40 Things We Learned in 2023

This year, we wrote 40 blog posts (including this one). Here’s our list of something we learned from each post. Let us know what you’d like to learn about next year! 

1. The Insured Cash Sweep service has been tested with billions of dollars and designed to comply with FDIC regulations. No ICS depositor has ever lost money in the system. | How to keep your cash safe in the wake of SVB's collapse
2. How did your CoS role prepare you to found a company? As a CoS, I had developed an understanding of how organizations should be run, how they should allocate resources, how to manage personnel effectively, and most importantly, how to ensure that all processes run smoothly and on time. | Ioanna Mantzouridou Onasi
3. There’s a 5-point framework that governs how political CoS operate and it translates neatly to the for-profit world.  | Learning from Politics
4. “Knowledge is a burden.” It is the weight we are asked to carry as Chiefs of Staff and a reminder to share the power of information with humanity and care. | Tim Gilligan
5. OKRs are about more than simply hitting numbers, they're about optimizing for learning. You're not just evaluating whether you met your objectives or not, you're also looking for insights that can help propel you forward. | OKRs: How to Go Beyond Copycatting Google
6. Paul Cohen, former CoS at One Medical, suggests that a Chief of Staff has three essential responsibilities: process, people, and portfolio. | Craft Your Own Chief of Staff Job Description
7. Classify decisions into Type 1 (irreversible) and Type 2 (reversible). Then, use RAPIDs to make Type 2 decisions faster and more effectively | Speed Up Your Decision-Making
8. At the Associate level, Chiefs of Staff are expected to be highly organized, efficient, and detail-oriented, but are typically not running self-directed projects. | Salary & Skills for Level 1 CoS
9. In general, OKRs are more strategic in nature, while KPIs are more tactical. OKRs are used to set high-level goals, while KPIs are used to measure progress towards those goals. | History of OKRs and KPIs
10. The purpose of Job Functions is to create clusters of similar jobs with shared requirements and opportunities for career advancement. | Designing Compensation Bands
11. Revenue Operations Managers often use process mapping to optimize the customer lifecycle. Chiefs of Staff should map key organizational processes to identify opportunities for improvement. | What CoS Can Learn from Revenue Operations
12. You will mess up and that’s ok. Everyone messes up and we are only human.  | Abby Owens 
13.  The superpower of a chief of staff is to be able to drop into a meeting and know when to speak up or not, whether you’re flagging a missed consideration, connecting a stray dot, or highlighting an effective or impactful new approach. | Ethan Senack
14. Even if the invitee books a time using a tool like HubSpot, Chili Piper, or Calendly, it will fall off their calendar if the inviter has not interacted with them before (i.e. they’re an “unknown sender”) | Fixing the Unknown Sender Issue
15.  Whether it’s improving internal systems or customer-facing products, the CoS and PM keep the user experience at the center. They serve as the voice of the customer/employee within the organization. | What Chiefs of Staff Can Learn From Product Management
16. The CoS role has, for some firms, become a cargo cult: companies have emulated the visible effects of achievement believing the real achievement would follow automatically. They hired CoS because great CEOs had them, not because they necessarily needed them or knew what to do with them. | Is the Chief of Staff Role Dead?
17. Constantly questioning how and why your company does things a certain way is critical to the analytics mindset. | What is the Analytics Mindset?
18.  To source data, it’s just a matter of understanding which tools your company is using and for what purpose. In an ideal state, the company may have documentation on which tools it uses and what data is collected in each. | How to Source Data for Analysis
19.  In a negotiation scenario, “No” provides a great opportunity for you and the other party to clarify what you really want by eliminating what you don’t want. | Learn to Negotiate
20. 1911: Frederick Winslow Taylor publishes “The Principles of Scientific Management” advocating for the “enforced standardization of methods, enforced adoption of the best implements and working conditions, and enforced cooperation” | The History of Process Improvement
21.  At the Sr. Associate / Jr. Manager level, Chiefs of Staff are not only expected to be highly organized, efficient, and detail-oriented, but also to run small self-directed projects. | Salary and Skills for a Level 2 CoS
22. Running a company hackathon can be a powerful way to stimulate innovation, engage employees, and generate fresh ideas to solve pressing challenges. | How to Run a Successful Company Hackathon
23. As a new hire, you have a unique advantage in that you offer a fresh eye. This means you have a genuine chance to assist a team with matters that may not be immediately apparent to them. | Dyna Shamshir
24. Try "wrong answers only." This approach encourages participants to provide unconventional and seemingly incorrect answers to brainstorming questions. | Mastering the Art of Brainstorming
25. Being a general business athlete is an asset! In all of my prior roles, I would struggle with keeping excitement alive for what I was working on. | Emily Smith
26.  A more proactive, data-driven approach should look to understand how teams are scoring across organizational root causes throughout the year and to intervene early when there are signs of concern. | Preventing Employee Burnout with Steph Newton
27. After a cold-email, I began a multi-year email exchange with computing pioneer Alan Kay, and one day asked him about the most interesting startups building the future of computing, and he introduced me to Croquet. | Saad Sahawneh
28. Busier teams don’t have time for mentorship or frivolous questions, but their younger team members pay the price of their impatience. | 6 ways to engage new grads in a remote environment with Kendall Wallace
29. Consistently demonstrating that decisions are made based on objective data, and not personal biases, can reinforce trust. Regularly sharing non-confidential data reports and how they influence decisions can help create a transparent culture. | Data-Driven Decision Making
30. When a new urgent issue hits, ask: Does this change the thoughtful work we’re doing to build toward our vision? | How to Prioritize During Permacrisis with Claire Podulka
31. Everyone has their ‘zone of genius’. It's about understanding your strengths and areas of expertise. Hand over tasks that can be executed by others more effectively. | Creating Work-Life Balance as a Chief of Staff
32. Whose job is it to create the AI future for your company? CEOs are too busy, department leaders are too siloed, and most internal ops people don’t have the strategic purview to find and fix the hardest problems. In many ways, the Chief of Staff is best positioned to take the lead. | Chief of AI
33. We analyzed publicly available data on ~400 alumni of the Chief of Staff Network, spanning educational history, work history, skills, endorsements, location, and more. | Chief of Staff Pathways Report 2023
34. The average salary dropped to $131k, from $153k last year. | Chief of Staff Salary Report 2023
35. We showcase 4 of the most common personas of Chief of Staff that we encounter, along with some typical variants.| Where do Chiefs of Staff Come From?
36. One of my biggest lessons learned over the years in leadership roles and especially over the last 20 months in my Chief of Staff role is the importance of Embracing Chaos. I'll share why it's hard, why it's good, and how to do it. | Embracing Chaos with Bonnie Brieden
37. When we say priorities, we mean that we don't have a clear vision. | Priority Should Be Singular with Claire Podulka
38. Chiefs of Staff have the vantage point and ability to align the marketing, sales, product, and customer success teams towards a unified go-to-market motion. | A Chief of Staff’s Guide to Go-To-Market
39. Level 3 is the Manager / Sr. Manager level; at this point, Chiefs of Staff begin to deal with more strategic matters and manage entire projects on their own. | Salary and Skills for a Level 3 Chief of Staff
40. The best is yet to come!