Proposals Don’t Have to Suck

Raise your hand if a proposal has ever made you cry in a parking lot.

Yeah. Me too... at least once. Back before I knew proposals could be any better.

Somewhere along the way our industry decided proposals are supposed to hurt. Cold pizza at 9pm. Seventeen versions of the same file. The SME who ghosts until the night before red team. The proposal manager running on Dr Pepper + spite.

Plenty of teams wear that misery like a badge. I never could. Those parking lot moments felt like a sign something was broken... and I wanted to fix it.

Miserable teams write miserable proposals. Tired writers hedge. Burned-out SMEs hand you three bullets + a resume from 2019. And the people you need most for the next bid quietly decide they’ll be “slammed” the week it drops.

A team that enjoys the pursuit shows up early, thinks harder, writes sharper, and raises its hand for the next one. Fun is a competitive advantage. So let’s build it on purpose.

The proposal manager sets the weather

Every proposal team takes its emotional cues from one person. The proposal manager.

Walk into kickoff frazzled, apologizing for the schedule, and the team hears “this is going to be bad.” Walk in with a locked plan, some energy, and a sense of humor, and they hear “we’ve got this.”

I played Division I basketball. The best point guards I played with weren’t always the best shooters. They set the pace, called the play, and made everyone around them look good. Same job here.

Here’s what that looks like on a live pursuit.

They carry the plan so nobody else carries the anxiety. Outline, assignments, review dates, and the submission date… all locked before kickoff ends. People relax when they can see the whole road.

They guard the team’s time like it’s billable. Because it is. Shorter meetings. Fewer “quick syncs.” No 11pm emails that imply an 11pm reply.

They absorb the chaos. An amendment drops at 4pm? The proposal manager figures out what changes, then tells the team once, calmly, with a fix already attached.

They keep selling the win. Why does this pursuit matter? What does winning mean for the people in the room… the program they get to run, the team they get to grow? Say it at kickoff. Say it again at pink team.

They celebrate out loud. Small wins, in the moment, by name.

And one non-negotiable. We don’t do all-nighters at Summit. Ever. If the plan needs one, the plan is broken… and fixing it before it breaks the people is the proposal manager’s job.

Your team will match your energy. Pick it on purpose.

Eight ways to make your next proposal fun

Try all eight. Or pick two for your next bid.

1. Give the pursuit a code name. “Operation Thunderbird” gets more energy than “RFP 70CMSD26R0042.” Let the team vote. Yes, it’s silly. It works.

2. Open kickoff with the customer, then the compliance matrix. Spend the first ten minutes on who the buyer is, what keeps them up at night, and what winning means for us. Then hand out assignments. People write better for a person than for Section L.

3. Play red team bingo. Build a card with squares like “world-class,” “feature with no benefit,” “passive voice,” “we’re excited to,” and “proof point missing.” First reviewer to call bingo picks lunch. Your reviews get sharper and your writers stop dreading them.

4. Make progress visible. A board everyone can see… sections moving from drafting to review to done. Dragging a card to “done” is weirdly satisfying, and nobody has to ask “where are we?” again.

5. Run a 15-minute daily standup that ends with a shout-out. What’s done, what’s stuck, who needs help. Then one person gets called out for something great. Every day. Out loud.

6. Start a traveling trophy. We love a Golden Highlighter… it goes to the best sentence of the pursuit. Silly trophies create real competition, and GovCon people are competitive by nature. (I’d know.)

7. Feed people like you mean it. Know everyone’s order. Stock the Dr Pepper. Remote team? Send a lunch credit on review day. Small gesture, huge return.

8. Submit early, then make some noise. Upload a day ahead. Screenshot the confirmation. Ring a bell, post the team photo, send everyone home. Then hold the internal debrief within a week, win or lose, over tacos.

Fun comes from a hundred small rituals. Pick yours and repeat them until they’re culture.

How to get great work from SMEs who hate proposals

Let’s be honest about why your SMEs dodge you.

They got a 40-page template, a vague assignment, and a deadline that collides with their billable work. They wrote something at 10pm. Then a red team reviewer who’s never done the job tore it apart in a comment bubble.

I’d hide too.

Your engineers, scientists, and program managers hold the proof that wins the work. The proposal manager’s job is to make giving it up feel easy… maybe even enjoyable.

Interview them instead of assigning them. Book 30 minutes. Record it. Ask the questions, let them talk, then have a writer draft from the transcript. Most SMEs will happily talk for half an hour about a job they’re proud of. They won’t write two paragraphs about it.

Ask for stories. “Describe your approach” gets you boilerplate. “Tell me about the time it went sideways and how you fixed it” gets you a discriminator. Try “What would you tell the customer over coffee?” and watch them light up.

Make the ask tiny + specific. “Write the technical approach” is a nightmare. “Three bullets on how you cut the schedule on the bridge rehab job, by Thursday at 2” is a five-minute task they’ll actually finish.

Protect their hours. Get the charge code set up and clear the time with their boss before kickoff. A SME choosing between your proposal and their utilization number will pick utilization every time.

Run interference on reviews. Reviewers comment on the work. The proposal manager translates those comments before they reach the SME. Nobody needs to read “this is weak” from someone they’ve never met.

Show them their fingerprints. After submission, send them the section with their story highlighted. Win the job? Tell them which piece of their work the evaluators called out in the debrief.

Brag about them to their boss. A two-line email to their manager about their contribution costs you nothing. It’s also the reason they’ll say yes next time.

The line: SMEs show up for proposal managers who make them look smart. Be that proposal manager.

Fun is what a good system feels like

Here’s the part nobody tells you. The fun shows up after the structure does.

When capture hands over real customer intel (we call it WINtel™), when the outline is locked on day one, when reviews have clear criteria... the team gets its brain back. That’s when the code names, the bingo cards, and the Golden Highlighter land. Throw a pizza party on top of chaos and it’s still chaos.

That’s why Propose sits in the middle of the Summit Win System™, between Position and Persuade. A great proposal manager runs that peak like a coach… clear plan, protected people, loud celebrations.

So here’s my challenge. Pick one idea from this list. Use it on your next pursuit. Then tell me what happened.

I’ll bring the Dr Pepper.