The Truth Is Out There
The simple shortcut to a smarter marketing plan
If you lead a marketing team, you're probably working on your 2025 plan.
Here's a simple two-part tip to make that planning process 10x better:
Stop staring at your spreadsheet and go talk to the two groups who matter most.
(1) Go Talk to 10 Customers
Seriously. Ten. Not one, not two. Ten. Volume matters here - not just for the additional data you'll get, but for the demonstration that you're serious about getting to the truth. Ask them:
What were you doing before you found us?
What was the moment you knew you needed something better?
Where did you go to look for new solutions? What else did you try?
What were you most curious about while you were thinking about buying our thing?
Where did you learn about us?
When in the sales process did you know we were the right choice for you?
What would have prevented you from working with us?
What’s the number one thing you can do now that you weren’t able to do before?
What’s the one thing you wish we did that we don’t do?
Take notes. Record the conversations if you can (then run them through AI). Buy them coffee or lunch, or donate to a charity on their behalf as a thank you. Follow up with your team about any lingering support or product issues they bring up. Close the loop.
Need help with how to ask these questions?
The Mom Test by Rob Fitzpatrick is a must-read for learning how to ask better questions without biasing the answers. It’s especially helpful for early-stage companies who are still figuring out what their customers will actually buy - but the fundamentals in the book re: asking better questions will be helpful to anyone, regardless what size of company they work for.
Forget the Funnel by Gia Laudi and Claire Suellentrop is also a fantastic choice, especially for more technical products where it might not be entirely clear what customers find most valuable about what you sell. Gia and Claire (who have a great Substack, too) also do this work with and for software companies if you’re looking for a hand on the customer interviews. (Hand up: many of the questions in my list above are stolen from them.)
(2) Go Talk to All Your Sales Reps
Yes, every single one of your quota-carrying sales reps. They’re on the front lines, talking to customers everyday. They’re the ones telling the story that sells your product. They know what works. And they know what needs work.
Here’s what to ask them:
What questions do you hear most often in a first sales call?
Where are the dead spots in our sales pitch or product demo?
What’s the most helpful piece of marketing content we’ve ever given you? Why?
If you could wave a magic wand and get one thing from marketing next year, what would it be?
What’s the biggest thing getting in your way of closing deals right now?
What specifically do you need to win one more jump-ball deal next year?
Where are we being too jargony, technical, or unclear in our message?
A few pointers on approaching these conversations:
Be humble. Asking your teammates what you're missing might feel a little uncomfortable. That's ok. Improvement starts by actively searching for what's not working - and spotting the gaps is a lot easier when you can borrow someone else's eyes.
Be curious about the simple stuff. Small tweaks move the needle. Actively listen for the ask for a better one-pager, a missing slide from the pitch deck, a smoother handoff process, or for the need for a reminder about a piece of content or talking points guide that already exists somewhere. You can often finish one of these 2% improvements in less than a week. So do it. Then go find another one.
Show gratitude and keep your word. Sales is tough. Acknowledge their hard work and let them know you’re there to help. And, as quickly as you can, deliver on at least one simple ask that comes out of your conversation. It’s sad, but salespeople don’t usually expect marketing to give them what they ask for. It’s your job to make sales fall in love with you. And as Sean Connery put it so nicely in Finding Forrester, the key to someone's heart is pretty simple: "Unexpected gift, unexpected time."
I promise you after these conversations, you will have more ideas than you know what to do with. You'll be on fire with ideas. And it’ll be shockingly easy to build yourself a to-do list for next year, sourced directly from your two most important sets of customers:
The people who buy your stuff.
The people who sell it.
It's wild to me how few marketing teams actually do this.
Get out of the spreadsheet. Get into the field.
The truth is out there.