Webinar | Ask a Chief Of Staff

Linds

Ask a Chief of Staff: Parachuting In & Delegating Out

WATCH THE RECORDING

Wednesday, July 21, 9:00 AM PT // 1 hour

When most people hear “chief of staff,” they think of government officials. But the chief of staff role has quietly been gaining traction in the private sector too.

Join us for our Ask a Chief of Staff series, where chiefs of staff and thought leaders will discuss helpful strategies for navigating the nuances of this unique role.

In this session, Clara Ma, Program Director of On Deck’s Chief of Staff Fellowship, will moderate a panel of fellowship alumni and chiefs of staff Ellise McDonald of Wise Systems, Kevin Dious of Reddit, and Matt Donne of Spring Discovery. They’ll discuss how to gain context when you’re dropped into a project, make your voice heard, and get buy-in when delegating tasks.

Keep an eye on this thread

During the webinar, we’ll be adding comments below with highlights worth saving and use this thread as a way to keep the spirit of the panel discussion, and the knowledge shared there, alive! 

We’ll also be posting any answers to questions that didn’t get answered IRL. So stay tuned to hear more from our panelists after the webinar ends!

Linds

Chief of staff skills as said by the chiefs themselves:

"Asking the right questions so you’re getting the right answer. Being a Chief of Staff means you're not afraid to be the player and the coach and get right in the game." - Ellise McDonald

"Helping to force them to understand that this is a non permanent solution, we can always iterate later, but we need a decision now." - Kevin Dious

"Stay optimistic in challenging situations. The work is a marathon, not a sprint." - Matt Donne

Linds

How to get better at the skills it takes to be a good Chief Of Staff

"Having patience in yourself and others is probably the most important thing. There is no one right way to do it and staying optimistic in challenging situations is the best advice…. having the understanding that its a marathon not a sprint is important to keep in mind." - Matt Donne (full quote) 😊

[Deleted User]

One more important CoS skill:

“A lot of the role is having a high EQ and understanding what people are good at” - Clara Ma

Linds

“A good meeting can make your day!” - Clara

After a meeting, how do you prioritize what to take action on vs what to delegate? As a CoS, you can do both:

• A lot of what Matt does as a gap filler is figure out what the individuals in the meeting are best at, and figure out what it is that they need support on. He’ll give them the tasks that need to get done or he’ll find an expert to help them achieve their goals. 
• Always identify people’s strengths and get them to stretch when they can….if they don’t have the knowledge, support them and hire an expert! 
• Kevin’s role is to follow-up and ensure things get done. His role is to make sure the CEO is good.

[Deleted User]

What are some do’s and don'ts of delegation: 

• Pro-tip: If the ask is coming from the CEO, people tend to get it done a little faster. ⏰ - Kevin
• Important to always remind people, especially if it’s a task that’s very much in the weeds, how the project fits into the larger goal of the company. Remind everyone that there are processes for a reason and outline the reason for the processes. - Matt
• How to follow-up on things that need to get done -- Very persistent. There’s a joint to-do list tracker for visibility. Always following up via Slack or phone call. ☎️ - Ellise

Linds

Do you feel like an organization needs to be a certain size to have a CoS?

• Doesn’t necessarily have to be a certain size. When it made sense for their company it was when the CEO got to a point where he needed someone to help him strategize and take on certain projects. They were a mid size company by the time they brought someone on vs. Matt was in the role early into the company’s creation. - Ellise
• Classic chief of staff role is wearing a bunch of hats 🧢 🎩 👒

[Deleted User]

While working with a CEO in the Chief of Staff role, Clara would always do a general feeling check-in. If the CEO was feeling stressed and unclear on what was going on, then Clara was not doing her job well. Her goal was to help the CEO use their brain 🧠 for the big strategy pieces and not worry about whether or not a cleaning person had been paid.

Linds

Working with our CEOs and other leaders

How did you go about building a relationship or trust with your CEO?

"The trust was built when I worked with all those other teams, I was cooking dinner, or taking the trash out , and managing cohorts, and he saw me work for 4+ months before he decided he wanted me as CoS."

"Being open and personal, letting him know why things  are lacking or when things are great."

Not being afraid to tell the CEO ”you did a bad job”, I am not a yes-person and that builds trust." - Matt

How did you go about establishing a relationship with you CEO?

“Taking out the trash” - we don’t like to say “oh that’s not my job”.

"Doing whatever it takes, staying up late, literally taking out the trash, doing QA work, making sure I was putting the customer first, etc."

"The CEO saw this and saw how hard I work for the company and that created trust between us." - Ellise

[Deleted User]

How do you give advice to the CEO on how to best use their time?

Talk through each project, listen👂️ and understand how the CEO is prioritizing projects. Ellise's CEO once said “think of your time as my time and make sure you’re prioritizing both”.

Linds

How many monitors do each of you use? 

• Kevin: ONE! But he recommends two or a BIG one
• Ellise: has two and she wants three!
• Matt: 2-3 screens, he sometimes recruits his iPad

🖥 🖥 🖥

Linds

Great webinar! I definitely knew NOT MUCH about the Chief of Staff role before attending, and I am so glad I got a glimpse into the work-lives of three incredibly generous and skilled professionals.

There were questions left unanswered after the webinar, so we'll post those here/below to keep the conversation moving: we want more!

Question 1

When you’re asked to parachute in and help a team out, what are some tips to ensure it goes smoothly (setting the stage, avoiding any resistance) ?

Linds

Question 2

With so many potential areas of focus, how do you pick your projects when your CEO doesn’t have clear sense of priorities themselves?

Linds

Question 3

What are ways you've overcome the perception that as a Chief of Staff you do only administrative functions as opposed to strategic functions, etc.?

clarama

Hi everyone! Clara here, the moderator from the panel :) Just wanted to answer some of these great questions that Linds posted!

Question 1

When you’re asked to parachute in and help a team out, what are some tips to ensure it goes smoothly (setting the stage, avoiding any resistance)?

I think one of the most important things here is to establish relationships ahead of time! Matt mentioned checking in with people in a day to day setting and Ellise also talked about catering to the personal side of people and not just their work sides. I agree with the both of them that it's important to build relationships and trust before you get to problem solving situations so that the rapport is already there and you're not starting from scratch. It's important to establish your own credibility and ability to gain context quickly so that when you do sit in at a meeting or start offering solutions, there's already a baseline of trust that things will get done and the solutions you offer are valid.

Question 2

With so many potential areas of focus, how do you pick your projects when your CEO doesn’t have clear sense of priorities themselves?

This is where CEO/Principal relationship building really comes into play! I would suggest two things here:

1) Work with your CEO to clearly define priorities. If everything is a priority, then it really means nothing is a priority. Pick 3-5 things that are CLEARLY top priorities (tie them to your north stars, your rocks, your OKRs, whatever it is that you use) and if anything else comes up, it bumps something from that list. Establish this cadence with your CEO and let them know that this is how you will prioritize your own work/tasks as well. You HAVE to be aligned on this matter.

2) Be willing to push back. Your CEO should trust your thoughts and opinions as well as value them. If they bring up a new priority item and you don't agree, you should have enough trust built that you can disagree. While your CEO/Principal may sit at the head/top of the company, you should have a good idea of what's going on on the ground floor so your insight here can be valuable in prioritization.

Question 3

What are ways you've overcome the perception that as a Chief of Staff you do only administrative functions as opposed to strategic functions, etc.?

Delegate out! Depending on where you've served in your org in the past or you're new to the company, your team members may have a preconceived notion of what functions you're supposed to serve. Make sure you clearly establish what your role is with your principal and then project that out to the company. It's totally fine to help out with the admin functions and I found myself filling those gaps when we didn't have an EA, but as your company grows, delegate those tasks out to the appropriate team members or hire someone to fill those gaps. Often times, Chiefs of Staff get stuck doing certain things because there really is no one else at the company to do them. Once there's a critical mass of those items that fall into a certain bucket, it's a good time to look at bringing someone to take care of those things full time.

Hope these answers helps and I'm always happy to connect further and chat more about the Chief of Staff role, whether it's on here or LinkedIn!