Proposals That Actually Convert

I Analyzed My Most Successful Proposals and Found These Patterns

Hi!

Proposals used to stress me out. I'd spend hours staring at a blank document, wondering how to start. So I spent a little time reviewing some of my most successful consulting proposals. I noticed patterns in the ones that landed me projects versus those that didn't. Thought I'd share what I found in case it helps with your next pitch.

As a side note, my friend Ben Childers, founder of Stratovation Partners, has a wholly different view on proposals. He doesn't think we should be doing them at all! I'll be chatting with Ben next week and sharing his approach and strategy soon after in another newsletter.

Before getting into proposals, a little housekeeping.

Announcements & Shares

Let's get together

It's always fun saying hi in person. For example, at Netroots Nation back in August, the person in front of me in the registration line was Myles Bugbee, founder of Persuasion & Pixels. We had a nice time talking while waiting, and that led to a newsletter that will be coming out next week.

I'd love to see you, too. Here are a few places I'll be -- let me know if you'll be at any of them!

• Grant Summit: Baltimore, October 29-November 1. One of the best-run conferences out there by the awesome team at the Grant Professionals Association.

• Cause Camp: Pittsburgh November 4-6. I grew up near Pittsburgh, so if you're hankering for hot Steelers takes or just want to know about local restaurants, it's my time to shine.

• NonProfit POWER: Baltimore, December 1-3. Different from most conferences, but well worth it if you're looking to connect with clients in a really intimate way.

My Chorus AI co-founder Tareq Alani will be speaking at the Environmental Grantmakers Association Fall Retreat October 19-22 in New Mexico, as well.

Other writers to check out

Will Robinson: longtime activist, communications strategist, and writer. I've been loving Will's think pieces on strategy and how he's charting new courses for the left.

Maya Kurien: writing about career changes at their most difficult. I've appreciated her honesty and willingness to address tough topics with personal stories.

Civic Shout: from the best in ethical list-building, Civic Shout's newsletter covers everything you need to know about email.

Jeremy Caplan’s Wonder Tools: if you love gadgets and new apps, or you're looking for suggestions to enhance your tech stack, this is a great read.

Now, let's shift our focus back to the heart of this newsletter: writing winning proposals that help you land more clients and grow your consulting practice.

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Back To Proposals...The Cover Matters More Than We Think

I used to rush my cover pages. Big mistake. I've learned that first impressions really do count. Now I make sure my cover includes my logo, the client's name, and a clear title. Nothing fancy, just clean and professional.

The executive summary that follows needs to show I've done my homework. I try to reference specific challenges the organization is facing. Consider including a brief statement about expected outcomes or ROI to immediately establish value. You're trying to illustrate you understand the client's core challenges and have a clear solution. Ask yourself: if the decision-maker only read this part of the proposal, would that be enough for them to say yes?

Timeline & Deliverables Dependencies

I've found that vague promises don't win work. For example, instead of saying "I'll improve your grant reporting process," write something like "I'll create a streamlined reporting template that reduces preparation time by 30%."

Breaking down my work into clear phases with specific dates helps too. Clients appreciate knowing exactly what they'll get and when.

I also explicitly state what's not included. This prevents misunderstandings later. You don't want a client expecting weekly check-in calls that aren't in scope. Spell everything out.

I also suggest clearly mapping out how each phase relates to the next and what needs to happen before we can move forward.

For each milestone in my timeline, I now explicitly state what I need from the client to stay on schedule. For example: "Week 3 - Stakeholder interviews: Requires confirmed interview schedule and contact information by end of Week 2." This clarity helps prevent delays and ensures clients understand their role in keeping the project on track.

I also build in buffer time for unexpected challenges and to account for common setbacks like delayed feedback or scheduling conflicts. In a strategic planning proposal, I included a two-week buffer before the final deliverable, noting: "This allows flexibility for additional stakeholder input if needed and accommodates potential scheduling adjustments during the holiday season."

When presenting timelines, I use visual elements like Gantt charts or simple timeline graphics that clearly show dependencies between different project components. This visual representation helps clients quickly understand the project flow and critical path.

Example of a Gantt chart from Wikimedia Commons

Explaining My Approach Without Sounding Preachy

I've sought a balance between showing expertise and not coming across as a know-it-all. I outline my process step-by-step, explaining how each phase builds on the previous one.

When I describe my methods, I focus on why they work for the specific challenge at hand. For an evaluation project, I explained how my participatory approach would increase buy-in from program staff. The client later said this demonstrated I understood their organizational culture.

Showcasing Your Team & Credentials Effectively

I've learned that clients want to know exactly who they're hiring. Even as a solo consultant, I now include a dedicated section about my background that goes beyond basic qualifications.

For each proposal, I highlight specific experiences relevant to their project. Recently, when pitching to an environmental nonprofit, I emphasized my previous work with conservation organizations rather than my general nonprofit experience.

I also include brief case studies of similar projects I've completed. For example, "For Organization X, I developed a donor engagement strategy that increased major gift retention by 35% within six months." These concrete examples demonstrate that you can deliver what you promise.

When collaborating with other consultants, I include their relevant credentials too. Clients appreciate knowing the specific expertise each team member brings to the table.

Addressing Risks & Contingency Planning

One section I now always include is "Project Considerations." Here, I proactively identify potential challenges and explain how I'll address them.

For instance, in a strategic planning proposal, I acknowledged that staff availability might be limited during their busy season. I outlined a flexible scheduling approach and alternative data collection methods to keep the project on track.

I've found that acknowledging potential roadblocks actually builds trust rather than raising flags. It shows I've thought through the project thoroughly and have plans in place for various scenarios.

I've also learned to go beyond just identifying risks. I make sure to include detailed mitigation strategies for each potential challenge. For example, instead of simply noting "Data quality may be inconsistent," you could write: "Risk: Data quality across departments may be inconsistent. Mitigation: We'll conduct an initial data assessment in Week 1 to identify gaps, standardize reporting formats across departments, and develop custom collection tools where needed to ensure consistent quality."

For high-stakes projects, I include a contingency section that outlines backup approaches for critical components. This might include alternative research methods if primary data collection faces obstacles, or flexible facilitation options if key stakeholders become unavailable. By presenting these contingency plans, I demonstrate foresight and preparedness that reassures clients I can handle unexpected situations.

I also include relevant policies on confidentiality and data security. For a recent evaluation project involving sensitive client information, I detailed my protocols for secure data storage and anonymized reporting.

Clarifying Assumptions & Prerequisites

I've learned the hard way that unstated assumptions can derail projects. Now I include a clear section outlining what I need from the client to be successful.

This includes specifics like "Access to program staff for 45-minute interviews during weeks 2-3" or "Historical program data from the past three years by project kickoff." Being explicit about these requirements helps clients prepare and prevents delays.

I also outline any technical prerequisites or environmental factors that might impact the work. For virtual facilitation projects, I specify the platforms I use and any preparation participants need to complete beforehand.

Pricing Without Awkwardness

Talking money used to make me uncomfortable. Now I present my fees clearly and confidently. I break down costs when it makes sense, showing the value behind my rates.

I've learned to be transparent about payment terms upfront. My proposals specify when payments are due and what triggers them. This prevents awkward conversations later.

I also include a section about how we'll handle scope changes. This protects both me and the client if the project evolves.

Making It About Them, Not Me

My early proposals talked too much about my experience and not enough about the client's needs. Now I focus on their challenges and how my work addresses them specifically.

I use "you" more than "I" throughout the document. Instead of "I excel at strategic planning," I write "Your team will gain clarity on priorities and next steps."

I've also learned to customize every proposal. Using the same template for different clients doesn't work. Organizations can tell when you've just changed the name on a boilerplate document.

Professional Formatting That Stands Out

I know it sounds minor, but proposal formatting really can impact client perception. Make sure to maintain consistent fonts and styling throughout, with clear section headers that make navigation intuitive.

White space can be your friend. Break up dense information with bullet points, charts, and occasional diagrams to make your proposals much more readable.

For longer proposals, I include a table of contents with page numbers. This simple addition has received positive feedback from busy executives who need to quickly find specific sections.

I also use my brand colors consistently but sparingly. A touch of color in headers or for emphasis creates a professional look without becoming distracting.

Comprehensive Follow-Up Strategy

My proposal process doesn't end when I hit send. I've developed a follow-up approach that keeps communication professional without being pushy.

I always send a brief email confirming the proposal was delivered and offering to walk through any questions. For more complex proposals, I suggest a specific time to review it together.

I've created a simple tracking system to note when to follow up if I haven't heard back. Usually, I check in after 5-7 business days with a friendly, value-focused message rather than just asking "Did you get a chance to review?"

When feedback comes in, I respond thoughtfully rather than defensively. Being willing to adjust aspects of my proposal based on client input has helped me save several projects that might otherwise have gone elsewhere.

Avoiding Common Mistakes

These are some of the most frequent mistakes I've heard about over the years:

Submitting a proposal with vague deliverables and an unclear timeline.

Too much dense, hard-to-read text. Now I use clear headers, bullet points, and plenty of white space.

Over-promising. Early in my consulting career, I committed to unrealistic deadlines to win projects. This led to late nights and weekend work. Now I set honest, achievable goals that I know I can meet.

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Final Touches That Make a Difference

Before sending any proposal, I take a break and then proofread it with fresh eyes. I've caught embarrassing typos this way.

I convert the final document to PDF to ensure consistent formatting.

After sending, I follow up to confirm receipt and offer to answer questions. This simple courtesy has helped me stand out from consultants who disappear after submitting their proposal.

What about you? Any proposal strategies that have worked particularly well in your practice? I'm always looking to improve my approach.

Until next week,

Sam

P.S. If you found this helpful, I'd appreciate you sharing this newsletter with other consultants in your network. We're building a community of social impact consultants who support each other's growth.