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Ask An Expert 20 May 25 2 Comments

How to Write Winning Proposals that Get 90% Strike Rate

By
Experiential Trainer, Author & Speaker

How to Write a Proposal that Gets Approved (90% of the time)

If you’re a freelancer or independent contractor who uses written proposals to win jobs, this blog post is for you.

Especially if you’re in the world of training, facilitation, or experiential learning – keep reading.

You’re going to get some hard-earned insights.

After 35+ years in the business and over 1,000 proposals written, I’m proud to say I have a 90%+ success rate.

Want to know how I do it?

I’m going to share the four essential elements I include in every single proposal – and how you can apply them to your own to achieve the same success I do.

Click play below to get started or continue reading…

The Power of a Well-Written Proposal

Let’s be honest – business still often boils down to relationships.

But for large projects, or any formal engagement, a written proposal is still a must.

Whether you’re bidding on a big team-building programme or submitting a quote for a leadership workshop, your proposal needs to reflect your professionalism, clarity, and unique approach.

The Four Critical Elements of Every Proposal I Write

Here’s a look at the four elements that I credit for my high proposal acceptance rate.

1. A Clear Understanding of the Client’s Needs

Right up front, usually on the second page after the logistics (like dates, location, number of participants), I reflect back what I heard in my initial conversation with the client.

This isn’t a sales pitch – it’s confirmation.

I use their words where I can, ensuring they feel heard and understood.

Sometimes, I’ve had clients tell me, “Oh, that’s not quite what we meant,” and I’m grateful for the chance to clarify before the work begins.

Tip: Misunderstandings are one of the biggest reasons things fall apart. Start by demonstrating that you’re aligned from the get-go.

2. Articulating the Difference You’ll Make

Next, I explicitly describe the difference I will make.

After all, why would someone invest in your services if there’s no clear transformation?

I describe what the outcomes will look, sound, and feel like.

For example, I might write:

“My practical training workshops will be designed to inspire, equip, and empower your staff.”

These powerful words are chosen deliberately.

I then align the program design, content, and delivery with those outcomes. That is to say, everything I say and do is filtered through the lens of the difference I have articulated for my client.

Each client is different, so the ‘difference’ I describe varies accordingly – but it’s always clear and intentional.

3. My Philosophical Framework (aka My Approach)

This is where I distinguish myself.

I explain *how* I do what I do. I even wrote a book about it – and I sometimes include it with my proposals.

But you don’t need a book.

What you do need is a clearly defined methodology. I usually describe five principles that underpin all my work:

  • Using the right activity at the right time
  • Sequencing and flow
  • Honouring choice (no one is forced to participate)
  • Encouraging reflection (because without reflection, there is no learning)
  • Making it fun—but not just for laughs. Fun should nourish the soul

And underpinning it all: every person should leave feeling seen, heard, and valued.

4. Investment (and a Risk-Free Guarantee)

Every client wants to know the bottom line.

On the last page of my proposals, I present:

  • A brief summary of who I am
  • The investment (yes, I use the word “investment” instead of “cost”)
  • A risk-free guarantee

For example, here is exactly what I wrote in a recent proposal:

“My fees are always based on your needs, the level of expertise I bring, and are always risk-free. That is, you’ll either love the program I design and deliver—or you don’t pay.”

That’s right. You don’t pay.

Now, no one has ever taken me up on that guarantee (thankfully) – and this is not surprising because I plan to exceed my client’s expectations every time.

But just including it gives your client confidence, especially if the decision-maker isn’t the one paying the invoice.

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What Else Goes Into a Winning Proposal?

I also include:

  • A brief breakdown of major program components (not every activity, but the general shape of the day)
  • Next steps or a clear call to action
  • An appendix with more details about me, if needed.

Tip: Keep it concise. Most of my proposals are 4–6 pages long.

Bonus Resources

If you found these ideas helpful, here are some recent videos and articles I think you’ll also enjoy:

How Do You Prep for a Gig    My Secret Sauce    Framing is Everything

Final Thoughts

If you’ve made it this far – thank you!

I hope this has helped you see proposals in a new light.

They’re not just a formality – they’re your chance to show your client that you “get” them, that you’ll deliver real value, and that they’re safe putting their trust in you.

Of the four elements I’ve shared – understanding the client’s needs, articulating difference, outlining your approach, and offering a risk-free investment—which one stands out to you as the most powerful for improving your proposal success rate?

Let me know in the comments below.

Your insights help others in our community sharpen their skills, too.

Now, go write that winning proposal.

And as always, have fun out there.

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Original post May 2025, last updated May 2025.

By - Experiential Trainer, Author & Speaker

Comments (2)

  1. Graham Monkman

    Many years ago, in another life, I was on a panel evaluating the credentials of advertising agencies to handle a new product launch. Mark, I wish those agencies had been aware of your four critical requirements for a successful proposal. Out of the twelve we interviewed only two showed any understanding whatever of our needs. We were a large provider of products for industrial markets, and one agency after another bored us senseless as they projected endless TV commercials for consumer products. And only one explained their philosophy in relation to advertising and communication, and how they would apply it to our markets . This company went into some detail about their strategic thinking and creative approach, in a light hearted discussion which, importantly, involved the audience. In other words, they ticked all the boxes embraced by your four points – interpreting needs, outlining points of difference, promoting business philosophies and creating a positive fun environment. This is a very valuable and excellently presented video. Congratulations Playmeo.

    1. Mark Collard

      Thank you so much for your detailed response Graham, it is much appreciated, especially so because it comes from an experienced viewpoint.

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