10 Questions to a Winning Proposal Strategy

Do you know how to develop a winning proposal strategy?

This article will help you do just that – develop a winning proposal strategy

If I’ve seen it once, I’ve seen it a thousand times. And to be honest, I can’t blame people for acting the way they do. Leaping before thinking. It gets the best of us on many occasions.

A new project gets announced. It’s exciting, large, sexy, and will keep your firm working for months, if not years. So, ‘let’s get down to business and win this damn thing’ is how the thinking usually goes.

A flurry of emails quickly circulates through the office. Everyone downloads the bid documents – Request for Qualifications (RFQ), Request for Proposals (RFP), or something similar. Calendars are checked, and meetings are booked. Everyone is brought together to determine how best to proceed.


It’s at this stage that most firms make a costly mistake.

With everyone sitting around an impressive boardroom table, freshly printed and sparsely highlighted bid documents in tow, the discussion almost invariable progresses very quickly to roles and responsibilities – who should do what, and when should the team reconvene to assess progress? And man, does that feel good. Making progress. Getting stuff done. Assigning people tasks. Scheduling meetings. Developing next steps. That’s what business is all about. Right? That’s how progress is made. And projects won.

Unfortunately, for too many firms on too many occasions, not enough time is spent answering a critically important question before getting down to the ‘real work.’ What’s the win strategy? If you can’t develop a compelling win strategy, your firm probably shouldn’t be pursuing the opportunity in the first place.


What’s Your Winning Proposal Strategy?

Developing a strong, compelling proposal win strategy isn’t easy. But when done well, it’s often the difference between winning and losing. And really, what’s more important than increasing your chances of winning? Nothing, that’s what.

Too often, firms believe an effective win strategy begins and ends with ‘our people, our project experience and commitment to customer service.’ At this stage, I would ask them what their competitors would say if asked about their winning strategy. Heads nod. And it’s quickly determined that most firms, without taking the time to think more strategically, will offer up the same basic building blocks for what differentiates their firm.

An effective win strategy often sits at the centre of three concentric circles – what your client values, what your firm can deliver, and the weaknesses of your competitors. As I said earlier, developing a compelling win strategy isn’t easy. But the rewards of thinking this through are enormous.

I read somewhere that ‘best practice’ indicates that 10 to 15 percent of the time spent on a proposal should be committed to developing a winning strategy. I’m not sure if that number is correct. But what I do know for certain is that you should not begin any real work on a proposal until you’ve convinced yourself that you’ve developed a compelling strategy to win it.

When developing a winning proposal strategy, it’s difficult to be highly prescriptive in a blog post of around 1,000 words. An excellent step in the right direction, however, would be to ask and answer the following 10 questions about the client, your likely competitors, and your firm.


  • Why does this project matter to the individuals involved – those directly impacted or those with a say in selecting the successful proponent?
  • What keeps them up at night, what are their concerns, and how could this project go right or wrong from their perspective?
  • Why does this project matter to the organization, and how does it contribute to its long-term objectives?
  • What are the objectives for the project, and how can your firm demonstrate its ability to help achieve them?

Your Firm

  • How can you best position your project experience to reinforce its relevance?
  • How can you tell the story of our people and link their experience and qualification to the project’s requirements?
  • How can you leverage everything you’ve learned over the years on similar projects and bring the learning to bear to the benefit of this client and this project?


  • What strengths do your competitors possess, and how can they be effectively neutralized?
  • What weaknesses do your competitors have, and how can they be exploited?
  • What competitive advantages does your firm enjoy over the likely competitors, and how can you make them an important element within your proposal?

You may not necessarily be the only firm to claim a competitive advantage in each area, but you must be able to ‘own’ it – to credibly convince someone that you can deliver that attribute better than any other individual or firm.

A winning proposal strategy begins in a place of honesty and deep introspection. They start with a deep understanding of the client, your competitors, and yourself. And it proves the adage that anything that worth’s doing is worth doing properly.

Ok, now let’s go win this damn thing. Good luck.