How To Spot (and Promote) a Trouble-Maker

3 minute read

16 January 2019

By Insights Team

Innovation Reporter, Upstart

If you’ve ever managed a trouble-maker, chances are that managing them was just another problem to be dealt with in the day.  Yet the right kind of disruptive person has the potential to be an asset rather than a liability. It’s what you do with them that counts.


There are many types of trouble-causers. Some just delight in the attention of the problems they create, they’re probably a lost cause and perhaps not right for your organisation.

And yet there’s another, more interesting kind, the ones who are always asking awkward questions. Often challenging, occasionally child-like and visibly frustrated, they’re likely to ask “why?” often, and publicly.

So What?

If your answer to their “why” is “because process” or “because that’s what we’ve always done” then these people have a short career in front of them in your organisation.

Industrial structures and mindsets don’t tolerate this kind of grit in the machine. Priorities set by management and “cascaded” into organisations ensure the machine runs smoothly. And for most of the 20th Century that worked.

Nails that stuck up got hammered down.

Now, digital tech is changing everything. In every sector, challengers are gaining mind share and market share from legacy players. From banking to media to healthcare, customers are in charge, and will move to new services with all the promiscuity of a teenager at a summer camp.

Your new trouble-causer will be seeing this - and their disruption comes from the inevitability of watching your organisation do things the old way this year, next year and forever after until retirement.

So Now What?

Stage 2 of our three-sprint Upstart Breakthrough Strategy process is “Think” Using design thinking-led tools we help you imagine the ideal or the currently unthinkable.  What if, instead of containing your troublemakers, you promoted them?

How would your straining-at-the leash team member cope if you gave them a budget, a team and a 90-day deadline to come up with and put into practice an idea?

That’s what corporate innovation units are doing. Depending on your point of view, they're either empowering the brightest and the best to act outside the rigid structures, or rounding up the troublemakers in one place.


One of the best example of promoting troublemakers is T-Mobile’s US CEO John Legere. As a leader, he took the helm of the stodgy German brand and made it the “un-carrier” - calling out the accepted but exploitative telco practices and putting customers first. Now it’s the fastest-growing carrier in the US and (potentially) about to swallow its rival Sprint. That would never happened with Business-As-Usual CEO.

If you’re struggling with trouble-causers, here are three things you can do:

Understand: Work out if they’re just the workplace attention-seeker or they’re the squeaky wheel which needs a generous amount of oil

Think: Imagine what would happen if you empowered them. Would they continue to make a fuss or relish the chance?

Plan: Create a realistic plan for this to happen under your watch. That way you will keep the value of their insight and motivation and maybe you’ll take the credit for creating the next visionary.

Because containment is not an option in the 21st Century.

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