Working with Senior Stakeholders on New Technology

Introduction

How do you convince or work with a senior stakeholder who’s pushing back on new technology when you need to win them over? My experience comes from two sides: the startup perspective and the corporate perspective.

Startup Perspective

In startups, the biggest issue is risk, specifically the return on investment. Cash is usually tight, and any project or investment you’re making is at the expense of another initiative. What you need to show is tangible proof there will be value.

Demonstrating Value

  • Talk to customers
  • Create a prototype
  • Prepare a full demo

Example: A friend working on an automated customer support system prepared a video demonstration showing how the solution would work. This helped de-risk the value by illustrating how it would look and how customers would react.

Corporate Perspective

In corporates, the big risk is compliance. For example, at Meta, we used to spend over 3000 FTE hours/year just keeping up with changing regulations.

Key Concerns

  • Compliance with regulations
  • Avoiding fines
  • Protecting user data

When introducing new technology that’s not well understood, the interactions aren’t clear. No director or senior leader wants to be slapped with a fine or, even worse, inadvertently leak user data.

Effective Approaches

  1. Show you’ve thought through various edge cases
  2. Provide detailed documentation
  3. Gather support from others in the organization
  4. Make your presentations easily readable

Remember, senior leaders don’t have time to go through extensive documentation. Lean on the trust and support of others who can vouch for your work.

Demonstrating Tangible Value Quickly

The most effective way to demonstrate value to stakeholders is to:

  1. Understand the metrics they’re looking at
  2. See how they’ve instrumented those metrics
  3. Establish a direct line of sight between your impact and the metrics they care about

Example: If they’re measuring the number of incidents, and you’re bringing in a new CI/CD tool, don’t focus on how it reduces time to go live. Instead, demonstrate how it directly affects the number of incidents.