How to Bring an Operating Model to Life (and Keep It Alive)

Learn the playbook and pragmatic tactics for early-stage fundraising from Mike Wilner, a startup founder, advisor, and author of Oversubscribed, a book on seed fundraising.

 min read
Last Updated: 
July 5,2021
Article Category

A Tactical Guide to Seed Fundraising

Learn the playbook and pragmatic tactics for early-stage fundraising from Mike Wilner, a startup founder, advisor, and author of Oversubscribed, a book on seed fundraising.

 min read
Last Updated: 
July 5,2021
Sachin Maini
Editorial and Content Lead
Heading 1
Heading 2
Heading 3
Heading 4
Heading 5

Heading 1

Heading 2

Heading 3

Heading 4


Paragraph text goes here

Block Quote looks like this
  1. List 1
  2. List 2
  3. List 3

Josefin Graebe’s Chief of Staff journey began seven years ago when she moved from Germany to the United States to work for German software company SAP in the Bay Area. At SAP, she had her first touchpoint with the role in reporting to the Chief of Staff to the Chief Marketing Officer. 

After a couple of years at SAP, she decided she wanted to move into a role at a consumer-facing company. After monitoring Uber’s job page for six months, she saw a position open up for Chief of Staff to the VP of Product and got hired for the role, where she served until being recruited by Lime to be the Chief of Staff to the CEO. She’s now working at Appfolio as the Director of Growth Strategy and Operations. 

Through these experiences, Josefin has gotten to know what it’s like to work as a CoS at companies of various sizes and stages. Across all of these companies, she noticed a pattern:

“All these companies faced similar challenges, just on a different scale. They all tried to figure out, ‘Hey, how can I translate strategy into results? How can I create an operating model, and how can I keep it alive?’”

Her experiences have lent her actionable insight into these questions. Below, she dives into the principles she’s devised for designing, implementing, and sustaining operating models, setting a company’s operating cadence, and more.

What is an “operating model”?

What is an operating model, and why is it so important? It is the set of systems, structure, processes, governance, behavior, and cadence that a company runs to execute on their strategy and turn it into results.

“The main goal of an operating model is to translate strategy into results.” 

Together, they define how the organization is run.

Inspired by Original Image from Bain & Company

According to this report from Bain & Company,  companies with thoughtfully designed operating models post better financial results than those without them. Companies that have designed successful operating models share one thing in common: they figured out how to align people, processes, and systems so that they work toward the same strategic priorities. 

However, the hardest part of implementing an operating model isn’t designing it, but bringing it to life and keeping it alive. That’s why the process of setting up an operating model should center around design principles —  an operating model is only useful insofar as it can be put into practice. 

4 Design Principles for Building An Operating Model

There are 4 core design principles to focus on in building an operating model: 

  1. Start with an MVP mindset
  2. Structure follows strategy
  3. Dance to your own rhythm
  4. Meetings matter

Principle #1: Start with an MVP Mindset

While listed as #1, having an MVP mindset is better regarded as principle zero because it can be applied to everything you do as a Chief of Staff. 

As most people in tech know, an MVP (minimum viable product) is the most stripped-down version of a product that still manages to deliver on that product’s unique value proposition. For a CoS, this might be more aptly thought of as a minimum viable process.

At its heart, an MVP is experimental. It’s a means of testing whether a product will be impactful while using as few resources as possible to do so. This experimental approach to product enables rapid learning, iteration, and, consequently, improvement. 

This same mindset is key to building operating models — because there is a surprising level of overlap between being a Chief of Staff and a product manager.

“As a Chief of Staff, you are technically a product manager. Your products are processes and systems, and your audience is all of the employees.”

Because of this, many of the same methodologies used by product managers can be used as a Chief of Staff in setting up your MVP operating model. For example, it can often help to try and apply an MVP mindset to everything you do—- including conducting your own user research, interviewing employees about what they really need, and continually testing and iterating based on that information. 

And just like a product manager,  building an MVP to test out your ideas before going to the lengths of compiling an in-depth, polished, process-heavy slide deck for your operating model is likely a good idea. 

An MVP should be the simplest possible version of the process you’re trying to create. With an initial MVP having been built, you then test and iterate on it until you see it gaining adoption. Only once it comes to life does it make sense to formalize it as a deck. 

Any systems or processes (and thus any MVPs) that a Chief of Staff constructs should be:

  1. Valuable. Add value to your company and its employees.
  2. Usable. Easy to understand and run.
  3. Inclusive. Rooted in the culture and values that your company lives and preaches every day.

Principle #2: Structure Follows Strategy

Building an operating model starts with defining strategy. This is because an operating model, and the systems that comprise it, must first and foremost be valuable. Their purpose is to serve a higher end—namely, the strategic success of the company. 

The structure of your organization and the design of the systems you implement will then follow from your strategic goals. Bridging that gap entails defining strategy, embedding strategic priorities in the org structure, and mapping talent so that you can help align high-performing talent with their areas of highest leverage.

Defining Strategy

As Chief of Staff, it’s typically your job to facilitate the annual planning process. Start with first principles by reflecting on and clearly defining the goals that will drive the rest of the planning process. Working together with the leadership team, you’ll think through and establish the strategic priorities for the year to come. 

Embedding Strategic Priorities in the Org Structure

With your strategy well-defined, your next task is to turn your attention to the org structure and examine how it might be adjusted to better serve your strategic priorities. This means organizing teams within the company so that they’re set up to successfully execute on strategy. 

Companies and their strategies grow and develop over time, and the org structure should follow. During her work at a previous company, for example, she found that their matrix structure no longer suited their strategy. In light of this, she spearheaded a company-wide shift to a functional reporting structure. 

Talent Mapping

This is a critical yet often overlooked step in the planning process. 

It can be extremely valuable to do talent mapping after composing your org structure. This means identifying high-impact roles within the new org structure, identifying your high-performing employees, and matching the high-performers to the high-impact roles. 

This is important because there’s no faster way to lose high potential employees than to keep them from making the impact they’re capable of. It’s important to stay actively attuned to your high-performers’ needs. 

As the Chief of Staff, you are the sounding board for the organization.”

This means listening to your employees —  and going out of your way to do so. They might not be eager to come forward with their dissatisfaction, so you need to position yourself as someone they can bring their concerns to. 

You can then funnel these concerns up to the leadership team. Even better, proactively reach out to them to make sure their needs for challenge and impact are being met. A preventative approach can go a long way in retaining top talent.  

If you have a well-developed HR team, you can partner with them in this endeavor. Together you can work to compile an organizational health deck composed of data on attrition, promotion, how quickly employees ascend the ranks of the company, where hires come from (internal vs. external), DEI, etc. 

A handful of concerns reported directly to you might be dismissed by senior leadership as anecdotes, so data can be used to build a more compelling look into the health of the organization. If the data reveal that talent is leaving and citing lack of challenge as a reason in their exit interviews, it’s time to look at the org chart and consider whether talent re-mapping might be necessary.  

In some cases, you might find a high-performer who feels unchallenged, but you don’t have a higher impact role readily available for them to fill or they’re missing a couple of the skills necessary for such a role. 

In this scenario, it’s best to talk to the employee in question, let them know their talent is recognized, and brief them on the skill gaps they need to fill over the next several months to be prepared for this next role once it opens. This can help make them feel valued, give them something to look forward to at the company, and reinvigorate their efforts toward professional growth. 

Translating Strategy into an Operating Model

The next step is to design your operating model itself. This should be done after the org structure is set and you’ve done talent mapping.

Your operating model has to serve not only your strategy, but also your people.”

Make this the last step of your annual planning process. At this point, you can now consider how your operating cadence and the broader operating model might be adjusted to best serve your strategy and your people. 

Reality won’t look as smooth as the overview provided here, though. Inevitably, nuances and complexities will arise during this process. One of the most daunting of these concerns is overcoming organizational inertia. Your operating model and cadence need buy-in from the people at your company in order to survive.

One challenge you are likely to experience is that employees will often be set in their ways and resist the changes you’re looking to implement. A few tricks for dealing with this:

  1. Get buy-in early on. This is a task where donning your product manager hat will be particularly useful. Get buy-in from your “users” early on before you’ve built anything. Interview them as a PM would in order to better understand their concerns. It’s much easier to create a solution that people love by involving them early on, rather than presenting it to them only once it’s finished and hoping that they like it. 
  2. Represent every team in the company. Not only should you talk to users early, but you should talk to members of every team. Make sure that you’re able to faithfully represent and consider the desires and concerns of each one, then build the operating cadence based on these collective insights. This will also help later on because you can demonstrate to those who are resistant that you did your best to take into account their needs and the needs of their team. 
  3. Find an executive sponsor. The support of someone such as the COO who serves in a leadership role will go a long way in helping you successfully bring your operating model to life. 

They won’t clear your path of all obstacles, but these tactics provide a strong foundation for breathing life into your operating model and driving enthusiastic adoption.

Principle #3: Dance to Your Own Rhythm

There’s no one-size-fits-all solution when it comes to operating models. This idea underpins the third principle for operating model design: “dance to your own rhythm.” 

Each company is unique, and each operating model should be too. The perfect model for Apple won’t be perfect for your company. You need something uniquely suited for your organization and its strategic needs in order to make it usable. The right model in the wrong company is the wrong model. If it’s at odds with the nature of your organization it will only create friction. 

So how do you develop an operating model that fits your organization? By identifying valuable norms and systematizing them. 

In doing so, you use the implicit idiosyncrasies of your company (the norms) to inform the actual explicit systems that make up your operating model and cadence. This creates alignment between your company’s unique identity/needs and the processes by which it operates—a dance to match your rhythm. 

Finally, it’s important to keep in mind that fast-growing organizations like startups are highly dynamic so your operating cadence should be too. It’s a good idea to check in every 6 to 12 months to ensure that the current operating cadence is fulfilling its purpose. 

The Meeting Matrix

One way to keep your operating model on track with a dynamic, evolving company is using a “meeting matrix,” which charts  recurring meetings within the company by their frequency and audience (i.e. who’s involved).

Image inspired by an image in Death by Meeting by Patrick Lencioni

While a meeting matrix won’t look the same at every company, Josefin finds the meeting matrix useful because 

“If you document all the meetings you have and categorize them by audience, it helps you to make sure that your operating cadence stays in sync as your company evolves, as your culture evolves, as your strategy evolves.

Just as the perfect cadence for Apple won’t be the perfect cadence for your company, the perfect cadence for your company last year likely won’t be the perfect cadence for your company today.

Operating cadence should therefore be dynamic, and having a meeting matrix for each stage in the company life cycle is one helpful tool you can use to ensure that it is.

Note that the examples below are not meant to represent best practices, but rather show what a company’s cadence might actually look like at each stage.

The Early-Stage Meeting Matrix 

This first matrix illustrates a cadence that would be appropriate for an early-stage startup of around 10 to 20 people.

The meeting cadence in the example above is fairly light compared with what you might find at a later-stage company. There’s no dedicated meeting for middle management and people managers. 

This is fine for an early-stage company, however, because it’s easy enough at this size for the team to stay aligned. Seeing this cadence at a larger company (50+ people) would be cause for concern because more is often needed.

The Scaling Company Meeting Matrix

A company that’s in “scaling mode” will need a heavier meeting cadence, and its meeting matrix reflects that. 

At the scaling stage, there are 3 adjustments that you might consider making:

  1. Create meetings for leaders to sync
  2. Make sure to keep strategic vs. tactical meetings separate
  3. Make time for succession mapping and 

More on each below. 

Create meetings for leaders to sync

One meeting type that may start to make sense in the scaling stage is the monthly “Leaders Sync” meeting. Consider instituting a meeting of this nature as a company scales to give senior leaders who aren’t execs, but who are still responsible for translating strategy into results, a place to convene on a regular basis. 

Forums like this can be quite important. For example, when Josefin was at Lime, it was in a “hyper-growth” phase. This meant that new executives were getting introduced, and some people who previously reported to the CEO were now reporting to the COO instead.

This separation is inevitable as a company grows, but it can be a bit painful, especially for those who are used to having a direct line to the CEO and the information that comes with that. 

Josefin navigated this tricky situation at Lime by encouraging executives to have transparent conversations with leaders whose reporting lines had changed. It’s important in such a scenario to explain that the team had grown too large and to provide insight into why some people were going to remain a part of it while others weren’t. 

But most importantly, she offered this new monthly Leaders Sync meeting for all the non-exec senior leaders to meet with the CEO so they could discuss strategy, performance, and whatever else they might need to run their teams successfully.

Keep tactics and strategy separate

As a company scales, another concern to be mindful of is keeping tactical and strategic meetings separate from one another. Strategic meetings should focus on the long-term goals of the company and the roadmap for achieving them. Tactical meetings hone in on more concrete, short-term actions that your company can take to execute on its strategy. 

It is usually best that these two endeavors remain distinct. As described in Death by Meeting:, leaders tend to reconsider strategic decisions when faced with tactical challenges.

Consequently, mixing tactical and strategic topics together in the same discussion should be avoided. Devise your meeting matrix to enforce this, separating the two so that strategic decisions aren’t made due to tactical challenges. This manifests as a weekly LT meeting (for tactics & alignment) and a monthly strategy meeting.  

If one of these LT meetings begins to devolve into strategic considerations, you can then pull the team back on track by reminding them that their strategy meeting is coming up and they’ll be able to discuss those issues there. For particularly urgent matters, they can move that meeting forward, if need be. The strategy meeting can then be deliberately prepared to handle these concerns and whatever other strategic issues require addressing. 

Preparation would include things like getting the right people in the room, making sure you have the necessary data on hand, and documenting the meeting more thoroughly. With this system in place, they can rest assured that they’ll have a well-prepared forum in which to discuss these matters. 

Make time for talent mapping and succession planning

Most companies have a performance review system, but many neglect a regular talent mapping process. This is a mistake.

A talent mapping process should involve sitting down with the company leaders and identifying skill gaps and needs in order to construct a talent acquisition and development plan for the next 6 to 12 months. 

In doing this, it’s important to create succession plans for crucial roles within the company. Especially in environments like Silicon Valley where the turnover rate is sky-high, this process warrants more frequent conversations.

The Enterprise Meeting Matrix
“Every meeting should serve a purpose.”

Chiefs of Staff should keep this in mind at all times, but especially at large-scale companies where meetings can grow redundant and meeting oversaturation is a real concern.  

For example, the enterprise company meeting matrix shown above is beginning to reach oversaturation. When this happens, look for places where meetings can be combined. In this matrix, for example, maybe the monthly business review for the last month of the quarter could be rolled into the quarterly leadership offsite. 

Likewise, the coffee chats, town halls, and all hands are probably a bit redundant and could be combined in some regard. The lines between these kinds of meetings are often blurry and employees often don’t really know the differences between them. 

If you find yourself faced with such overlap, return to first principles and ask what you’re trying to solve. Then work from there to structure the meetings so they’re actually solving that problem. This might mean dedicating one type of meeting to sharing information top-down (from leadership to the rest of the company) while making another that’s driven by employees and gives them the opportunity to ask questions of executives. 

The idea is to establish clarity and focus in your cadence. Make this cadence clear not only for yourself and the LT, but for all members of the organization. 

One tactic for doing so is to make your company-wide meeting cadence accessible to the whole team. This fosters transparency and gives employees the opportunity to ask questions about these meetings.

Regardless of your company’s scale, one thing you should likely do is go on a “listening tour “prior to implementing any disruptive changes in cadence. 

This means asking people how they feel about those meetings that might be changed and, if changes definitely are going to be made, helping them to understand why. During this process you can also sit in on meetings to see which ones need to be made less frequent or killed altogether. 

Principle #4: Meetings Matter

As mentioned earlier, any system or process you build as CoS should be valuable, usable, and inclusive. Meetings are the bedrock for ensuring that your organization is inclusive. They’re the vehicle that brings everyone at your company to the table. And they really matter.

Kevin Fishner, Chief of Staff at HashiCorp, speaking on the First Round Review podcast, put it well in saying that: 

“It’s very possible that for many employees, their only face-to-face human interaction for that day is through a meeting. If that meeting is good, then their day is good. If that meeting is bad, then their day is bad.”

Therefore, it’s important to strive to structure your operating model to make the company meetings both valuable and inclusive. A few ways to ensure this:

  1. Break the meeting cycle with deliberate meeting design
  2. Optimize meeting size

Break the meeting cycle

The “meeting cycle” refers to the loop that often occurs where a topic comes up in a meeting and someone suggests, “Let’s take this offline.” When it comes up later on, someone then says, “Let’s talk about it in the meeting.” 

Original Source: @lizandmollie 

Then, when broached at the next meeting, it again gets taken offline, the cycle repeats, and the can just keeps getting kicked down the road. According to Josefin, this tends to happen for three reasons:

  1. You don’t have the right people in the room to properly address the topic. Deciding who needs to be in the room can easily become a political issue and is usually up to the Chief of Staff to solve. 
  2. It’s unclear who holds the decision-making authority on this issue.
  3. You’re missing the data you need to confidently make the decision.

Breaking the meeting cycle, then, is a matter of tackling these three issues through deliberate meeting design.  

Find the right meeting size

Setting the right sizes for various meetings is a key component of effective meeting design. Tackle this challenge using a first principles approach by constructing a table that outlines the problems and goals of each meeting. 

Seeing these problems and goals lends insight into how many people are needed for that particular meeting. For example, the purpose of an all-hands is information sharing, so there’s no real cap on the number of attendees. LT and strategy meetings, however, involve data, in-depth discussions, and decision-making. They typically shouldn’t exceed around 10 people.

For most meetings, anyone who doesn’t need to be there probably shouldn’t be there. One way to determine who does or doesn’t need to be there is to pour through documentation from previous meetings and look at:

  • Who was there?
  • What decisions were made? 
  • Who was needed to make those decisions? 

Use these past meetings to predict who will be needed in future meetings. This can be a collaborative effort with HR. There are also frameworks like Bain’s RAPID that can help you decide who should be in the room.  

To effectively gauge and set the size of a meeting, one simple method you can use as a rule of thumb is Amazon’s two pizza rule — meetings should be small enough that two pizzas can feed the whole group (you can even add a fun twist by hosting a Zoom pizza cooking party/meeting for your team). 

Downsizing meetings will inevitably lead to some team members feeling left out. As Chief of Staff, make sure the people not in the room don’t experience this FOMO. A few tips to support those who can’t be there:

  • Share the meeting agenda with them beforehand. Give them the freedom to speak up if they feel that something on the agenda demands their presence.
  • Share the meeting notes with them afterward so they’re kept in the loop.
  • Provide a different, async forum for them to stay connected on these matters (e.g. a Slack group for the LT where you post updates from the exec team at the same time the meetings used to happen). Ask for their questions and encourage them to share their concerns.
  • Finally, frame the changes being made as an experiment. Let them know that if these changes end up being for the worse, you’re amenable to switching things back to the way they were. Offering this will provide comfort and promote buy-in for those who are hesitant. If a change really does make a positive impact, they’ll likely come around and support it after this has proven to be the case. 

This experimental approach can be applied to most of the changes you implement as Chief of Staff. They tend to be “two-way door decisions”  where you can walk back out the same way you walked in if need be, which is consistent with having an MVP mindset.

Bringing An Operating Model To Life

In sum, the key to  designing an operating model that can be brought to life, and kept alive, rests with these 4 core principles:

  1. Embrace an MVP mindset. Think like a product manager and test out the minimum viable process for any system you want to implement. You can almost always go back to the way things were if something you try doesn’t work out—use this knowledge to give yourself the freedom to experiment.
  2. Start from first principles/strategy. Use strategic priorities to help shape your org structure and talent map to make sure your high-performers are in your high-impact roles. Then develop your operating model in light of these strategic and structural considerations. 
  3. Dance to your own rhythm. No two companies are alike. Set a cadence that works for your organization and its unique qualities and needs. Your organization will also be different a year from now than it is today, and your cadence should reflect this. Check in every 6 to 12 months and evaluate whether changes need to be made. 
  4. Meetings matter. They’re the place where your operating model comes to life. Design meetings and set your cadence deliberately. Make sure each meeting serves a purpose and that participants are clear on what that purpose is. Only the people who need to be in the room should be there, but it’s your job to ward off FOMO for those who would still like to be there by keeping them up to speed.

Building your operating model with this in mind should provide a strong foundation that you can return to again and again as you continually hone your own operating models and sharpen your craft as Chief of Staff. 

Get tactical advice sent straight to your inbox every month.

Aaron Appleton
Abhijeet Patra
Abhishek Anirudhan
Ada Nguyen
Adam Gelman
Afraj Gill
Akanksha Manik Talya
Alexandra Barr
Alexandra Worthington
Ali Greenberg
Alice Wilson
Allison Dea-Kemp
Amine Aboura
Amrutha Adusumilli
Amy Story
Anastasia Chapman
Andre Bjork
Andrea Torres
Andreas Klinger
Andrew Rea
Andrew Yu
Andy Barr
Angie Ryan
Ani Pai
Ann Ferracane
Ann Miura-Ko
Anna Drabovskaya
Anne Bosman
Anthony Nardini
Ari Calumpang
Ari Gootnick
Arielle Tannenbaum
Ash Wesley
Asher King Abramson
Asher LaBostrie
Ashna Mahtani
Ashwin Lalendran
Asta Diabate
Barry Conrad
Bea Aguila
Becky Stephens
Benjamin Plummer
Bernadeth Madlangbayan
Blake Arensdorf
Blue Davis
Boydie Maraj
Brandon Taleisnik
Brandon Zhang
Brennan Foo
Brett Wietecha
Brianne Ilagan
Callie Cox
Callum McDonnell
Cam Sadler
Candice Ammori
Carly Dalgleish
Carolyn Wakulchik
Chai Flores
Chaitanya Choudhary
Chamod Gamage
Chance McAllister
Charles Cushing
Charles Liu
Charlie Taibi
Charm Lagura
Chioma Kalu
Chris Moreno
Clara Ma
Conor Brady
Cooper Charlton
Craig Montuori
Cullin McGrath
Curtis Sandy
Danitra Blue
David Booth
David Fallarme
David Hoang
David Jeon
David Weinstein
David Zhou
Denise Devlyn
Dishita Shah
Don Ho
Donté Verrill Huffman
Eade Bengard
Edgar Brown
Egor Zaitsev
Eliot Gattegno
Eliza Popa
Emily Edmonds
Eric Friedman
Erik Torenberg
Erika Batista
Fadi Hindi
Fernando Wittmann
Flo Bühringer
Gajus Kuizinas
Gautam Shewakramani
Gianna Chan
Gonz Sanchez
Haleigh Wilson
Harry Siggins
Harshita Jain
Hayley Wade
Heath Jamieson
Holly Stinson
Ilia Schelokov
Imran Mumtaz
Jack Fritzinger
Jackie Miller
Jackie Williams
Jackson Steger
Jacob Ruiz
James Sinka
Jamie Farrell
Janel Loi
Jared Gordon
Jason Piersialla
Jenna Kellner
Jennifer Dyck-Sprout
Jill Kismet
Joanna Cohen
Joe Penn
Jolisa Masucol
Jon Kent
Josefin Graebe
Josh Sushan
Julia Culhane
Julian Weisser
Julie Carroll
Juraj Pal
Karel van der Vyver
Karthik Puvvada (KP)
Katarina Smith
Katie Kent
Katya Delaney
Kaylyn Lu
Keith Williams
Kelly Hook
Kelly Kang
Khanh Nguyen
Kieran Ryan
Lana-Lea Dennis
Laura Thompson
Lauren Hoffman
Laís de Oliveira
Lei Ugale
Leon van der Vyver
Lili Welch
Lital Zigelboim
Logan Pugh
Lorenzo Castro
Lucas Hasselfeld
Lucas Vieira
Manar AlSagob
Maranda Dziekonski
Marc Havercroft
Margot Black
Maria Jimena Sanchez
Mariya Boykova
Marshall Kosloff
Marty Bode
Matias Sanchez Sarmiento
Max Nussenbaum
Michael Bassani
Michael Butler
Michael Gill
Michelle Kwok
Mike Daugherty
Mike Wilner
Mindaugas Petrutis
Mindy Zhang
Ming Lu
Minn Kim
Mohga Koshty
Morris Huang
Naida Rosenberger
Natalie Toren
Nate Snow
Nathan Cheng
Neha Khurram
Niko Zona
Noémie Federico
Nur Sevencan
Olga Stogova
Oliver Fisher
Oscar Ramos
Owen Willis
Pablo Martinez-Falero
Pablo Pinto
Patrice Madurai
Patrick Blumenthal
Paul Gleger
Paula Abarca
Paulina Sicius
Pawel Cebula
Payam Salehi
Peter Martin
Peter O'Rourke
Phillip Lemmons