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Your Most Common Proposal Challenges (and how to solve them)

Juggling RFP deadlines, stakeholder feedback, and customer questions can make it difficult (if not impossible) to reflect on your proposal approach and ways you can improve. To help you on this journey, we’ve compiled a few of the most common proposal challenges and steps you can take to solve them. 

If your challenge is…

Not enough time to write proposals.

By far one of the most common proposal challenges is not having enough time to actually create the proposals. Writing a thoughtful proposal requires having space to deep dive into the customer, your solution, and how the two work together (not to mention your competitors for those RFP situations). We’ve shared plenty of hacks on how to save time, write faster, and create a repeatable process, but there is a point where you can’t optimize anymore. 

That’s when the best solution is to get help. 

Solution: Get Help

Help with proposal writing falls into three main areas. 

Option 1: Hire Employee

If you are often creating proposals, especially RFP responses, sometimes hiring an employee is your best option. Having an employee on staff means they are an expert in your company, can be dedicated solely to growing your company, and have a direct stake in your company’s success (i.e. their salary). Depending on how often you’re creating proposals, this might be the most cost effective option for your company. 

Need help hiring a proposal writer? Our Hiring & Onboarding services help you find, interview, and onboard proposal writers aligned with your company. Learn more here. 

Option 2: Hire Temporary Writer

In some cases, you know you have a busy season and only need help during that time frame. Many companies turn to temporary proposal writers in this case to have extra help when things get busy. This has all of the benefits mentioned above without the long-term commitment of a full-time employee. 

Option 3: Work with Proposal Company

There are many cases where you might prefer to outsource your proposal writing to a company. If you don’t have enough proposals to fill the time of an employee, if you like having an outside perspective as part of your sales process, or if you rarely respond to RFPs and need help for just a few, then outsourcing your proposal writing to a company could be a good fit. There are all types of support available, from monthly retainers to one-off projects and everything in between. 

Yes, we offer proposal writing support. Check out our offerings here.

Your competitors always win.

There’s nothing more frustrating than putting in a ton of effort to respond to an RFP only to find out that your biggest competitor won…again. 

It can be discouraging to have this happen, and you may feel like giving up to stop “wasting” your time responding to RFPs. 

But it doesn’t have to be that way. Instead, you can focus on your win strategy.

Solution: Create Better Win Strategies 

Too many companies see an RFP that aligns with their offerings, quickly draft a proposal, and send it in hoping for a win. Sometimes this strategy works, but most of the time it doesn’t.

If you’re serious about pursuing RFPs, doing some prep ahead of time will dramatically improve your win rates. What type of prep should you do? 

  • Learn how your competitors pitch their offerings

  • Uncover common customer pain points

  • Develop relationships with buyers

  • Draft key content to have on hand

  • Outline your win themes based on competitive research

  • Form partnerships as needed

These are just a few examples of steps to take before the RFP is released. If you’d like help creating your win strategy, book our consulting services or sign up for the Bid to Win: Advanced RFP Strategy course.

Your team doesn’t have a proposal background.

Many RFPs have instructions on how to create a compliant response. It stands to reason that your team should be able to figure it out on their own, right? 

Wrong. 

Top companies spend at least six months training their proposal writers on how to create proposals that win. If your team has little to no training, then expecting them to write winning proposals against your biggest competitors is like sending your high school’s top track star to the Olympics with no prep (okay, maybe not quite as dramatic, but you get the idea). 

The solution to this is, of course, training.  

Solution: Training

A first step in training your proposal team is to first decide what areas they need to grow. A few key skills for proposal writers include: 

  • Project Management

  • Understanding RFPs

  • Creating Competitive Strategy

  • Strategic Proposal Writing

  • Technical Writing

  • Design

Once you’ve identified your team’s gap, find trainings in that area.

Need proposal writing training? 

Here’s how ours align with the above skills:

We also offer team trainings on any of the above topics and can create custom workshops based on your team’s goals! Learn more and schedule a Discover Session here

Lack of process.

If a customer asks for a proposal or an RFP lands on your desk and you don’t know what to do, then lack of process might be your challenge. 

It doesn’t have to be that extreme though. Even some companies who send out a dozen proposals a month suffer from an ill-defined process. If at any step in the proposal development process you have to ask for clarity or struggle to know what is “right”, then process may be your issue.

Solution: Create structure

The more structure you have with proposals, the better your team will be. Especially with RFPs, there’s no time to waste trying to hunt for the right piece of content or getting approval. 

If process is your issue, here are a few common first steps:

  • Make sure your content library is up-to-date with approved content

  • Have a clear Go/No Go process so you can instantly decide if it’s worth responding to an RFP or not

  • Document approvers, SMEs, and points of content and share with everyone on your team 


The above are a great first step to improving your process challenges. 

Still need more help? With our custom consulting service, we’ll review your process and help you establish a stronger one. Or if you only need help with crafting your content library, then check out our proposal writing services.

You’re ready for RFPs but don’t know how to get started. 

Many companies have a goal to secure a large (often government) contract. But if you’ve never responded to an RFP before, then there’s a bit of a learning curve. 

In this case, it’s best to learn from an expert to save time and ensure you present your company in the best possible way. 

Solution: Guidance 

Many of the solutions in this post can help you enter the world of RFPs. Here at Utley Strategies, we have three main ways to help you with this: 

  • RFPs 101. This work-at-your-own-pace course introduces you to RFPs and the procurement process so you know what to do when you encounter an RFP. 

  • Proposal Support. If you need help writing, we offer VIP Days and take on a limited number of proposal writing projects each month.

  • Proposal Session. Sometimes you just want to talk through your current proposal, an opportunity, or your strategy. In this case, our Proposal Sessions might be a good fit. These one-hour sessions give you direct access to our founder, Demi Utley, to discuss your current challenges and develop a plan–without the commitment of a full project. 

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