I’ve heard the story a hundred times: You have a great idea that could push your company into a league of its own, but your boss wants to play it safe. It feels like no matter how much you research, prepare, and present it, the idea just isn’t taken seriously. What’s going on here? Why are so many innovators discouraged from shaking things up?
The truth is, this story is never as simple as it first appears. I like to remind my clients that wisdom is found in both positions. On one hand, the risk of innovation could have a big payoff or keep a company from falling behind the competition. On the other, it could be a costly detour that underperforms expectations, tipping business-as-usual success into tightening-the-belt budget cuts. And budget cuts could lead to opportunity costs, as the company plays it safe and misses out on promising opportunities it could otherwise seize.
At any moment, either of these positions could be defensible. But you have a particularly strong case for why taking a risk is worth it. So, how do you convince your boss to say Yes to innovation?
Understand their position
The first step is to understand your boss’s point of view. In his book The 7 Habits of Highly Effective People, Stephen Covey differentiates wanting to be understood from understanding. It’s easy to spend an entire conversation waiting for a chance to talk and not letting up until the other person “gets it.” That’s speaking to be understood, and you can imagine just how big a problem this becomes if your boss is doing the same thing to you. No one hears the other. They just assert their position, become frustrated that it isn’t being understood, and then the conversation ends.
But there is a better way to connect with your manager. After all, you already know what you believe and want your boss to understand it. And now, you know that speaking merely to be understood won’t make that happen. Instead, take this chance to understand what your boss believes. Ask questions. Look for the wisdom in their position.
Once you understand their position, you can address it.
Perhaps your boss already feels overwhelmed by all the plates spinning at work. That’s your chance to assure your boss that you’ll take complete ownership of this transformation. Then, you can explain how the innovative idea will decrease complexity and save time for the team—and thus for your boss. Now that you understand your boss’s concerns, you can point out how counterproductive it would be to say: “I’m way too overwhelmed to green-light changes that reduce my workload.”
Or, perhaps you learn that your boss has been in this situation, said Yes, and things didn’t work out. Understanding this gives you the chance to pinpoint what went wrong. Maybe someone hastily implemented a new fad without any research and it turned out to be a costly mistake. In that case, it wasn’t “innovation” that went wrong. It was a lack of research. By understanding this, you can address the concern by providing a report on success rates and an implementation plan.
Understand their hesitancy
You might even discover that your boss is generally on board but needs to take things slow and start small. Notice that this isn’t a challenge to your vision—it actually supports it. Your boss may just need to see a few quick wins before exploring larger ones. This could be a savvy plan, balancing costs and benefits before fully committing. It also gives you a great opportunity to prove yourself and earn trust.
Of course, the source of resistance isn’t always so clear. People are complicated, after all. Sometimes, we make decisions without knowing why, or without being comfortable sharing why. If it’s clear that your boss’s refusal won’t be changed by seeing evidence and you think something else might be afoot, that’s worth understanding too. Maybe they have a history of being self-conscious or sensitive about being outperformed by an employee.
Working around troubling personalities like this can be difficult, but it’s not impossible. This doesn’t require dishonesty. Tell the truth. Your boss has the opportunity to green-light an innovative new strategy. Ask for their advice. See if they can critique your existing plan. In other words, get them involved so everyone can share in the glory, and your idea has a better chance of success.
After all, innovations don’t happen in a vacuum. They’re created, resisted, and implemented by people. Being innovative isn’t just about generating new ideas, but also about understanding and overcoming the resistance to those ideas.








