Ever find yourself in a room full of higher-ups, sweating bullets as you pitch your heart out, only to see them zone out or worse—laugh? Oh, let me spill the tea. I was in a board meeting once, about 10 years into my career. I had this revolutionary idea to shift our entire product strategy. Picture this: me, so young and full of fire, walking into the lion’s den. I laid down my plan like it was gospel, but what did I get? Crickets. Yup, talk about a gut punch to my young exec ego.

This epic fail taught me that it isn’t just about the idea; it’s about how you package and deliver it. It’s like dating; you can’t just walk up to someone and say, “Marry me.” You’ve got to woo them first. So, if you’ve ever found yourself in a similar pickle, wondering why the heck you’re not getting through, then you’re in the right place, my friend. This is no doom and gloom tale. It’s a wake-up call to arm you with what you’ve been doing wrong and how to knock it outta the park next time.

We’re diving into three colossal trip-ups that screw up your chances of becoming the influencer you want to be in your workspace: the wrong mindset, the wrong approach, and the wrong timing.

The Wrong Mindset

Let’s kick this off with mindset, the invisible puppeteer pulling the strings behind most of your decisions, actions, and yep, failures. When you strut into that room, are you going in thinking, “My way or the highway”? Because if you are, oof, prepare for some roadblocks ahead, my friend.

This attitude stems from a toxic misconception: “If they don’t get it, they’re the problem.” Newsflash: if they don’t get it, you’re the problem. Why? Because it’s on you to translate your vision into something that makes sense to the people who matter. Your view is not a universal truth; it’s subjective. A steak might be divine for a carnivore but anathema for a vegan. You’ve got to tune your message to resonate with your audience’s frequency.

Let’s get this straight: the “My Way or the Highway” approach is career sabotage, period. It ignores organizational culture, existing systems, and most importantly, the human beings you’re trying to influence. What you’re essentially saying is, “I don’t care how things work here; my idea’s better.” In most cases, that’s just waving a red flag in front of a bull.

So, how do we flip the script? It’s all about reframing the narrative. Instead of going in hot, start by getting into their shoes. Say to yourself, “I’ll spend time understanding why we do things the way we do here, and then propose how we can improve it.” It’s not as sexy as thinking you’re the savior they’ve been waiting for, but trust me, it’s far more effective.

The magical word here is empathy. If you can understand their pain points, fears, and ambitions, you’re better positioned to tailor your pitch in a way that addresses their needs, not just yours. And just like in real life, understanding someone takes time, so invest it wisely. You wouldn’t propose on the first date, would you? (If you would, we’ve got bigger issues to tackle!)

Let’s get to some practical tips to shift this beast of a mindset:

  1. Be a Listener: Spend more time listening than talking. When you listen, you gather intelligence. Simple as that.
  2. Ask Questions: Yeah, it might seem obvious, but are you really doing it? You’d be amazed at how much you learn by just asking questions.
  3. Seek Feedback: Share your idea in its embryonic stage with a few trusted colleagues or mentors. Their input can help you tailor your proposal to be more relatable to a broader audience.

By making these small shifts in your mindset, you transform from the “annoying outsider with a harebrained idea” into the “innovative problem solver” they didn’t even know they needed. And in the business world, that’s like upgrading from a scooter to a jetpack. So, which ride do you want?

The Wrong Approach

Alright, you’ve dialed back the ego and tuned into empathy. You’re no longer the crusader who’s gonna save the world in one go. But even after fixing your mindset, there’s another booby trap waiting for you: the approach.

Here’s where Hollywood does a disservice to us all. Ever watched a movie where the protagonist makes a dramatic pitch, and the room erupts into applause? Yeah, that’s the “Mic Drop Fantasy,” and in real life, it rarely happens. Most decisions in a business environment don’t come from one dazzling presentation. They’re the result of a series of smaller, smarter moves that build up to an undeniable argument for action.

If you’re expecting to waltz in, dazzle ’em with your brilliance, and waltz out, you’re setting yourself up for disappointment. Don’t be the guy that goes, “Why didn’t they just say yes?” Instead, be the savvy player who realizes, “This is step one. I’ll play the long game, form a logical argument, and sell it to all the stakeholders.”

This is what I call the art of “incremental influence.” Instead of going for the homerun, aim for first base. Then second. Then third. You get the point. Build your case over time, layer by layer, until the value of your proposition is so glaringly obvious, they’d be fools to ignore it.

So how do you practice this art? Here are some techniques:

  1. Start Small: Pilot your idea on a smaller scale first. Prove its efficacy in a controlled environment, then leverage those results to win over bigger fish.
  2. Keep It Consistent: Stay committed to your idea, but adapt your pitch. Each stakeholder has unique concerns; address those, and you’re more likely to win their support.
  3. Get Allies: Identify key supporters within the organization and get them on your side. Their endorsement can add weight to your proposal and make it more palatable to decision-makers.

Remember, you’re not on a game show where you have to answer before the buzzer sounds. Take your time, strategize, and treat each presentation or discussion as a round in a longer game. Along the way, you’re not just selling your idea; you’re building relationships, earning trust, and gaining a deeper understanding of the ecosystem you’re operating in.

And let’s kill another myth here: playing the long game isn’t synonymous with being manipulative. What it means is that you’re savvy enough to understand the complexities of human decision-making. You’re navigating the labyrinth of corporate culture, egos, and red tape to bring about a change that you genuinely believe will add value.

In short, the long game is about being patient, persistent, and ridiculously prepared. So throw out that misguided belief that one presentation will seal the deal. This is real life, not a scripted drama. And in real life, the big wins often come from a series of smaller, smarter victories.

The Wrong Timing

Let’s assume you’ve got the mindset and approach all dialed in. You’re no longer that “my way or the highway” lone wolf, and you’ve tossed out that Hollywood “mic drop” dream. But here’s the kicker: you could still fail spectacularly if your timing is off. Yup, timing can be a silent killer, and it doesn’t care how brilliant your idea is.

Look, pitching a new process smack dab in the middle of an ongoing project is like changing the tires on a car that’s already in motion. Not only is it risky, but it’s also incredibly tone-deaf. It screams, “Hey, I don’t give a flying flip about your timelines, stress levels, or the fact that you’re already neck-deep in work.”

There are two kinds of people who typically mess this up: the dreamers and the doers. The dreamers are so enthralled by their vision that they can’t wait to make it a reality. The doers, on the other hand, are the “action Jacksons” who feel they need to constantly shake things up to prove their worth. Both have their merits, but neither is excused from the cardinal sin of poor timing.

Here’s where the “Don’t rock the boat” principle comes into play. If everyone is rowing in unison, trying to navigate through turbulent waters, the last thing you want to do is stand up and declare, “Hey, why don’t we try paddling backwards?” Not only will you throw everyone off, but you might also end up swimming with the fishes—professionally speaking, of course.

So, how can you time it like a pro? It’s all about the art of finesse. Here are some actionable tips:

  1. Do Your Homework: Before making your grand proposal, understand the rhythms and cycles of your organization. When is the budget season? When are performance reviews? Knowing this can help you identify when people are most receptive to new ideas.
  2. Play the Political Game (Without Being a Sleazeball): Every office has its politics. Navigate it wisely, not sleazily. If Jane in accounting hates change but loves chocolate, maybe bring some Godiva to your next meeting. It’s not bribery; it’s strategic congeniality.
  3. Spot the Golden Opportunities: Sometimes, the stars align, and the universe practically hands you the perfect moment on a silver platter. Maybe it’s after a project wraps up, or perhaps it’s when the CEO is feeling particularly visionary. Seize those moments.

In a nutshell, great ideas aren’t enough. The landscape you’re operating in has its own rhythms and rules. Being oblivious to them is like trying to pitch a tent in the middle of a hurricane. Smart timing requires situational awareness and the ability to read the room, not just a killer PowerPoint deck.

And there you have it, folks. You could be a genius, but if you’re walking into rooms at the wrong time, you’re just gonna look like a joker. Nail the timing, and your influence will go through the roof.


We’ve broken down three epic ways people bomb when they’re trying to be influential stakeholders: wrong mindset, wrong approach, and, last but definitely not least, wrong timing. I hope you’re still with me because these pitfalls can make or break your career, no cap.

So, quick recap because repetition is our friend here. The first killer is having the wrong mindset, that whole “my way or the highway” vibe. Remember, nobody likes a dictator unless they’re in a history book or a Netflix drama. Ditch that nonsense and opt for empathy. Feel the room, understand the dynamics, and then make your play.

Next up was the wrong approach. Now, don’t get it twisted. This isn’t about your pitch being trash or your ideas being stale. No, sir. This is about playing the long game and ditching that “one and done” mindset. Hollywood’s got us thinking that we can walk in, drop some verbal bombs, and peace out. In reality, building consensus is more like a slow dance than a rap battle. And hey, slow dancing has its charms too, right?

Lastly, timing is everything. Be the maestro, not the rogue drummer going off-beat and ruining the entire symphony. Know when to step up and when to sit down. You gotta be patient, like a lion stalking its prey. Don’t pounce until the time is right, or you’ll just end up as a meme in the office Slack channel. Trust me, no one wants to be that guy or gal.

So, here it is, plain and simple: Pick one of these pitfalls and focus on flipping the script for the next month.

Feeling too high and mighty? Work on your empathy game. Find someone at work you can learn from, and make it a project. Think you’ve been too pushy with your ideas? Take a step back and lay the groundwork before your next pitch. And if you’re that person who loves to throw curveballs in the middle of projects, start jotting down your “brilliant” ideas and save them for the right moment.

In the end, influencing stakeholders isn’t some arcane art or mystical skill. It’s about knowing the game, from the rules to the players to the timing. And hey, if a former boardroom disaster like me can figure it out, then you definitely have a shot. Go out there and crush it, friends. You got this.

About the Author: Geoffrey Byers
Geoffrey is one of the world's foremost Designers. He is also a Serial Entrepreneur, Author, Speaker, and Mad Scientist. Hypothesis-Driven experimentation is his love language.