The Checklist Is Not a Checklist

Or: How I Learned to Stop Worrying and Love Expectations

In order to facilitate clarity and fairness, organizations will try to document job expectations explicitly. These expectation documents walk like checklists and quack like checklists, but they aren’t checklists! A common understanding between managers and team members of precisely what these tools are — and aren't — is absolutely critical to meaningful and equitable leveling and performance assessment.

I’m willing to bet that if your creative team is situated within a larger organization, documentation exists that attempts to enumerate the requirements and expectations of each role and level. Sometimes this documentation will have an excitingly sleek name like “The Job Family Matrix.” Sometimes it’ll be called “expectations_final_rev_UPDATED.xls.” But either way, it’s there, and everybody knows where to find it.

This documentation is used in hiring (to write job descriptions and bring candidates in at the right level), it’s used in promotions (to recognize scope of contribution for existing team members), and it’s used in performance assessment (to compare achievement against expectations). Those are some pretty key areas of utilization!

I’ll opine in another essay about the hiring process in general, and that will certainly include thoughts about this kind of documentation applied to that endeavor. But here I want to focus on the thorniness of this subject in relation to performance assessment and promotion.

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A job where you show up every day and take wild guesses about what you should be doing — about what will be rewarded and what will be punished, about what might lead to advancement and what might lead to stagnation or even termination — is probably not going to be very satisfying. 

In a workplace, expectations must be explicit. It is incumbent upon the organization to ensure that team members have a common, transparent, easily-accessed explication of what is required of them, and to trust that this will be used to assess their performance and their level.

So the organization, probably mostly in good faith, will set about writing all this up. Here are the specific ways in which the role of Designer is different than Sr. Designer, or here are the duties of an Artist III that will have to be demonstrated by an Artist II wanting to get ahead.

In a thoughtful organization that actually understands itself,¹ there will be a fair amount of detail here — a large number of specific expectations will be enumerated.

But if you’ve ever been in involved in the creation of expectations documents, you’ll probably have noticed a curious property they possess. Beyond a point, adding more detail doesn’t help. It hurts. A 100-item list is not 10x more informative than a 10-item list. In fact, it’s almost certainly less informative. 

The law of diminishing returns looms large here. For one thing, every bit of detail added to one expectation creates the sense that all the others need more detail, too. Without it, the detail in the one actually increases the perception that the others are more open to interpretation. Chasing that across the entire set is bound to fail.

In addition, too much specificity can work against equity. Remember, “equitable” and “equal” are not the same thing. Especially on a creative team, you need the ability to recognize…well, creativity. You’ve probably tried to build a team made up of diverse skill sets to form a high-performance whole. You don’t want eight million job descriptions that are wrought so finely only one person in the world could possibly fit them. That will never be fair.

No, ideally, you end up with expectations that are specific enough to be meaningful, but broad enough to be equitably applicable across actual individuals, projects, sub-teams, and specialties in the real world.

In order to do that, the documents will essentially end up describing a necessary but insufficient set of expectations. That is, some level of expectation will end up implied, but not explicitly documented. Everyone involved must understand and agree that it is simply not possible or desirable to make all expectations explicit. 

I know this. You know this. If you woke them up in the middle of the night, the team members know this. But it’s so, so easy to forget. Ambitious people want to know how to get ahead. Everyone wants to know how to do a good job. And we all want to get (and give!) meaningful, equitable feedback. 

So the organization hands employees something that looks an awful lot like a checklist of expectations, the employee checks all the boxes on the list, and then you as a manager have to say, “Ah, I see the confusion. This checklist is not a checklist, you see. Isn’t that clear now?”

Performance-assessment regimes interact with these expectations in various ways. For instance, the process may invite an employee to submit a retrospective of their own performance, and perhaps solicit additional input from peers. To facilitate this, the system will often include a rubric or template for individuals and their managers to structure their feedback.

Maybe it’s “The Eight Behaviors” and “The Ten Skills,” or “My Three Areas of Impact” and “My Key Areas For Growth.” Whatever. This will sit on top of the expectations documentation, and offer that documentation as details to be included in the assessment.²

This is all fine and necessary, especially in standardizing reviews between individuals. Look, people self-report in wildly different ways, managers might have to evaluate individuals with whom they’ve spent widely varying amounts of direct time, and some people may get peer input from multiple cross-functional partners. Apples may need to be compared to oranges. The template helps.

Besides the standardization, it also helps keep the manager focused on comparing performance and level against established expectations, and not, say, how eloquently one or another team member might write their own or their peer reviews.

But there’s a real danger that these templates can somewhat obfuscate the nature of the expectations. “Look,” a team member explains, “here are examples of me doing a great job in all ‘Eight Behaviors,’ therefore I deserve a bonus and a promotion.” If you have managed creative professionals, I am 100% sure you have had this conversation.

Alas, it just isn’t necessarily true. This failure seems to stem from an overreliance on that assumption (described above) that the individual being assessed understands that these are necessary but insufficient metrics. It’s not wrong to expect them to understand this…but it’s a bad assumption that they do!

Of course, it’s also possible that the expectations are not ideally formed. While it’s certainly true that excess specificity can be the enemy of equity, the inverse happens too. I’ve seen so many expectations that are too vague or multivalent to have much meaning. Demonstrating “teamwork” or “domain mastery” or “problem solving” could really be anything, you know?

A designer, say, could easily — and rightly — claim their advanced level of domain expertise by noting their adoption of some cutting-edge new tools or tech. And yet they might be blind to the fact that even so, every one of their designs failed multiple reviews. 

Their assessment is not wrong, but they’re kind of missing the point. Yes, they could be said to have “checked the box” for domain expertise, but can that exist in a vacuum? Their manager might think the answer is obvious: adopting tech is a means to create a commensurate improvement in quality (or efficiency or productivity or whatever the metric is). That’s obviously implied!

But does the box get checked? How obvious was that implication after all?

Also, some enumerated expectations I’ve seen, like “thrives in ambiguity” or “remains effective under pressure,” feel to me essentially like tacit acknowledgements that the team will be poorly led. Of course, what those expectations are intended to acknowledge is that the workplace is dynamic, that no one can perfectly predict the future, and that creative work, especially, has an ineffable element of chaos to it (I named this channel Ars Pandemonium for a reason!). All true!

Still, these leave a bad taste in my mouth — I feel like I, as a leader, am asking you, as a team member, to preemptively let me off the hook for mistakes or weaknesses in my leadership. And in fact I will force you to do that by holding your performance review hostage to it.³

But being all of that as it may, here we are. A team member believes they have met all the documented expectations, and now you have to tell them that…actually, there are also a bunch of other invisible, indeterminate expectations that they didn’t meet. How can that feel fair? How can it be fair?

Well, as long as organizations are structured with a system of leaders and managers and contributors and tasks and performance assessments and incentives and remuneration and a ladder to climb, we’re probably stuck with something like what we currently have.⁴ It’s probably as fair as it’s going to get. And it can be gotten right.

I won't pretend even for a second that I’ve always gotten it right (spoiler: I haven’t). But from my own work and watching managers whom I respect navigate these issues, I think three key practices can at least mitigate the problems, while maximizing value and fairness from the system.

• Communication. (Duh.)

Hardly seems like this should have to be said, but it nonetheless emerges as the biggest problem, time and again. Assumptions thrive in silence. Communicate frequently and broadly that those performance evaluation expectation documents that look like checklists are not, after all, checklists. Doing this might make you sound like an idiot! (Ask me how I know.) But I figure better to sound like an idiot while telling the truth than look smart allowing a falsehood to fester. 

It is important to explain that expectation documents — explicit and transparent as they may be — will never be more than enumerators of a necessary but insufficient set. And be clear that just adding more detail would create at least as many problems as it might solve.

Furthermore, I personally think it’s reasonable to be transparent and forthright that there will always be managerial perception, judgement, qualitative analysis, and context to any performance evaluation. Pretending the system has somehow created true objectivity is a credibility booby-trap. It hasn’t. It can’t. Hopefully it has created an environment which better promotes fairness and equity, and that’s the best it will ever do.

• Continuous feedback. 

An individual’s personal assessment can drift radically away from their manager’s due to the different lenses with which they look at the same set of expectations. Earlier I proposed an example of a team member who believes they have met their expectation of “domain expertise” because they’ve mastered a new tool or technology, even while their manager believes they have not, in fact, met this expectation since the resulting work has not been of sufficient quality.

It’s incumbent upon the manager in this situation to be continuously giving the feedback to the team member — before their performance review — that while the adoption of the new tech is good, it only works to their benefit if it creates higher quality work. The team member might very well point to the expectation and say, “hey, it doesn’t say so here!” At which point…well, see Communication above. As tough as that conversation is, it’s so much tougher during an actual performance review.

• An open mind. 

Notwithstanding the scenario above, sometimes a team member has a really insightful interpretation — or a really legitimate critique — of an expectation.

Now, I believe there is real risk in assuming too close a parallel between creative direction and directing creatives, but here’s a situation where I feel a strong overlap.  When I provide creative direction, I try to give folks the benefit of the doubt. I want to experience the assignment from their point of view. I’ve had amazing creative minds on my teams, and I’ve often been delightfully surprised at the work they’ve presented to me. Not always what I was predicting, but oftentimes better.

Similarly, any number of times over the years directing creatives I found myself surprised by an accomplishment a team member called out in a performance assessment. It had never occurred to me that they might have interpreted the expectation in that way!

The world is overflowing with things I don’t know, and generally the folks I’m working with are so smart and capable I’d be foolish not to at least hear them out. Sure, there might be some adjustment or realignment to be made, and sometimes we’re just not going to see eye-to-eye. But sometimes being open has helped broaden my own understanding of the expectations, to the benefit of the whole team. And since we’ve established that some level of interpretation is always present, I figure if I don’t listen to their interpretation, they’re just going to be guessing at mine.

However, do note that this requires the utmost care. Leaving open too broad an interpretive palette negates the point of having a consistent set of expectations in the first place. It opens the door to all kinds of unconscious bias. That said, the notion that any of this is truly objective is nonsense, and with a thoughtful, transparent approach, this can really help individuals find the feedback that will most help them thrive.

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And that’s the point: as always, it’s critical for both manager and team to keep in mind the actual problem they are trying to solve. We want to try and help people grow — to develop valuable skills and to unlearn bad habits. The goal is to have a healthy team with equitable opportunities and rewards for everyone.

Unless your title is Sr. Director of Box Checking or something, the goal is never to complete a checklist.

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P.S. I’ve heard it over and over through the years, any time explicit expectations come up: how in the world can we calibrate the notion of “meeting expectations,” with the constant drumbeat of “our team has very high expectations.” It leads people to think managers are sitting around saying:

“I expect you to exceed expectations, therefore if you exceed expectations it means you meet expectations. If you actually meet expectations, it means you underperformed!”

This sounds absurd (and hopefully, in a well-managed organization, it would be) but it is also an interpretation that is really, really easy to empathize with. Ah, the joys of management.

1. Which is…none of them. No, no, that’s too cynical. But I’ve been involved in the writing and revisions several of these documents, and it’s amazing to see the disconnects they uncover. Probably a healthy exercise to perform even if only for that!

2. It’s worth noting that even on teams managed using more precise (or at least more finely quantized) goal/result schemes, like OKRs or KPIs for example, those schemes still exist within a broader expectation framework.

3. Story time. I once had a team member march into my office upon having been asked to self-assess their ability to “thrive in ambiguity” (it was a survey, not a performance review, but the point stands). Pointing their finger at me, obviously quite angry, they all but shouted, “I shouldn’t have to ‘thrive in ambiguity!’ That’s your job, not mine! You’re the damn director, I hold you responsible for giving me direction!” Not wrong. Harsh, but not wrong.

4. Of course, teams and companies don’t need to be structured like this — and I know of a few that aren’t. But my experience certainly suggests that plenty are.