You Don't Get Comfortable Selling Yourself Before You Start. You Get Comfortable by Doing It.
For founders, sales isn't just a business capability. It's a practice in being seen, risking rejection, and learning to talk about your value without hiding behind your expertise.
I have been staring at myself in a Zoom window trying to record a video for my website.
I know what I want to say.
I know the work I do.
I've spent much of my career selling ideas, services, organizations, opportunities, and other people's work.
But selling myself is different.
Because when someone rejects an idea I'm representing, they rejected the idea.
When you're a founder selling your own expertise, it can feel like they're rejecting you.
Intellectually, I know that's not true.
Emotionally? That's a different story.
And apparently, I'm not the only founder wrestling with it.
The Connection Lab conversation we weren't supposed to have
This week's Connection Lab was supposed to be about what makes a manager worth following.
We barely got there.
Instead, one of our regular participants, Mike Sweeney, started telling us about some of the work he'd been doing to generate new business.
He'd recently reached back out to former clients—people he hadn't talked with in a long time—to let them know what he was doing now and reopen those relationships.
That alone felt significant.
Because sending an email like that sounds easy until you're the person who has to hit Send.
Suddenly, all sorts of questions show up.
What if they don't respond?
What if this sounds desperate?
What if they don't remember me?
What if they aren't interested?
Who am I to ask them for an introduction?
I told Mike that part of building a sales process is learning to wrestle with exactly that discomfort: our egos, our imposter syndrome, and our reluctance to ask other people for help.
And then we started workshopping his pitch.
That's when the conversation got interesting.
Expertise can become a hiding place
Mike has done a lot of things.
So when we asked him to explain how he helps customers, he naturally started explaining his methodology.
He has a six-step iterative process.
I stopped him.
Not because the process doesn't matter. It does.
But not yet.
A potential customer doesn't begin by wondering about your six-step process.
They're wondering:
Can you help me with something I care about?
That's a surprisingly difficult shift for people who sell expertise.
We have spent years acquiring knowledge, developing methodologies, earning credentials, solving complicated problems, and learning how to do things other people can't do.
So when someone asks what we do, we start unloading the evidence.
Here's my methodology.
Here are my credentials.
Here's everything I've done.
Here's how my process works.
Here's everything I know.
It feels safer.
Expertise gives us something concrete to stand behind.
But the customer isn't trying to understand everything you know.
They're trying to understand what your knowledge could do for them.
At one point I told Mike:
“You keep coming back to trying to sell yourself. And you don't need to sell yourself. You need to sell your expertise, and you need to build rapport.”
But there's another side to that.
Later in the conversation I said:
“People are not just buying what you do, they're buying you. They're buying the relationship they have with you.”
Both things are true.
And that's what makes selling expertise so damn uncomfortable.
You are part of the product. But you shouldn't make yourself the pitch.
If you're a consultant, coach, advisor, creative, freelancer, or professional-services founder, there's very little distance between the business and the person selling it.
Your judgment matters.
Your experience matters.
Your personality matters.
Your ability to listen matters.
Trust matters.
The relationship matters.
You are part of what the customer is buying.
But that doesn't mean the sales conversation should be a performance about how impressive you are.
Your job is to help someone see themselves in the story of what you've already helped someone else accomplish.
That's why stories matter so much.
Instead of explaining every capability I have, I can tell a business owner about another owner who had become too deeply involved in everything happening inside her company. We improved her visibility into the business, reorganized some of how the team worked, found places where she was overinvesting and underinvesting, and helped the company grow.
Or if I'm talking with a very small business owner, I might tell my Band Wife story—how my husband and I changed pricing, became more selective about the work we accepted, improved our contracts, created additional services, and significantly grew the band's revenue.
Those stories do something a list of credentials can't.
They let another person think:
I wonder what she would see in my business.
That's the opening.
Unfortunately, knowing this doesn't make doing it comfortable
This is where Chad Keller jumped into the conversation.
Chad described his own struggle with recording video.
He had decided he needed a YouTube channel.
Then he procrastinated.
Eventually, he essentially forced himself to sit down and record.
But instead of making one video, Chad decided to make ten.
His reasoning was smart: if he made one, it would be easy to find a reason not to make another one the following week.
Ten created momentum.
And the early videos?
Not particularly good, according to Chad.
But that wasn't the victory.
The victory was that they existed.
He told us that he hoped people eventually found him through video seven or eight because he could already see himself getting better at presenting, telling stories, and making his ideas relatable.
Then he said something that captures the entire lesson:
“You've got to have the terrible so that you can have the good.”
That's not really advice about YouTube.
That's capability development.
You cannot think your way into confidence
I've been working on my own sales language for months.
I'm testing positioning.
I'm refining stories.
I'm working with a business advisor who holds me accountable for my sales plan, outreach, language, and follow-through.
I'm still road-showing the pitch.
Because there is no magic paragraph that suddenly makes selling comfortable.
There are reps.
You tell someone what you do.
They look confused.
You try another version.
Someone lights up.
You pay attention to what you said differently.
You tell a story.
Someone asks a question you didn't anticipate.
You adjust.
Someone says no.
Someone introduces you to somebody else.
Someone says, “Wait, I need that.”
And slowly, you get better.
The sales script isn't creating the confidence.
The conversations are.
Chad described using short networking conversations almost like batting practice: tell the story, hear yourself say it, notice what lands, notice what feels awkward, change it, and try again.
That's what I mean by getting your reps in.
Rejection is data
There's another uncomfortable part of this.
You can get better at all of this and people will still say no.
That's sales.
But a no isn't necessarily a verdict.
It might mean wrong customer.
Wrong problem.
Wrong language.
Wrong timing.
Not enough trust.
No budget.
No urgency.
Or yes, sometimes it means they simply don't want what you're selling.
That's useful information too.
The job isn't to build a sales process where nobody rejects you.
The job is to become capable of distinguishing between the no that should teach you something and the no that simply means:
Not this person. Not this opportunity. Keep going.
That's harder when your identity is tangled up with the thing being sold.
A rejected proposal can start feeling like rejected expertise.
A LinkedIn post nobody responds to can feel like nobody cares what you have to say.
A video with 17 views can feel like evidence that you shouldn't have made it.
It isn't.
It's one rep.
Courage in business is usually much less dramatic than we make it sound
We like entrepreneurial stories about giant leaps.
Quit the job.
Raise the money.
Launch the company.
Bet everything.
But much of the courage required to build a business is remarkably ordinary.
Send the email.
Ask for the introduction.
Tell someone you're looking for clients.
Say what you charge.
Follow up.
Publish the post.
Tell the story.
Ask for the business.
Turn on the camera.
Hit record.
Do it again.
And again.
And again.
That's how the capability gets built.
Which brings me back to this Zoom window
During Connection Lab, I admitted something.
I can facilitate a live conversation without much trouble. Put me in a room with people, and my energy is big.
Ask me to record a marketing video by myself?
I shrink.
I hesitate.
I become overly conscious of my voice, my face, my words, my opinions.
Some of that comes from earlier in my career, when I was a media-trained executive at the beginning of social media. Having a public opinion wasn't encouraged. It could create professional risk.
I learned to be careful about being visible.
That training stuck with me longer than I realized.
So today I'm staring at the little camera on my computer and taking my own advice.
I'm uncomfortable.
I'm overthinking how I look and what I sound like.
And part of me would much rather write another article, adjust another page on my website, help somebody else with their business, or find seventeen other productive things to do.
Those things are comfortable.
This isn't.
This is a rep.
And maybe that's the work.
Not waiting until I feel completely confident selling myself.
Not eliminating the possibility that someone might reject me.
Not finally discovering the perfect pitch that makes all of this easy.
Just building the capability to show up before I feel ready.
Because the founder who is afraid to sell doesn't necessarily need another sales system.
Sometimes we need enough practice to discover that we can survive being seen.
And then we need to do another rep.
Connection Lab with Stephanie Kord Miller is held every Wednesday at noon ET. Each week, thoughtful leaders, entrepreneurs, and builders come together to explore one important question shaping the future of leadership, AI, trust, and organizational change.
If you'd like to think through these ideas with us—not just read about them—I hope you'll join the next conversation.
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