The Box-Ticking Illusion

Ticking off “the boxes” must be one of the most alluring paths for leaders, and one of the biggest pitfalls.

It’s so alluring because it promises a systematic approach to predictability, safety and control – but that promise is empty. The real work, the kind that actually sustains and accelerates growth, lies beyond the comfort of checklists and conventional wisdom.

It starts with setting aside the way that may look right and instead doing what is right: asking the hard questions, the uncomfortable questions, the questions that may not have “right” answers at all. 

The way I see it, if you’re only checking boxes – DE&I checkboxes, innovation checkboxes, process checkboxes, growth checkboxes – you’ve beautified the facade of your business or your self… but underneath it’s all the same. It’s operating exactly the same – but now with a new and improved exterior. Do you know that lipstick on a pig analogy?

Here it is. 

If you’ve checked off the DE&I box without really asking why you’ve operated without it – it’s a disservice to the initiative as a whole. 

If you’ve developed your innovation checklist without asking why you haven’t innovated previously – will it really make any difference?

If you mindlessly box-check a best practice protocol (only the best way anyone has done it thus far) you ignore the opportunity for a better way forward. 

The pig looks pretty good checking all those boxes... But it’s still a pig (I love pigs by the way, but just work with the analogy here)... 

And I get it – in a world filled with rapid change, the risk of being canceled and extreme performance demands – it’s easier, safer and simpler to check the box. But while it may all look “right” it fails to ask the hard questions: Why did you end up there in the first place? What values, ethics, beliefs have yielded your current results? Questions that dig deeper into the subtext of how you’re operating – as an individual and within a culture. 

Checking boxes can give you that warm fuzzy feeling – you know that one? I get it.

Sometimes I create checklists after the fact just so I can cross them off and feel like I accomplished something. It’s so seductive; it reassures us and our stakeholders that we're making progress, even when we might be marching in place. We’re left inadvertently reinforcing the status quo while sacrificing the potential of meaningful, transformative and even exponential results. 

Box checking is a surrogate for the real work that needs to get done —the work of grappling with complex problems, dealing with why your results are what they are, and truly inquiring into what else might be possible. Asking those kinds of questions will start to shift what’s underneath the surface and yield real change. 

If you want to dive into this with me more, we just kicked off a partnership with Intro – an app to book time with me personally. It’s a super-cool way to connect 1:1 – to get into some of the hard questions that will make a difference for you and your organization – or anything else I might be able to support you with. Check it out and I’ll look forward to seeing you there. 

To be clear – there’s a time and place for checkboxes: pre-flight checklists, tax compliance checklists, and anything else that you want to function exactly as it has. But for the rest of what we’re dealing with, at least if we want to grow, the checklist approach will just hold you back. 

I think that our greatest challenge and most significant opportunity – personally and professionally – is orienting ourselves and our companies towards doing the real work. Work that pushes the boundaries, that leads transformation and ultimately delivers sustainable change. Checking boxes may offer a temporary illusion of progress, but it's the courage to look beyond them that will define us.

Let's not just check off the box of doing things right; let's do the right things.

It's a subtle but powerful shift that can move mountains—or better yet, build new ones.