Why your best proposals keep losing to your competitors and what’s the real reason behind it
I was on a call recently with several other MSP sellers when one of them got blunt.
“I’m almost at the point where I won’t even meet with them if I can’t get in front of the decision maker.”
It was a sincere and fair frustration. He was burning hours on deals where the owner, CFO, or business partner never showed up. An office manager ran the process. An IT contact collected the quotes. Somebody promised to bring it back to the team or quietly overstated their authority. And the deals died the way they always die.
I have lived this exact pain more times than I can count. Twenty years selling to construction firms in Arizona. Some of my biggest losses were not because we lost on price or scope. They were because I never got to the person whose actual job was on the line if the IT failed. I built proposals for office managers and IT contacts. I lost to whoever was cheapest, every time.
But here is the part of this conversation that should land hardest with builders.
The exact same thing is happening to you.
Not in your IT purchases. In the proposals your firm submits to a client.
The Filter
Every buyer has a filter between the seller and the principal. Always has. The filter exists for a good reason. Owners and CFOs have a hundred things on their desk, myself included. Somebody else has to do the legwork.
The problem is what the filter does to the proposal that comes out the other side. When I cannot get the decision maker in the room, here is what is actually happening to my deal.
I cannot find their real pain, because the person who feels it is not in the meeting. The office manager collecting quotes is not the one losing sleep over downtime. This is a task on her list, not a problem she owns. So I cannot build a proposal around what is actually driving the decision. I build it around what the filter told me, which is surface-level by definition.
Without the real pain to anchor to, I have nowhere to position my company. No way to show how Dimensions is different. There is no problem deep enough to make our value matter.
So I become a number. The decision maker I never met looks at three proposals that all read about the same, and picks on the one variable left.
Price.
I did not lose that deal in the proposal phase. I lost it the moment I accepted I would never talk to the person with the pain, and did not adjust my process.
Now Look at Your Project Side
Replace MSP seller with general contractor or subcontractor. Replace office manager with project manager, procurement coordinator, or owner’s rep. Replace IT decision with capital project.
Same problem.
Your firm submits a proposal on a job. The owner has hired a project manager to run procurement. Sometimes there is a developer, an owner’s rep, an architect, a construction manager, and a CFO. All of them are filters between you and the person whose name is on the building.
The PM collects proposals. The architect scores them on technical merit. The owner’s rep flags concerns. The CFO does a spreadsheet comparison. Somewhere in there, three or four bids that all “look about the same” get put in front of the principal, who is asked to make a decision in twenty minutes between meetings.
And what gets chosen?
The cheapest one. Or the one that survived all the filters. Almost never the one that was best for the actual project. You did not lose that bid because you were not the right firm. You lost it because nobody who actually mattered ever heard the case for why you were.
This is the exact same dynamic I deal with selling IT to your firm. The only difference is the industry. And the consequences for you are bigger than they are for me, because the building gets built either way. Just maybe not by the firm that should have built it.
And Now AI Has Joined the Filter Party
This is the part that has changed in the last twelve months, and it deserves more than a passing mention.
The buyer’s filter used to be people. The PM read the proposals. The architect’s team scored them. The CFO ran the spreadsheet. Imperfect, but human, and humans can be reached, persuaded, asked clarifying questions.
That filter now has AI in it.
Owners and PMs are dropping proposals into ChatGPT and Claude and asking the model to summarize them, compare them, score them against the RFP, and flag risks. CFOs are using AI to do the financial walk-through that used to take an analyst three days. Procurement teams are using AI to write the questions they ask sellers and the framework they use to evaluate the answers.
I am not making a value judgment on this. We run AI in our own business. AI in the buying process is here, and it is here to stay. But here is what AI in the buyer’s filter is doing to your proposal, and you need to understand it.
It is flattening. AI is exceptional at finding the common dimensions across a set of proposals and producing a comparison table. Price, schedule, team, references, deliverables. Every proposal you submit is now being machine-scored against every other proposal in a format that is optimized for “all things being equal.” Which means the things that make you genuinely different, the unstated context, the relationship, the way you would actually run the project, the trust you have built with this client over years, are exactly the things the AI cannot see.
It is filtering you out before you reach the principal. The PM no longer needs to read all five proposals. The PM reads the AI summary, then looks at the two or three the AI flagged as worth a second look. If your proposal had a piece of differentiation that did not survive the summarization, you never made it to the shortlist. The owner never even heard your firm’s name.
It is making the principal feel less needed than ever. Owners and CFOs already had every reason to skip the meeting. Now they have an even better one. The AI gave them the comparison. The PM gave them a recommendation. Why would they spend an hour with you?
This is not paranoia. This is the new shape of the buying process. The contractors who win in this environment are the ones who figure out how to either get past the AI filter, get to the principal in spite of it, or build a relationship that exists outside the filter entirely.
What I Have Learned to Do Differently
Most sellers, when they hit this wall, treat it as binary. Either the decision maker is in the room or the deal is dead. It is not. You do not need the decision maker in the room. You need their input, and there is more than one way to get it.
The honest move is to respect the buyer’s process and find a workaround. Sell them on why getting more involved actually serves them, not you. Show them how their input means a proposal that does not pile in services they will never use. Show them how it means less back-and-forth after the proposals land, because you built it right the first time. Show them how it means the work gets tailored to what actually keeps them up at night, not what your assessment happened to flag.
If they say no anyway, get their input asynchronously.
In my world, when I cannot get the owner or CFO into the meeting, I ask the gatekeeper to put a small set of questions in front of them. Not a survey. Not a form. Five questions designed to do four things at once: pull out the information I need, get to the real motivation behind the spend, set my firm apart from everyone else in the running, and not sound like sales questions.
Here is the set I have landed on for IT decisions.
FOR THE OWNER-PRINCIPAL YOU CAN’T GET TO
- You have not outsourced IT before (or you are changing providers). In your own words, why does making this move now make sense for the business?
- A year from now, what has to be true for you to say this was clearly worth it?
- What does your current setup get right today that you would be unhappy to lose in the transition?
- How are you thinking about this spend: a cost to manage down, or an investment that should return something? And if it is a return, what return?
- Is there anything specific you would want to see in our proposal that we have not asked about?
Notice what these are not. They are not “what is your budget” and “what is your timeline.” Those are the questions everyone else is asking. These are the questions of a partner trying to understand a business, not a vendor trying to win a quote.
Now the Builder Version
Here is the version of those questions adapted for a builder submitting a proposal to an owner client, with the principal nowhere in the room.
FOR THE OWNER-PRINCIPAL YOU CAN’T GET TO
- What does success on this project look like to you personally, separate from the budget and the schedule?
- A year after the doors open, what has to be true for you to say this was clearly worth the investment?
- What is the part of this project that, if it goes wrong, you would be most upset about? What is the thing that has to go right?
- How are you thinking about this build: lowest delivered cost, best long-term value, fastest time to revenue, or something else? If we had to choose one, which one wins?
- Is there anything specific you would want to see in our proposal that we have not asked about?
And for the subcontractors reading this, there is one I would push you to add to the list, because subs feel the filter even harder than primes. Most of you never get within a hundred miles of the actual owner. The GC’s procurement team is your filter, and they have their own incentives.
FOR SUBS BIDDING THROUGH A GC – THE ONE EXTRA QUESTION
“What is the GC’s biggest concern about our trade on this project, and what would they want to see in our proposal that addresses it?”
That question, asked of the right person at the GC, will tell you more about how to win the bid than any spec sheet. Because it surfaces the thing the GC has not told you yet. The trust deficit. The bad experience with someone else last year. The scheduling worry. The owner’s specific pet peeve about your trade. The unspoken thing that is going to come up in the internal conversation you will never be in.
Ask it. Even if the answer is short, the fact that you asked changes how the GC reads your proposal.
The Bigger Point
The deeper truth in all of this is that the buying process has gotten farther and farther from the people whose decisions it actually serves. Owners are busier, organizations are bigger, filters are thicker, and now AI is summarizing what gets through.
The sellers who win in this environment, whether they are MSPs selling to construction firms or contractors selling to owners, are the ones who refuse to accept that they will never reach the person who actually feels the pain. They respect the buying process. But they find a way to get the principal’s voice into the deal, even if the principal will not get into the room.
Because here is the truth that has not changed.
The proposal that wins is almost never the one with the lowest price. It is the one that solves a problem the principal actually has.
You cannot solve that problem if you never hear them describe it. And you will not hear them describe it if you let the filter, human or AI, decide what you get to know. Ask the questions. Even if they go through a middleman. Even if the answers come back in two sentences. The fact that you asked changes the deal.
It always has.
For over 20 years, Computer Dimensions has been the trusted IT partner for Arizona’s architecture, engineering, and construction industry. We help AEC firms communicate better, collaborate smarter, and actually use the technology they’ve invested in. Because in construction, the tools only work if your team does.
IT Built For Builders.
