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How the Most Successful Leaders Manage the Brilliant Naysayer

By: Mike Maddock



Your company has a senior person who is legendary for saying, “No, it will never work.” Learn to manage—not fall victim to—this type of person. Here’s how:

In my book Free the Idea Monkey, I asked the question that everyone on your team has probably asked more than once: “What if Harold doesn’t approve?”
And with these five words, discussion of a potentially brilliant idea comes to a screeching halt.
Most every company has a Harold (or Harriet). Typically, he has been with the company for 20-plus years. He knows more about industry norms, the company’s intellectual property, your IT capabilities, what legal will and will NOT go for, interoffice politics, and the CEO’s family than anyone in the building.
And, unfortunately for you, good old Harold can effortlessly—and with absolutely no malice intended—recite four to six reasons why your idea won’t fly. He’ll tick down a veto list that may include chemical theory, legal compliance, union issues, patent law, an MIT-funded research study from the 1940s, and two similar ideas that failed in 1985.
Harold often hangs his hat in R&D, but sometimes he’s in IT, legal or operations. I’ve even seen Harold in marketing. Everyone loves Harold. He’s charming, always willing to provide a bit of historical perspective, remembers everyone’s birthday, and is willing to lend a hand—as long as your initiative doesn’t put the status quo at risk.
And at times, everyone also hates Harold because at a brainstorming session he is, unwittingly, at his worst. If you want innovation, Harold is your proverbial skunk at the proverbial church picnic (i.e., the unwanted guest).
He will sit with his arms folded and jaw clenched and wince at just about every idea. He’ll often say things like, “I am trying to be really open minded here, but…” and eventually the air will leave the room as Harold explains in detail why the idea in question won’t work.
His heart is pure. He isn’t objecting for the sake of objecting. In his mind, “somebody has to save the company from these crazy Idea Monkeys,” and that somebody is him.
Odds are, Harold is the most feared (and revered) person in the organization.
Harold doesn’t know it, but he is often singlehandedly keeping your company from moving forward.
Winning Over Harold and Harriet
So how do you contend with this well-meaning Harold in a way that leverages his wealth of knowledge without demotivating your team? Here are five techniques I’ve used to win over a Harold:
1. Stop denying that you have problem. 
A while back, my firm was asked by a retailer to come up with new things it could offer that would be consistent with the brand yet boost margins. During the kickoff meeting, it became apparent that there was a high-ranking Harold on the leadership team, but the CEO assured us she could control Harold and that we should not modify our process in any way to accommodate him.
Fatal mistake. At seemingly every turn, Harold found a reason why things did not work. Despite nudges, begging, sucking up and private conversations, nobody could keep Harold from “helping” things stay off track. It was brutal. Ideas were dismissed before they got enough attention to make them viable. Don’t think rank alone will quell the righteous might of your Harold. If you have a Harold working with you, step No. 1 is to acknowledge he is there and is not going away.
2. Play by (some of) his rules.
To be successful, an innovative idea must meet the criteria of company leadership. If you have a Harold, he qualifies as company leadership. In fact, his voice may be more powerful than the CEO’s since oftentimes the CEO will check in with Harold on all major initiatives.
Make sure you go to Harold and get an extensive list of criteria from him. What qualifies as a good idea? What technical challenges must we overcome? What operational hurdles are deal breakers?
The more rules the merrier. Allowing Harold to set some—and agree to almost all—success criteria enables you to neutralize him. You can show him that you are creating and eliminating ideas based on his wishes. He can take credit for the ideas since his criteria are helping to shape them. Harold likes setting rules so let him.
3. Bring in the cavalry (I mean experts).
Your challenge is that Harold knows more than you. But Harold’s challenge is that he is “in the jar.” The way he thinks about new ideas is constrained by the corporate container he finds himself working within. And unfortunately, his own expertise is keeping him and everyone else from realizing the possibilities all around him. You must fight fire with fire. As part of your innovation process, bring in outside experts—people Harold will recognize as peers—from parallel industries.
What’s a parallel industry? One that does the same thing you do but is in no way competitive. For example, hospitals often look to the hospitality industry for expertise.
Experts from these parallel industries can share with Harold emerging technologies, new techniques, new discoveries and new ways of looking at old challenges.
You might expect Harold to be offended or feel challenged by the import of outside expertise; my experience has been that these outside experts, and what they have to offer, are liberating for him. One Harold left an expert roundtable with 27 pages of notes. Harold doesn’t feel threatened because these experts aren’t directly in his field, and he loves learning about anything that could come to bear on “his” company.
4. Give Harold exclusive access to experts.
Consider giving your Harold the opportunity to work alone with the outside experts—no one else allowed. For one thing, this appeals to his ego. (We are only having the most important people meet.) And for another, if there are only peers in the room, communication tends to be easier and more candid. These outside experts can help Harold by challenging his prejudices, which is to say: Tell him he is way off base with his concerns.
During a recent project, we had a Harold constantly uttering the four-letter word “CAN’T” regarding a wish an innovation team had. They wanted to allow consumers to be able to build their own online solutions, using company-provided resources. Harold was convinced it was an impossible IT and legal challenge. It was only when a former IT executive from a large investment firm showed him how he had met a similar challenge five years earlier that our Harold got on board.
5. Stage an intervention.
If the above strategies don’t work or you no longer have the willpower left to make them happen, I suggest you just put the following note on Harold’s desk:
Harold, this message is from someone in the company who cares. I’d tell you who I am, but, frankly, I am afraid you might misinterpret this note as something other than an act of love or great respect.
First of all, I want you to know that you are really, really, reeeeeeeaaaally smart. You know more about this company than anyone else. I am amazed by your ability to keep track of all the things going on around here—past and present. I learn from you every time we are together.
But I wish that you would use your superhero powers for innovation good, not evil. I wish that you would use all that you know to construct new ideas—not tell people why they won’t work. If you don’t think this is possible, I wish that you would switch jobs. You’re too smart and know too much not to be creating new ideas every day.
Published: May 16, 2013

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Mike Maddock

Mike Maddock is a serial entrepreneur, author and a keynote speaker. He has founded 5 successful businesses, including Maddock Douglas, an internationally recognized innovation agency that has helped over 25% of the Fortune 100 invent and launch new products, services, and business models and create cultures that know how to innovate. He co-chairs the Gathering of Titans entrepreneurial conclave at MIT, is past president of Entrepreneurs’ Organization and current chairman of Young Presidents’ Organization. Mike currently writes for Forbes and is the author of three books about innovation: Free the Idea Monkey to Focus on What Matters Most. Brand New, Solving the Innovation Paradox and Flirting with the Uninterested, Innovating in a "Sold, not bought," Category.

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