Nova Chief of Staff

About Nova Chief of Staff:

Shine bright in your career! Nova is the premier destination for Chief of Staff:
* Education
* Certification
* Development

Go big, get prepared.
The Chief of Staff position is a dynamic role that can add tremendous value to a growing organization. But with educational and programmatic resources few and far between, the role is often overlooked and misunderstood.

That’s where Nova comes in. Get empowered with the knowledge and confidence you need to stand out and make an impact in top positions with senior executives.

Through consulting, coaching, and a first-of-its-kind Chief of Staff Certification program, Nova supports:
* Current Chiefs of Staff
* Executive Assistants
* Businesses
* Operations Managers
* Highly Organized Leaders
* Consultants
* Undergraduate/Graduate Students
* Anyone interested in the CoS role or program development

Certification:
Nova's CoS Certification program equips aspiring leaders to function at the highest levels of a company. Through hands-on job experience and expertly crafted online curriculum, Nova coursework prepares students for the ins and outs of the CoS role so they can hit the ground running in their current or future job.

Consulting:
Nova also provides fractional CoS consulting to mission-driven, high-growth startups. Looking to maximize your time, and the impact of your company's vision and strategy? Nova's fractional CoS can be your right hand + execution-focused, strategic thought partner. From business planning, to exective level project management, to board meetings + materials development, Nova will allow you, the business leader, to focus on what's most important. 

Coaching:
Introducing Nova’s newest offering: CoS Coaching. Receive one-on-one, direct access to an experienced Chief of Staff to level-up your impact. Our coaching sessions cover:
* Business Planning
* Strategy & Prioritization
* Business Process
* Engagements & Comms

Learn more at NovaChiefofStaff.com!

Owner | Founder, Consultant, Coach

T-Mobile

Created and led the Business Office for the T-Mobile Business Group (B2B), supporting the President, SVPs, and the business organization of 5,000+ employees. This includes leading and creating the fabulous team responsible for various Chief of Staff duties including: 

-Business Planning: strategic planning, rhythm of business, SLT priorities, corporate/board deliverables, session management and strategy, leadership offsites.

-President Engagement Planning: internal and external events, recommendations, customer networking, travel preparation and coordination.

-Employee Experience & Engagement: new and existing programs driving culture, development, feedback, DE&I, and listening. Analysis, insights, and executive summaries to drive programs forward.

-Events including all-employee (5,000+) and Senior Leadership Team off-site & strategic planning events.

-Various programs & projects including: org charts, pitch decks, customer escalations, planning calendars, playbooks, facilities & operations, etc. 

-Built a Chief of Staff team of 7-8 employees to support our leader and fill gaps in the organization. Defined all roles, processes, & systems, and ran a highly effective & collaborate Chief of Staff team, filled with incredible people who were collaborative, challenged, and loved their work.

Chief of Staff, President of T-Mobile Business Group

Retail Strategy, Consumer Experience

Executive Leadership Program (L2E)

Nordstrom

Business Process, Project Management, Nordstrom Technology Group

Buy Planner & Vendor Management, Special Occasion Dresses, Merchandising Group

Buy Planner & Vendor Management, At Home Hard Goods

Online Buy Planner & Vendor Management, Soft Accessories

Assistant Buyer & Vendor Management, At Home Hard Goods

Assistant Buy Planner & Vendor Management, Trend Accessories and Belts

Washington DECA

Board Fellow

Nutraceutix, Inc.

Sales & Vendor Management

Macy's

Sales Manager

Suncadia Resort

Restaurant and Food and Beverage Supervisor

Salish Lodge & Spa

Server

University of Washington

General Administration

Starbucks

Barista

Come join the Chief of Staff revolution! 

With two decades of experience in some of the biggest companies in retail, food/beverage, and technology, I have a history of stepping into new roles, new industries, and new businesses, and transforming teams from the ground up over and over again. I’ve seen the tremendous impact of a Chief of Staff in streamlining organization processes, improving employee culture, and advancing the goals of executive leadership in a business environment. 

That’s why I’ve built, tested, and implemented a successful Chief of Staff framework, so students, professionals, and organizations can benefit from the wealth of tools, resources, and knowledge I’ve accumulated during my career.

As the Chief of Staff to a President at a Fortune 40 company—a multibillion-dollar business with 5,000+ employees—I built the president’s Chief of Staff model from the ground up to create a highly successful team, drove efficiencies, and established executive back-office structure that will be in place for years to come.

As a highly versatile leader with a strong orientation for action, I’ve been able to quickly develop sound but flexible business processes and systems which enable teams to scale at a rapid pace, with an executive presence that offers leaders confidence and trust. Now, I’m sharing that with motivated leaders looking to level-up their skills, career options, or organizational effectiveness.

My work style is upbeat, curious, dynamic, collaborative, and culture-first. I have an unwavering curiosity, and a genuine passion for leadership and work culture. To help others blaze their optimal career path, I offer fractional Chief of Staff consulting and a first-of-its-kind Chief of Staff Certification course through Nova.

Learn more by reaching out, or see our offerings at https://www.novachiefofstaff.com/

CEO vs. Chief of Staff vs. Executive Assistant...  
 
as the human body: 
 
CEO is the Brain. 
Chief of Staff is the Nervous System. 
Executive Assistant is the Heart. 
 
 
🧠 CEO=- Brain 
 
→ Sets the vision and direction, like the brain directs the body's functions. 
 
 
🌐 Chief of Staff = Nervous System 
 
→ Carries through the brain's direction while coordinating, communicating, and executing. Similar to the nervous system's role in the body. 
 
 
🫀 Sr. Executive Assistant = Heart 
 
→ Provides vital support and ensures smooth operations, akin to the heart sustaining the body. 
 
__ 
 
Do you use analogies to describe these or other C-suite roles? Please share in the comments. 
 
(Analogy credit: Neha Panchal) 
 
__ 
 
♻️ Engage and share to support this post. 
 
👋 Follow Maggie Olson for daily CoS & leadership insights

Maggie Olson

Founder & CEO @ Nova Chief of Staff | Acclaimed Fortune 40 CoS to President | First-of-its-kind Chief of Staff Certification Course | Keynote Speaker | Team Trainer | Building Confidence Around the Globe 🌎

Chad Ruppert

The Chief of Staff role is one of the most misunderstood in business. 
 
The vague title doesn’t help, nor does the fact that many people are doing the work of CoS under a completely different title. 
 
Think Biz Ops, Business Planning, Strategic Planning, or Executive Business Partner, to name a few. 
 
So, let’s clear things up. 
 
 
Here’s a breakdown of three roles most commonly confused with Chief of Staff: 
 
💼 Chief of Staff Definition 
 
The strategic right hand to a business leader focused on execution, alignment, and driving key initiatives.  
 
Prioritizes what matters, ensures transparency across the leadership team, and turns vision into action. 
 
 
💼 Executive Assistant 
 
A logistical powerhouse managing calendars, travel, expenses, and tactical support. 
 
Keeps the executive on track and operations running smoothly. 
 
→ Confusion Level: 4/5  
→ Cheat Code: EA = tactical partner, CoS = strategic partner  
 
 
💼 Chief Operating Officer  
 
Owns the operational backbone of the business, ensuring scalability, efficiency, and execution of company-wide initiatives. 
 
Manages teams, oversees processes, and drives performance.  
 
→ Confusion Level: 3/5  
→ Cheat Code: COO = supports business, CoS = supports leader  
 
 
💼 HR Executive  
 
Leads hiring, employee relations, culture, and training. 
 
Ensures policies align with company goals and support a thriving workforce.  
 
→ Confusion Level: 2/5  
→ Cheat Code: HR = company's people, CoS = business leader's initiatives  
 
 
The CoS role is unique because it adapts to the leader's needs and exists FOR the leader. 
 
It’s not just about culture, operations, execution, or strategy—it’s all four… and more.  
 
As the Chief of Staff role gains traction, understanding matters.  
 
So let’s set the record straight:  
 
A Chief of Staff is a business leader’s strategic, execution-focused partner—turning vision into reality.  
 
♻️👋 Engage, share & follow Maggie to support this post.

Kristin Hathorn

Stop underestimating your Executive Assistant,  
 
And invest in them like you would a member of the C-suite.  
 
Most leaders are underutilizing the incredible power their EA brings to the table. 
 
It’s time to stop missing out on this asset and start unlocking your Executive Assistant’s full potential. 
 
How do you do this? 
 
Here are 5 ways to invest in your Executive Assistant 
 
1️⃣ Connect them intentionally within your organization. 
 
Help them build their internal network by introducing them to a cross-functional peer who complements their strengths. 
 
2️⃣ Give context, not just tasks. 
 
Help them understand your priorities, goals, and obstacles by walking them through your top 3 strategic goals and how they connect to the company’s vision. 
 
3️⃣ Ask them to co-pilot a challenge. 
 
Don’t go it alone. Invite them into your thinking process by bringing them into a decision you’ve been sitting on and talking it out together. 
 
4️⃣ Give precise, purposeful feedback. 
 
Tell them exactly how they made your day easier this week, and offer specific guidance that builds confidence and strengthens their impact in the organization. 
 
5️⃣ Encourage growth. 
 
Support learning opportunities, assign projects that stretch their skill set, and invest in their curiosity and long-term goals. 
 
The takeaway: 
 
Treat your EA like the strategic partner they’re capable of being, not just the person managing your calendar. 
 
You’ll gain more than efficiency. You’ll unlock stronger support and elevate your leadership. 
 
In the comments: Leaders, what’s one way you invest in your EA? 
 
♻ Share to spread awareness.  
 
👋 Follow Maggie Olson for daily CoS and leadership insights

Invest in your EA

CoS ≠ EA  
  
But too many companies make the same mistake.  
  
They take a high-performing Executive Assistant, tack on Chief of Staff responsibilities, and expect them to succeed in both roles.  
  
It doesn’t work. ❌  
  
Not because an EA or Chief of Staff isn’t capable, but because the job itself becomes impossible.  
  
A Chief of Staff simply cannot be as effective in their role while still managing EA duties.  
 
 
Here are 10 Reasons why leaders should never blend these two critical roles:  
  
1️⃣ They Require Different Skill Sets  
  
↳ EA work is tactical and CoS work is strategic  
 
↳ Expecting one person to master both is unrealistic  
  
2️⃣ Both Are Full-Time Jobs  
  
↳ Each role demands 100% focus  
 
↳ Splitting time means neither will be done well  
  
3️⃣ Impossible Workload for One  
  
↳ Managing calendars and leading initiatives don’t mix  
 
↳ One will always suffer under the weight of both  
  
4️⃣ Strategy Goals will get Lost  
  
↳ Chiefs of Staff need flow time for big problems  
 
↳ Admin tasks will always take priority if combined  
  
5️⃣ Pay Doesn’t Match the Work  
  
↳ Many get a title change but no real raise  
 
↳ Extra responsibility without fair compensation  
  
6️⃣ Role will Lack Authority  
  
↳ Chiefs of Staff need decision-making power  
 
↳ If they are still viewed as an EA, they may struggle  
  
7️⃣ Burnout Happens Fast  
  
↳ The workload is unsustainable  
 
↳ This leads to frustration, mistakes, & turnover  
  
8️⃣ Role Perception will Skew EA  
  
↳ EA tasks = seen as an EA  
 
↳ This can limit influence as a strategic leader  
  
9️⃣ Conflicting Mindsets  
  
↳ EAs focus on quick execution, CoS work longer-term  
 
↳ Switching between the two constantly isn’t effective  
  
🔟 Both Roles Lose Impact  
  
↳ Combining roles = one overwhelmed person  
 
↳ The company loses out on true impact of two roles  
 
 
In short,  
  
When EAs and CoS collaborate, they create an unstoppable force.  
  
But combine the two roles, and you’re setting both up for failure.  
  
Leaders who understand this build stronger teams, empower their Chiefs of Staff to lead, and give their EAs the focus they need to excel.  
  
What’s your take? Have you found success in a combined role? They definitely exist!  
  
 
♻️ Engage and share to support this post. 
 
👋 Follow Maggie Olson for daily CoS & leadership insights

CoS ≠ EA

You say you value your Executive Assistant. 
 
But what does your bonus policy look like? 
 
Executive Assistants drive measurable impact at every level of an organization. 
 
Yet too often, when it comes to bonuses and recognition, they are excluded. 
 
If your bonus policy does not reflect the value your EA brings, you are overlooking one of the most influential roles in your company. 
 
Here is what your work looks like with an Executive Assistant: 
 
⚡Time management 
 
→ They manage calendars in a way that protects priorities and frees up hours you didn't know you had.  
 
⚡Anticipate needs 
 
They identify problems early and resolve them before they affect you or the company's progress.  
 
⚡Protect energy 
 
They filter distractions so you can focus on decisions and outcomes. 
 
⚡Executive bandwidth 
 
They move between planning and execution to keep projects and operations on track. 
 
⚡Influence and trust 
 
They support the team's alignment and strengthen the company's culture. 
 
⚡Operational support 
 
They run systems, workflows, and processes so you can stay focused on achieving goals and company growth. 
 
If your EA is essential but excluded from the bonus pool, the message is clear: 
 
You are not valuing one of your most important drivers of success. 
 
Leaders, it is time to align your compensation policies with the reality of the EA role. 
 
♻ Share to help spread awareness of this crucial role.  
 
👋 Follow Maggie Olson for daily C-suite leadership insight.

Is your Executive Assistant reporting to the right person?  
  
If it’s not the leader they support, the answer is probably no.  
  
Some think an EA should report to the Chief of Staff.  
  
But here’s the truth...  
  
The close relationship between the EA and the leader is critical for success.  
  
The EA should report to the leader they support.  
  
Why?  
  
For these reasons:  
 
 
👉 Maximized EA Effectiveness  
  
Direct access to the leader allows the EA to manage key tasks—calendar, inbox, expenses, logistics, travel—without unnecessary roadblocks.  
  
The more difficulty the EA has reaching their CEO, the less impact they will have.  
  
👉 Increased Chief of Staff Focus  
  
Offloading major work streams to the Chief of Staff should be avoided, this includes managing the CEOs EA.  
  
EA and CoS can work beautifully together, but it's the partnership - not hierarchy - that moves mountains.  
  
👉 Enhanced EA + CEO Relationship  
  
The EA’s close relationship with the leader drives success.  
  
Taking the EA out of direct reporting weakens this bond and the critical insights that come with it.  
  
 
In short...  
  
While the EA plays a critical role in supporting the CoS, direct access to the leader is paramount.  
  
There are exceptions, but generally it’s not ideal.  
  
Executive Assistants should report to the leader they support.  
 
  
In the comments: What’s your take? If you report to the CoS, how has it worked for you?  
  
Ps. Share exceptions below too— I know there are some!  
  
 
♻️ Engage and share to support this post. 
 
👋 Follow Maggie Olson for daily CoS & leadership insights

Is your Executive Assistant reporting to the right person

🎁GIVEAWAY ALERT 🎁
 
Nova Chief of Staff is turning TWO! And we have so much to celebrate.
 
From 2024 to 2025, our community grew fast:
 
🚀 600 ➡️ 1,500 students
 
🌎 20 ➡️ 45 countries
 
👥 3 ➡️ 8 full-time Nova team members
 
🎓 2 ➡️ 5 learning paths
 
📍 1 ➡️ 3 in-person trainings each year! 
 
 
💫 In honor of Nova’s birthday on 11/1, we’re celebrating with a massive giveaway!

 
Here’s what’s up for grabs:
 
🎁 11 enrollments at 2023 pricing — $995 (save $855!)
 
🎁 1 FREE enrollment to Nova’s Online Chief of Staff Certification Course ($1,850 value)
 
 
To ENTER do the following:
 
1. Like, comment, AND reshare this post to be entered to win!
 
2. View the Nova Chief of Staff course syllabus at https://lnkd.in/ekBc2Q5R
 
 
- Enter through Thursday 11/13
 
- Winners announced Friday, 11/14
 
 
Thank you for helping us grow, learn, and lead together these past two years.
 
❤️ Maggie & Team Nova
 
 
♻️👋 Engage, share & follow Maggie to support this massive giveaway!

Curious if you’re a Chief of Staff? 
 
You might already be doing the job. 
 
Dozens of titles exist for the work of Chief of Staff, and one of the most common "ahas" is someone realizing they are a Chief of Staff under a different title.  
  
Companies may choose not to use the Chief of Staff title because it's unfamiliar, they don't love it, or maybe it's reserved for C-Suite only. 
  
But in fact, the Chief of Staff role - title or not - often exists throughout a company supporting leaders across many different leadership levels (director, VP, etc.).  
  
Here are fifteen signs that YOU are a Chief of Staff: 
  
- you're the leader's right-hand 
- you improve process & drive efficiency 
- you have a strong influence on the team 
- you exist to make the leader's role easier 
- you may act as proxy and advise your leader 
- you're proactive in finding biz improvements 
- you're in the know about everything going on 
- you're focused on the strategy of the business 
- you jump into projects & lead them to completion 
- you lead important, strategic initiatives for the leader 
- you ensure your leader is prepared for everything 
- you make strategic recommendations constantly 
- you prepare important materials for your leader 
- you often oversee the leader's events & comms 
- you're a trusted partner to the leader & the team 
  
If most of these are true, YOU are a Chief of Staff. 
 
Identifying that the work you're doing IS Chief of Staff work is critical to your success.  
 
You'll open doors, find resources, and finally have a charter for your role.  
 
Are YOU a Chief of Staff?  
  
Ps. If this list describes your EA, promote them. 
(and backfill their core admin duties) 
  
📖 Find this cheat sheet and a dozen more resources in Nova's Free Resource Library.  
 
 
♻️ Engage and share to support this post. 
 
👋 Follow Maggie Olson for daily CoS & leadership insights

Curious if you’re a Chief of Staff?

You might be a Chief of Staff and just not know it yet. 
 
Here’s the thing, many Chiefs of Staff don’t start with the title. 
 
Sometimes the work hides behind labels like Business Manager, high-impact EA, Director of Ops, or Special Projects Lead. 
 
The title might be different, but the work (and the impact) is there. 
 
So if you’ve been wondering if you’re unofficially the CoS, here’s your checklist to figure it out. 
 
 
Signs you're a Chief of Staff (title or not): 
 
- You’re the leader’s right hand 
 
- You improve processes and drive efficiency 
 
- You have a strong influence across the team 
 
- You exist to make the leader’s role easier 
 
- You act as a proxy and trusted advisor 
 
- You proactively identify business improvements 
 
- You stay in the know about what’s happening 
 
- You focus on the strategy behind the execution 
 
- You lead cross-functional projects to completion 
 
- You run key strategic initiatives for your leader 
 
- You make thoughtful, strategic recommendations 
 
- You build materials that drive high-level decisions 
 
- You often manage internal comms or events 
 
- You’re trusted by both the leader and the team 
 
 
Does the majority of this list sound like you? 
 
You’re already operating as a Chief of Staff. 
 
And knowing that *matters.* 
 
It provides new insights, resources, and opportunities for growth. 
 
And leaders: 
 
Does this list sound like your EA? PROMOTE them to CoS. 
 
And backfill for their core EA duties. 
 
♻️👋 Engage, share & follow Maggie to support this post.

Signs you're already a CoS

Assya A. B. Joseph, mCMI

Four conferences in about a year. First time bringing my family. 💕 

LOVED having Cole there snapping some photos. 

LOVED having Max there for the last few minutes of day 3 (he was sad the banners were being taken down, sweet boy). 

Thankful, thankful, thankful for an incredible team & so many Nova students who continue to trust us in such major ways. 

Excited for the conference break until April & then we do it again, 3 more times next year. 

Proud of the 5-star reviews that come in on Google after every training. 

🌟 Go Nova! 🌟

🫶👏

What does being “strategic” really mean? 
 
Throughout my 20's I heard a lot about "being strategic." 
 
I figured I should "be more strategic" but I didn't really know what that meant.  
 
After years in leadership positions in large companies, I get it now.  
 
Because being strategic in this role isn’t about showing up with an MBA, a consulting background, or the perfect case study. 
 
It’s about how you think. 
 
How you frame problems. 
 
How you anticipate what’s coming next, and shape the path forward. 
 
Strategy for Chiefs of Staff is often using information found between the cracks, to set the plan for what's ahead.  
 
- The dots you connected after 1:1s 
- The information that has to feed a process 
- The plan based on deep diving into the background 
 
It’s the discipline of connecting context, people, and priorities—then turning that insight into motion. 
 
Here are five ways the best Chiefs of Staff think and operate more strategically: 
 
1. Long-term thinking 
 
Think beyond this week and this month. 
 
Ask, “What actions now will create impact over the next quarter or year(s)?” 
 
Strategic Chiefs of Staff design for future impact, not just immediate output. 
 
 
2. Anticipate conflicts 
 
Identify potential friction or risks early. 
 
Plan how to address them before they become problems. 
 
Strategy often looks like prevention, not reaction. 
 
 
3. Problem-solving 
 
Look past surface-level issues. 
 
Break challenges into manageable parts and focus on solving the right problem one at a time. 
 
Solving the right problem saves time, energy, and trust. 
 
 
4. Prioritize high-impact work 
 
Not everything is the highest priority. 
 
Focus on the work that drives the most value and ensure your leader’s time is maximized. 
 
Protect time like it’s a strategic asset—because it is. 
 
 
5. Connect the dots 
 
Bring together information, trends, and insights to help organize thoughts and simplify decision-making. 
 
That’s the quiet superpower of a strategic Chief of Staff. 
 
–– 
 
Being strategic isn’t about having all the answers. 
 
It’s about asking better questions, seeing systems, and steering the team toward what matters most. 
 
The best Chiefs of Staff don’t just execute the plan. They help create it. 
 
That’s strategy. 
 
♻️👋 Engage, share & follow Maggie to support this post.

5 ways CoSs can think and operate more strategically

"Dang, I really miss the 9-5."  
 
(said no one ever)  
 
We hear a lot about the perfect "work-life balance." But what's more realistic?  
 
Work-life integration. 
 
Work-life balance is out.  
 
Work-life presence is in.  
 
The goal?  
 
Be *incredibly present* no matter what you're doing. And set up your day to allow for it.  
 
As a LEADER, I don't tell my team exactly when to work and when not to work.  
 
They're adults. We talk about work expectations, getting the job done, and doing it well.  
 
As a BUSINESS OWNER, I prefer some weekend work at a coffee shop over five back-to-back 9-5s away from my family. 
 
Some things that have worked for me/my team:  
 
- expectations are around work not time 
- mtg days are only Tuesdays & Thursdays  
- Appt? Just let us know, no approval needed 
- Slack check-ins & check-outs since we're virtual 
- no expectation to open/reply to weekend emails  
- the understanding that urgent things *will* come up 
 
The fact is, we've got to get the work in... 
 
But the reality is, we're better at work when we have some creativity & control around how we set it up. 
 
Find a rhythm that allows you to thrive, both at work AND at home.  
 
__ 
 
Now, how to get your C-suite leader on board? Let's share some creative ideas in the comments. 👇  
 
__ 
 
♻️ Engage and share to support this post. 
 
👋 Follow Maggie Olson for daily CoS & leadership insights

I’ve gone from 0 to 50,000 followers on LinkedIn in 2 years. Here’s exactly what I did: 

(hint: #7 is a great place to start) 

When I built my business a few years ago, some very smart people told me I needed to build a personal brand to support it. 

I’d never thought about that, afterall, us Chiefs of Staff are most comfortable behind the scenes— and that’s always been me. 

But, they told me posting everyday on LinkedIn would be a great start, and I was beginning to listen. 

I spent a few months doubting myself: 

- but what will I say? 
- who will listen? 
- do I really want to be “public?”

And then, I said f-it let’s go, and I went all in. 😇

Here’s the thing: it’s still early days. It’s not too late, and whether you’re a business owner or an employee of a business, a personal brand can *only* help. 

I’ll expand on these tactics in a newsletter soon (subscribe in the comments) but here’s the quick & dirty:

1️⃣ Post Consistently 

 →  # per week & timing

2️⃣ Optimize Your Profile 

→ see link in comments

3️⃣ Land on 3-5 Content Pillars 

→  what you’re going to talk about

4️⃣ Max Out Connection Requests 

→  every single week, w/ a note

5️⃣ Write in Easy to Follow Formats 

→  lists & short paragraphs like this post 

6️⃣ Mix Up Content 

→  text, images, graphics all help 

7️⃣ Comment, Comment, Comment 

→  on people’s posts with audiences you want
→  some of my comments get more views than posts! 

8️⃣ Write Posts with Strong Hooks 

→  or they’ll literally never be seen 

9️⃣ Promote as Little as Possible 

→  give 10x more than you sell

🔟 Be You 

→  always!

LinkedIn has become a huge outlet creatively, a place to practice writing, and a strong funnel of awareness for my business.

And the best part? It’s an extremely kind platform to be “public” and 99.9% of people on here are respectful & professional. 

Start commenting. Start posting. 

It’s still early days. 

💕

Below: 

- What else do you want to know? 

- If you have a goal for 2026 that relates to building your personal brand, share it below. Let’s hold ourselves accountable! 

- And find someone great to follow in the comments. 

♻️ 👋 Share & Follow Maggie Olson to support this post. 

💻 Subsribe to my newsletter in the comments for expanded personal brand tips, coming soon.

Let’s talk about the levels of a Chief of Staff.  
  
Often, I see complex leveling frameworks trying to be used as the black & white solution to exactly how the levels in a C-suite organization should play out.  
  
EA is this, Sr. EA is this, CoS is this. Etc.  
  
I fight this… hard. Why?  
  
Because outside of writing job descriptions, those frameworks fall flat in the real world.  
  
Chiefs of Staff don’t fit neatly into boxes.  
  
They’re managers, directors, VPs, and execs. They’re individual contributors and people leaders. They’re brand new to the workforce and C-suite veterans.  
  
That’s what makes this role so complex and so compelling.  
  
It's about the person. Not the resume.  
  
Here are three real-world examples to help explain this further:  
  
 
✨ Juan, Chief of Staff  
  
📍 Level: Manager | 3 years’ experience | $110K base  
  
→ Hired by a Midwest EdTech CEO at an early-stage startup  
→ Paid with a mix of equity + incentives  
→ Seen as a high-potential operator and future exec  
  
Scope: Prepping the CEO, running all-hands, managing internal ops, owning team culture, and jumping into whatever’s needed.  
  
 
✨ Molly, Chief of Staff  
  
📍 Level: Director | 8 years’ experience | $175K base  
  
→ Hired by a healthcare EVP after years in program leadership  
→ Naturally gravitated toward strategic support and cross-functional work  
→ Finally realized this was the job she’d been doing all along  
  
Scope: Leads cross-company projects, strategic planning, and executive team initiatives.  
  
 
✨ Dasha, Chief of Staff  
  
📍 Level: VP | 27 years’ experience | $300K base  
  
→ Hired by a retail CEO who needed a seasoned #2  
→ Former founder, C-suite exec, and industry insider  
→ Serves as advisor, proxy, and filter between the CEO and the org  
  
Scope: Runs CEO meetings, drives strategic initiatives, and leads a small internal team.  
  
—  
  
Three examples out of thousands.  
  
Thousands of paths, thousands of backgrounds, thousands of different paths & experience levels.  
  
ALL making great Chiefs of Staff…And ALL of their work dependent on what that business (and the business leader) NEED.  
  
In the comments: Who do you identify with best from this list?  
 
 
♻️👋 Engage, share & follow Maggie to support this post.

Many Levels of CoS

I use ChatGPT more than I use Instagram, email, & Google combined. I can’t be the only one thinking about these quirks. 

(Aka complaints, tips, & annoyances)

I’m not a UI expert and I’m not a techie.

But I am a Chief of Staff turned CEO of a fast growing company. 

And I use ChatGPT hourly most days. 

6️⃣ Extremely Random Musings: 

1) Why (why!) as one of the richest companies in Silicon Valley, does predictive text not work on the ChatGPT app. 


2) For a technology platform that is used hourly by said power-user, the mobile & desktop interfaces need to be much more similar. 

If I’m on the desktop version all day & new chat is in one spot, when I switch to mobile at night new chat should be in the same-ish spot. It feels too different. 


3) A few weeks ago for whatever silly reason I found on the internet, I named my ChatGPT “Quinn.” (for everyone who’s also named yours, plz share the name in the comments.) 

But omg, last week “Quinn” started calling ME Quinn. I could see how futuristic robot world could go incredibly wrong here. I corrected it & we’re back to normal, for now. 


4) At Our last training conference, I learned the concept of a “go word” from one of our students, and for some people I feel like it’s going to be life changing:

You train your ChatGPT to allow you to send prompt after prompt through but until your “Go Word” is used, it won’t return results for you. 


5) As we know, tech platforms (aka their investors & stakeholders) want you on their platform longer & longer. Unfortunately I’m seeing that now in a big way on ChatGPT in recent weeks. 

Everything I query, even after 4 rounds of grammar & spell check, Quinn asks if I’d like a different take, another small correction, a slight improvement. OMG no… this will have the opposite effect. 


6) Can we not relate everything I do in ChatGPT back to my work? Seriously though: 

- researching a recipe and it finishes the query with how Chiefs of Staff exist in a variety “of flavors.” 

- doing travel planning and it relates where I’m going to “the journey of EA to CoS.”

- My kids medicine is not “like the fix every CEO needs when they hire us.” 

Lol. 


If you’re like me & you have a list in your phone of ChatGPT or LLM oddities, please share below. 👇 

Or maybe you have a solve for predictive text?! Ty!

♻️👋 Engage & share to support this thread. And follow Maggie Olson for daily CoS & Founder content.

If you’ve ever been a Chief of Staff, you know the role changes you forever.

It shapes how you think, lead, communicate, and operate in every room you enter. 

This week, I’ve been reflecting on the pieces of my own Chief of Staff experiences that I’m most grateful for.

Here are mine:

→ Incredible proximity to senior leadership
→ Learning to build influence without authority
→ Partnering closely with & learning from talented EAs
→ The blend of art and science throughout the CoS role 
→ The chance to lean into what I’m naturally good at
→ Solving messy, ambiguous problems over and over 
→ Managing big, high-stakes initiatives & stakeholders 
→ Learning directly from so many experienced leaders 
→ Seeing how a business truly operates, top to bottom
→ Exposure to so many people across organizations 
→ Contributing & leading major company priorities
→ Studying how leaders think, speak, and make decisions
→ Understanding what strong & weak leadership looks like
→ Seeing how multi-million dollar decisions get made
→ Working in a role built on trust & learning how to build it 
→ Experiencing how major events are run behind the scenes
→ The ability to be lead with listening and curiosity 
→ Practicing ruthless prioritization in real time
→ Confidence that I can lead BIG things

That last one hits home for me. 

I never would have had the confidence to step into a Founder role and build a company without my Chief of Staff experience. 

It simply shapes you. 

✨ 

What are you most thankful for from your Chief of Staff role? 
Share in the comments. 

♻️👋 Engage, Share and Follow Maggie Olson for daily CoS and leadership content. And, Happy Thanksgiving! 🦃 

(Stay tuned for a special Nova Black Friday announcement later this week... you won't want to miss it.)

Am I using AI intentionally? 
 
A year ago, I made a simple mindset shift with how I was using AI. 
 
I replaced anything I planned to Google, with ChatGPT instead.  
 
Not only because the results are far better, but more importantly, to build comfort using AI and to begin to learn the vast use cases it supports. 
 
I don’t google anything anymore, personal or professional. 
 
And when I forget and do, I end up regretting it. 
 
Here’s what this looks like in practice. 
 
 
✅ Swap Google for ChatGPT  
 
→ Build familiarity and learn the ways ChatGPT can help you, from life to work.  
 
 
✅ Stream-of-consciousness prompting 
 
→ When I am needing something vague and complex I “talk it out.”  
 
→ I’ll speak ideas or half-formed thoughts into ChatGPT to ensure I’m giving enough detail and setting up the results for success.  
 
 
✅ ChatGPT is a starting or an ending point, but not both 
 
→ A starting point that offers ideas or things to think about (with many prompts). 
 
→ An ending point for a grammar check and preserving content (one prompt). 
 
 
✅ Plan to re-prompt a few times 
 
→ That’s how it works. Each iteration sharpens your thinking. 
 
 
Here’s what I’ve noticed since making that shift: 
 
I save hours each week. 
I’m thinking about things in different ways.  
I’m learning faster because I ask better questions. 
 
AI isn’t replacing the way I work. 
 
It’s supporting it… immensely.  
 
I’ll pass the reflection to you: 
 
➡️ How are you intentionally using AI right now? 
 
♻️👋 Engage, share & follow Maggie to support this post.

Happiest thanksgiving to everyone who knows their role 😇

There’s a connection in here to Chief of Staff but we’ll leave that for tomorrow (or for you to help me with in the comments). 

Gobble gobble! 🦃

What do Chiefs of Staff and one of the most successful executives in media have in common?

Everything.

The path between operational execution and strategic scale can be hard to see while you’re walking it.

But it’s where leaders are BUILT. 

And why a successful Chief of Staff role develops *world-class leaders.*

Barry Diller started his career in the mailroom and went on to become CEO of Paramount Pictures. Today, he’s the founder and chairman of IAC and Expedia Group. 

His career has been defined by risk-taking, instinct, and *relentless execution.*

I’ve loved his book. 

Wonderful storytelling, a humble leader, and incredible parallels between his early career and the similarities found in his success to a strong Chief of Staff or strategic operator.  

His journey relates to many navigating the CoS journey at the beginning: 

…lacking confidence but holding the determination to *figure it out.*

7️⃣ Takeaways for Chiefs of Staff from Barry Diller’s book (& my thoughts): 

- He admits he “couldn’t add beyond basic math” and was financially illiterate while leading a company with 600M in debt. His solution? Jump in the deep end and fake it until he made it.

(Find resources & figure it out) 

- He talks about how managing top-down is nearly impossible if you haven’t managed from the bottom up.

(ahem: influential leadership). 

- He calls instinct, influence, and execution a kind of poetry — and says instinct is what he prizes, not experience, research, or data.

(Instinct > data is the hill he’ll die on) 

- He believes metrics applied to basic decisions waste time and money, and that staying naive and underexpertised helps you recognize a good idea.

(Deep industry expertise is overrated) 

- He says this process became his baseline mantra: “muck around enough until the gears finally mesh and you figure it out.” 

(Dive in & learn above all else) 

- He recalls standing in front of bankers, tasked with explaining how he’d turn around a company, and thinking, “Me? Well I couldn’t do much but I could tell a good story.”

(Storytelling is everything) 

- His philosophy with less experienced employees, “drop them in the deep end and see who survives. Promote the ones who do.”

(Simply obsessed & totally agree) 

That’s the essence of the Chief of Staff role.

You’re dropped into the deep end to learn how to navigate a new business, a new leader, a new team, and a role without clear direction. 

You lead with influence, high EQ, humility, and excellent execution. 

And somewhere along the way you look back and realize you just received an undergrad + MBA level education in less than 2 years. 

And you’re unstoppable. 

Thank you, Barry, for the great story. 

And the lesson that even the greatest executives lack confidence & expertise. But above all:

*They have the determination to figure it out.*

👇Did you read? Let me know your take below. 

♻️ 👋 Engage with this post to show your support & follow Maggie for daily CoS content.

I’ve spoken to thousands of aspiring & existing Chiefs of Staff. Here is the advice I give most often: 

I’ve been a people leader for 20 years, a Chief of Staff for five, and an entrepreneur for three.

Here’s the advice I give most often to everyone regardless of their role: 


1️⃣.  Raise your hand, share your value, & ask for what you want. 

Someone else is out there advocating for themselves and helping a leader understand why their team would be better with them. 

Don’t miss out because you’re waiting to be tapped on the shoulder. 

2️⃣.  Lean into your strengths.

Most people lack confidence based on what they think they’re *not* good at. 

I entered my MBA program surrounded by engineers and had major confidence issues around high-level math. Turns out, those engineers were all there to be more like me: to learn people leadership and communication skills. Which apparently they viewed as far more valuable (I can see that now). 

Switch the narrative in your head and lead with your unique value, and the confidence knowing that you can figure out what you have to, but it doesn’t have to be now. 

3️⃣.  Network network network & never stop. 

The higher level the role, the less cold applications are going to work. For Chief of Staff & executive-level jobs you need to already be in someone’s brain when they consider who they’re going to hire. 

Data shows that connectors get connected. Weave networking into your professional rhythm. 

And when you network consistently & maintain strong relationships, you always have people to call when you need help with something like, deep financial analysis where you may be softer in experience. 

4️⃣.  Build systems, processes, & tools to support yourself & the business. 

Whether your executive & their team adopt many or few of the tools you implement, you *must* build these systems, tools, & processes for yourself to thrive in your role. 

Executive back offices are constantly changing, and to support this we have to have places for all the things to land and starting points to see things clearly, recommend strategic changes, and take true ownership where needed. 

One of the first things a CoS (and many other roles) should do is document current state, but flexibly, knowing it will change. It will lead to #5. 

5️⃣. Be the person who finds & recommends solutions.

No matter what role you’re in, the person who’s known for just *getting sh$t done* is talked about in rooms they’re not in. 

Take it a step further and stop asking, start recommending solutions, and using the assumptive close framework to lead with a bias for action. 

__


Sometimes it helps knowing that we’re all working on the same things. 

Pick one or two, make a goal, and go get after it! 

Anything jump out at you? Share in the comments. 

♻️ 👋 Engage & share to support this post. Follow Maggie Olson for daily leadership.

taplio

Maggie Olson's Linkedin Analytics

Maggie Olson

Performance ScoreMaggie Olson's LinkedIn Performance

Maggie Olson's Best Posts (last 30 days)

Ready to grow your LinkedIn presence?

taplio

.css-6ytdur{background-image:linear-gradient(284deg, rgba(39, 43, 72, 1) 0%, rgba(33, 47, 183, 1) 100%);color:transparent;-webkit-background-clip:text;background-clip:text;}Maggie Olson's Linkedin Analytics

Maggie Olson

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Maggie Olson's LinkedIn Performance

Maggie Olson's Best Posts .css-1emoo84{font-size:var(--chakra-fontSizes-md);font-weight:400;color:var(--chakra-colors-gray-600);}(last 30 days)

Ready to grow your LinkedIn presence?

Maggie Olson's Linkedin Analytics

Performance ScoreMaggie Olson's LinkedIn Performance

Maggie Olson's Best Posts (last 30 days)