Small victories are a key part of many healthy organization’s culture, the act of celebrating or at the very least recognizing when something minute happens. As a leader tasked with building out a whole new practice in an established nonprofit, I’m already thinking about the small wins we can get on the board to show we’re moving, changing, acting, but then, is this a distraction, or good practice?

(I’m raising my hand here to say that no, I’m not an org dev expert, not a culture maven, but I’ve been increasingly sensitive to these areas of modern work for many years, and at Alluma I have a unique opportunity to put some of this possible wisdom into action.)

Despite knowing small wins will build trust, will show what our vision looks like and get our staff excited about this work, I’m conflicted, and reading my brother Brandon Greene’s piece on Radical Ambition today really hit home. So I’m thinking about the ways we identify when small wins really are sufficient, and what the possible markers are to suggest you need to skip the chaff and aim big, bold, tenacious.

As Brandon writes:

As I have been pouring over the articles contained within the project, it has made me think a lot about the work that I am engaging in. I have been wondering if it is audacious enough? At the same time, I have wondered just what would it take move something as bold at the government level?

He’s responding to the stunningly powerful work of the #1619 project in the New York Times magazine, a uniquely audacious project worthy of ALL our attention. If you haven’t read it online or purchased a rapidly out-of-stock copy, go do that now, I’ll wait here.

Lately my colleagues and I have been observing small changes, small wins, plans to achieve incremental progress, and sometimes yes, that is enough, for now. But all too often, we recognize that taking a ship that is sailing into a storm and applying “incremental changes” will still result in a wreck.

How Can We Think Bigger?

I think having a diverse perspective in a team is a key way to avoid obsessing over small wins instead of seeking major changes. It increases the safety of the crowd, the wisdom of the crowd and in a trusted environment, lets voices of concern be heard, voices that say ‘we’re not doing enough to really matter here”. By diversity I do mean ethnic and gender and age, and also a broad range of field experience; not just folks with the exact same career paths.

Second, you need a broad view, a clear sense of what your peers and maybe competitors are doing; are you a feature or two behind? A version of automation short of your nonprofit peers? Go ahead and push for small wins, incremental change. But, if you find yourself struggling to see a path that leads to your team, your organization out front, incremental ain’t gonna cut it. Now is the time to go big. Audacious.

Third, or once you realize you’re past small wins, you do need to look at culture. If you don’t invest in more open, inclusive and reflective culture at this point, you’re stuck for some time. This is when your team needs to see things differently, and learn to work differently. Talk to the amazing folks at the Justice Collective, Human Workplaces or someone like Luke if you need help on building culture that enables innovation and change.

What do you do when you realize your culture of small wins isn’t enough? Here’s some of what I’ve found helpful as a starting point:

• You go read about doing it different.
• Start to incubate bigger ideas- write them down, share them, get champions, do them!
• Don’t be afraid to go causal- diagram out why the current small steps can’t get you to the place you want to be! This helps make the case for folks who like details and safe plans.
• Go above your managers if they do not support your ideas of thinking bigger. Don’t ignore them or disrespect them, but don’t let them hold the team back.
• Write about your work- share it with staff, share it on the web, chances are it will help you think differently about your work.
• Lastly, make sure you’re investing in a culture of reflection- the act of dissecting past wins and failures is key in thinking bigger and better about how to launch forward.

If you’re struggling to get your ideas over the hump, think about where it is that you do your best thinking- for me, the wilderness and places by water help me get out of my zone, find what helps you think freer and embrace that however you can!

If we don’t start now, we’ll never get there. Don’t look back in five years and think “if we had just…”. Every shady street started with a row of saplings.
Joy Bonaguro