The one about sloppiness and formatting is a huge one for me.
When you correct people on these things, it can seem like you're being nit-picky or majoring in the minor, but -
• It reflects the level of care behind all aspects of the work. If they couldn't be bothered to make it look clean, how rigorous was the analysis behind it?
• It affects how people receive the work. Whether they are detail oriented or not, we all feel the difference between sloppy and polished work.
I hate feeling like I’m nitpicking when I point out details. Luckily most of the folks I’ve hired and worked with in recent years get the importance of details. But I remember times in the past when I had to remind myself that I was justified in pointing out sloppiness. In those cases, I took extra care to frame my message so the recipient couldn’t shrug off the feedback by labeling it as “you’re just nitpicking.”
As part of preparing for their 2024 goals, I've asked all my direct reports to review this, comes with at least two key takeaways and one example of a time they acted like an owner and one example of when they did not.
I love this whole article but I'm currently kicking myself for not knowing the text formatting hack in emails before this. The amount of time I've spent manually formatting over the years ..... so painful
Another tip is that when you're pasting text from different sources or documents and want it to all look streamlined you should use the keyboard function: "command+shift+V" then you may not need to use the Clear Text feature at all!
I learned this in my first job working at a law firm. I saw a couple of paralegals who were lax on details because “they knew the lawyers would catch mistakes.” But finally, the lawyers had to put their foot down.
Seeing what a burden it created for them made me realize the importance of “imagine this was going straight to the client” type effort.
When I was earlier on in my career I only learnt this lesson by failing and realising what the consequences of my mistakes were. That's partially why I do my best to let people I'm leading fail rather than micro-managing so they don't, otherwise they'll never truly learn the 'this is going straight to the client' lesson.
Great question. I’ve had cofounders mention they appreciated my ability to disagree and commit, especially because our company had a debate culture and it can be tough to know when to relent. Disagreeing and committing probably varies from person to person, but here’s how I think about it:
1. Have I made as strong of a business case as I could make? If I don’t think I’ve explained myself well, I take responsibility if my audience isn’t persuaded. So I’d want to at least take another stab at explaining my idea more effectively before disagreeing and committing.
2. Do I believe the other party understands what I’m saying? If the answer is no, then I may keep attempting to explain. If the answer is yes, they understand what I’m saying, but still disagree or believe another idea makes more sense, I’m more likely to disagree and commit.
3. How bad is the alternative to my recommendation? If I think the alternative would ruin the company, I’m going to keep fighting for my POV.
4. Do I think that alternative could work? Most of the time, I can see the merits of alternative ideas, and after hearing other people’s arguments, I’m on the fence. I find for many strategic decisions, there’s not a clear right answer. If there were, we wouldn’t be debating, we’d already have made the decision. Through the process of hearing my colleagues’ arguments, I’m often convinced that their POV or idea makes more sense than mine.
Btw I say “their ideas” and “my ideas” to make it simpler, but in reality, it doesn’t matter who came up with an idea. The end result is to do what’s best for the business. At the end of the day, I feel equally good if we go with my or someone else’s idea, as long as it was the best decision we could make given the info we had.
I really enjoyed this article! I find that the best operators are those who have built their own self-management systems. I live and die by my Notion, it's my second brain and I don't know what I'd do without it!
Great insight, I’ve found this to be the case too. Some write stuff in a notebook, some jot items on Post-it’s every day, others put everything in their calendar, others use Notion/Asana/Trello, etc. I used to want folks to use the same process to stay organized, but for years now, my stance has been “as long as the work gets done, use whatever system you like.” I try to keep team-wide process light.
My system probably seems chaotic and not-optimized to folks on the outside, but it works for me and I love it. My to-do list is a mix of Google Calendar events, Notion, texting myself, and Post-it’s. :]
Second, great question. Re: your actions potentially putting a $150M contract at risk, are there checks and balances in place to prevent any one person from jeopardizing the project? Ideally there are others (your manager, your skip level manager, colleagues) who are involved. If you feel on an island and believe a big contract might be risk, definitely raise your hand. When you raise your hand early, there’s almost always lots of options and ways to solve. It’s when we raise our hands too late that there are often bigger, more expensive consequences and fewer ways to resolve.
In terms of spending time to address weaknesses vs asking for permission to fail so you can learn, I’d say to do both. Both go hand-in-hand because you learn by trying to address the weaknesses, and this will involve your manager’s support anyway.
It also depends what your weaknesses are. I’m a proponent of choosing roles where your weaknesses are less relevant, so the impact of those weaknesses is minimized. In the essay, I mention working on weaknesses just enough so they aren’t debilitating and don’t prevent you from doing work you love to do.
Hope this helps. Also I’m kind of digging this advice column format so keep the questions coming when they pop up. :]
Many excellent tips in this article.
The one about sloppiness and formatting is a huge one for me.
When you correct people on these things, it can seem like you're being nit-picky or majoring in the minor, but -
• It reflects the level of care behind all aspects of the work. If they couldn't be bothered to make it look clean, how rigorous was the analysis behind it?
• It affects how people receive the work. Whether they are detail oriented or not, we all feel the difference between sloppy and polished work.
I hate feeling like I’m nitpicking when I point out details. Luckily most of the folks I’ve hired and worked with in recent years get the importance of details. But I remember times in the past when I had to remind myself that I was justified in pointing out sloppiness. In those cases, I took extra care to frame my message so the recipient couldn’t shrug off the feedback by labeling it as “you’re just nitpicking.”
As part of preparing for their 2024 goals, I've asked all my direct reports to review this, comes with at least two key takeaways and one example of a time they acted like an owner and one example of when they did not.
This is EXCELLENT.
Yesss. Love this Ashley, thank you for sharing!
I also told them to read 15 Principals of Managing Up - this content is SO good.
I love this whole article but I'm currently kicking myself for not knowing the text formatting hack in emails before this. The amount of time I've spent manually formatting over the years ..... so painful
I use the clear text feature daily myself. It’s a gift that keeps on giving.
Another tip is that when you're pasting text from different sources or documents and want it to all look streamlined you should use the keyboard function: "command+shift+V" then you may not need to use the Clear Text feature at all!
“Your manager can’t always be your safety net.”
I learned this in my first job working at a law firm. I saw a couple of paralegals who were lax on details because “they knew the lawyers would catch mistakes.” But finally, the lawyers had to put their foot down.
Seeing what a burden it created for them made me realize the importance of “imagine this was going straight to the client” type effort.
When I was earlier on in my career I only learnt this lesson by failing and realising what the consequences of my mistakes were. That's partially why I do my best to let people I'm leading fail rather than micro-managing so they don't, otherwise they'll never truly learn the 'this is going straight to the client' lesson.
This is great advice!!!
"Be as self-directed and independent as possible."
My favorite point.
When I heard it at first, I thought it was about never asking for help.
But it's about being able to take yourself from point A to B. This includes reaching out to the necessary people to help overcome obstacles.
Exactly Tiger re: reaching out to the right people to get what you need
I'd love to hear your thoughts on when "to disagree and commit"? when should you stand your ground and keep pushing?
Great question. I’ve had cofounders mention they appreciated my ability to disagree and commit, especially because our company had a debate culture and it can be tough to know when to relent. Disagreeing and committing probably varies from person to person, but here’s how I think about it:
1. Have I made as strong of a business case as I could make? If I don’t think I’ve explained myself well, I take responsibility if my audience isn’t persuaded. So I’d want to at least take another stab at explaining my idea more effectively before disagreeing and committing.
2. Do I believe the other party understands what I’m saying? If the answer is no, then I may keep attempting to explain. If the answer is yes, they understand what I’m saying, but still disagree or believe another idea makes more sense, I’m more likely to disagree and commit.
3. How bad is the alternative to my recommendation? If I think the alternative would ruin the company, I’m going to keep fighting for my POV.
4. Do I think that alternative could work? Most of the time, I can see the merits of alternative ideas, and after hearing other people’s arguments, I’m on the fence. I find for many strategic decisions, there’s not a clear right answer. If there were, we wouldn’t be debating, we’d already have made the decision. Through the process of hearing my colleagues’ arguments, I’m often convinced that their POV or idea makes more sense than mine.
Btw I say “their ideas” and “my ideas” to make it simpler, but in reality, it doesn’t matter who came up with an idea. The end result is to do what’s best for the business. At the end of the day, I feel equally good if we go with my or someone else’s idea, as long as it was the best decision we could make given the info we had.
I really enjoyed this article! I find that the best operators are those who have built their own self-management systems. I live and die by my Notion, it's my second brain and I don't know what I'd do without it!
Great insight, I’ve found this to be the case too. Some write stuff in a notebook, some jot items on Post-it’s every day, others put everything in their calendar, others use Notion/Asana/Trello, etc. I used to want folks to use the same process to stay organized, but for years now, my stance has been “as long as the work gets done, use whatever system you like.” I try to keep team-wide process light.
My system probably seems chaotic and not-optimized to folks on the outside, but it works for me and I love it. My to-do list is a mix of Google Calendar events, Notion, texting myself, and Post-it’s. :]
I agree - it doesn't matter what the system is as long as it works for the person!
This is one of the most insightful articles I have ever read. Young people could learn so much from this before they start their career.
Thank you for your positive feedback Hadshal!
Once again, I'm here commenting without reading. Already got the like before anything else. rsrs
You’re awesome, thank you Danilo 🙏
First, congrats on your new role Kimia!
Second, great question. Re: your actions potentially putting a $150M contract at risk, are there checks and balances in place to prevent any one person from jeopardizing the project? Ideally there are others (your manager, your skip level manager, colleagues) who are involved. If you feel on an island and believe a big contract might be risk, definitely raise your hand. When you raise your hand early, there’s almost always lots of options and ways to solve. It’s when we raise our hands too late that there are often bigger, more expensive consequences and fewer ways to resolve.
In terms of spending time to address weaknesses vs asking for permission to fail so you can learn, I’d say to do both. Both go hand-in-hand because you learn by trying to address the weaknesses, and this will involve your manager’s support anyway.
It also depends what your weaknesses are. I’m a proponent of choosing roles where your weaknesses are less relevant, so the impact of those weaknesses is minimized. In the essay, I mention working on weaknesses just enough so they aren’t debilitating and don’t prevent you from doing work you love to do.
Hope this helps. Also I’m kind of digging this advice column format so keep the questions coming when they pop up. :]