Still Trying to Measure Impact One Grant at a Time? Here’s Why That Doesn’t Work

Value Stream Consulting
Jun 9
3 min read

Updated: 5 days ago

In the past few articles, we’ve been exploring the strategic importance of initiatives, those often-missing links between mission and grantmaking. We’ve highlighted how initiatives create structure, connect portfolios, and help foundations move from activity to purpose.

That work sparked a wave of thoughtful questions from our community. One question kept coming up: What exactly happens at the initiative level when it comes to measurement?

This article answers that question head-on. It may not have been in our original sequence, but it's a timely and necessary addition, especially as technology begins to change what’s possible.

Grants Generate Outcomes. Initiatives Make Impact Measurable.

Every grant manager is fluent in outcomes: services delivered, individuals served, reports submitted. These are critical, short-term signals of execution.

But if your foundation wants to understand whether it is moving the needle on a systemic issue, whether it's shifting conditions, access, or opportunity, you need to measure at the initiative level.

That’s where impact lives.

What Happens at the Initiative Level?

An initiative is a coordinated, multi-year strategy. It integrates multiple grants and partners around a long-term goal, such as increasing economic mobility, improving public health, or reducing disparities in access.

At this level, measurement becomes about tracking progress toward a clearly defined change. That progress must be observable, realistic to monitor, and grounded in data that reflects the broader landscape, not just individual programs.

Measuring Impact in Practice

Let’s say your initiative focuses on improving economic mobility for youth in underserved communities. Instead of just tracking how many youth complete training programs, you would monitor:

Postsecondary enrollment trends across target ZIP codes
Youth employment rates for ages 18–24
Growth in median income for youth-headed households
Declines in high school dropout rates in funded districts
The number of youth engaged in mentorship or career navigation
Longitudinal progress of a youth cohort over a 3–5 year period

These indicators can be sourced from public data, education departments, labor statistics, and standardized grantee reports. Measured together, over time, they reveal whether the initiative is contributing to its intended impact.

Where AI Comes In: A New Era for Measuring What Matters

This is where emerging technology, especially AI, adds new power to the equation.

Today, AI can already assist with:

Consolidating grant reports into standardized, comparable formats
Detecting trends and anomalies across large data sets
Linking qualitative and quantitative data across grantees and time periods
Suggesting thematic insights by analyzing free-text grantee narratives

In the near term, AI will go further. Foundations will be able to use AI to:

Seamlessly search internal reports, CRM fields, and historical initiative records
Cross-reference those with public datasets (e.g. Census, education, health)
Generate initiative-level dashboards that identify emerging impact patterns
Uncover unexpected secondary outcomes, changes you didn’t initially set out to measure, but which reflect meaningful change

Imagine launching an initiative to improve youth employment, only to discover, via AI-augmented analysis, that it also reduced youth homelessness. These are the types of insights that will soon move from anecdotal to actionable.

But that’s only possible if your foundation is already measuring, and managing, at the initiative level.

Practical Guidance for Grantmakers

To move from tracking activity to measuring long-term effectiveness:

Define initiatives with a clear impact goal.
Design grants that contribute to that goal from multiple angles.
Identify a small number of credible indicators tied to that goal.
Use a mix of public data, grantee reports, and external validation.
Leverage AI and automation to synthesize data and surface insights.
Track progress consistently, year over year, not grant by grant.

But There’s a System Problem...

Most grant management systems weren’t built for this. They focus on grants and programs, not strategic, cross-cutting initiatives.

In a previous article, we recommended funders create a separate structure for initiatives, use initiative-specific goals in planning, and supplement their systems with tools that can track broader progress.

We’re doubling down on that advice here, and adding this: prepare now for how AI will reshape your measurement capacity. The foundations that do will be the ones that not only measure impact, but understand it deeply.

Our Recommendation

If your organization wants to track its true contribution to mission-level change:

Start managing and measuring at the initiative level.
Enhance your systems, workflows, and culture to support that shift.
Embrace AI to unlock insights across both internal and public data sources.

Initiatives are where strategy meets measurable change, and where AI will help us see what’s truly working.

Still trying to measure impact one grant at a time? It’s time to zoom out, and design for what matters.