In the agile community, we tend to focus a lot on teams. This is a natural thing to do as building high performing delivery teams is where agile started. We tend to see management as an impediment to good team functioning. We talk about "the frozen middle" and "lack of executive support". We teach scrum masters and product owners how to shield their teams from management.
If we are going to stay in delivery team land, this is fine. We can build high performing teams and shield them from management as we always have, but if we want to take agile further - build truly agile organisations rather than just agile delivery teams - we need to take a different approach to management. We need to start engaging them as allies rather than treating them as the enemy.
There are limits to how far we can go with just teams. By just optimising delivery within a larger organisations that is dysfunctional, we sub-optimise. Teams will deliver efficiently, but they will not be delivering the right things for the organisation and its customers. The work that makes it into the teams will not be the right work. The system that feeds the teams is still broken.
If we want agile organisations, we need to fix the whole system, not just delivery teams. As Deming said -
"The workers are trapped in a system and the system is owned by management"
So to fix the system, we need to fix management.
Easy to say, much harder to do.
The big problem we have with reaching out to senior leaders is that many large organisations (the sort that can afford agile coaches) tend to be very hierarchical and as a lowly agile coach, it is often difficult to navigate the layers and get access to the people who can fix the system. In some large organisations, senior leaders are revered almost like demigods... a hush will descend on the room... A GM has graced us with their presence. Everyone put on a tie and look smart. There is actual, real fear of these people. You can feel it when they walk in the room.
But you know what? Once you do get to talk to senior leaders, you find out that they are people. People, doing pretty much what the rest of us do - working in a job and trying to do their best at it in an environment that keeps shifting around them (only they tend to wear nicer suits while doing it). Just like us they are trying to make the best decisions possible with very limited information and under enormous time pressure.
They are also quite often extremely isolated. Particularly in companies with a very aggressive management culture. They have to be seen to have all the answers. Reaching out to their peers for help is equated with weakness and they will be eaten alive. Often they feel overwhelmed and really struggle with uncertainly. This manifests in many ways, from the overly aggressive crash or crash through manager to the indecisive, won't make a decision without mountains of data manager and everything in between.
In short, they are people. Real people, just like the rest of us, dealing with the same real problems the rest of us deal with, but often without the support network of peers that the rest of us can draw on for support.
They are often actively looking for advice and help on how to do better (ever wonder why there are so many management books on Amazon?). What we need to do as agilists and coaches is to show them that we have something to offer that they can make use of in what they do. We need to be able to show that we can help them.
Again, easy to say... but how do you get access? How do you start that conversation? You start with what you have. You obviously have access to someone on the organisation, otherwise you wouldn't be there. Ask to talk to their boss to find out what problems they have with the way things run and how you can help solve them. It really doesn't matter how low in the organisation you start, just get started. Talk to their boss. Have a conversation about their role and the challenges they face in it. Find out what their biggest pain points are.
Frame the conversation around the agile transition that is happening lower down - "Change is happening, how can I help make your job easier in the face of that change?" That way it looks like they are managing change rather than asking for help.
9 times out of 10 it will be a plea for data to help them understand progress without the usual gantt charts. That's an easy one to solve. It doesn't really matter what the problem is, use your skills and techniques as an agilist to help them - problem with scheduling work? Teach them Kanban. Problem with resource management? Teach them WIP limiting.
Once you have that initial conversation going, expand it. See what you can offer for their other non-agile problems. Become a trusted advisor.
Then ask to talk to their boss. And so on up the chain. Also ask to talk to their peers in other areas of the business. Use them as a bridge into areas you don't have direct access to. Build a network of introductions upwards and outwards.
Providing coaching and advice to executives is one of the most valuable things we can do as coaches. If we really want to transform organisations and unlock their potential, we need to get senior leadership on side and involved. We can't do that if we stay down at the team level. We need to show that we have something to offer at their level as well and the only way we are going to do that is by becoming their trusted advisors. We need to become coaches for the organisation, not just its teams.