Getting the boss involved in your Digital Insurgency

Driving a Digital Insurgency can be dangerous work - as we discussed two weeks ago - your boss might be 100% against it ("But! Nobody told you to do that!" | LinkedIn). You can accept the risk - or reduce it.

Going 'all-in' every time on your Digital Insurgency might work a few times - but statistically you will hit a barrier and the mistake could be costly. Preferably you don't follow the Bill O'Reilley school of stakeholder management and start 'doing it live' - instead sit down and map out a better approach.

I talked to a couple of great leaders in this space to get their feedback. Brigadier General (retired) David J Anderson has been helping drive the Canadian Armed Forces Digital Transformation for several years. He talked about the importance of doing an Intelligence Preparation of the Battlefield (IPB) - of your boss and the system. It is important to know the following:

• What motivates your boss? How do you help them achieve their goals?
• What interests you boss? Do they align with your goals?
• What is their past history? Will they have blind spots or strengths that you can work with? What have they seen previously that would resonate with them?
• What are their peers and boss interested in accomplishing? Could you help your boss align with those efforts?
• What is the context that they are approaching this position?

You shouldn't do the IPB by yourself. You might want to sit down with your peers and co-workers to share notes. The answer might be that your boss will 100% not support this effort - so for the interest of the insurgency you will want to give your notes and work to another 'insurgent' in another section. You would hope that the other insurgent will have success, get support and that shift will change your boss' motivation and interest. If your 'boss' boss' is interested - that might help get your boss interested.

If there is a small window with your boss - you will want to focus your attention and build success. As BGen (ret'd) Dave Anderson would say, "relationships matter." Further, you never want to sacrifice the small wins for your boss for the big wins. If you are trying to do an insurgency from the bottom-up, the small wins aggregate to the big wins. As Dave would say - "change is change."

Philippe Beaulieu Brossard, Co-President of the Archipelago of Design and Prof leading the strategic design curriculum at Canadian Forces College, has another perspective. When I sat down with him, he highlighted that the new leader might think and act differently than your assumptions based on previous experiences. The new leader might surprise you.

Philippe related a great example from the conduct of Exercise Strategic Bridge as part of the National Security Programme (NSP) at Canadian Forces College, a programme for CAF and WoG senior security leaders. Teams were given the task of reviewing the Canadian Indo-Pacific Strategy to expand its shelf life towards 2028 after months of working on an innovative vision for Canada and the region. One team in particular advocated for a bold vision towards 2040 that many thought too “dreamy.” But when they briefed a panel of senior leaders, the panel selected their vision out of three proposals. As Philippe suggested: “What does this tell you: you should always try to give to your boss what the organization needs, not what the boss initially thinks that the organization needs.” Do the IPB that Dave Recommends, but remember that you might very well change the assumptions of your boss. Your boss might surprise you.

How do you get your boss onside? Do a collaborative session with your team and boss and find the barriers and challenges using Design Thinking. You might already know the answers, but it is to "get the buy in to your team and your boss." If it is a one person plan - it is an issue. The outcomes:

• Here is where we want to go.
• Here is what we need to get there.

Sometimes the Commander or boss needs this to understand the complicated space. They need a collaborative session to understand the space and map out the outcomes.

Lastly - don't pitch it as a Digital Transformation - as your boss might already have a negative reaction from past experiences. Instead - use a terminology that may have less baggage such as organizational development or modernization.

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