David Hoang — Writing — leadership

Operator Mode

Sun, 15 Sep 2024 00:00:00 GMT

I love Paul Graham’s writing. Hackers and Painters is one of my favorite books of all time. Graham’s thoughts on art and science resonate with me as a designer who studied fine art. The internet broke when the long-time Silicon Valley investor wrote about Founder Mode. There’s been a shift in tech’s factory reset moment during the past few years. The professional management class is getting slashed with the reduction in workforce and the advancement of AI capabilities. Graham’s essay references a talk by Airbnb CEO Brian Chesky about Founder Mode vs. Manager Mode.

As always, the internet had a lot of opinions that obviously have to be binary and polarizing towards one direction; classic Silicon Valley hopping on bandwagons. My critique is not Graham’s writing. In fact, he’s right. What’s wild to me is management somehow got conflated to professional management consulting. More accurately, it’s BCG Mode, not Manager Mode. Instead of picking sides, I’m going to propose a different mode.

Operator Mode.

While we talk about founders and C-suite professional managers, the majority of people working at companies are operators. Tech loves adopting words from the military. An operator is someone who…well, operates—plans and executes. Above all else, I consider myself a company operator (who comes from a design background). In this issue, I’ll share how I think of my role helping founders in running their companies.

Operators that add value

In my experience, there are two primary regrets founders have. The first is raising too much money that results in higher demands from the board. After that, it’s building a leadership team from a professional management class. Both result in the founder losing control and getting tucked in a corner as a Chief Strategy Officer or an honorary title.

It sucks to see that happen. Instead, founders are better equipped to find operators that add value to their needs. There are three core areas I believe are most valuable for founders: managers with strong craft, expansive experience, and scaling the mission.

1) Craft-oriented managers

The concept of professional managers is the biggest mistake. A professional manager is perceived as someone who is hands off, focuses on administration of management, and a master bullshitter. Trust me, these people exist and it's true. Let me ask you a question. As a designer, how would you feel if the person that has authority over your job has a degree in Design Management but has never been a designer? Imagine an army general who has never seen combat, only studying philosophy and tactics. In my opinion, that's not management.

Most direct reports don't expect their manager to be the best designer on the team, but they need to know that at one point they were in their career. In order to grow in your craft—one of the top performance indicators in every career ladder—you need someone who knows the craft to elevate yours.

Founders don't need professional managers. They need strong craftspeople who know how to manage. From first-line manager to executive, the best managers are the ones who are in the role to scale the craft, not something self-serving.

Whether it's being the founding designer or needing to fill gaps with team churn, the craft-oriented manager has no problem rolling up their sleeves.

2) Expansive experience for the company

An operator brings their experience to expand what the startup is capable of. That is the value of bringing someone in. It might be hiring a sales leader to build out a team as the startup expands into the enterprise. Perhaps the company is about to IPO and needs a CFO who has repeated experience in this. The one thing an experienced operator cannot do when joining a startup is live through the past experience of the company’s existence. This is why expansive experience is the biggest value add for startups growing: helping the founder get to where they want to be.

3) Scales the culture

The last one might be the most important. Operator Mode is scaling the culture of the company, not destroying it. When I decide to join a company, I make sure I’m aligned with the culture and values of the company. It’s impossible to align 100%, but I understand it’s part of my job to scale the culture, so I better be on board with it.

When good operators join companies, they transform the culture for the positive. I only join companies where the culture and mission resonates with me deeply because I feel it's my responsibility to help grow it. I'll never have the same influence as the founder, and that's precisely the point. What's important is for them to have other people they trust to scale the culture, not constantly combat it.

My belief is this doesn't mean to blindly execute without question. In fact, the best mission-driven operators will challenge founders on the hardest parts and hold them accountable.

Leading while in Operator Mode

The goal of an experienced operator is to not be a professional manager. The purpose is to help the founder achieve the vision, hopefully with a desired outcome for everyone at the company. It's difficult to achieve both, but that should be the motivation. Let me share three areas I focus on to help founders and why I think they want me in the first place.

Filling founder gaps

Operator Mode is about filling the gaps of the founder, not replacing them. I remember talking to a former colleague at Replit. One of the main reasons we joined was to work with an inspiring founder like Amjad; give him the amplification (but also counter-balance) to be the best founder possible. The goal is not to silence founders but make them better.

The responsibility in Operator Mode is to find areas you can take over for the founder to be more effective. Most pure founders don’t love managing, and they need managers they can entrust to look over the things they care about. I find the duty of an experienced operator to a founder as a crucial one. Founders have been grinding and putting their heart and soul into their company, and now they entrust you with it.

Scaling the entrepreneurial spirit

When it comes to entrepreneurship at scale, there is nobody who personifies that more than Claire Vo. The CPO of LaunchDarkly's philosophy is that she joins companies to help inject innovation. She reminds teams how to work like a startup and not to be a bureaucratic professional management machine. Vo is in the weeds by reviewing designs, getting into the work, and even building Chat PRD on her own time. Having a leader who builds and stays close to the craft is the only way they can help you grow. I still design, craft prototypes, and conduct research. The only difference is they serve a different purpose: to guide, invoke ideas, and stay sharp with the tools.

Operator Mode is leading in executing your craft

Whether a founder, operator, or executive, the goal is leading towards shared outcomes; fulfilling the mission while leading a great exit. Your craft may come in many forms. It might be design or engineering. It might be business growth or recruiting. Good managers know how to right-size process and scaling. Despite their abundant experience, they’ll start with first principles to devise what’s needed, not blindly run a playbook. The balance of craft and management is why I continue loving Operator Mode.

Originally posted on Proof of Concept

Crafting a leadership portfolio

Sun, 08 Jan 2023 00:00:00 GMT

One of the top questions I get asked is what a portfolio for a manager should look like. Unsurprisingly, the answer is like any design answer: it depends. The ultimate output of a portfolio looks different based on so many factors: whether you're in brand or product, the type of management role, and what you're optimizing for. In this post, we'll look at the goals of a manager’s portfolio, what you are optimizing for, and the core elements of a portfolio. There are a few common artifacts you'll have as a manager: résumé/CV, portfolio deck, and website. The last two might be the combo of your portfolio.

Setting clear portfolio goals

The truth is at some point in your management career you will not need a portfolio! You will be reached out to by recruiters or apply based on your experience and credibility, which is a much harder thing to maintain than a portfolio! You might be optimizing your portfolio for different reasons than looking for a new career opportunity. For example, you might want to get into public speaking at meetups and conferences. The content you show there is going to be much different than what you show in a career portfolio.

A leadership portfolio might not be optimized for looking for work.

What type of role am I looking for?
What size team do I want to take on?
What type of industry/product do I want to work on?
Who do I want to report to?

Questions to ask:

Who is the audience for my portfolio? Is this to attract a potential new role, increase speaking engagements, or network?
What type of leader are you? Do you want to emphasize certain skills? Do you want to eventually lead larger teams? Do you want to stay close to the product and lead that way?

Differences between a portfolio for managers and individual contributors

Depending on the level or the role, you may or may not show the work you directly contributed to. For example, if you're interviewing for a product design manager role at an early startup or at an agency, it's very possible that part of your responsibilities is doing the work. If you're interviewing for a VP of Design role, you won't be showing any pixels you pushed (at least I'd hope not!)

Similarities

Learning about what you're like as a person and working with you
You’ll still have case studies that show business and customer impact

Differences

Your case studies will be more focused on what you put in place to enable teams to do the work
You’ll showcase tools you’ve created, such as 1:1 docs, frameworks, and others
Visualize your process of how you got work done
Though it’s good to show business outcomes as an IC, as a manager, this will be expected in your portfolio

Capturing the content for your portfolio

Building a portfolio takes a lot of time, but you can start capturing data of what you'll put in it as you go along. As a manager, the type of impact you make looks different than when you were an individual contributor (IC). Your IC portfolio is more around your work, process, and craft, and the management portfolio focuses on how you manage towards outcomes leading a group of humans. Keep an Infinite Slide Deck to track your work.

Keep a management journal

Journal your experiences as you’re doing the work. It’ll help you keep track of data and moments you want to share later. Trust me, it’s hard to remember later on. As you keep your journal, capture key metrics you’ll need to remember to tell the story.

Career Management Doc by Jessica Ivins
Hype Doc by David Hoang (inspired by CMD)

Constructing the portfolio

My portfolio is a Keynote deck. You can use anything that can be exported as a PDF you can share. I also highly recommend building a website that will be your digital portfolio. The website can serve as general content and the portfolio deck can be more detailed. You may not want to disclose every single detail of your portfolio online, and that's where a website might serve better to speak to things at a high level. It's common for design managers to have absolutely no portfolio published online.

Platform

I recommend having a website and a presentation deck ready to go. The content does not have to match 1:1 but it’s nice to have a website where you can have a general overview and a deep dive slide portfolio.

Elements of your portfolio

About / your leadership story
Career history
Management philosophy

Management approach and frameworks

A few images and slides on your approach to management. This might include your leadership philosophy, what methodologies you subscribe to, etc.

Work

Company and role overview

Summary of your role (Ex: Head of Product Design at Company A, leading growth, product design, and content design.)

Hierarchy of portfolio

Company-level
Initiative level
Project level

Include

Visuals of early ideation, decision points, and final outcome (credit who worked on it)
Company goal
Core metrics

Case studies are different for managers. Though you’ll show project work (presumably what you did leading your team), the story you tell is slightly different. The core elements are:

Executive summary: What were the business goal and customer opportunities? What processes and frameworks do you put in place to drive outcomes for your team?
How did you manage towards outcomes?
Success metrics you put in place for your team
What did people on your team do?

Build a web presence

This can be a complement to your slide deck. I recommend managers have a website. Elements to include:

About

The section that includes details about you:

Bio: A manager should have a quick bio to give an overview of a career summary. Keep it about two or three paragraphs
Resume or CV: This can be a downloadable PDF
Philosophy and leadership principles: A nice section to share a bit about your approach and philosophy to leadership. This isn't essential though very nice to have

Writing

I recommend that managers have a blog, whether on their personal website, or Medium. Writing articulates what it’d be like to have you as a manager or your philosophy. A few examples of good ones:

https://nlevin.medium.com/inside-figma-the-product-design-teams-process-3897332d8565

Featured

Work: Case studies and portfolio pieces you might want to include online. Be mindful of the company metrics you share publicly in case it's confidential

When you're done building your portfolio, you'll have your about page and at least one case study of a project you led.

Best practices and tips

There is no one-size-fits-all approach for a leadership portfolio. However, here are some tips to keep in mind as you build your portfolio.

Focus on outcomes and impact

Focus on outcomes and impact; present your work at a level higher than you might be used to. Your portfolio will look more like case studies of your time at the company and with your teams vs. individual projects.

Tell the story of the product you impacted during your tenure: what difference did you make in the customer’s journey with that product? Who did it impact? At what scale?
Tell the story of how you impacted the business during your tenure: did you launch a new product? A new business line? Impact revenue or go-to-market?
Tell the story of how you impacted people during your tenure: did your team grow? Did you branch out to hire new disciplines? Did you set up a career ladder and promote? Who were your successes?
Tell the story of how you influenced cross-functional team members -- both at your peer level and up/down. Did you help them understand the customer better? How did design impact their roles and outcomes?

Show what your team did and give them credit

It’s okay to show the work of your team. In fact, you should. However, make sure you give them credit.

Display your IC work somewhere to de-risk

Even as a manager, people want to know you used to be a good designer! I recommend including a few pieces of content around your work when you were an IC. No need to go in detail and include this as part of your overview.

Share what you learned

Part of what people will expect from leadership portfolios is the lessons you learned along the way. It will be more authentic if you talk about the lessons and address the “What would you have done differently?”

Example narratives you can tell

Organizational excellence: example of how you identified a gap in how your team worked and solved it
Leading through changes: How you led and kept your team resilient during challenging times
Creating effective processes
Teams you’ve built
Initiatives that you led
How you evaluate work
How you ensure design quality at scale