used to get a firm grasp on my day-to-day focus and intentionally shift my energy to high-impact problems as I tried to keep up with my scaling startup.
1. Defend your priorities
The first step is to limit your to-do list to ensure you’re working on the right things day-to-day.
I’m a big fan of limits. Digital to-do lists tend to expand endlessly. I see it with my clients all the time: the infinite nature of task tracking software doesn’t help with decision making.
I like to use Post-its as physical bounds. Put a Post-it that lists your top five priorities for the day next to your keyboard. If you make a list in a notebook, that’s fine, but don’t let it run down the page. For example, you might choose one big task for the day (something that requires lots of focus) and three smaller tasks (things that may take an hour of concentrated effort between meetings).
Making it tangible also helps protect priorities. A Post-it note is not only visible to you but to others around you. When I used to get the shoulder tap from product managers, I could point to the Post-it on my laptop and say, “Is that more important than these things? Nope? Okay, talk to you next week.”
2. Know your no’s
Your “no” is as important as your “yes.” Focusing your to-do list is only possible if you recognize what you aren’t doing.
We fear refusing colleagues’ requests because we want to be useful and valuable, but when we don’t say “no” enough, we take on too much and end up creating less value anyway. If saying no is difficult for you, write templates that you can copy and paste.
And remember, “no” now doesn’t mean “no” forever. You may choose to consciously ignore or pause on an area of responsibility for a time. Set expectations by making it clear to your team, manager, and peers. Help them understand your key priorities.
When the no’s add up, it may be time to consider the next hire. But if you’re always taking things on, you won’t even realize it.
3. Avoid being the gatekeeper
Get out of your team’s way by creating public frameworks and processes that help your direct reports make quality decisions. Design principles, for example, empower your team to make decisions that align with your vision and quality bar — and make it so you’re not the only gatekeeper.
If the quality bar is in your head and you’re the sole arbiter of what “good” looks like, you’ll start racking up “decision debt” — an ever-growing list of approvals to catch up on. This creates an unscalable pressure and keeps you focused on details rather than the big picture.
Define and circulate the frameworks that determine good work.
Learn to delegate tasks that may not be priorities for you, but could be great learning opportunities for your team.
Look at your list of to-do’s and for each one, ask yourself: is it high effort or low effort? Is it high impact or low impact? If you’re a visual person, plot your tasks in the Impact vs. Effort 2x2 diagram here.
Tasks that aren’t uniquely high impact for you as a leader are candidates for delegation. You’re not reducing your responsibilities or shirking work. Rather, you’re maintaining responsibility for outcomes while giving your direct reports more pathways for growth and development.
5. Coach more, direct less.
One of the best ways for a leader to get out of the decision-making cycle is to develop coaching skills. Learn to ask your team good questions and be patient as they arrive at their own answers, rather than jumping in with your own ideas. Listen and empower.
It’s natural to look for solutions when you’ve been problem solving your whole life. But coaching your team allows them to forge their own path, which develops them and frees you up to focus on high-impact work as a leader.
6. Invest in yourself to maximize your learning and energy
Your company will scale whether or not you do, so the question is, will you grow with it or get left behind?
Investing in your personal development and learning is critical to your ability to scale.
We all understand this intuitively, but when we have packed calendars and feel “needed,” it can be difficult to step away from our day-to-day. Still, invest in yourself no matter what.
Netflix CEO Reed Hastings speaks of how heads-down he was running his first company, PureSoftware. It felt selfish to take a day off for leadership development. He says:
“I was too busy chopping wood to sharpen the axe. I should have spent more time with other entrepreneurs. I should have done yoga or meditation. I didn’t understand that by making myself better, I was helping the company, even if I was away from work.”
You are the only one responsible for your ability to keep up with a scaling company. And when you actively develop yourself and optimize your energy, you’re demonstrating to your team that you value learning instead of overwork and burnout.
You can tell a leader from a follower when they become responsible for outcomes instead of execution, and know how to stay focused on what matters. Redefine success for yourself … because “busy” isn’t success at all.