"But! Nobody told you to do that!"

I was talking to a Digital Insurgent I know this week, and he shared something I hear often inside a bureaucracy. He was driving change and making the organization better - and then his boss dropped that great line, "But - nobody told you to do that!" Because he is in the military, it was followed up with a "Have you spoken to the Chief (Army Commander) about this?"

What is your mid-level boss so afraid of?

The perfect boss for a Digital Insurgent, is one that is excited to make change, experienced in change management, will mentor you and then enable you. When you bring up a scheme, they start scheming, they get other schemers - and before you know it, five people are on a whiteboard! Motivated, laughing and wanting to work late on this problem. If you have this leader – cherish it. Make sure you protect them.

The next level down - one that I had once, and enjoyed working for - is indifferent to change, but will not get in your way. They are not ‘promotion focused’ and instead, are along for the ride. They may even protect you. They know you are plotting to drive change and when people complain about your schemes - they shrug their shoulders and say, "let him try it."

The most difficult boss for a Digital Insurgent is one that is very risk adverse and isn't looking to prove themselves for promotion - instead they want to reduce possible issues so that they don't ‘not’ get promoted. If you are doing something that they don’t understand or wasn’t ordered by their boss – they will seek to stop it immediately. These bosses are frustrating and can kill any digital insurgency.

I had one of these experiences before, I was walking down the hallway and the Army Commander saw me. I had worked on a few files for him and even though I was mid-level – he knew me. He asked me how I was doing and any ideas to drive digital. Did I have ideas! I pitched him by greatest hits, and we were soon scheming together. He said, “Caleb, send me an email with that idea flushed out. Let’s do it!”

I got back to my desk and forwarded the briefing note I was working on. I was happy, finally some change! The next day I got a reply. I scrolled right to the bottom.

My email was forwarded by the Army Commander, “this is great, can we drive this and get an update in a few weeks?”

Deputy Commander, “where is this coming from? I have never heard of this idea?!?!”

---- you can see where this is going -----

One Star General, “we should be focused on what we are working on. Give me a brief on what this is, and we can hand the idea over to the proper staff officer. Caleb should be focused on other stuff.”

My boss, “hand this over to this other person and focus on what you are working on. Nobody told you to do that.”

The idea was handed over – and immediately died. If I was a braver man, I sometimes thought it would have been funny to forward the entire email chain back to the Army Commander and say, “this is why nothing moves forward.”

Being a Digital Insurgent can be dangerous work!

That incident didn’t really impact my career. I was known as a schemer, and it was considered a useful trait. Further, I knew I was retiring from the Army in 8 months and political infighting didn’t hurt my feelings anymore. It was not the same for a good friend.

He was also working on the digital file and saw an opportunity to really drive change. He took the initiative and took his shot. He sent an email to the One Star General outlining a great idea. The One Star didn’t protect him, and his boss crushed him for the initiative. “Nobody told you to do that!” My friend got a bad performance report that year and was pushed back from promotion for two years. He had to do mundane jobs and missed his window for a command billet.

Lessons for a Digital Insurgency

The first lesson is for all the senior leaders that want to see initiative and innovation. If someone is brave enough to give something a go – you must protect them – otherwise the mid-level leaders will crush them.

The second lesson is that an insurgency is dangerous stuff. You must be very strategic about it. If possible – don’t leave a paper trail and make sure you take calculated shots. Don’t just take one shot with one email – be Mao Zedong about it – overwhelm the person with multiple insurgents from different directions.

The last thing is to not take the “but, you were never told to do that!” too seriously. As Lt. Aldo Raine, Inglorious Basterds said – after being asked if he was worried about getting into trouble, "Nah, I don't think so. More like chewed out. I've been chewed out before."

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