How bad is it? A methodology for managing mistakes

The cost of perfection is infinite. So how do you right-size your efforts when you have a high quality bar but limited resources?

We’ve all had the impulse to work on something for just a little bit longer. Perhaps late at night or after some rapid edits, you have the nagging pull to check your work for the fifth or sixth time. Perfectionist polishing has its own magnetic field. Whether its fear of finishing or fear of failure, we can feel foibled by our own human fallibility. I have been known to struggle against my physical limitations — eyes bleary, brain no longer absorbing all the details. My body tightening at the thought that after all this effort, I still might — *gasp* — make a public mistake!

The burn and burden of perfectionism can arise in any org, leaving many asking, “At what cost?” Besides weighing you down with excess mental baggage, these moments consume focus, crowding out space for broader impact beyond the one deliverable. Is it worth your health, your sanity, to pursue the impossible goal of perfection? Eventually I realized that my answer is no. I committed to rationalizing my efforts. Afterall, not all errors are created equal. Mistakes are inevitable. It was up to me to learn how to deal with them. So I came up with some heuristics. It began with learning to assess the impact of a mistake. And it ended with learning to calibrate to my context. I dig into both steps below.

Step 1: Understand the impact of your mistake

Early in my career, I attacked every error with the same level of ferocity, whether it was a formatting error or a forecasting error. When I finally realized I need to draw boundaries, CGP Grey ‘s taxonomy of mistakes provided a starting point. Grey takes a structured look at mistakes, defining types and matching the best responses to each:

CGP Grey’s “Menagerie of Mistakes” (from timestamp 14:15) categorizes the big and the small, starting with glitches — mistakes that are good at blending into the background. Source: CGP Grey was WRONG

Glitches and Blunders

Glitches are mistakes that are good at hiding in plain sight. Blunders are embarrassing, visible, but still harmless mistakes (think Bushisms). Glitches and blunders become more common the more you have to do — putting on a sweater backwards before you rush to work, calling someone by the wrong name after you’ve just met a dozen new team members. These are worthy of grace, of laughing it off.

Errors of all varieties

Errors range from the trivial to the significant, and are more varied in how people perceive size, importance, or even if there’s an error at all. Grey playfully names their species, including:

  • Error Trivialis
  • Bad Takeus
  • Technically Correctus
  • Error Factualus
CGP Grey’s “Menagerie of Mistakes” (from timestamp 14:15) describes different error types. Source: CGP Grey was WRONG

Notably, every error requires a judgment call, weighing the cost of fixing the error vs. the benefit of moving on. Unless, that is, you make a catastrophic error — one that fundamentally breaks what you’ve made. They demand a do-over, a recall, or some equivalent.

Step 2: Calibrate to your context

Grey’s mistake taxonomy leaves the critical last mile to the audience, using one keyword to back out of any specific guidance: “perceived.” As political strategist Lee Atwater famously stated, “Perception is reality.” As such, I’ve learned to consider what I perceive, what my stakeholders perceive, and how to mediate between the two. Said another way, three pieces of context guide my error response: my objective, the work’s development stage, and organizational expectations.

Know your objective

Your primary goal should inform what kinds of mistakes are acceptable. If you’re a history teacher, for example, factual errors would undermine the entire endeavor, whereas technically correct errors (e.g. omissions) are necessary to manage class time constraints.

My objective in this blog post is to help ease the mental burden of navigating uncertain expectations in one’s career. Thus, while I can’t afford a bad take, I may well make some trivial errors without impacting this post’s clarity, accessibility, or truthiness. In setting your own boundaries and standards, you tap into your own intrinsic motivation — which leads to better work.

Adjust to the stage of development

As work goes from concept to finished product, it’s rarely worth aiming for perfection until the clear shape of what you are driving towards emerges. In copy editing, for example, editors target attention towards one focal problem to solve per editing round — nailing the story, then nailing the flow, then word choice. Trying to do all three at once tends to fragment attention and drive anxiety born of ineffective strain. Rather than wasting attention, I’ve learned to focus it and let go of certain errors before their time has come to be addressed.

Calibrate to your organization’s expectations

Almost more important than whether you correct a mistake is agreeing with those impacted about how to manage mistakes. As we noted above, mistake tolerance is highly subjective and varies by industry, organization, and team. Some optimize for speed and fast feedback, allowing mistakes to abound in support of rapid iteration. Some are highly image-conscious and demand perfection as a proxy signal for competence and trustworthiness. Notably, the latter is not a sustainable strategy; such organizations are often marked by high turnover (e.g. management consulting).

Regardless of your org culture, set expectations. Have discussions early and often about what your colleagues need and expect from you. Understand how much they want to co-create versus review polished work. Convey where you are in the development process. Gauge whether your teammates can engage with ideas before they are fully fleshed out. Whether you agree or not with your colleagues preferred approach, knowing is half the battle.

Mistakes will be made

Cringy as mistakes may feel, Grey gives us a reality check: “If you make things, there will be errors.” Unless lives depend on it, there is no truly “right” or “wrong” approach to managing mistakes. What matters is that you have one.

Your Reality Checklist

Five new realities and seven mindset shifts to get you work-ready

Source: The Cowl

Dear graduates,

You have amassed incredible book smarts in the last four years. Now it is time for you to build professional smarts. For me, as a first-generation Jamaican American, I didn’t have many examples in my private life of how to navigate the professional settings I ended up in — finance and strategy consulting firms. I had to learn that hustle, diligence, and many other things that I thought I’d learned in school all look quite different in a workplace. Below are five key differences I observed, and seven mindset shifts I had to undergo to effectively adapt.

Five new realities of how school differs from the workplace

1. The role of analytical skills

In school I gained the impression that I could think, plan, or brute-force my way into almost any opportunity I wanted. In retrospect, these tactics worked well because I was either undertaking something entrepreneurial, like starting a student group, or operating within a well-defined system, like a class scoring rubric. Most workplaces, by contrast, are somewhere in between. Systems are loosely-defined, with unspoken rules and silent expectations. Consequently, communication skills and other “soft skills”, like people skills and team collaboration, are more “make or break” than the analytical skills you learn at school.

2. The belief in objectivity

In academic courses, every attempt is made to set an objective grading rubric, to pre-define standards of what “right” is and what “good” looks like. While some companies try to come up with a trajectory map that emulates this specificity of standards, I have never seen one that wasn’t wide open to interpretation. Phrases like “produces consistent, high-quality work” on qualitative rating systems where the highest score is “exceeds expectations” are typical. These are vagaries layered on moving targets. Thus, it becomes your responsibility to manage not only your own performance and development, but also how you are perceived.

3. The idea  — and relevance — of a “right answer”

When a teacher poses a question to a class, more often than not there is a right answer ready to hand. Not so in business. More likely than not, the question is being asked *because* there is no ready answer. In strategy consulting (which is essentially project-based problem-solving for companies), I’ve found there can be multiple, equally valid answers to a question. Which answer you should lead with is context-dependent. The expansive number of unknowns also means you can expect to be wrong more often in the working world. In finance, peers often told me “as long as I’m right more than I’m wrong, I’m in good shape” — and these were peers putting other people’s money and, thus, livelihoods on the line with their decisions. Still, they were confident enough to take action and take responsibility for the consequences.

4. How you engage with authorities

Without a right answer at the ready, and with a lot of subconscious expectations, many managers struggle to give explicit guidance. Instead, most managers provide general guidance and are prone to make corrections after the fact. It is up to you to figure out what you don’t know you don’t know, so you have a comprehensive understanding of your development areas and how to meet or exceed expectations. This requires you to build rapport with and learn from peers and authorities alike. You build rapport by taking an interest in how they operate and what you should emulate. Figure out how you can make your boss’ life easier and also how to gracefully communicate your and your project’s needs.

5. How you define success

In school, there is a fairly narrow path to “success,” defined by grades and how advanced or complex the subjects you study are. By contrast, career success is deeply individual. Choosing your major in college may seem overwhelming but is finite compared to the unlimited number of career choices you will have. These choices will be multifaceted. You will need to balance your goals, financial needs, passions, and strengths. Rather than be overwhelmed, you simply need to be informed about the implications of each choice for your future opportunities, and to accept that you may not have the exact perfect job all the time. Indeed, a perfect job may be mythical, as no one likes their job all of the time. 

Seven mindset shifts to get “work-ready”

The above differences may sound straightforward on the surface, but they require a number of mental shifts to psychologically prepare for the working world. Below are seven “From / To goals” that will set you on a strong footing for your foray into the working world.

1. Thinking of work tasks as “assignments” Big-picture thinking about team objectives

Rather than thinking of your tasks as things to tick off a list, you need to think carefully about how your work will be used. Questions you might ask yourself include: Who is using what I am making? What will they expect to see? Are there examples or precedents I need to model my work after? How much of this is custom content vs. standard content? How can I simplify things to make this immediately usable or actionable?

2. Perfectionism Growth mindset

Rather than investing an infinite amount of energy into a project, you need to learn to invest the right amount of efforts to get the job done. There is no time to examine every alternative or to leave no stone unturned. This means you have to let go of any fear of being imperfect or wrong, as you calibrate with and for your team or client.

3. Expecting a roadmap Learning to navigate

While there may be a few examples to learn from that help you make a preliminary plan or guide for your work and career, some aspect of your work will include uncharted territory. You will have to develop the skill of navigating as you go, in a way that progresses your objective as new information becomes available.

4. “Big reveals” Bringing people with you as you produce work

Just working hard won’t necessarily win you appreciation or reward. Hoping people notice your work without sharing your progress or involving others also leaves you at risk of going in the wrong direction. Rather than revealing all your hard work when it’s done, validate your approach with your boss and pick up tips from your peers along the way. Involve your team in your journey.

5. Assuming people think like you Listening to and managing people

Eliminate the word “should” from your vocabulary when thinking about others. Empathy is your most powerful tool for understanding coworkers and managing your boss, your teammates, and other co-workers.

6. Thinking a role is too good or not good enough Focusing on learning and strong execution

Knowing how to execute simpler tasks inside and out means you will be competent enough to teach others and to find efficiencies. Taking on “stretch roles” that are beyond your current experience or knowledge is equally important. Don’t be afraid to take informed risks. Be confident in your capacity to learn, adapt, and step up.

7. Always sticking it out Recognizing if an environment is unhealthy or just a bad fit

Only you know your tolerance-level for unhealthy work environments, which, unfortunately, there is no shortage of. If staying is important to your next professional or financial goal, you may stick out a job with a terrible boss or insane hours for several years. But notice how it’s impacting your sense of confidence and sense of self, and consider if there are alternatives that get you to the same place. And make sure you find a mentor or peer to talk it out with.

With that, class of 2020, I welcome you to the “real world.” I wish you a strong start, many adventures, and the confidence that comes with knowing that all of my friends from school have pretty much found their happy places.