Reflection

Recently at work, there was some tension within the company. We had started working on a project—let’s call it Project Kiwi. About three weeks into the project, the company decided to pivot and prioritize another initiative, which I'll refer to as Project Berry.

The first time I was made aware of Project Berry was when I saw the mocks and was given a date to build it against. Immediately, I was concerned:

• The new deadline was set before engineering had a chance to realistically evaluate the scope.
• Expectations around timelines and complexity were significantly misaligned – aggressive and not within ball-park at all.
• This was the third time in a row leadership dropped a project mid-build and I was losing faith in their decision making capability.

Resolving these misunderstandings required substantial effort from me, the CEO, CTO, and product lead.

This week, I wanted to take the time to reflect on how I could have done better and take away one lesson.

Let’s talk about Context Gaps and how they influence Decisions.

Decisions

In tech—and really, in most business contexts—decisions typically boil down to one person.

Ideally, the person making a decision should be the one with the most complete and relevant context. Unfortunately, reality is messy.

In my situation:

• My team had the most technical context and was fully aware of the hidden complexities and costs.
• The Decision Maker held business context like customer expectations, deadlines for demos, and strategic priorities.

Neither side had the full picture, ultimately leading to tension in a high pressure environment.

The Context Gap

When two logical, well-intentioned parties disagree, it's often because each lacks key context held by the other.

Bridging this context gap is critical:

• Decision makers need comprehensive context to make the best decision.
• Non-decision makers benefit from transparency as it builds trust and helps in flagging the relevant information to the decision maker

The foundation for bridging context gaps is trust. Without it, excessive energy goes into persuading each other rather than collaborating constructively.

My Mistakes

From the POV of the non-decision maker, I made two mistakes:

1. Misidentifying the decision maker: I initially misunderstood who the ultimate decision maker was. In this case, the decision maker was the CEO who was putting pressure on the product lead. Even if I convinced the product lead, the decision would likely have remained the same unless they successfully convinced the CEO.
2. Failing to set expectations: I didn’t proactively communicate the complexity of the system’s that my team owns. As a result stakeholders had a lack of context and inadvertently causing unrealistic expectations to bild.

Decision Maker’s Mistakes

From the decision maker’s POV, they should have proactively sought out necessary context.

Without actively seeking out the right context and repeatedly making mistakes, their credibility—and consequently trust—erodes.

Takeaway

This experience was humbling. Especially recognizing my own areas for improvement. As a manager and someone who regularly makes decisions for my team, it reminded me of the importance of:

• Bridge upwards by proactively maintaining channels with leadership to set realistic expectations
• Bridge downwards by proactively listening to my team (direct reports and non-direct) to better understand their pain points. How could I expect to make them more productive (my role as a manager) if I don’t understand their problems?
• Don’t take the trust that I’ve built with my own team and leadership for granted.

Localizing Context

Reflecting further, I've become increasingly convinced that founders who can both deeply understand user pain points and build solutions themselves are uniquely positioned to disrupt established industry leaders.

The advantage these founders bring lies in their ability to localize context to a few key individuals. They immerse themselves directly in user experiences, thoroughly grasp their pain points, and then immediately translate that context to a tangible solution. This avoids the costly and loss-ful step of transferring context between parties.

Big organizations struggle with these challenges, as they rely on multiple layers of communication where context can be diluted or misinterpreted. By contrast, small teams and startups, localize context to a few key individuals and allow them to make better decisions.