Issue 42: The Adaptable Chief of Staff as a Pioneer

Lessons from a seasoned Chief of Staff on driving innovation and growth

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Tech Week, (presented by a16z) is a week of 500+ events hosted by VCs and startups to bring together the tech ecosystem. NY Tech Week takes place June 3-9.

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In this week’s issue, we’re featuring guest author Ethan Summers, Chief of Staff at Empirix Partners, a strategic sourcing and procurement advisory.

During Ethan’s colorful career, he routinely chose or ended up in “first on the ground” positions for a new business, unit, team, or product. What prepared Ethan most for the Chief of Staff role was becoming the second CEO of a consumer electronics startup, Fledging, in August 2020. 

While Fledging closed in late 2022, the lessons learned from the major wins and losses refined Ethan’s perspective on one of the roles most unique to the Chief of Staff: The Pioneer. 

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The Adaptable Chief of Staff as a Pioneer

A pioneer is usually the first person to make meaningful progress in a new area. Examples include exploring new lands, new problems, or new industries. In the startup world, they’re go-to-market specialists.

The big difference between a pioneer and an explorer is that the explorer might make a great map, but the pioneer establishes a foothold in the field: the first town, the first working solution, the first product-market fit. 

It's the difference between Becquerel’s discovery of radiation and Marie Curie’s groundbreaking advancements in medical applications.

🏅 Why Executives Need Pioneers

Executives live in the top-left quadrant of the Eisenhower Matrix: everything is both urgent and important. This means their opportunity cost is sky high and makes waste their highest risk.

Courtesy of Ambient.us

3️⃣ factors create a high risk of waste relative to the executive’s other opportunities:

Discovery: The executive might have to spend a lot of time and effort exploring new opportunities. By their nature, most opportunities end with “No.” Executives have a lot of opportunities to discover, too. That’s a lot of “No.”

Development: Good opportunities need to be developed. Though the risk of failure is falling, the time costs – for learning, experimenting, implementing, etc. – grow quickly. 

Skills: An executive’s main job is running their organization, function, or business unit. Their skillset is built for this. Startup executives may point to their founder status as proof they’re great pioneers. That’s true and definitely worth celebrating, but they’re no longer only founders: they're executives. 

Pioneering a business unit, team, process, go-to-market strategy, or anything else requires a deep understanding of the executive’s strategy, risk-adjusted time for discovery and development, and a particular skillset. 

That’s where the pioneer comes in. 

🌟 What Makes a Great Pioneer?

The skill that matters most when it comes to being a pioneer is adaptability. 

Opportunities need to be pioneered. They need to be discovered and developed, or canceled, as quickly as possible. This requires supreme adaptability.

That’s why Chiefs of Staff thrive in the role of pioneer.

With a highly adaptable mindset, they routinely discover new problems and opportunities, develop solutions, prioritize relevant to strategy and resources, and gather alignment for the long-term solution.

Often, the “opportunity” is mandated by the Principal or the organization’s needs. This creates even more urgency while making the discovery process start too late. Chiefs of Staff become great at unraveling assumptions to understand the true opportunity. They may find it’s worth development or that they need to raise the true risks with their executive.

A few other skills typical to great Chiefs of Staff turn their adaptability into a true superpower: Culture/Structure, Operations, and Strategy (our favorite acronym for the Chief of Staff role).

Culture/Structure: Culture is what people do. Structure defines culture. Whether you favor the first term or the second, they can be considered identical for the pioneer’s sake. Structure is how the proposed solution will actually be implemented, supported, and transitioned from the startup phase of a venture, to the growth phase, to the franchise phase. 

Operations: Discovery without development solves little. Operations are the key to developing a new solution. It’s important to note that Operations should be thought of more like a scientific experiment than an assumed solution. Great pioneers rapidly deploy experiments to validate their discovery, and only build the solution once the experiments confirm a great opportunity. 

Strategy: More than understanding what the strategy is, the pioneer has to understand why the strategy exists. Also known as the “commander’s intent,” this is a crystal clear statement of purpose that keeps the pioneer aligned to the vision of the future while adjusting to reality. 

🌕 Here’s a real world example to put this into perspective

John F. Kennedy set one of history’s most inspiring and audacious moonshots: putting an astronaut on the moon. To achieve this, he appointed James Webb as Administrator for 3-year-old NASA, making Webb the pioneer for the moon landing. 

Culture/Structure: From focusing NASA on the moon landing, to building public and private partnerships, to recruiting some of the world’s bravest and smartest astronauts for a dangerous mission, Webb established the structures that created the culture that achieved the moonshot. 

🧭 Commander’s Intent: During a tour of NASA Space Center in 1962, JFK asked a janitor what he was doing. The janitor’s response? “I’m helping put a man on the moon, Mr. President.” In this possibly apocryphal story, the intent was so clear that every person at every level of contribution understood how their work helped achieve the commander’s intent. 

Operations: Putting an astronaut on the moon required an exhaustive list of technology, process, and people that didn’t exist. In partnership with many others, Webb rapidly experimented with hundreds of concepts. 

🧭 Commander’s Intent: Webb knew that he needed to rigorously test to ensure that the right people were sent to the moon with the right technology to touch down, walk the surface, record the event, and return home. 

Strategy: The strategy was a globally publicized moon landing by American astronauts. 

🧭 Commander’s Intent: Put an astronaut on the moon and bring them home safely. 

📖 The Pioneer’s Playbook

Like all great Chiefs of Staff, you’re probably thinking, “This is a great story, but how do I actually do it?”

The good news is that a toolbox already exists. It comes from the world of startups, where turning radical innovation into the new industry standard is the name of the game.

The pioneer’s go-to-market playbook:

1. Define

2. Build

3. Run

4. Staff

5. Integrate

6. Transition

🎯 1. Define

Also known as “discovery” in the truest sense of discovering a thing with no assumptions of value or solution. Discovering the opportunity is the single most important step. First, you have to understand the problem so well that you can easily explain it to anyone. Then, you have to align the opportunities and risks with your organization’s strengths and weaknesses. Once this is ready, you have to reconnect with your executive to present this more true perspective, evaluate it against the strategy, and make a Go/No Go decision.

Great tools include:

• Customer discovery

• Competitor analysis

• Alternatives analysis

• Strategy evaluation

🏗️ 2. Build

There are two phases here: experiment and development.

🧪 2.1 Experiment: During the experimentation phase, you rapidly and rigorously test probable solutions. The idea isn’t to prove your or your executive’s idea. It’s to objectively determine which ideas have the highest chance of strategically aligned success. Importantly, you need a clear hypothesis for each experiment that you try very hard to prove wrong. The most durable hypothesis advances to development.

Great tools include:

• Ideation

• Experimentation

• Post-experiment analysis

• Peer review

• Speed

🛠️ 2.2 Development: The most promising experimentally tested idea should advance to development. In this phase, you establish the minimum viable solution for the problem. This is the fastest, cheapest version of the solution. It’s meant to validate your experiment at a higher level, to justify more investment.

Great tools include:

• Ghost prototyping

• Rapid prototyping

• Pilot programs

• Customer demos

🏃‍♂️ 3. Run

Once you have a working minimum viable solution, it’s time to run it! Your goal here isn’t to build a permanent, long-term solution. Like any pioneer, you’re establishing a viable mix of technology, process, and team that continues to validate the opportunity while beginning to create actual value for your executive. Projects either have a clear path to profitability here, or they’re somewhat profitable. You may have a hodge podge team and tech stack in place.

Great tools include:

• 3^rd party technologies and products

• SOP-based processes and procedures

• Partial and/or short-term FTE support from your organization

• Contractors

👥 4. Staff

Staffing the team is the “rubber meets the road” moment for the opportunity because it represents the commitment of real resources for the long-term. It’s important to objectively re-evaluate the opportunity-solution set against the strategy. Situations change quickly. Your goal with staffing is to begin building a team who can take over most of your responsibilities as you prepare to move on to the next opportunity. Critically, you need to staff the person who will become the leader of the new solution. You’ll also want to document processes for training and integration purposes.

Great tools include:

• Strategic realignment

• Recruiting

• Process documentation

• Training

🧩 5. Integrate

It’s finally time for your project to formally join the organization. Though this has been happening throughout, this step is where it becomes official. Integration is crucial because organizations are living systems. Just like an organ recipient’s body can reject the organ, the organization can reject the new product, process, team, or business unit. Your goal is for the receiving team to happily accept your new solution by making it part of their strategy and operations. You’re very close to moving on.

Great tools include:

• Stakeholder analysis and discussions

• Recruiting an internal champion

• Transition planning, schedules, and training

• Updating the strategy based on the new capability

🦋 6. Transition

Congratulations! You’ve turned an idea into a useful addition to your organization’s mission: The new leader is in place. Documentation is rigorous. A team is staffed. The capability makes your organization that much better. Continue to support the capability as an advisor, just like a founder/CEO can become a board member. Your founder’s experience can serve the capability for years. 

As an important note, sometimes the Chief of Staff may transition roles to become the capability’s leader. This is a great achievement, but don’t build the capability with you as the leader in mind. 

Great tools include:

• Strategy refresh

• Stakeholder summaries

• 1:1’s with the new leader

• Retrospective analysis with your executive

Whether you run this strategy in a week for a process change or a year for a new business unit, you can trust the playbook because it’s time-tested by Nobel Prize winning chemists, NASA Administrators who put astronauts on the moon, and US Presidents solving intractable challenges. By framing your Chief of Staff role as a Pioneer, you’ll be able to implement truly innovative and strategic solutions that align with overarching goals, leading to a profound transformation of the organization's capabilities and future prospects.

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📖 Additional Chief of Staff Related Reads:

How to Self-Manage Even if You Have a Manager (Your Future Self Will Thank You)

How To Prioritize When Everything Feels Like A Priority

Meet the Empirix Partners Team: Chief of Staff Ethan Summers

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