Making Sense of Your Own Context Window

It's impossible to exist in the world of startups today and not be inundated with all things AI, at all times. You've probably encountered the concept of context windows. Simply put, a context window in the realm of LLMs refers to the amount of text the model can receive as input when generating or understanding language.

When I read Scott Stevenson 's Tweet (or X? what do we call these now?), I stopped in my tracks. We've all been on teams where we draft and share user manuals, but context windows have never been a part of the discussion.

The best founders are self aware, deeply curious, and always looking for new ways to grow. They structure teams from a place of deep understanding about their own working styles.

What can be learned about building teams by understanding your context window?

Personally, I'm pretty confident I would have saved myself a lot of heartache and heartburn over the course of my career if I had used this as a lens.

Three Types of Context Windows

The concept applied to human decision-making can be a way to explore your "short-term context window," or the recent history and information you use to make choices.

There are three main types of short-term context windows:

Narrow Focus

Leaders with a narrow window focus heavily on immediate details and short-term goals. They excel at tackling tactical problems but might miss broader trends. Founders with narrow focus might gravitate towards deep dives into specific tasks like product development, fundraising, or marketing campaigns.

Balanced Focus

These founders can consider both immediate issues and the bigger picture. They can make strategic decisions informed by current needs and long-term vision. Founders with this type of focus often excel at juggling multiple priorities and seeing the bigger picture.

Wide Focus

Leaders with a wide window prioritize long-term vision and strategic goals. They excel at innovation and seizing opportunities but might miss critical short-term issues. It's common to see them thrive when they get to focus on high-level strategy and future planning. Operational details? Those, on the other hand, might be a major source of struggle.

It's important to underscore Scott's original point - one type of context window isn't better than another. Any attribute can be either a strength or liability depending on your relationship to and understanding of it.

Do one of these context styles seem most like you? It's ok if not. Most people have a dominant style with spill over into another. But if I were a betting person (which is basically anyone in venture), I'd guess one type of focus resonated most. So, now what?

Building Strong Founders + Teams by Context

If you can understand your own way of processing information and relating to the world, it becomes infinitely easier to build teams that allow you to operate in your zone of genius with the majority of your waking hours.

So what does that mean if we use context windows as a frame? Based on your own focus type, here are some ways you might think about leaning into your strengths and building your team.

For the Narrow, Recruit Wide

Surround yourself with generalists who can handle various tasks with minimal supervision. Utilize freelancers or outsource non-critical functions. Tactically, this can include:

• Action Team: Build a team strong in execution. Hire detail-oriented individuals excelling at project management and meeting deadlines.
• Advisory Board: Establish an advisory board with experienced founders who can offer a broader perspective and help identify potential long-term risks.

Habits:

• Daily Stand-ups: Implement daily stand-up meetings to get a quick pulse on project progress and identify any roadblocks requiring immediate attention.
• Chunking: Break down large goals into smaller, more manageable tasks with clear deadlines. This keeps your focus tight and progress tangible.

Frameworks:

• SWOT Analysis: Regularly conduct a SWOT (Strengths, Weaknesses, Opportunities, Threats) analysis to stay grounded in the present reality while identifying potential future looking problems early on.

Balanced? Build with Experts

Build a core team with strong domain expertise in key areas like marketing, engineering, and finance. Delegate execution but maintain close oversight. Tactically, this can include:

• Cross-Functional Teams: Create cross-functional teams with members from different departments. This fosters communication and ensures all perspectives (short and long term) get considered.
• Dedicated Strategist: Hire a strategist or consultant to focus on long-term planning and scenario building, to complement your tactical strengths.

Habits:

• Devil's Advocate: During team discussions, assign someone to play devil's advocate, challenging assumptions and ensuring decisions consider both short-term feasibility and long-term impact.
• Weekly Reviews: Schedule weekly reviews to assess progress toward immediate goals while revisiting long-term objectives and adjusting strategy as needed.

Frameworks:

• The Balanced Scorecard: Utilize the Balanced Scorecard framework to track progress across financial, customer, internal process, and learning & growth dimensions, ensuring you're making balanced decisions.

Wide Pairs Best With the Operator A Team

Build a strong leadership team with operational experience to handle day-to-day tasks. Hire a COO or experienced manager to bridge the gap between vision and execution. Tactically, this can include:

• Strong COO: Hire a Chief Operating Officer (COO) with a detail-oriented mindset. This frees the founder to focus on vision and long-term strategy while ensuring daily operations run smoothly.
• Data-Driven Culture: Implement a data-driven culture where decisions are based on real-time data and analytics, helping bridge the gap between long-term vision and short-term execution.

Habits:

• Strategic Thinking Time: Block out dedicated time for strategic thinking, away from daily distractions. Use this time to research emerging trends, brainstorm new ideas, and refine your long-term vision.
• Future Vision Exercises: Conduct regular team exercises where you envision the future state of your company and industry. This helps bridge the gap between long-term goals and present actions.

Frameworks:

• Scenario Planning: Employ Scenario Planning to consider different potential futures and develop contingency plans. This ensures your company can adapt to changing market conditions.

You may also want to consider the Habits + Frameworks listed above for other context types. There's a lot to learn by exploring the way others think!

Universal Truths, Independent of Context Windows

No matter what context window, or type of focus, feels like you're "just right," there are some universal truths about building great teams.

First and foremost, team dynamics are crucial. Hire people who can challenge your thinking and offer diverse perspectives. Surrounding yourself with Yes People is an expensive, often deadly, mistake.

But vibes alone won't make a team great. (Womp womp, I know. That's a buzzkill for some.)

Operational excellence is essential. And it bringing operational excellence to Day 0 is a competitive edge. This is a different article for a different day, but some things to consider as you continue to think about context windows:

• Regular Team Meetings: Regardless of window size, maintain regular meetings (daily for micro, weekly for macro/visionary - or some combination thereof) to keep everyone informed and aligned. The point is consistently showing up to exchange information and ideas with a dedicated cadence is critical for keeping the mission moving forward, aligned and on time.
• Documentation: Create clear documentation for processes, goals, and communication protocols, especially for founders with a micro-focus. Building knowledge repositories early on become like the Old Testament for a startup - foundational for all the books to follow.
• Communication Style: Tailor communication to your team. Macro/visionary founders may benefit from concise updates, while micro-focused founders might need more detailed information. You'll set your team up for success if you can tell them how best to communicate with you so they can get what they need to deliver on the mission. But communication is also a two way street. Knowing how your team needs to receive communication helps you be a better servant leader (if that's your thing).

The best team structure adapts to your context window, not the other way around. But by understanding your short-term context window, you can create a team structure that optimizes learning and decision-making in a way that accelerates success.