Fundraising Sessions
CHICAGO WOMEN IN PHILANTHROPY
Friday, August 7, 2026 · Impact House, 200 W Madison St
Facilitated by IntuWork Consulting
THE DAY
At a glance
Coffee & Connection
Everyone
Welcome & Icebreaker
Diane & Margaret
Setting the Stage
Diane & Margaret
Volunteer Leader Roles in Fundraising
IntuWork
Break
Volunteer Leader Roles in Grant Writing
IntuWork
Giving Circle Strategy
IntuWork
Lunch
CAM
2027 Priorities & Commitments
IntuWork
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WELCOME & ICEBREAKER · DIANE & MARGARET
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SETTING THE STAGE · DIANE & MARGARET
Why we are all in one room
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SETTING THE STAGE
How we work today
Say the hard thing
If something is not working, this is the room to name it.
Everyone talks, nobody dominates
Some of you do this for a living. Leave room for the people who do not.
We are not solving everything today
The parking lot is real and we will come back to it.
We speak about CWIP, not about individuals
Nobody's giving, capacity, or generosity gets discussed, in here or after.
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Volunteer Leader Roles in Fundraising
Not a fundraising class. A working conversation about what raising money for CWIP asks of us, and where the lines are.
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BEFORE WE START
Let us start with what today is, and what it is not.
This is not
- A training on how to fundraise.
- Some of the best fundraisers in Chicago are sitting in this room. We are not here to teach you your job.
- A session about asking your own network for money.
This is
- A conversation about fundraising for CWIP specifically.
- What that means for us, given who we are and who is in the room.
- And where the line sits between a space that stays safe and an ask that is fair to make.
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SESSION 1
Before we say anything, we want to hear you
"What makes raising money for CWIP feel different from the fundraising you already know?"
Sixty seconds, popcorn style.
A word or a phrase is plenty. There are no wrong answers, and nobody is called on.
Every seat sees it differently.
Grantmakers, grantseekers, master fundraisers, first-timers. That range is exactly why we are in one room.
Whatever you name, we work with it.
Most rooms land on the same tension, and the rest of this morning is built around it.
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SESSION 1
Where CWIP stands today
Stronger than we tend to give ourselves credit for. Worth saying out loud.
Luncheon sponsorship in 2025
up from $58K in 2020
of total CWIP revenue
now comes from one event
of classifiable Luncheon revenue
is foundation gifts
members
with a year-round giving program still to be built
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SESSION 1 · NAMING IT
One question still ahead of us.
CWIP has grown faster than its answer to one question: what are we raising money for?
It is already in motion.
IntuWork is building the fundraising plan and the case for support as part of this engagement. Neither is finished yet.
We are not settling it today.
It deserves more than a rushed half hour, and the answer belongs in the fundraising plan, not in a retreat room.
But we are not working around it either.
After the break we spend twenty-five minutes on it, and what you produce becomes the raw material IntuWork drafts from.
Everything you build this morning is a first draft, and first drafts are exactly where strong cases start.
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SESSION 1 · THE HARD PART
CWIP works because it is a room where nobody is being worked.
Members tell us the same thing in interviews. CWIP is a safe space. Grantmakers and grantseekers sit together and think, without anyone being solicited. That trust is the asset. It is why many people join.
And CWIP still has to be funded.
Both are true. Neither cancels the other. The question we get to work together is: how do both stay true at once?
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SESSION 1 · WHERE IS THE LINE?
Three situations. Is this a fair ask, or is it a place we hold back?
A colleague at an unrelated sector event asks what you have been up to lately.
You are at the CWIP Summer Social. A member mentions her foundation is opening new affinity work.
You sit on a grant making committee. A peer suggests CWIP apply to your fund, knowing you're on its board.
You will not agree on all three. That is the useful part.
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SESSION 1 · TOGETHER
Our rules of the road
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Type what the room agrees on. This becomes the standing guidance for every CWIP leader, not just today.
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SESSION 1
A peer perspective
How someone who lives on both sides of this has handled it.
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SESSION 1 · WHAT IS NEXT
CauseCue Cards
We build CWIP's case for support together, then practice it until the words are yours.
Draft
6 min
You write one sentence, on your own.
Sharpen
6 min
Pairs. Cut it down. Make it sound like a person.
Coalesce
4 min
We take the strongest lines and build the shared set.
Practice
10 min
Two role plays. Real situations, not hypotheticals.
Your CauseCue Card is on the table. Let's use it.
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SESSION 1 · DRAFT
In one sentence: what is CWIP, and why does it matter?
Write it the way you would actually say it, not the way a brochure would.
Then one more line: if someone gave CWIP money, what would it do?
If you get stuck, finish this instead: "CWIP is the reason I…"
One sentence. If it needs a second sentence, it is not finished yet.
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SESSION 1 · SHARPEN
Read yours out loud to your partner. Then cut it in half.
Partners take turns. Read it aloud, do not hand over the card.
Listener: say back the one phrase that actually landed.
Both of you rewrite using the phrase that landed.
Reading aloud is the point. Anything that sounds false on the page sounds worse in the air.
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SESSION 1 · TOGETHER
Our case for support
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Type the strongest lines as they come. These go on the back of everyone's card and into the follow-up email.
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SESSION 1 · ROLE PLAY, ROUND ONE
Scenario A: the ordinary case.
You are at a sector event. A program officer you know casually asks what you have been up to.
You have ninety seconds. Use your sentence.
Partner: play it straight, then push once. Ask something a real person would ask.
Switch at the halfway mark.
Nobody is closing a gift here. You are making CWIP a thing they remember on Monday.
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SESSION 1 · ROLE PLAY, ROUND TWO
Scenario B: the hard one.
Same partners. Switch who goes first.
A peer who has heard of CWIP asks: "How is that different from CFW?"
Answer it cold. No notes.
Partner: if the answer is fuzzy, say so.
Hold on to how this one felt. We come back to it in the giving circle conversation.
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SESSION 1 · DEBRIEF
Before we break
What landed?
Which line got a real reaction from your partner.
What felt false?
The part you would never actually say out loud. Cut it.
Where did you hesitate?
If you paused before asking, that is the line we drew earlier doing its job.
What happens Monday?
You made the case. Then what? That is the gap we are closing next.
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Break
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Volunteer Leader Roles in Grant Writing
The leadership role in grant writing is not writing. It is deciding what we are asking for, and that decision is still ours to make.
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SESSION 2
CWIP doesn't have "staff"
Which means the question is not who to delegate this to. It is who among us does what.
The Board
Approves the plan and the targets. Signs every funding agreement and grant contract. Gives personally.
Fundraising Committee
Carries the work day to day. Owns the prospect list, the pipeline, and who solicits whom, in the proper context.
Chicago Association Management (CAM)
Gift processing, receipts, acknowledgments, the donor database, sponsorship invoicing, event operations.
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SESSION 2
The foundation picture
of classifiable Annual Luncheon revenue
comes from foundation gifts
paid staff
Every relationship CWIP holds is carried by a volunteer
What that means for you
- Foundations renew when the relationship stays warm between asks. That tending is a leadership role, not a writing role. 1.
- None of it requires you to be a fundraiser. It requires knowing what CWIP is asking for, which is this morning's real work. 2.
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SESSION 2
Where do you see yourself in this?
Use your notecards. Three minutes, then we hear a few out loud.
Where could you add the most?
Shaping the case, opening a door, stewarding a relationship, or something else entirely. No wrong size.
What would get in the way?
Time, clarity about roles, the line we drew this morning. Name it plainly. This is the room for it.
What you name becomes design material.
Challenges surfaced today become requirements for the fundraising plan, not complaints about it.
Nobody is signing up for anything.
This is a conversation, not a commitment. Commitments come this afternoon, and only from you.
Grantmakers and grantseekers see different obstacles. That is exactly why we ask the whole room.
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SESSION 2
Every funder asks the same thing first.
"What will this money do?"
It is the one question CWIP has not needed to answer until now, because the Luncheon answered it for us. Between you, this room has read thousands of proposals. No group in Chicago is better equipped to shape the answer.
The next twenty-five minutes are yours. What you produce becomes the starting material for the case for support IntuWork is drafting, and the Fundraising Committee will review.
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SESSION 2 · YOUR EXPERTISE, OUR OPPORTUNITY
The goal on the table is $250K to $500K a year.
Say we got there. What would CWIP do?
Not a wish list. What would CWIP do that it genuinely cannot do now?
Be concrete enough that a program officer could picture it.
Then pick the one you would fund yourself, and be ready to say why.
You have all sat on the other side of this. Answer it the way you would want it answered.
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SESSION 2 · TOGETHER
What the money would do
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Type it as they say it. This is the raw material for CWIP's case for support, and it does not exist anywhere else yet.
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SESSION 2 · PRIVATELY
On the back of your card. No names said out loud.
Is there a funder relationship you would be willing to open a door to? Write it down.
If the answer is no, or not right now, write that. It is a real answer.
Cards go to the Fundraising Committee, not to the room.
The committee maps this privately, funder by funder. Nobody is put on the spot in front of their peers.
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SESSION 2 · GOING DEEPER
Workshop 4: Major Donors
Jarel Loveless, for the whole group, at our next convening.
Individual giving is the one priority on our list with little infrastructure behind it. Workshop 4 is where we build that.
Who
Everyone in this room.
When
[ NEXT CONVENING DATE - TBD]
Details and the invite come with the follow-up email on Wednesday, August 12.
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SESSION 2
Before lunch, three things are true
CWIP now has a first answer to what the money is for.
It is a rough draft, it is yours, and it is more than existed at nine o'clock this morning.
No one was volunteered in public.
The cards go to the Fundraising Committee. They map the relationships privately.
There is no staff, so the committee is the engine.
That is exactly why the handoffs have to be clear. We come back to that after lunch.
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Giving Circle Strategy
The Collective Impact Fund. Where it stands, what it risks, and the direction we need from you before fall planning.
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SESSION 3
Where the concept stands today
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SESSION 3
Three partnership paths
Each carries different implications. Which makes you curious, and what would you want to know before CWIP approached anyone?
CFW
Chicago Foundation for Women
Closest mission fit, fastest credibility. Also the option most likely to blur the line.
First Women's Bank
Corporate partner
Lowest-hanging fruit. Brings a sector we are underrepresented in and does not compete on mission.
The Trust
Chicago Community Trust
Relationship at peak warmth from the 2026 honoree year. Highest ceiling, most complex to structure.
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DECISION POINT
What are your thoughts?
Three questions. We are asking for a directional read on each, so fall planning starts with your voices in it.
Is a giving circle the right vehicle for CWIP?
If yes, is it a sector-professional fund, or something else?
Which partnership path do we explore first, and who owns that conversation?
What you decide here shapes what moves into fall strategic planning.
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SESSION 3 · ON YOUR OWN FIRST
Answer question one for yourself. Before anyone else talks.
Yes, no, or not yet. Write it down.
Then one line: what would have to be true for you to change your answer?
We do this alone first so the first confident voice at your table does not become everyone's answer.
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SESSION 3 · SMALL GROUPS
Threes and fours. Where do you land, and why?
Everyone says their answer to question one before anyone debates it.
Then work questions two and three.
Pick one person to report a single sentence.
Rectangular tables, so keep the groups small enough that everyone can hear.
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SESSION 3 · REPORT OUT
Where the room lands
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One line per group. Type it as they say it, in their words.
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SESSION 3 · THE SIGNAL
Straw poll
Hands, not ballots. We are taking a direction, not passing a motion.
Yes, pursue it
The concept is worth designing. Fall planning picks it up.
Not yet
The identity work comes first. Revisit once we can answer the CFW question cleanly.
No
It is not the right vehicle for CWIP. Put the energy elsewhere.
Whatever the room says, it goes in the follow-up email on August 12.
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Lunch
Hosted by CWIP
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2027 Priorities & Commitments
Thirty minutes. Two priorities chosen, ownership named, and a commitment from every person in the room.
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SESSION 4 · TOGETHER
What should lead in 2027?
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Given everything today, what should CWIP's fundraising priorities be?
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SESSION 4
If the group needs assistance, five potential priorities for the year ahead
Re-engage quiet funder relationships
Warm paths back, mapped privately by the committee
Build a premium sponsorship tier
Increase the top levels of financial sponsorship
Diversify into new corporate sectors
Look at the Chicago Metropolitan Area revenue sectors and diversify
Build year-round individual giving
Set a 12 month goal from members
Develop a process for conversion with the next awardee(s)
Multi-year partnership while the warmth is at its peak
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SESSION 4 · CHOOSE
Which two lead?
Hands up for your top choice, from either list. One vote each, we count out loud.
Then hands for your second.
If the top two are obvious, we move on. If they are not, we talk for two minutes.
Two priorities with real owners will beat four good intentions every time.
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SESSION 4
The handoff we have to get right
Two committees touch the same sponsor. Here is the short version; the full model comes in the follow-up.
BEFORE
Fundraising Committee
Identifies the prospect, makes the approach, negotiates the commitment, keeps the pipeline.
FOR THE EVENT
Annual Luncheon Committee
Owns the sponsor's experience. Recognition, seating, program, the day itself.
AFTER
Fundraising Committee
Thank you notes, reports back, and starts next year's conversation. A sponsor is not a transaction that ends with the luncheon.
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SESSION 4 · CLOSING
Commitments
One commitment each, completed before December 31, 2027.
It can be small. It has to be specific.
- "I will make one introduction to a bank contact by September 30."
- "I will open one funder door if the committee asks me to."
- "I will bring three prospect names to the Fundraising Committee in Q1 quarter."
- And the one we all share: every board member makes a personal gift at a level meaningful to them.
Everyone writes a card. We read six aloud. All of them get collected, and all of them go into the 2027 plan.
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SESSION 4 · WRITE IT
Your commitment card. One thing, and a date.
Name, one commitment, and the date you will have it done.
Before December 31, 2027. Specific enough that you would know if you missed it.
If you are stuck, take one of the five conversations or make one introduction.
Every card gets collected. Whether or not yours is read aloud, it counts.
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SESSION 4
The committments
Six read aloud
Volunteers first.
Everyone else hands the card in
Jaelyn collects at the door. Nothing gets transcribed from a recording.
All of them are real
Every commitment goes in the follow-up email, attributed, so the room can see the whole set.
These commitments become the foundation of CWIP's 2027 plan.
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SESSION 4
What happens by Wednesday, August 12
You get the case-for-support points
The lines this room built, plus a follow-up email template you can use.
You get the full commitment list
Every card, attributed, so we all see the same set.
The giving circle signal goes to fall planning
Whatever the room decided, written down and carried forward.
Workshop 4 details follow
Major donors, whole group, at our next convening.
The case for support gets drafted
IntuWork drafts it from today's material. The Leadership Team shapes and approves it.
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Most consultants deliver promises.
We help nonprofits deliver on theirs.
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Parking lot
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Jump here whenever something good comes up that is not today's business. It gets captured, not dropped.
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OPTIONAL · 60 SECONDS, NO DISCUSSION
Fundraising Committee Charter
The draft charter is in your packet. We are not working it today. Comments to Sarah by [DATE].
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Leadership Retreat