Three questions a good marketing advisor asks before you spend another dollar
Most founders don’t have a marketing problem. They have an order-of-operations problem.
The usual sequence goes like this. Revenue flattens, someone recommends an agency, the agency sends a proposal, and the founder spends a week deciding whether the proposal looks reasonable. The question being answered is “is this agency any good?” The questions that should have come first never get asked.
There are three of them, and a good marketing advisor asks them in this order.
1. What should we actually do?
Before anyone talks about channels or vendors, you need a diagnosis. What is holding growth back right now? It might be traffic. It might be conversion on the site. It might be that customers buy once and never come back, which no amount of new ad spend will fix.
A useful test of the diagnosis: can you explain in two sentences why the next dollar should go to this channel and not another? If the honest answer is “because the agency we spoke to does paid social,” the diagnosis came from the vendor, not from the business.
Write the answer down before anyone sells you anything. It should name one or two problems, not ten.
2. Who should do it?
Only once you know the job can you pick the right shape of help. Some jobs suit a specialist freelancer: one channel, a clear brief, a founder who can manage the work. Some need an agency, because the work spans several channels or needs cover when someone is away. Some belong in-house, because the knowledge has to stay inside the business.
The mistake is choosing the shape first. Founders who start with “we need an agency” end up with an agency, whether or not the problem needed one.
A practical check: for each job on your list, write down who will manage that person or team week to week. If the honest answer is “nobody,” keep the scope small until someone can.
3. What should it cost?
This is the question founders feel least sure about, and the one vendors are happiest to answer for you.
Start from your total marketing budget, not from the proposal. Gartner’s 2026 CMO Spend Survey puts total marketing budgets at 7.8% of company revenue on average. Gartner’s sample leans toward large companies, so treat that as a sense-check rather than a target. It is still useful: if one proposal would eat most of your budget before a dollar goes to media, the scope or the partner is wrong for your stage.
Then split the budget between people and media. A brilliant team with nothing to spend can’t prove anything. A big media budget with nobody competent running it burns faster.
Finally, ask for the price line by line. If a partner can’t explain what each line buys, you can’t judge whether it’s fair.
Why the order matters
Answer the questions in reverse and you get the most common failure: a founder picks the partner they liked best on a call, accepts the scope they were offered, and finds out six months later that the work was aimed at the wrong problem.
Answer them in order and most decisions get easier. You can compare proposals against a plan you already own. You can turn down good agencies that are wrong for this particular job. And you can tell, month by month, whether the work is moving the number it was hired to move.
Where an advisor fits
You can do all of this yourself, and many founders do. What helps is someone who has read a lot of proposals, knows roughly what good work costs, and isn’t selling the service being recommended. That’s the gap Connectwright was set up to fill: work out what to do, place the right agency or freelancer at the right price, then stay on to oversee the work.
Whoever helps you, keep the order. What first, who second, cost third.
Connectwright is a marketing advisor for founders, based in New York. Partners it introduces pay it a referral fee, and you’ll always know before you sign.
