Most people figure out how careers actually work by making expensive mistakes.
They stay quiet in meetings when they should have spoken up. They underestimate what their non-corporate experience is worth. They go into salary negotiations without a strategy and walk out with less than they deserved. They build surface-level professional relationships and wonder why nothing ever materializes from them.
The hard part is that nobody teaches you this stuff. Not in college. Not in orientation. Not even in most first jobs.
Which is exactly why I sat down with Kimberly Kanary, a VP of marketing who has built her career across some of the most recognizable brands in the country, including Smucker's, Jif, and Pillsbury, and has spent over a decade in jewelry retail leadership, as well as time in real estate and Fortune 500 banking.
Kim has been in the room. She has built and led teams, hired and passed on candidates, and navigated her way from an entry-level intern to executive leadership. In this conversation, she shares what she actually looks for when she hires, what holds women back before they even realize it, and what she would tell her college-senior self if she could.
This is the kind of perspective that takes most people years of trial and error to collect.
Consider this your shortcut.
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Kim started college debating between communications and law. She took classes in both, tested different paths through internships, and made her decision from the inside out rather than from the outside in.
That approach...staying curious and getting exposure before committing...is exactly what she recommends for anyone who feels uncertain about their direction early in their career.
Her advice: do informational interviews. Reach out to people whose backgrounds you admire, ask for 20 minutes, and just listen. Most people want to help because someone helped them along the way. And if you don't hear back right away, follow up. Being persistent is OK. Being desperate is not.
Clarity unfortunately doesn't show up as a lightning bolt most times. It builds gradually through exposure, conversation, and action.
Kim's first big surprise entering the workforce wasn't the workload or the politics. It was the realization that your education alone doesn't carry you as far as you think it will.
The classroom gives you a clear path (think assignments, grades, a defined finish line). The workplace doesn't work that way. And that gap between structure and ambiguity is where a lot of new professionals lose their footing.
What fills that gap? Soft skills. The ability to build relationships, collaborate, listen, and navigate dynamics you can't find on any syllabus.
The hard skills get you in the door. The soft skills determine what happens after that.
Kim has interviewed a lot of people. Here is what consistently separates the candidates who get offers from the ones who don't.
Preparation is non-negotiable. Not a quick scroll through the company's website, but real preparation: knowing the role, understanding the company, and showing up with questions that prove you've been thinking carefully.
Practice out loud. This one surprised even Kim when she first learned it in crisis communications training. What sounds great in your head doesn't always land the same way when you say it. Record yourself. Watch it back. You will catch filler words, nervous habits, and patterns you didn't know you had. It's uncomfortable, but it works.
If you don't have corporate experience, use what you do have. Class projects where you had to solve a real problem. Internships. Volunteer work. Student leadership. Those experiences absolutely count. The goal is to show that you know how to approach challenges and that you're capable of learning, not that you already know everything.
Ask genuine questions. Curiosity signals engagement, and engagement signals potential.
Kim has seen the same mistakes repeat across candidates at every level.
Showing up knowing almost nothing about the company or role is the most common one. It signals that you're not that interested even if you are.
Letting confidence tip into arrogance is another. There's a balance between presenting yourself well and taking over the room. Be self-aware about that line.
And filler words and mannerisms (the ums, the nervous hair-twisting, the looking away mid-thought) can create an impression you don't intend. Most people don't notice these things about themselves. Recording yourself before interviews is one of the best ways to catch them.
This was one of the most honest things Kim said in the entire conversation, and it's worth sitting with.
You can be fully qualified and still not feel confident. Those two things develop on different timelines, and one does not automatically produce the other.
Kim's advice: don't wait for the confidence to arrive before you act on it. Sometimes you have to project it outwardly before you fully feel it inwardly. And over time, the act of presenting yourself confidently actually builds the real thing underneath.
She also made a point that a lot of women need to hear: stop beating yourself up over failures longer than they deserve. Take the lesson, decide what you'll do differently, and move on. The mistake is not the problem. Dwelling in it is.
One of the career moves that changed Kim's trajectory the most wasn't a planned promotion. It was a moment when her boss left and no one was sure who was going to pick up the responsibilities. Kim raised her hand.
She didn't know how to do everything she was taking on. She said as much. But she showed up willing to ask questions, figure it out, and get it done. That single moment of stepping forward when it would have been easier to step back accelerated her growth in ways that staying comfortable never could have.
The version of this that applies to most early-career professionals isn't always that dramatic. It's the task force nobody volunteered for. The extra project someone needs help with. The little opening where you could stay quiet or step up.
Those moments add up.
Getting to the VP or C-suite level is possible. Kim has lived it. But she's honest about what it costs.
Senior-level roles require long hours, availability at inconvenient times, and a willingness to sacrifice certain things most people aren't fully prepared for. If you want that path and you're clear-eyed about the trade-offs, go for it.
But Kim is equally clear that not wanting that path is completely valid. Not everyone wants to manage people. Not everyone wants to be an executive. Knowing what you actually want, and being honest with yourself about it, is a form of ambition in its own right.
The thing she cautions against either way: burning yourself out in the process. You can put in the work. Just don't make yourself the sacrifice along the way.
Kim loves negotiating. And she thinks most people get it wrong in the same predictable way.
The biggest mistake: making the negotiation about you instead of the business. "I've been here two years" is not a negotiating argument. "I've been here two years and I'm now responsible for X, Y, and Z" is a different conversation.
Tie everything back to business value. What are you taking on? What's the scope of the role? What have you contributed?
Her other advice: be realistic, practice the conversation out loud with someone you trust before you have it, and don't nitpick every detail. Identify the two things that actually matter to you and go after those.
And if you don't ask, the answer is always no.
The professional relationships that actually open doors are built over time, with genuine interest and consistent follow-through.
Kim's rule: don't meet someone for the first time and ask them to be your mentor. That puts them on the spot before there's any real relationship. Instead, lead with genuine curiosity. Ask to learn about their work, their path, something specific you admired. Let the relationship grow from there.
And then follow up. This is where most people drop the ball. You have a great informational interview, you feel energized by it, and then six months pass and you never reached out again. That's not building a relationship. That's a one-time interaction.
Real connections require maintenance. It doesn't take much: a check-in, a shared article, a quick note when something they said stuck with you. But it has to be consistent.
Kim was direct when asked what skills matter most in 2026.
Communication. Written and verbal.
In a world that increasingly defaults to text speak, shortcuts, and emoji, the ability to write a clear email, hold a calm and organized phone conversation, or present with presence in a room is becoming rarer and more valuable.
Technology matters and young professionals have a real advantage there. But the fundamentals are making a comeback precisely because they're disappearing. If you can communicate clearly across contexts, you will stand out.
Her other advice: don't only invest in the things you're already good at. Pick one challenge area and start chipping away at it. Not everything at once, just one thing. Gradually, you start to round out the gaps instead of being defined by them.
Kim's answer to this question was unexpectedly reassuring.
She wouldn't change anything. Every experience, the good decisions and the mistakes, put her exactly where she ended up. Changing one thing could have altered the whole trajectory.
What she would reinforce: keep raising your hand, even when it's uncomfortable. Invest in your emotional intelligence and your ability to read the room. Push yourself to grow, but not at the expense of your relationships. And when you win, actually let yourself celebrate it without becoming arrogant, without letting your guard down, but genuinely acknowledging what you accomplished.
Mistakes are coming. So are wins. The goal is to keep learning from both.