On Challenging the Process (and Leader)

As I continue to meditate and think about leadership I also want to capture a few thoughts about how to challenge the process and how to do it in a way that is respectful.

Why? Because challenging the process can also mean that you are challenging a leader (or the much larger leadership). But you can do it in a way that doesn’t have to be interpreted that way.

There is an art to this, by the way, that is learned over time so it’s interesting to think that if I had heard this advice when I was 22 I’d have really no idea on what any of it means, as least pragmatically.

Conceptually, leadership and challenging a leader is easy. In practice, it’s really, really hard to do well. A few notes taken from years ago during a leadership workshop:

  • Developing the art of challenging the process without challenging the autority of the leader takes time and a ton of practice.
  • When you are given an instruction, follow through immediately, and then find the time to debrief later.
  • Avoid verbalizing your frustrating with the process in front of other team members and especially in front of your team while your leader is present.
  • The powerful principle here is that public loyalty can create private leverage. This can’t be overstated as I’ve seen this work time and time and time again. In practice, this means that you’re a public fan and a private critic of the process (and perhaps the leader).
  • Do not confuse your insights with moral imperatives. This can get a bit touchy, but, having good dialogues with trusted friends, coaches, and mentors can help you figure out the difference.
  • If you can’t get beyond some of these issues with the process (or leader) then you need to exit and leave the team.

Here’s some additional wisdom to remember which I wish I would have taken a lot more when I was younger:

Remember that “no” does not necessarily mean your boss is not open to change. It may simply mean your idea isn’t any good or currently relevant to the larger tasks at hand.

But, as a leader, our job is to create opportunities for those who report to you to challenge the process because we simply do not gain anything by not knowing what they are already thinking.

If our staff has the expressed and explicit permission to challenge the process:

  • Everyone wins, organization and team-wide.
  • The business continues to remain relevant to the real needs internally and externally.
  • We can create environments that attract great talent and also can attract great leaders.
  • Nothing ever goes underground or festers and we minimize resentment and bitterness to grow.

A final thought per my notes: Can we build a model of execution that is dedicated to the mission but not married to the model itself?


I love walking through these old notes, they are great food for thought.