Estimated read time: 4 minutes

Written by Cassie Rice, Chief Operating Officer

Org charts are clean by design.

A box for each role, a line showing who reports to whom, a tidy hierarchy that looks reasonable in a board packet.

Fundraising doesn't actually work that way, and the gap between the chart and the reality is often exactly where a major gift program loses ground.

An org chart tells you nothing about who actually has influence over a major gift decision, who gets pulled into asks informally, or where decisions really get made.

When those two pictures diverge enough, the chart stops being a useful tool and starts being a source of confusion.

Where the Org Chart Breaks Down

A few patterns show up again and again when we look past the chart to how decisions happen:

The person with formal authority isn't the person with real influence.

A development director might sit above a senior major gift officer on the chart, but if that officer has a fifteen-year relationship with the organization's top donor, real influence over that relationship doesn't run through the chart at all.

Cross-functional influence gets ignored.

A program director who happens to have a close relationship with a prospect because of shared professional interests often has more actual sway over that relationship than their position on the chart would suggest.

Decision-making bottlenecks aren't visible in reporting lines.

If every major gift over a certain size needs informal sign-off from the ED, that's a real constraint on how fast a program can move, and it's invisible on a chart that only shows who reports to whom.

Why This Matters More During Growth or Campaigns

A slightly misaligned org chart is a minor inefficiency during steady-state operations.

It becomes a real liability the moment an organization tries to scale a program or run a campaign, because the increased workload of campaigns necessitate efficient, clear decision-making

If the real decision-making structure doesn't match the formal one, campaigns hit friction that nobody quite knows how to name, because officially, the process should be working fine.

How to Find the Gap in Your Organization

The chart won't show you the gap. But a few honest questions will:

• For your top five donors, who actually has the most influence over the relationship, and does that match who's formally responsible for it?
• When a major decision needs to get made quickly, who actually has to weigh in informally before anything moves, even if they're not in the formal approval chain?
• If your development director left tomorrow, would decision-making authority actually transfer cleanly to whoever's next on the chart, or would there be a period of real confusion?

Closing the Gap Without Redrawing the Whole Chart

You don't need to reorganize the entire structure to fix this. A few practical steps:

Document real influence alongside formal roles, even informally.

A simple internal note on who actually drives key donor relationships is more useful day-to-day than the org chart itself.

Build board relationships into planning explicitly.

If a board member's personal relationship with a donor matters to an outcome, treat that as a resource to coordinate, not an invisible variable.

Clarify informal approval bottlenecks and decide if they're worth keeping.

Sometimes an informal sign-off step exists for good reason. Sometimes it's just a habit that's slowing things down and nobody's questioned it.

A Quick Gut Check

Before your next planning cycle, ask:

• Does your org chart reflect who actually drives your top donor relationships, or just who reports to whom?
• Is there a decision-making bottleneck that exists informally but isn't acknowledged anywhere?
• If someone new joined the team, would the org chart alone give them an accurate picture of how things really work?

The org chart is a useful starting point. It's not the whole truth, and treating it like one can leave real influence, real bottlenecks, and real risk invisible until they cause a problem.

Wondering where the gaps are in your own organization?

Sometimes the way work actually gets done looks very different from the structure on paper. GPG can help you identify where roles, decision-making, and donor relationships may be creating friction, and build a clearer path forward.

Talk With GPG About Your Fundraising Program

The post The Fundraising Org Chart is Lying to You appeared first on Gail Perry Group.

Estimated read time: 5 minutes

Written by Jen Herrmann, Vice President of Business Development

When we dig into why a major gift program is struggling, the answer is rarely a strategy problem.

It is ambiguity, and it shows up in two distinct ways that are often lumped together but need to be diagnosed separately.

The first is pipeline ambiguity: a lack of clarity about a prospect’s current stage, whether discovery, cultivation, solicitation, or stewardship, and the next action required to advance the relationship.

The second is portfolio ambiguity: a lack of clarity about who is responsible for setting and executing the strategy for a managed prospect, including coordinating everyone involved in the relationship.

A major gift strategy is only actionable when every managed prospect has three things: a clearly defined stage, a specific next action, and one person accountable for moving the relationship forward. When any of these is unclear, ambiguity begins to undermine execution. 

Pipeline Ambiguity: What It Looks Like

Pipeline ambiguity is uncertainty about where a prospect stands in the relationship-development cycle and what must happen next to advance the relationship.

It shows up in familiar ways:

• A prospect remains “in cultivation” for eighteen months because there are no clear criteria for determining readiness for solicitation.
• A promising prospect is identified but never meaningfully qualified, remaining indefinitely between identification and active cultivation.
• A solicitation occurs, but the prospect’s response and the required follow-up are not clearly recorded, leaving the relationship stalled.
• A major gift is received, but no stewardship plan is established to guide the next phase of the relationship.

A program can have a capable team and strong prospects and still leak results if relationships remain indefinitely in one stage or move through the pipeline without a defined next action.

Portfolio Ambiguity: What It Looks Like

Portfolio ambiguity concerns accountability for the relationship. It rarely announces itself. Instead, it shows up as small, recurring frictions that seem minor in isolation:

• A donor receives a call from the executive director and a separate email from the major gift officer in the same week, on unrelated topics, because neither knew the other had reached out.
• A gift officer hesitates to move a relationship forward because they are unsure whether the executive director wants to make the ask.
• A board member develops a strong personal relationship with a donor, but staff members do not know the details, so cultivation and stewardship fall through the cracks.
• A prospect sits untouched for months because everyone assumes someone else is responsible.

None of these incidents will sink a program on its own. Multiplied across a full portfolio and a full year, however, they can mean the difference between a program that reaches its goals and one that quietly underperforms.

Why Both Are So Common

Many organizations lack shared definitions for the stages of donor development. A prospect may be labeled “in cultivation,” but the team has no common understanding of what that means, what evidence supports the designation, or what must happen before the prospect advances.

At the same time, most organizations define responsibilities by title rather than by donor relationship. A job description may say that a major gift officer “manages a portfolio of prospects.” It rarely specifies what happens when the executive director also knows a donor personally, a board member has an existing relationship, or the donor’s interests shift toward a program area with its own staff contact.

Real donor relationships do not follow organizational charts or advance simply because they appear in a database. They require clear stages, purposeful next actions, and one person accountable for coordinating the strategy. Without those standards, ambiguity fills the gap.

How to Find Both in Your Own Program

Both kinds of ambiguity are easiest to identify by testing your team’s certainty, not reviewing its policies. Pull up your top ten prospects and ask:

• What stage of the pipeline is each prospect in, and what evidence supports that designation?
• What is the next action required to advance the relationship, and when should it occur?
• Who owns the relationship and is accountable for setting and executing the strategy?
• Does everyone who may engage the prospect understand who is coordinating the relationship?
• Is there a shared, current record of the pipeline stage, next action, relationship owner, and most recent contact?

If your team hesitates over more than one or two of its top prospects, you have found the gap.

Fixing It Without Adding Bureaucracy

The fix is not a heavy process. It is a clear, simple standard applied consistently:

Establish shared criteria for each pipeline stage and a defined next action for every managed prospect. “In cultivation” should communicate more than a general status. The team should understand what that stage means, what must happen before the prospect advances, and what action comes next.

Name one owner for each managed relationship and document it somewhere everyone can see. Not a rule of thumb, but a specific person tied to a specific prospect who is accountable for setting the strategy, coordinating the people involved, and ensuring that agreed-upon actions occur.

Create a default rule for anyone who wants to engage a prospect they do not own. Usually, the rule is simple: coordinate with the relationship owner first. It must be an established norm, not an unspoken expectation.

Hold brief, regular reviews to confirm stage, next action, and ownership. This is especially important for prospects who have remained in the same stage longer than expected and for high-profile relationships involving an executive director, board member, and gift officer.

A Quick Gut Check

Before your next portfolio review, ask:

• Could every relevant member of your team identify each top prospect’s current pipeline stage and next action?
• Could they also name the relationship owner without hesitating?
• Has a prospect remained in the same stage for months without anyone flagging it?
• Has a donor been contacted by two people in the same week without either knowing about the other outreach?
• Are the pipeline stage, next action, and relationship owner documented somewhere, or does that information live only in memory?

Ambiguity rarely presents as a crisis, whether the uncertainty concerns where a prospect stands and what should happen next or who is accountable for the relationship.

It shows up as a slow leak, and it is one of the most fixable problems a major gift program can have.

Wondering where ambiguity may be showing up in your own major gift program?
Sometimes an outside perspective can uncover the gaps that are hardest to see from inside your organization. Contact GPG to Learn More

The post The Silent Killer of Major Gift Programs: Ambiguity appeared first on Gail Perry Group.

Average reading time: 4 minutes

Written by: Gina Vaughn

When we recently assessed a regional organization’s development team and processes, we learned that their weekly meeting was a status update.

Everyone reported where their prospects stood, the ED asked a few questions, and the meeting ended.

Functional, unremarkable, easy to sit through without really engaging.

We recommended a specific change to the format.

Instead of status updates, each officer would bring one specific ask or decision they were genuinely stuck on.

The team would spend the meeting problem-solving that one thing together, out loud.

That's the whole recommendation.

It's not complicated. It's also not something most teams think to try until someone from outside the day-to-day points it out.

Why It Worked

A few things happened that a status-update meeting had never produced:

Officers stopped carrying stuck relationships alone. 

A hesitant ask, a donor who'd gone quiet, an awkward family dynamic; these things used to sit in one person's portfolio until they either resolved themselves or quietly went dormant. 

Once we built in the structure for surfacing them, they got worked through as a team, often within the same week they came up.

The team started learning from each other's judgment, not just their results.

Watching a colleague talk through how they'd handle a tricky ask taught officers things a status report never could.

Over months, the whole team's instincts sharpened, which is exactly the kind of shift we look for as a sign an engagement is working.

Stuck decisions stopped costing weeks.

A donor conversation that might have sat unresolved for a month because nobody wanted to be the one to push it forward now got unstuck in a ten-minute team conversation.

None of this usually shows up as a single dramatic gift (although sometimes it does!).

It shows up as dozens of smaller moments where a relationship moved forward a week earlier than it would have, an ask got made instead of avoided, a stuck conversation got resolved instead of dropped.

By year-end, those dozens of small compounding wins added up to a result nobody could trace back to one cause, because there wasn't one. 

This Is Easy to Miss Without an Outside Read

If you asked this team's development director what changed, the answer may be "we changed our meeting."

That's not a satisfying answer for a board that wants a tidy explanation for a great year.

But it's the true one, and it's exactly the kind of structural gap those of us at the Gail Perry Group spot: something a team is too close to its own routine to notice on its own.

What This Means for Your Team

You don't need a bigger budget or a bolder campaign to see this kind of shift.

You need an honest, and often outside, look at whether your team's regular touchpoints are solving problems or just reporting on them.

A Quick Gut Check

Before your next standing team meeting, ask:

• Does this meeting change any decisions, or does it just report on decisions already made?
• Are officers surfacing what they're actually stuck on, or performing progress?
• If this meeting didn't happen this week, would anything meaningfully different occur as a result?

We see this exact pattern often enough that it's become one of the first things we look at with a plateaued development program.

Sometimes the biggest lever isn't a bigger prospect.

It's a five-minute change to a meeting nobody thought to question, and it's easy enough to begin this week.

Curious what your team's version of this is?

A Development Audit gives you that outside look at the structures, systems, and habits shaping your fundraising program, plus practical recommendations for what to evolve. Contact GPG to learn more.

The post One Meeting Change, One Record-Breaking Fundraising Year appeared first on Gail Perry Group.

Estimated read time: 4 minutes

Ask most organizations what happens to a major gift officer after three or four strong years, and you’ll get a vague answer.

Maybe a raise. Maybe a higher-capacity portfolio. Rarely a clear answer about what comes next.

That vagueness comes at a cost.

When a strong major gift officer leaves, the organization loses more than an experienced team member. It risks the donor relationships and institutional trust they built, while facing a year of ramp-up for their replacement.

A promotion track is essential to retention, not a nice-to-have.

Why Fundraising Roles Often Lack a Clear Path Forward 

Many nonprofit organizational charts do not offer fundraisers a defined path from associate to officer, senior officer, and director.

This gap is not necessarily a budget problem. It is a design problem. Organizations often build their structures around headcount and titles without creating meaningful growth opportunities for the people already succeeding in critical roles.

What Could A Growth Track Look Like?

A real promotion track for fundraisers doesn't have to mean a bigger title every year. It usually includes some combination of:

Expanded scope, not just expanded portfolio. Moving from managing a portfolio to also managing or mentoring newer officers, owning a specific donor segment strategically, or leading a piece of campaign planning.

Increased autonomy and voice in strategy. Senior fundraisers who've proven their judgment should have real input into how the team approaches its top donors, not just execution of someone else's plan.

A defined path to leadership, even if it's not the top development job. Not everyone wants to manage people. Some of the best fundraisers want to stay donor-facing forever, and that's fine, as long as there's a track that rewards depth of expertise, not just a track that requires becoming a manager to get recognized.

Compensation tied to demonstrated impact, not just tenure. A raise for staying is different from a raise for growing. Fundraisers notice which one they're getting.

When There Is No Path Forward, Strong Fundraisers Leave 

Without a clear promotion track, talented fundraisers face a choice: remain in a position with limited opportunities for advancement or pursue their next step elsewhere. Many eventually choose to leave, often without signaling their intentions until they have accepted another offer.

By the time the exit interview happens, the decision may have been taking shape for months, largely unnoticed.

A Quick Gut Check

Before your next review cycle, ask:

• Can your strongest fundraiser describe what their role could look like in two years? (Can you?)
• Is there a path for growth that doesn't require becoming a manager of people?
• Have you had an honest conversation with your top performer about what they actually want next, or are you assuming they're satisfied because they haven't said otherwise?

If your strongest fundraiser cannot see a clear future within your organization, they may begin looking for one elsewhere. 

We'd love to have you join our annual Major Gifts Officer Bootcamp 2026. Portfolio management, cultivation strategy, the ask, stewardship -- all of it, live, with expert coaching built in. Secure your seat before registration closes.

The post The Promotion Track That Keeps Fundraisers From Leaving appeared first on Gail Perry Group.

Estimated read time: 5 minutes

Picture two candidates for a gift officer role.

Candidate A has a decade of fundraising experience and interviews with total confidence.

Candidate B has less traditional fundraising experience, but spent a decade building long-term relationships in a completely different field such as sales, education, or ministry.

Most hiring processes are built to find Candidate A, but it's not always the best or most straightforward solution.

Sure, prior fundraising experience is genuinely useful. It means someone understands moves management, knows how to structure an ask, and won't need training on the basics. That's real value.

But it's also the easiest thing to screen for, which means most job descriptions and interview processes optimize for it.

This is often at the expense of a trait that matters deeply: the ability to build authentic relationships with people who have real wealth and real discretion about where it goes.

But it’s only part of the equation. Here's the part that gets missed just as often, in the other direction: relationship building isn't the finish line.

We've seen officers who are wonderful with people and still don't raise money, because they treat every touch as a chance for a nice conversation rather than a deliberate step toward a gift. They build real trust and then don't know what to do with it. The relationship becomes the whole job instead of the vehicle for the work.

The officers who actually succeed do both.

They build the kind of trust that makes a donor comfortable talking about their values and their family, AND they understand moves management well enough to know when a relationship is ready to advance, and how to advance it without rushing or stalling it.

One without the other shows up in the numbers. 

Pure relationship-builders often produce warm donor sentiment and flat revenue. Pure process-followers often produce efficient pipelines and donors who feel handled rather than known.

It's about listening well enough, over enough time, that a donor comes to trust you with their values, their family dynamics, and eventually their money: and then knowing how to translate that trust into a structured next step.

Some people are naturally good at the relational half regardless of their job history.

Some people have run development shops for a decade and still haven't developed it.

And some people are so good at the relational half that no one questions why their portfolios never move toward asks.

What Predicts Success

Across the leaders we've worked with, a few traits show up again and again in the ones who thrive, regardless of their resume:

1. Genuine curiosity about people
This is the top trait that separates good process-followers from good gift officers.

Not performed interest. Curiosity about what makes someone tick, what they care about, what keeps them up at night. Donors can tell the difference between an officer who's asking questions to get to the ask, and one who's genuinely interested in them as a person. Only one of those builds trust that lasts.

2. Comfort with silence and slow timelines
Major gift cultivation isn't fast. It can take months or years to move a relationship to the point of a significant gift. Officers who need quick wins or get anxious in the absence of immediate progress tend to rush the relationship, and rushed relationships produce smaller gifts or no gift at all.

3. Emotional steadiness
Rejection, awkward silences, donors who go quiet for months- these are normal parts of the work. Officers who take them personally burn out fast or start avoiding the hardest, most important conversations.

4. The ability to represent the mission with credibility
This one's less about personality and more about fit: does this person actually believe in what the organization does, deeply enough that they can talk about it with real conviction? Donors can tell when someone is reciting talking points versus speaking from genuine belief.

5. Willingness to work a structured process
This is the trait that separates good relationship-builders from good gift officers. It means treating every coffee, every visit, every conversation as a deliberate move in a cultivation plan, not just time well spent with a nice person. It means being able to say, specifically, where a prospect sits in the pipeline and what the next step is. Relational instinct without this discipline produces donors who adore the organization and never get asked.

What This Means for Your Hiring Process

If your interview process is mostly about resume review and past performance metrics, you're screening for execution skill and missing relational skill almost entirely. And if you're screening only for warmth and likability, you may be missing whether a candidate can actually move a prospect toward a gift. A few adjustments help:

• Ask behavioral questions about how a candidate has built trust with someone over time, not just how they've closed asks
• Pay attention to how they talk about past donors or clients: as people, or as targets
• Ask a candidate to walk through a real prospect relationship, start to eventual ask, and listen for whether they can name the stages and the moves, not just the rapport
• Consider candidates from outside traditional fundraising if they've demonstrated real relationship-building in another field
• Don't assume years of experience equals relational skill. Ask what they actually did in those years.
• Don't assume a warm, well-liked officer is a productive one. Check the pipeline movement, not just the donor sentiment.

A Quick Gut Check

Before your next major gift hire, ask:

• Does our job posting and interview process actually screen for relational skill, or just fundraising process knowledge?
• Have we talked to references about how this person builds trust, not just how they perform against a number?
• Are we open to a candidate who doesn't look like a traditional fundraiser on paper, but shows the traits that actually predict success?
• Can this person point to specific prospects they moved from one stage to the next, or only to relationships they enjoyed?

The best gift officer isn't always the one with the most fundraising experience. It's the one who can build the kind of relationship a donor trusts enough to be transformational, and who knows how to turn that trust into forward motion.

The post Hiring for Major Gifts: What Predicts Success appeared first on Gail Perry Group.

Estimated read time: 4 minutes

There's a version of "high-performing" that shows up in board decks: goal met, deadlines hit, dashboard green across the board.

That version isn't wrong; it's just incomplete.

It tells you what a team produced, not what made the team capable of producing it.

The first definition also breaks down at the exact moment you need it most, which is when something isn't going well.

Look closely at fundraising teams and boards that hold up under real pressure, and the same few habits show up again and again.

Here are three of them.

Habit 1: They Name Problems Before Problems Name Them

Take an annual fund team in the final push before December 31.

Gifts are trickling in slower than projected.

In a team that's only high-performing on paper, this is the time everyone puts their head down, works longer hours, and says nothing.

The manager finds out the numbers are soft when the year-end report lands, not before.

In an actually high-performing team, someone says it out loud on November 15: "We're behind pace, here's what I think is driving it, here's what I want to try in the next two weeks."

That's not a weaker team because it's naming a problem.

It's a stronger one, because the problem gets a plan instead of a quiet countdown to a bad number.

Trait 2: They Ask the Uncomfortable Question in the Room, Not Around It

Take a capital campaign steering committee three months into solicitations, watching a handful of lead prospects go cold.

A steering committee that isn't high-performing tends to split into two camps that never actually talk to each other: the ones privately worried the goal was too ambitious, and the ones publicly insisting everything's fine.

Nobody says either thing in the room.

A high-performing steering committee has the conversation everyone else is avoiding.

Someone asks: "Is this a timing problem with these specific donors, or a sign the goal needs revisiting?"

That question doesn't feel comfortable, but it's also the only way the committee finds out which one is true before it's too late to adjust.

Both of these examples point to the same underlying skill.

Neither team is more talented or works harder than a struggling one.

The difference is whether the people in the room can say the true thing before it turns into a bigger problem.

Trait 3: Their Board Asks with Curiosity, Not Blame

Boards run into the same test, just with different stakes and less day-to-day visibility.

A board that isn't high-performing tends to find out about a struggling campaign the same way an average community member finds out: secondhand, and late.

A high-performing board asks for the unfiltered version regularly (not just when leadership decides it's time to share it) and it asks with curiosity instead of blame.

"What's actually happening here" lands very differently than "who let this happen."

That distinction, curiosity over blame, is often the entire difference between a board that helps a struggling campaign recover and thrive.

Why This Is Worth Naming Out Loud

Fundraising runs on relationships that can't be faked under pressure.

A donor can tell when a gift officer isn't confident

A board can tell when leadership is managing the story instead of managing the campaign.

Whatever is actually true about how a team works together eventually shows up in front of the people you're asking to invest.

None of these three traits requires a personality overhaul or a new hire.

They require a much smaller thing: a standing habit of saying the true, uncomfortable thing before it's forced out by circumstance.

A team that can do that consistently will outperform a team with better talent and worse candor almost every time.

So if you're taking stock of your own team or board this fall, go beyond the productivity question.

Also ask: what's the last hard thing someone said out loud here, before they had to?

That answer is the real measure of how high-performing you are.

Ready to strengthen your team?

If this article resonated with you, the Major Gift Officer Bootcamp takes these ideas even further. Together, we'll explore the practical systems, strategies, and habits that help fundraising teams communicate more effectively, build stronger donor relationships, and achieve better long-term results.

Registration is now open for our September cohort. Learn more.

The post Three Habits of A (Truly) High-Performing Fundraising Team appeared first on Gail Perry Group.

Estimated reading time: 4 minutes

Here's one of the most demoralizing feelings in this work:

You're doing everything you're supposed to be doing. Discovery visits, cultivation touchpoints, portfolio strategy.

You've been consistent. You care deeply about the mission.

And it still feels like nothing is moving the way it should.

When that feeling persists, it's natural to conclude that you are what's wrong.

That's almost never the right conclusion. Here's what's usually actually happening.

There are only three real explanations, and one of them has a straightforward fix. Keep reading to find out which one you're dealing with.

Structural Barriers vs. Strategy Gaps

When a fundraiser is doing the right work and not seeing the right results, it's almost always one of two things, and neither one is the fundraiser's fault.

The first is structural barriers. An over-full portfolio with no prioritization support. A CRM that gets used for data entry but doesn't support strategic decision-making. Administrative tasks crowd out cultivation time. A culture that rewards busyness over impact. These aren't personal failures. They're organizational design problems. And they are fixable, but only if someone names them.

The second is the timeline. Major gift relationships take 12 to 24 months to build from a meaningful first conversation to a six-figure ask. If you've been in your role for 18 months, you are building a pipeline that will produce results… but not yet. The cultivation work you're doing right now is the foundation for gifts that will close in year two and beyond.

Why This Matters to Name

Development directors leave, on average, after 18 to 30 months. Which means most organizations lose their development director exactly when she is beginning to see results from her early relationship building. The sector loses talent at precisely the moment the investment begins to pay off.

This creates a tragic pattern: the development director who has been doing everything right — building real relationships, running disciplined discovery, cultivating with genuine care — gets frustrated and leaves.

The new director starts the cycle over. And the donor relationships that were close to moving forward get reset.

The way to interrupt this pattern is to distinguish clearly between what is a strategy problem, what is a structure problem, and what is simply a timeline problem.

A Useful Diagnostic Question

When the work feels hard in a way that doesn't match the effort you're putting in, ask yourself:

When I think about the high-priority work that isn't getting done, is it because I don't know how to do it, or because something keeps getting in the way of doing it?

• Strategy gap: you need more knowledge, a better framework, or a sharper approach. This is the easiest problem to solve.
  
• Structure gap: you need something in the organization to change: staffing, systems, expectations, role clarity. This requires a harder conversation, but it's a tractable problem.
  
• Timeline gap: you need to trust the work and keep going. This is the most important thing to distinguish, because it's the one that requires patience rather than change.
  

If it's a strategy gap, that's exactly what the Major Gift Officer Bootcamp is built to close. Twelve weeks, live, starting September 16: frameworks for portfolio strategy, discovery visits, and moving relationships forward with confidence, not guesswork.

The Fundraisers Who Build Programs That Last

The development directors who build major gift programs that genuinely perform over time don’t contain some mystery trait that the rest of us don’t seem to possess.

Instead, they are the most consistent. They do the right work, protect the time it requires, trust the relationships they are building, and know the difference between a problem to solve and a process to trust.

If you're in the middle of the timeline right now — doing the work, seeing slow movement, wondering if it's working — keep going.

The relationships you're building today are the gifts you'll close in year two or three.

And if it's a structure problem: name it. It's worth saying out loud.

And if it's a strategy gap: the fastest way to close it is training built specifically for the work you're doing right now. The Major Gift Officer Bootcamp starts live September 16, twelve weeks, and once the cohort begins, registration closes. Reserve your spot.

The post Why Fundraising Feels Hard When You’re Doing Everything Right appeared first on Gail Perry Group.

Estimate read time: 4 minutes

Here's something we’ve learned after years of working with nonprofit organizations:

A predictive variable in major gift success isn't always the prospect list. It isn't always the campaign case. It isn't always the staff size or the budget or the technology.

It's the relationship between the executive director and the development director.

And it's almost never talked about explicitly.


This partnership sets the direction. What happens next depends on who's actually running the plays, keep reading.

What the Partnership Looks Like When It's Working

When this relationship works well, the division of responsibility is clean and complementary:

•  The Executive Director opens doors. The development director walks through them with a strategy.

•  The ED carries the mission story and organizational credibility. The development director translates that into specific cultivation plans and prospect strategies.

•  The ED makes the relationship moves that only an ED can make: the personal call to a top prospect, the authentic conversation with a board member, the testimony that needs to come from organizational leadership. The development director identifies what's needed and makes sure it happens.

•  Neither person manages the other. They manage the work together.

This is not a management structure. It's a working partnership, and the distinction matters.

Partnerships require explicit conversation, shared understanding of each person's role, and regular check-ins to make sure both people are getting what they need from the relationship.

What Goes Wrong When the Partnership Is Strained

Three common failure patterns, all of which damage major gift outcomes:

The ED is absent from the cultivation work.
She trusts the development director to manage the major gifts program entirely, reviews reports, and doesn't make the relationship moves that only she can make. The development director, however talented, can't move key relationships forward without the organizational credibility that only the ED carries. Major gifts stall.

The ED is over-involved.
She second-guesses strategy, attends every cultivation meeting, and inadvertently crowds out the development director's ability to build her own relationships with donors. The development director's effectiveness is undermined, even when the ED means well.

The role division was never made explicit. 

Both people are operating on different assumptions about who owns what, leading to gaps, duplicated effort, and resentment neither person names.

The partnership sets the strategy. Someone still has to run it: the discovery visits, the portfolio moves, the specific next step with each donor. That's the major gift officer's job, and it's exactly what the Major Gift Officer Bootcamp trains: twelve weeks, live, starting September 16.

The Conversation That Fixes Most of This

One structured conversation between the ED and development director, twice a year, that covers:

• Who owns which relationships, and which ones the ED needs to be personally active in.
• What the ED will do specifically in the next 90 days that only the ED can do.
• What the development director needs from the ED to do her best work.
• Where there's role ambiguity that needs to be resolved.
  

That's it.

Most of the failure modes described above don't require complex interventions. They require a direct conversation that most ED and development director pairs haven't had.

Schedule that conversation. Have it honestly. The major gift program will be better for it.

If you're an executive director, what are the three relationship moves only you can make in the next 90 days?

If you're a development director, have you given your ED the specific guidance she needs to be an effective partner, or have you been hoping she'd figure it out?

A strong ED/development director partnership gives your major gift officers clear direction. The Major Gifts Officer Bootcamp gives them the skills to execute it — live, twelve weeks, starting September 16. Register today.

The post The Partnership That Predicts Major Gift Success appeared first on Gail Perry Group.

Estimated reading time: 3 minutes

Here's a question every executive director eventually asks.

Usually quietly, and usually after a stretch of soft major gift numbers:

"Is my development team actually performing? Or am I confusing activity with results?"

It's harder to answer than it looks. Because most development performance gets measured by dollars raised, which matters… but misses a lot.

A team can hit annual fund goals while a major gifts program stagnates. An MGO can stay completely busy while their portfolio barely moves.

Activity and forward movement are not the same thing. Here's how to tell the difference.

Some of what follows comes down to structure. Some of it comes down to skill, and skill can be built. Read on to see which is which.

The Four Indicators of Genuine Major Gift Performance

When GPG assesses a development program, these are the four things we look at:

1. Portfolio movement. Are major donor relationships actually advancing — moving from identification to discovery, from discovery to cultivation, from cultivation toward solicitation — or are they sitting at the same stage month after month? A portfolio that isn't moving isn't a cultivation program. It's a maintenance program.

2. Discovery visit activity. Are new major gift prospects being identified and genuinely engaged on a consistent, ongoing basis? A development team that isn't regularly running discovery visits is managing the current portfolio, not growing it. The pipeline that closes gifts in year three is being built right now… or it isn't.

3. Quality of donor strategy. Is there a real, written, individualized plan for each major relationship? A specific next step grounded in what the fundraiser actually knows about this donor? Or is strategy implicit, informal, and reactive?

4. Executive director's presence in the cultivation work. Is the ED actively involved in major gift strategy alongside the development team — not just reviewing reports — and making the relationship moves that only an ED can make? When EDs are absent from this work, the development director can't move key relationships forward, regardless of how talented she is.

Indicators 1 through 3 are skill-based: they're about what your major gift officers know how to do. If those are the ones falling short, that's exactly what the Major Gifts Officer Bootcamp builds: twelve weeks, live, starting September 16, on portfolio strategy, discovery visits, and donor planning.

Why These Are Hard to See From the Inside

The team sees the activity. The executive director sees the reports. Neither view tells the complete story of what's actually moving, what isn't, and why.

That's not a failure of leadership. It's a structural limitation.

Internal teams often can't clearly see their own blind spots, especially when the team is working hard and committed.

A development assessment creates that clarity: not as a judgment of the team, but as a map of what the program needs to reach its potential.

The Goal: Capable, Not Dependent

The point of an assessment isn't to find problems. It's to find the highest-leverage opportunities: the two or three changes that would have the most impact on major gift results. Then, you build a plan around those specifically.

Organizations that work with the Gail Perry Group leave with a clear, prioritized roadmap: what to build, what to restructure, what to invest in, and what to stop doing.

The value isn't only the findings: it's the direction that follows.

Your development team is almost certainly working hard. The question isn't whether they're working. It's whether the structure around them is built to support the results your organization is capable of producing.

If it's the team's skills that need building rather than the structure around them, that's what the Major Gift Officer Bootcamp is for. Live, twelve weeks, starting September 16: Reserve Your Spot

The post What a High-Performing Nonprofit Development Team Looks Like appeared first on Gail Perry Group.

Estimated Read Time - 4 minutes

We hear this frustration from leaders constantly:

"The board says they want to help with fundraising. They show up to meetings. They believe in the mission. And when it comes to actually doing anything… silence."

Here's the thing: that's almost never a reluctance problem. It's a preparation problem. And it is completely solvable.

The Real Diagnosis: Ambiguity, Not Resistance

Board members who don't help with fundraising are almost never opposed to it.

They genuinely don't know what to do.

Nobody told them clearly.

And because they're accomplished professionals who don't like appearing uninformed, they say yes in the meeting… and then do nada.

The board members who become your strongest fundraising partners aren't always the ones with the biggest networks.

They're the ones who've been given the clearest, most specific guidance.

What Activated Board Fundraising Actually Looks Like

There's a meaningful difference between an educated board and an activated one.

Educated boards understand the campaign goal. Activated boards have personal ownership in the outcome.

Here's what activation requires:

1. A small, specific list. Three to five donors each board member genuinely knows and cares about. Not "reach out to your network." Named people with named relationships.

2. A framework for a conversation that they can make their own. Not a script. The shift from "ask your friends for money" to "introduce someone you care about to something you believe in" is enormous. Most board members, when they finally hear that reframe, lean forward.

3. A clear understanding. What they're asking prospects to consider at this stage, and what they are absolutely not expected to close alone?

4. Explicit permission to pass the torch. To say "let me connect you with our development director" rather than carrying the full conversation themselves.

The One-to-One Briefing That Changes Everything

The board conversation that converts ambiguity into activation isn't a presentation at a board meeting.

It's a one-to-one conversation with each board member, about their specific three to five prospects, what they know about each person, and what a first conversation could realistically look like.

One hour. Per board member. Worth every minute.

Because here's what happens when a board member finally gets it: when they realize fundraising isn't asking strangers for money but connecting people they love to a mission they believe in.

Their body language shifts. They lean forward. The skepticism converts to advocacy.

And you know what’s funny? That board member — the one who brought in the $4 million lead gift — is often the person who was most skeptical in the beginning.

A Note on Timing

This activation work needs to happen before the campaign, not during it.

Once active solicitation begins, there's no time for the preparation that makes board members effective. Build the activation now. Then, when the campaign launches, you'll have a board that is ready and genuinely excited to help.

The question worth asking your board isn't whether they want to help. They do

The question is whether you've given them something specific enough to actually do.

Board activation is some of the most impactful work our consulting team does, and one of the most directly tied to campaign and major gift outcomes. gailperrygroup.com/consulting

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