If you're ever trying to sell a product to me, just know that I'm a nightmare to track down, to actually get on a demo, and then to get me to say yes. It's probably not that I don't like your product; it's simply that my schedule is a mess, and pinning me down is no easy feat. So salespeople who give up early on me get nothing, but those salespeople who are aggressive, borderline pushy, and in my face typically will get a deal if the product fits.
I'm celebrating twenty years in leadership this year, which means it's twenty years of me hiring people. I can tell you I've hired people simply because they are more aggressive than others in their approach. They refuse to let me go without giving them an answer, and they refuse to let weeks go by without knowing that we're going to hire them. The best salespeople are super aggressive in their hiring process, and it shows up the day they start.
It's always a fine line between being aggressive and being labeled as pushy or annoying.
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Where this always shows up is at work, when you're trying to get something accomplished, asking for a raise, raising a concern, or just simply trying to get a point across.
The reality is, most people give up way too early.
They send one email, ask one question, bring something up once in a meeting, and then assume silence means no. Sometimes silence just means someone is busy. Sometimes it means they forgot. Sometimes it means your request is sitting somewhere around number 47 on their priority list, and unless you bring it back to the top, it's probably going to stay there.
I've learned over the years that the people who tend to get things done are usually the people who are willing to keep pushing. They follow up. They ask again. They schedule the meeting. They walk into your office. They send the text. They make it slightly uncomfortable for you to continue ignoring the thing they need an answer on.
That doesn't mean you should become the person everyone avoids. You still need a level of self-awareness. If someone has told you no five times, you probably have your answer. If someone has asked you to stop, stop. But there is a massive difference between ignoring a clear answer and refusing to accept no answer at all.
This matters especially in your career.
If you want a raise, don't mention it once six months before compensation reviews and hope your boss remembers. Keep the conversation alive. Ask what needs to happen. Ask where you stand. Ask what specifically would need to be true for you to earn more money, and then keep coming back to it, while finding the balance in how you bring it up and approach it.
The same thing applies when you're trying to move into a new role. One conversation about your career aspirations isn't a career development plan. If you want the next job, people should probably know you want the next job. They should know what you're doing to prepare for it, what you've accomplished, and why you think you're ready. That requires repetition, and repetition can sometimes feel uncomfortable.
I think a lot of people worry so much about being annoying that they end up becoming invisible. They want to be polite. They don't want to bother anyone. They don't want to come across as needy, difficult, or overly ambitious. So they sit quietly and wait for someone else to recognize what they want, what they need, or what they're capable of.
A lot of people worry so much about being annoying that they end up becoming invisible.
The problem is that organizations are busy places filled with busy people. Your boss has their own priorities. Recruiters have dozens of candidates. Executives have hundreds of problems. Customers have their own schedules. If something matters to you, you cannot assume it matters equally to everyone else. Sometimes you have to create the urgency yourself.
There is an art to knowing how hard to push, but I'd rather occasionally dial someone back than constantly try to pull ambition out of them. Careers tend to reward people who are willing to ask, follow up, push, and make themselves difficult to ignore. You don't need to be obnoxious, but every once in a while, being a little annoying might be exactly what gets you the answer you were waiting for.