Dotting Your I’s and Crossing Your T’s: Grown Up Edition

Hannah Fleishman
5 min readJun 14, 2018

Anything worth doing is worth doing right.

But what happens when everything is worth doing?

The best people I’ve ever worked with carry a sense of urgency. They push projects forward, they hijack meetings that don’t have agendas, they don’t wait for someone else to respond first in the email thread. Their nickname in middle school was probably ‘Next Steps’.

We can always count on these people to get stuff done. And as a result, we end up asking these people to do more of said ‘stuff’. You know how it goes: word on the street is you drive results, and we got some results that need driving. That’s the double-edged sword of being effective.

The problem is, these people are allergic to the words “That’s not my job.” They will say yes to the task, project, or program you put on their plate. And it’s not to please you, it’s because it probably is worth doing and will benefit your company, customers, or community in some small or big way.

People today care more about mission than money; they’re truly invested in the success of your organization and want to help it make an impact. If you give them an opportunity to do that, they won’t turn it down.

That’s where the idea that anything worth doing is worth doing right, breaks. You can’t give 100% to every task, project, or program if your to-do list is only getting longer, not shorter. The math won’t work. (Don’t fact-check me on that, I went to a liberal arts school.)

So what happens when we don’t have enough percents to give to all the work on our plates? We get sloppy. We forget to dot our i’s and cross our t’s. Lately, I’m doing and seeing more work I’m not proud of. Work that was rushed. Work that was resented. Work that was a jump ball between teams. Work that was reckless.

From careless typos and outdated website copy, to uninspired campaigns and recycled content, it seems that urgency is trumping quality. That’s why I’m starting to shift my thinking from, “the best people I’ve worked with carry a sense of urgency” to “the best people I’ve worked with know how to balance urgency and good work.”

Christian Kinnear, HubSpot’s Managing Director of EMEA, is one of those people. Working with Christian is “the dream.” He has a big, demanding job, and a growing family, but never makes you feel rushed with his time and always does thoughtful work.

I recently worked with him on an article about time management for managers, and he walked me through how he prioritizes his workload. Oh em gee. His operating system for bandwidth is like a science project. (Again, liberal arts major here so I use ‘science’ loosely.) And it shows. People love working with Christian, not because he’s the fastest person in the room, but because he knows how to balance urgency and good work.

When we were little, school teachers told us to dot our i’s and cross our t’s for a reason. Because quality matters. Our work is a reflection of us, of our team, and of our organization. Do good work, and leave sloppy for the joes. (Sloppy joes don’t get enough air time, in my opinion, so just let me have this.)

These are a few ways I’m *trying* to work smarter, not harder so that I can pay more attention to detail at scale:

  • Create a Process for Repeatable Tasks: If you’re getting asked the same questions over and over, or are being pulled into similar projects constantly, there’s an opportunity to streamline your knowledge. Instead of doing it yourself, teach people to fish. Create a step-by-step guide, run a workshop, or publish templates and resources. Chances are, the task doesn’t need you, it needs what you know. So teach it.
  • Say “No” Sometimes: Next time you get a request for help, don’t isolate it. Taking it on will cut into the time you had planned to spend on something else. Evaluate the request based on whether or not you can afford to take that time away, or delay that time. If you can, reshuffle your priorities and reset deadlines. If you can’t, say no.

Warning: This might not feel good. I said no to someone last week, someone I really like working with, and it felt wrong. Kinda like when I bought my first fur vest because they were really popular and girls looked really great in them, but when I got one and put it on everyone said it was cute but inside I was like THIS JUST ISN’T ME and never wore it out of the house. (It was faux fur, relax.)

  • Ask Three, Then Me: Resourcefulness is an underrated skill. Elementary school teachers tell students to “ask three, then me”; meaning, ask three other students before going to the teacher for help. At work, we should do everything we can to find an answer to our question first; Google it, look on your internal Wiki, create an free account and play around, read user reviews, etc. There are usually a million ways to figure something out yourself before asking someone, and that will help you learn more in the long run.
  • Put Proof Reading on Slow Motion: Spellcheck will only get us so far. Whether it’s an email to your leadership team or a blog post, proof read it. Then proof read it again. Then do it a third time. Sloppy writing sends a strong message and can easily be fixed.
  • Have One To-Do List: Things are going to fall through the cracks. That’s just life. But you can make sure 98% of things don’t, by having a little Christian Kinnear-inspired operating system of your own. I see people jumping between Post-it notes, Google Docs, and their calendars to figure out what’s on their task list. Similarly, I used to think of my inbox as my to-do list so I was tackling urgent, incoming stuff and not spending enough time chipping away at big projects. Now I use Trello, and make it a priority to update it every morning, and after every meeting with action items.

Work isn’t going to slow down. But, you probably have more control over the pace at which you tackle it than you think you do. If you’re asking yourself ‘Is this good or just good enough?’ then you probably didn’t give it 100%.

I may not know math, but I know that anything less than that isn’t good work.

What helps you balance urgency and quality? Please share — I’d love to get more advice on this.

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Hannah Fleishman

Director of Employer brand & Internal Comms at HubSpot. I like puns.