90 Pieces of Advice for 90 Days

One of my favorite parts of working at TeamSnap is the opportunity to mentor people. It's how I learn the most. Before I head out on sabbatical next week, here are 90 pieces of advice I shared with the company for the 90 days I'll be gone.

1. Nobody knows what you’re thinking. Say out loud what you want and what you need.
2. Despite the previous advice, most of us imagine that we know exactly what other people are thinking. We’re probably wrong.
3. Most deadlines are fake. If there aren’t consequences attached to missing it, it’s not a real deadline.
4. The best gift you can give a co-worker is candid feedback.
5. Just because the CEO says he thinks something is a good idea doesn’t mean he thinks you should go do it. The CEO thinks lots of things are good ideas in the abstract.
6. Public thanks and recognition are 10,000 times more valuable than a gift card.
7. Collaboration is beautiful, but every project needs a final decision maker. Many projects spin out of control because nobody knows who owns the final decision.
8. Most meetings waste most of the attendees’ time. If you own a meeting, own it.
9. If a meeting isn’t useful to you, leave. Or don’t attend in the first place.
10. Most status updates are more effective in writing than via a meeting.
11. If you’re not constantly learning new skills, you’re falling behind.
12. You can expense an almost unlimited number of books to help you with your career. Despite this, most employees expense exactly zero books.
13. The larger the project, the harder it should be to get approved.
14. If you don’t know why you’re being asked to do something, don’t start until you find out.
15. Ask “Why?” often.
16. If you don’t understand something, ask. It’s 99% likely others also don’t understand but are too embarrassed to ask the question.
17. Invest in learning to write in plain English. It’s a superpower.
18. Similarly, do whatever it takes to get over your fear of speaking in public. Communication skills are rocket fuel for your career.
19. Assume positive intent. Most people are trying to do the right thing, even if it rubs you the wrong way.
20. When you’re not happy with someone else, the best person to talk to about it is that someone else.
21. Ask for what you want, even if you don’t think you’ll get it. Often you will, but if you don’t ask you never will.
22. Discussing your salary is never something you should be shy about. Most employees treat it like a horrible taboo. It’s not.
23. If you’re thinking about leaving, tell your manager. Maybe the things you want are available here.
24. If you’re somebody’s manager and they surprise you by leaving, you didn’t have a candid enough relationship with them.
25. Tell the truth. Always. If you can’t tell the truth, be truthful about that.
26. Plan for the first ten minutes of every meeting to be social time.
27. The best way to reduce costs is to not do stuff in the first place.
28. Doing one thing really well is usually better than doing lots of things half-assed.
29. Most of us are smart enough to figure out how to do most things. Don’t be afraid to say yes just because you haven’t done something before.
30. Add jokes everywhere you can. The world needs a laugh.
31. One space after a period. Not two.
32. If you are asking a person or a group to decide between several options, come in with your recommendation rather than simply presenting a list.
33. Your manager is more worried about you leaving than you are about getting fired.
34. If it’s not a hell yes, it’s a no. For most everything.
35. Two words we don’t use nearly enough are “I disagree.”
36. Saying “I disagree” is healthy conflict. Acting with disagreement is unhealthy conflict.
37. Your CEO and other leaders are dying for you to reach out and ask for a meeting.
38. A list of priorities includes an order. If there’s no order, it’s just a list of ideas.
39. The main advantage of working remotely isn’t “No pants.” It’s the ability to work asynchronously and get way more done than if everyone has to work at the same time.
40. Company culture changes as we grow. This is only a bad thing if company culture changes in a bad way.
41. Take real vacations. Unplug. Turn off Slack and email. Don’t think about work.
42. Give tons of credit to others. It costs nothing and pays back multiple times over.
43. It usually takes less time to test something with real customers than it does to argue everyone’s opinions about what customers might prefer.
44. Admit when you’re wrong. Not just grudgingly but enthusiastically and publicly.
45. You can always replace a semicolon with a period; if you can’t, it should probably be a comma.
46. Read The Personal MBA and learn the basics of business, no matter what your job is.
47. Stop being afraid to ask for better equipment to do your job. Your time costs the company thousands of dollars every week; a tiny improvement in efficiency pays off.
48. Most job interviews are a bad way to figure out if someone can do the job. They’re a good way to figure out if you want to work with this person every day.
49. Share more about your personal life with your coworkers. They do want to know.
50. Most presentations would be better as a memo.
51. There’s a difference between a slide deck that you’re sending someone to read and a slide deck you’re showing as part of a presentation. If you’re using the same deck for both, you’re doing it wrong.
52. Most presentations do not need slides unless you have something that is best explained visually.
53. Block out time on your calendar for focused work, not just for meetings. Also, for working out.
54. Sometimes a person outgrows the company. Sometimes the company outgrows a person. This is natural and not a failure.
55. Most people can take much more direct feedback than you imagine.
56. If nobody ever tells you what you need to work on to improve at your job, you’re not hearing the truth. Everyone has things they need to work on.
57. It’s hard to ship the minimum viable product unless everyone really believes they’ll get a chance to work on version two.
58. Improving process doesn't feel like doing work, but it's often the most valuable work you can do.
59. Hiring more people is often the least efficient way to get more done.
60. There are no proper channels. Hierarchy is B.S. If you have something that leadership needs to know, just send a Slack or an email.
61. Leadership needs to know a lot more than leadership ends up hearing.
62. If you’re afraid that a question is too impertinent to ask, you should definitely ask that question.
63. Most people have imposter syndrome most of the time. It’s not just you. We all think that we’re about to be found out.
64. If something seems really time-consuming or inefficient to you, there’s probably an easier way to do it. Ask someone.
65. If your team isn’t constantly reviewing the success or failure of past decisions, you’re very likely making the same mistakes again and again.
66. If you keep asking your manager for permission to do things and they keep saying yes, maybe stop asking and just do the things.
67. If you’re constantly having to give approval to do things, your people don’t have enough autonomy.
68. Honestly, when your kids interrupt a meeting, it’s kind of delightful. That goes double for your pets.
69. “Design is not just what it looks like and feels like. Design is how it works.” - Steve Jobs
70. Companies rarely regret over-investing in design.
71. Most enterprise software sucks so bad.
72. Infrastructure and Finance don’t get enough credit. Most jobs can have an off day. They can’t.
73. Repetitive stress injuries are no fun. Invest in an ergonomically sound work environment.
74. It’s OK to cry at work occasionally. It's not OK to cry at work all the time.
75. If you can’t decide between option A and option B, there’s almost always an option C you haven’t thought about.
76. If you have to talk yourself into hiring someone, don’t hire them.
77. Projects running long and meetings running long are symptoms of the same problem.
78. “We’ll worry about that later” always seems like a good plan at the time. Less so when later happens.
79. Find someone to challenge your ideas and your beliefs. You’ll ultimately end up stronger.
80. Your most strongly held beliefs are the ones most likely to be wrong.
81. People respond predictably to incentives, with predictably unintended consequences.
82. There is nothing more humbling than watching a customer use a product you designed.
83. Spend more time with customers. Lots more time.
84. Most advances in software development make it easier to do hard things and harder to do easy things.
85. Humans are terrible at assessing risk. That’s why people are afraid of flying instead of afraid of driving to the airport.
86. The best return on investment for one hour of your time is to learn the keyboard shortcuts for the software you use the most.
87. Automate everything you can. At work and in life.
88. Eat a healthy diet, get exercise, sleep a lot. Entire industries are built around helping you do each of those the “right” way. There is no right way.
89. Replace social media, news consumption and TV with reading and creating. Watch your mood soar.
90. Don’t put off happiness until the future. Start on your bucket list today.