Proposal Mastery: Affecting Proposal Outcomes through Content and Leadership

By Olessia Smotrova-Taylor

What separates outstanding proposal managers from mediocre ones is the ability to lead their teams in developing winning content on top of running a smooth process. No matter how compliant and attractive the document may be, most often it is the substance that will distinguish a winning proposal from the rest. Many proposal managers rely on Subject Matter Experts (SME) to create the substance, but most SMEs require guidance, facilitation, and significant rewrites in order to produce something innovative and compelling. Rarely is a proposal team blessed with a solution architect who can guide the SMEs. In the majority of cases, a truly top-flight proposal manager steps up to become that solution architect, to ensure that their proposal content shines.

As a proposal manager, you are the person who is ultimately responsible and most invested in whether the proposal wins or loses. As a result there are certain things you cannot afford to do when it is your win rate on the line. If you relinquish ownership over the content of the proposal and relegate yourself to merely running the process, then you put yourself at risk of “garbage in, garbage out. Just as a master programmer is more valuable than a junior code monkey who stops caring once the code compiles, a master proposal manager who ensures that the information running through the proposal process will return a meaningful sales document adds tremendous value to the process. Claiming to be “all about compliance” is another major no-no. Those proposal managers who are all about compliance will inevitably dump every single “shall” from the RFP into the outline, without weeding out obvious statements that do not require a response, such as “the contractor will acknowledge the receipt of CAC cards.”The absolute biggest mistake you can make is praying that the SMEs take care of the content, instead of coaching them to do it, the way a seasoned proposal professional like you would.

The other skills you must develop in order to ensure you have the final say include learning how to facilitate solution development to coax better approaches from SMEs; mastering the art of coaching non-professional proposal writers to drive content to a winning quality; running airtight in-process reviews; learning how to tell good content from bad content; and how to roll up your sleeves, interview SMEs, and fill the graphics and text gaps yourself if the team is not operating to your satisfaction. The end result is an increased win rate for you, and promotion from the general population of perfectly adequate proposal managers into the realms where the superstars live and work.

In order to reach proposal mastery, there are six steps you can follow in every proposal.

Step 1: Become an Overnight Expert in the New Proposal’s Subject Matter

You may ask, “But how am I supposed to validate the content of a proposal I’m managing if I don’t know the subject matter well?” Good question. Fortunately, there are exact how-to techniques to help you master any subject matter in a week or less, which are well-established and used by a variety of other professions, including journalists and Navy SEALs, which a proposal manager can use to become independent of any given industry. Becoming an expert at becoming an overnight expert is a skill just like any other. It’s actually easier than it seems, and you probably have done parts or all of it before, consciously or unconsciously.

The process happens in several phases.

The first phase of becoming an overnight expert is an “absorption phase.” In this phase, your mind acquires passive vocabulary and starts connecting all the pieces of information together. You have to first approach the subject with confidence and curiosity, or what Shunryu Suzuki calls the beginner’s mind. In other words, you have to find your Zen while drinking from the fire hose. Suspend any panic or insecurity you may have about learning a new subject; remember, it is expected that you won’t understand much right away. Instead, focus your energy on absorbing as much as possible as quickly as possible. It’s much easier if you relax while paying attention as the information flows through you; this attitude actually recruits your subconscious mind to work for you instead of against you as you begin to familiarize yourself with the material. The hardest part is staying relaxed and ale rt, instead of relaxed and tuned out. If you find your attention wandering, force yourself to focus back.

Start with the Objectives and Background part of the Statement of Work (SOW), and understand what the opportunity is all about, and who is doing what to whom and for whom. Then read any materials you have about the opportunity.

The easiest way to begin identifying what you need to research is to thoroughly break apart the SOW into its constituent parts. Work front to back, and draw a Work Breakdown Structure to create a graphical representation of the document. This way, you will be able to visualize how all the moving parts fit together. Once you have this representation, find documents on the web that show different facets of the program and subject matter (but don’t read them yet beyond an initial scan to confirm that they are useful). If a subject is completely new, find a primer on websites such as Wikipedia. Write out the key terminology and look up acronyms and concepts – it is just like learning a foreign language.

Apply speed-reading techniques to process the mountains of material you turn up – take a class on it – it is a time well-spent. In a nutshell, when you face a giant stack of documents to read through, preview each document first for structure, organization, and key landmarks. Isolate necessary information into sections; the most critical sections to read in detail versus what you only need to skim. Make sure you take notes as you read; studies show that people who write down notes retain information up to 70% better than those who do not. Finally, organize information the way it would be useful for the proposal, to make it easier to map one-to-one for tasking SMEs.

The next phase of mastering new subject matter is the “active listening phase. Ask questions using a brainstorming checklist (yes, you should not go into a brainstorming session without an agenda and a checklist of questions you want answered when developing a solution), and listen to the SMEs discuss the subject matter. Pick out the words you know, and focus on things that currently make sense. When your mind drifts, forcefully direct it back to the material or discussion. Continue to take detailed notes, pondering the meaning behind each point. You can actually fool your brain into listening better using physical cues, such as making eye contact with the person who is talking, and maintaining an attentive posture (leaning forward slightly, with your body pointed toward the person you are listening to). Paraphrase and repeat the points the other person is making, in order to clarify your understandin g in your own words.

The third phase is the one I consider the most fun but nerve-wracking – this is where you start passing yourself off as a “junior expert”, to see how long you can keep up the appearance of expertise. Do not readily confess your ignorance in the field. Instead, look for opportunities to put yourself on the spot, and enjoy the adrenaline rush. If you have done your homework right, you can command respect from your SMEs as a knowledgeable person and actually begin to deepen your understanding of the subject. Remember – you can always go back to a failsafe excuse: “I am not an expert in the field, I am a proposal manager.” The real point of the game is to participate actively in discussions, and process information as it comes to you in context. The best questions to ask are “Did I hear it right? You said that …” and “Who is this?” or “ What is this?” (if it’s not in the information you were given to read on the pursuit – and is not distracting from the main conversation). Before you speak up, ask yourself, “is this an annoying question that would distract the group and destroy my credibility, or is it a question that helps everyone, including me?” The goal is to get to a contextual understanding – you don’t have to understand every term you encounter.

The fourth phase of mastering a new subject is the “common sense” phase. This is where you focus on acronyms, terms, and concepts you don’t understand and relate them to things you do understand. Isolate the obstacles to understanding: often there is something that you don’t understand and that causes your brain to stall. Each time you encounter a familiar concept, think about it in detail, and relate the unknown material to what you know. Figure out what the system/service/ product does, translated to a common language; deduce what the customer wants in a nutshell and why. This is the phase where you begin to simplify your mental picture of the SOW. Picture yourself as the user who needs this system/service/product, and not a provider. Translate everything technical and complex into simple, practical terms; what is the customer’s problem, and what are the biggest challenges and day-to-day strugg les? If you can’t figure it out yourself, ask an SME to explain it to you as if you were a seventh-grader.

The fifth, and final phase of subject matter mastery is the sorting phase. Sort the disjointed information into “buckets”, and ask questions to figure out the 8Ws about each main topic:

    • Why
    • What
    • Who
    • How
    • When
    • Where
    • Wow

This focuses the SMEs and helps them fill the gaps. As you stay with the subject matter, patterns will emerge. Figure out what are the most important parts necessary to win this proposal (hint: that would be the benefits to the customer from the customer’s standpoint). Keep pointing the SMEs to what’s needed to win this proposal, and push the SMEs to come up with innovative solutions.

Step 2: Initiate and Facilitate Solution Development Sessions

Before you hold a solution development session, determine what Nirvana looks like for the solution. Then, when you gather the SMEs together, assess where the company is right now in relation to that ideal. Be creative; go for quantity of ideas at first, withholding judgment initially when getting the ideas out. Listen and say what you LIKE about the idea, what are your concerns, and make constructive suggestions for each concern raised. Encourage everyone to piggyback on each other’s’ ideas. To cut down on brainstorming time, use solution development checklists for the management and technical solutions, and use templates and process for the rest, including past performance, resumes, plans, cost, etc.

Another technique for generating great content is to master is the art of the SME interview. Before you go into a one-on-one or few-on-one session like this, prepare all the RFP criteria and figure out what questions you need to ask. Record the interview, as you may miss information when typing notes. Ask all the 8Ws and make note of actions and decisions that need to take place; after getting through the facts, prompt them to talk about their feelings on certain subjects to get to the stories and anecdotes.

Step 3: Give Ample Direction and Help to SMEs

It’s important to remember that you are the expert in writing a proposal, and that proposal writing is very different from academic, technical, or intramural business writing. First and foremost, coach your SMEs to write just as they would say the sentence aloud. This encourages clear writing. Provide the SMEs with the resources they need to orient themselves quickly, including just-in-time training in writing and detailed work packages or outlines for their sections. Remove bottlenecks proactively for them, both upstream and downstream, to ensure they encounter as few snags as possible while retrieving important information. As the proposal manager, you have to be the advocate and cheerleader for your team, providing mid-process coaching and facilitating meeting to encourage collaboration and peer reviews. Make it easier for the SMEs to download content from their brains by interviewing and recording and transcribing the material, or using a tool such as Dragon Naturally Speaking that uses speech recognition to type spoken words. Finally, don’t be afraid to redirect resources if a SME isn’t working out where they’ve been assigned.

Step 4: Run In-Process Reviews

An in-process review (IPR) is one of the key tools in your toolbox to track progress in addition to status meeting agenda. This is where you read through every single section of every single document that is in progress, using track changes and the comment function in Microsoft Word. It is a rolling review – work doesn’t stop while you go over the documents. Ideally, you should do an IPR every 1-3 days to ensure there is no time lost, to prevent writers’ drift, and to offer timely directions. This way, there are no embarrassing surprises for you during formal reviews.

Step 5: Tell Good Content from Bad Content

While you are conducting IPRs, be sure to read every proposal section to check if the content is rotten. Don’t get stuck on writing quality – look for substance above all – especially focusing on the worst content offenders, including cut-and-paste, off-topic writing, bland fillers and lack of substance, missing “how”, and lack of benefits language. Identify specific gaps using 8Ws, checklist questions, and compliance items, and devise a recovery strategy to get back on track.

Step 6: Fix Yourself Whatever isn’t Working

Forget about the principles of good management – your end goal is winning. You don’t get an award for “doing work through others” as a manager would; you get rewarded (hopefully) for getting a contract award. As a proposal manager, you are the most invested in producing a winning finished product. So, roll up the sleeves and fill the gaps, refine benefits, redo weak approach write-ups and graphics, and have the SMEs vet the accuracy. Put your personal stamp all over the proposal; pore over every word, including tables, and ensure they’re up to your standards. Check the cost volume to make sure it matches the technical proposal. One great technique to ensure your document flows nicely is to read it aloud after the editors have finished working on it; you will catch many boo-boos and awkward or unclear phrasing this way. In other words – leave absolutely nothing to chance.

Once you apply these six steps to a proposal effort, you will notice a drastic difference in the final product – and will likely impact the proposal outcome. This is when you reach proposal management mastery.

P.S.: If you need Business Development, Capture Management, Proposal Management and Writing, or Proposal Training Support, contact us at 301-384-3350 or at We have 800+ fully vetted capture and proposal managers, technical writers, graphic artists, orals coaches, editors, subject matter experts, and other proposal support. We have supported 18 out of the top 20 Federal Contractors and have won $18 Billion since 2005.


Olessia Smotrova-Taylor
OST Global Solutions, Inc.

One thought on “Proposal Mastery: Affecting Proposal Outcomes through Content and Leadership

  1. Great post. As an orals coach, I typically get called in after the written proposal has been submitted. (It’s better when I work with the proposal team from the beginning, but that happens infrequently.)

    I agree with how you’ve defined the PM’s role. I see my role as the orals proposal manager, subordinate to and working in tandem with the PM, in much the same light. I believe in actively shaping the oral proposal’s strategy and message, which is or should be a version of the written proposal’s strategy and message. (When the written proposal was mostly about compliance, I have my work cut out for me.)

    Over the years I’ve changed how I work with a proposal team to conform much more to your model. I used to confess ignorance of the subject (the solution being proposed), but mastery of the process (of making an oral proposal). Now I spend much more time learning the subect and understanding the solution.

    I’m going to send a link to your post to some of the BD people I work with, because I think they’ll find it invaluable. Thanks.

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