6 Things That Helped Me Build Confidence as a Woman in Sales
I was 23 years old when I started my first full-time job.
I had a degree in Insurance and Risk Management, my first full-time role as an insurance broker, and a dream of building a fulfilling career.
But the reality?
I had never sat across the table from a CEO. I had never negotiated a six-figure business decision. I had never been responsible for advising organizations on hundreds of thousands—sometimes over a million dollars—in annual insurance costs.
Yet that was exactly what my job required.
Every day, I was expected to walk into meetings with CEOs, CFOs, and executive teams who had decades more experience than I did. They understood finance. They understood business. They understood leadership. Somehow, I was supposed to earn their trust and convince them to let me advise them on how to manage one of their largest expenses.
To make things even more challenging, I was a young woman in an industry segment that was roughly 90% male and selling to leadership teams that also were predominantly, male.
There were plenty of moments where I questioned whether I belonged in the room.
But over time, that started to change.
I realized that confidence and business acumen isn't something you're born with. It isn't something you magically wake up with after a promotion or a certain birthday.
Confidence and business acumen is built. One uncomfortable experience at a time.
Whether you're in sales, healthcare, marketing, finance, real estate, engineering, or any other profession, the process is the same. The terminology changes, but the principles don't.
These are the six things that made the biggest difference for me.
1. Read the Books That Successful People Recommend
One of the fastest ways to shorten your learning curve is to borrow someone else's experience.
There's an average saying that the average CEO reads 52–60 books per year (roughly one book a week). I wanted to read the same books, and I didn't just read them—I highlighted them, took notes, and looked for opportunities to apply one new concept every week.
Every great sales conversation, leadership lesson, or negotiation strategy has probably already been written about by someone who has spent decades mastering it.
A few books that had a huge impact on me early in my sales career include:
Every chapter gave me another tool to bring into conversations, and every tool made me a little more confident.
2. Find a Mentor (and Choose Carefully)
People spend more time researching what to watch on tv than they do choosing a mentor.
Don't do that.
Look for mentors the same way you'd look for a job.
Interview them.
Watch how they lead.
Pay attention to how they treat people when no one is watching.
Ask yourself:
"Do I want my career to look like theirs?"
The best mentors don't just give advice.
They challenge you.
They ask difficult questions.
They hold you accountable.
And remember—mentorship should be a two-way street.
Ask yourself what value you can bring to the relationship. Respect their time. Follow through. Show initiative.
The best mentor relationships are partnerships, not handouts.
3. Job Shadow Great People—Even If You Don't Get Paid
Early in your career, your greatest currency isn't money.
It's exposure and time.
Find someone who consistently performs at a high level and ask if you can simply watch.
Sit in on meetings.
Observe difficult conversations.
Listen more than you talk.
Take notes.
Ask thoughtful questions afterward.
Be a sponge.
Those experiences are worth far more than another hour of busy work at your desk.
You don't become confident by reading about difficult conversations.
You become confident by watching hundreds of them happen in real life.
The reps matter and if you aren't getting them in, you aren't getting better.
4. Practice Being Uncomfortable
This might be the most important lessons on the list.
Confidence doesn't grow inside your comfort zone.
It grows every time you willingly put yourself in situations where you might fail.
Go to networking events where you don't know anyone.
Message people you admire.
Practice your elevator pitch.
Volunteer to speak.
Lead the presentation.
Introduce yourself first.
Ask the question.
Take the meeting.
You will stumble.
You will say the wrong thing.
You will leave thinking, "Well, that went terrible."
Good. In 10 years, you will admire those moments.
Those moments are education.
In the beginning, it can feel like you're "wasting time" on opportunities that probably won't lead to business.
But they aren't actually wasted.
They're giving you something even more valuable: experience.
You're learning how people communicate.
You're discovering what decision-makers care about.
You're figuring out how to ask better questions.
You're figuring out how to be on your toes.
You're becoming more comfortable talking about business.
None of that happens sitting behind a computer making cold calls or sending emails all day.
Real confidence is built in real conversations.
5. Surround Yourself with People Who Raise Your Standards
The people around you quietly shape your expectations.
They influence what you think is possible.
Most successful people will tell you they got to their success because they were constantly delusional. They were always reaching for an unreachable target.
One exercise I recommend to everyone is making two lists.
The first list includes ten people you admire.
People who inspire you.
People whose careers, attitudes, leadership, or discipline make you think, "I want to be more like them."
Then ask yourself:
"How can I spend more time around these people?"
Maybe it's coffee.
Maybe it's volunteering together.
Maybe it's attending the same professional association.
Maybe it's simply engaging with their content online.
Now make a second list.
Write down ten people whose negativity consistently drains your energy.
The people who complain about everything.
Who criticizes every opportunity or worse, everybody.
Perhaps they always have a reason why something won't work.
You don't have to dislike them.
But you don't have to let them shape your mindset either.
Success is contagious.
So is negativity.
Choose your environment wisely.
6. Never Stop Learning
The more you know, the more confident you become.
Learn your industry.
Learn your niche.
Understand the financial side of the business.
Study leadership.
Learn communication.
Understand how your customers make decisions.
When you speak the language of your clients, something changes.
You stop sounding like someone trying to sell them something.
Instead, you start sounding like a trusted advisor. Like a peer.
And people buy from people that they like and trust.
Education creates competence.
Competence creates confidence.
Confidence creates credibility.
The sales—and the opportunities—will follow.
Final Thoughts
Looking back, I realize none of these things made me successful in my role overnight.
When people get into sales, they want the hack, the quick fix, the quick solution, but the truth is, it doesn't exist. Ask someone how they reached their success, and they'll have trouble giving you specific answer.
That's because it didn't happen after one meeting, one conversation, one book, one mentor, one uncomfortable experience. It all compounded over time.
If you're early in your career—or you're stepping into a new role where you feel like everyone knows more than you—remember this:
No one starts as the expert.
Every confident professional you admire was once the youngest person in the room, wondering if they belonged.
Keep learning.
Keep asking questions.
Keep showing up.
One day you'll look around the room and realize you aren't trying to belong anymore.
You're the person someone else is looking up to.
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