We’ve all been there: an external stakeholder places unreasonable demands on your work or team.
Some real-world examples:
Legal says we’re not allowed to make a change, even though there are thousands of companies much bigger than ours that are already live with this change.
Security makes simple things impossible because the only thing they care about is security.
Sales forces a specific solution because it is what the customer asks for, even though it may not be what they actually want or need.
The reason this happens is pretty simple: everybody is too focused on staying in their lane. Nobody wants to shake things up and everybody operates in the safe comfort of their silo.
Since the change legal requested is guaranteed to make the company lose millions, I’ll ask legal pesky questions to provide as much context as possible. I want to be able to tell whether the changes are in the best interest of the company, not just from an insular legal perspective
I’ll pepper them with many questions, like:
Why do we need to implement the change?
How is our company different than hundreds of other bigger companies that don’t have this legal change?
Must we be the first? Why not wait until more companies adopt it.
What happens if we don’t implement it?
Would we get a warning first or immediately get a fine?
How much time would we get to fix it before being fined?
Asking these questions usually isn’t appreciated, because they frequently don’t have all the answers to your questions. Every question you ask makes them look bad, and as a consequence you look bad too. To them, it feels like you’re challenging their expertise and not taking their judgement seriously.
That’s absolutely not the reason. I’m not trying to challenge their mandate, I’m trying to understand all the options that are available and figure out the best course of action. I’m trying to steer the conversation away from aa single insular area of expertise to a playing field based of common interest: what is the best decision we can make for the company while taking into account all the different perspectives?
Collaboration becomes impossible if the only thing the people you must collaborate with care about is a their silo. You’ll be busy discussing low-value side-quests with a complete disregard for how it impacts the real-world business.
The real-world doesn’t care about your silos. The problems with problems is that they don’t respect the artificial boundaries of your expertise. The paradox of collaboration is that you need troublemakers to have the best collaboration possible.
You need the misfit who gently tells legal their request is unreasonable, given all the facts. The troublemaker who warns security their demands will backfire in the real-world. The rebel who asks sales to directly talk to the customer so they can figure out what they really need.
For the best results you must have productive friction without rubbing each other the wrong way. Strong collaboration requires troublemakers who are unafraid to challenge the status quo.
The problem is that we like strong collaboration but we absolutely don’t like opinionated troublemakers.
We Like Collaboration, We Don’t Like Troublemakers
If you think of troublemakers, leaders like Elon Musk and Steve Jobs immediately come to mind. They are extremely innovative leaders and both polarize and cause lots of friction wherever they go. But the end result frequently (not always!) is something far better than it could have been without their intervention.
If your organization struggles to collaborate: you need more troublemakers. You need people that cause friction and force people to think outside their box. You need people who cause a ruckus and pull people away from the railroad to go offroad together.
Like Elon and Steve, you need troublemakers who are unafraid to rub people the wrong way. Don’t mistake this to mean you must rub people the wrong way. You need people who see things differently together with a broader perspective. They will try to get others to develop a fresh perspective beyond their limited scope of expertise.
Don’t try to replicate Steve and Elon. If you make trouble: don’t be a dick and try to preserve the relationship.
Winning by doing the right thing in the long-term is far more important than winning any single battle on the short-term. Otherwise you may get ousted, like happened to Steve Jobs.
Here’s to the troublemakers.
Even though it’s not always appreciated: keep causing a ruckus as your company needs you much more than they’ll ever give you credit for.