Member Directory

Only 1 month in so still trying to figure it out, but having a task list with the following has been extremely helpful for me thus far: 1. item 2. description 3. notes 4. hyperlinks 5. next follow up dates 6. next follow up step

You're a catalyst, and should act like one; spread yourself broadly, always ask where you can be adding value, and don't get too bogged down in the operational weeds!

It's a myth that you can read your CEO's mind. (If you really can read minds... let's talk.) But you can learn the right questions to ask your CEO regularly that get you pretty damn close.

Listen first, and ask a lot of questions!

Critical listening is key

Just keep swimming - some days are better than others, but keep the big picture in mind. I bet you're doing some pretty incredible things day-to-day when you step back for a second! Keep going.

The To-Do List/Waiting List combination provides me with the security of knowing what I need to do and what I need others to do for me.

Talk to everyone at your company! No, seriously, everyone. Whether you are just starting out or whether you are 6-12 months in, you should try and carve out at least 30 mins of time with as many people as possible. Ask what they do, listen to how they contribute to the business, and ask a few pointed questions, like "what is the company strategy", "what is the company culture", "where are the headwinds", "who are the inspirational leaders", etc. There is no better way to paint a holistic picture of an organization than by talking to the sum of its parts. Once you have that picture, go to work with your C-Suite team on ways to highlight and foster the good, and systematically course correct the bad.

Make your company values explicit via canonized principles. Weave those principles into EVERYTHING you do to create a shared framework for how decisions are made based on what you collectively value. Principles alignment can and should be attached to performance reviews, OKR planning, product roadmapping and more. You are what you do, not what you say.

Over-communicate. It's never enough.

Step 1: Find ways to make your boss's life easier (e.g., management reports, calendar audits, performance dashboards) Step 2: Once the format is locked, automate them! This frees up time to focus on the next big idea

Don't be afraid to speak up with your observations and propose changes / adjustments to your company's strategy or the CEO's tactics, especially early in your tenure.

Be crystal clear on your focus (Principal, Leadership Team, Organization) and get yourself OKRs that will drive your focus and impact :)

Learn how to shuck oysters. 1) It'll provide perspective on what it means to get your hands dirty. 2) Oysters are delicious.

You're a leader of leaders. Trust is everything - with your executive partner and with the broader organization.

Active listening is probably the most underrated yet universally useful concepts I've come across over the years.

Every minute you spend communicating context up, down, and across the organization is a minute well spent!

You need to be proactive and find the missing gaps between leadership team and rest of the team

Spend time with your CEO outside of the work relationship to build a deeper level of trust!

Nothing is more important than trust: others' trust in you and your own trust in yourself.

Your principals team is also your team. Stay close to them and make it a point to regularly sync.

Listen first, always

Get really, really good at writing — Hemingway will become your best friend.

Speak up, give your opinion, and become a sounding board for your CEO.

Be a good listener, make everyone feel comfortable and accountable

Prioritize projects like a portfolio focused on impact and return.

Be as transparent as possible and ruthless in prioritization.

Learn by/while doing and always leave time for yourself.

Build key relationships throughout the organization.

Be curious, open minded, and people loving!

Have the confidence to handle ambiguity.

Think a step ahead

Build trust.

To build trust, find something that an exec (other than one you're supporting) needs done, do it.

Trust your crazy ideas...then design a plan that inspires others to take the leap with you.

The key to an effective partnership with your principal and peers is transparency and for the CoS to be sparring partner and perspective bringer.

Superhuman and Todoist can make you a master of following up.

Always be considering how you can make your manager not just 2x more effective, but 10x more.

When you're working in a high velocity environment like a startup, it's even more important to build networks within your org with leaders and employees who can tell you what's really going on. It can be tempting to only invest your time in building relationships with the exec, but if you want to be a great counsellor to your principle (in my case our CEO) you need to know what's happening at the front line. The insights you can glean from key, high-performing employees and more people leaders shouldn't be underestimated!

Always assume best intentions (and make that clear)

Think of yourself as the exec team's ambassador and get the details right. Learn the name of the cleaning staff. Arrive to meetings on time and with energy. Crack jokes. Distill key messages, and repeat them over and over again. You're accountable for getting sh*t done -- and that means taking responsibility for the mood in the room.

Collaboration and communication is key to everything

Embrace the three pillars of being a COS - i.e. strategy, operations, and administrative - as all three are crucial for any business operation, and as a COS you are likely well placed to be influential in these activities. ALSO - be a force multiplier for your leadership, and a reach extender for your staff!

Set expectations up front. For example, I let people know I'm very responsive. I respond to every email I receive in the same day, even if I can't take action immediately and I let the sender know I'm working on it.

I am still pretty new to the COS world, but as a general rule of thumb, insatiable curiosity made this role very attractive as an avenue to have another period of hyper learning growth as you get to participate in many facets of a company!

Being a Chief of Staff means no day is ever the same. You can prepare the best you can, but you'll inevitably pick something up that you didn't anticipate for and you'll need to find your way to make sure it doesn't get dropped.

I'm pretty new to the role, but definitely delivering on everything that you say you will do is huge. Developing that trust early is everything for a good relationship with the executive team.

A quote from Jim Baker "prior preparation prevents poor performance:

Never stop being curious - dig into how every single thing works - in order to build the credibility and knowledge you need to advise.

5-10 minute "walk and talk" with the CEO at the end of every day when possible

Separating the signal from the noise to inform recommendations is as important as the outcome of the final decision.

Patience... has been useful for me. Observing opportunities and letting them emerge organically.

Make your boss’s life easier. Help the company. Relationships matter. No assholes allowed.

Rather than always beating yourself up how you could do things better/differently, remember to ask yourself is this "good enough"?

Be open minded and learn as much as you can from the (most probably) amazing people you are working with.

Getting comfortable saying no, is more important than saying yes in the COS role!

Set up a daily sync with your exec first thing in the morning.

Create, maintain, refine: create a system, maintain your system, refine your system.

The one answer to have is "got it".