What 3 Questions Should You Be Asking Your Leaders?

Mark Fowler
6 min readOct 13, 2019

At my day job, we’re working hard to promote continuous improvement, leading with culture, and planning for the future by being forward-thinking with our current talent. This sometimes means promoting unique individuals, teaching and mentoring others, or even removing ones that would likely thrive in another company. We call this “talent planning” and is what my mind has been focused on over the past few weeks (besides learning Golang and Machine Learning in AWS). I’ve jotted down a few verbal notes over the past few days and wanted to capture them as writ and share them here.

What are you doing to succeed in an overly-constrained environment (aka day 1 mindsets)?

Most of us can probably think back to a job where we assumed a new role with a new and exciting company. We came in with exuberance, initiative, expecting to make significant impact in this role. We didn’t know about the silos, we didn’t know about the crappy architecture, we didn’t know about the mounds of technical debt we’d be dealing with on a daily basis, and we didn’t know about the difficult business partners with bassackwards, slow-as-molasses mindsets. We made plans and decisions without those shackles in mind.

Fast forward through a few bumps and bruises later, perhaps a few failures and project battle scars, and now we have some constraints that we know about. We now know that Frank and his team are going to say no. We know that Sally and her team are going to ask “why?” And we know that Jim and his team are going to pad their estimates and timelines. We may not realize that this knowledge is now influencing how our decisions are made. The challenge is keeping that “day 1” mentality while living in an environment rife with impediments and constraints.

Those constraints will never go away, at least, not in their entirety. There will always be constraints that impede our absolute progress. We need teams with mindsets where they’re constantly looking for ways to initiate positive change, to break down impediments and eliminate waste. We need to grow a continuous improvement culture that isn’t hindered by being overly constrained. We need to stop being victims, aggressively eliminate victim mentality.

Free your minds from constraints!

When our teams and leaders see a problem, what are they doing to solve it? Are they bringing solutions to the table? What bottlenecks are they seeing and how can they exploit those? And what are they doing to help their teams achieve this mindset? Answering these questions with action is what is meant by initiating positive change. Go back to day 1 mindsets.

What are you doing to help your peers succeed (aka one team or whole team approach)?

Most of us learned about this important point all throughout school. We were generally put in to teams for projects, assigned a specific role on that team, and relied on to execute all the deliverables tied to that role. It was a matter of winning. It was for the team. If everybody on the team won, then the team literally won. That’s a bit dramatic, but you likely know what I mean. We were schooled in team-based cultures for larger projects.

After school, many of us then went to work. We started careers, and mentioned team projects on our resumes, but only listed individual skills, individual positions, individual progress. We still worked in teams on projects, but when it came time for performance reviews most of the callouts were related to how you did as an individual. You know the questions: what do you want to be in 5 years? What have you done to continuously improve? What failures did you experience and what did you learn from them? It wasn’t until recently that I found leadership that actually asks how my team did? And, more importantly, what I do to help my teams succeed?

To take the perspective one step further, perhaps a better gauge of individual performance factors, in addition to the above, goes something like this: what have you done to help your peers succeed? I find that when a portion of my focus is on helping my peers succeed, they’ll likely be more willing to help me succeed when they’re needed. In an agile network, one doesn’t succeed alone, no matter how agile someone is. You succeed in an agile network by collaborating with a team, relying on them just like you did on school projects.

We need teams and leaders that are thinking about their peers and how they can help them succeed in the overly constrained environment we’re operating in. What have you done to help your peers succeed? Are you executing your role the way your peers would have you? Do you show them the respect they deserve?

What are you doing to create new leaders & experts (aka clone yourself)?

My career has made sure that as many smart people as possible will, or already have, cross my path. Some of them I reported to, some of them reported to me, and some of them I just naturally gravitated towards. You see, I love working with smart people. I love learning from them, soaking their inputs up like a sponge.

As does happen in a career, smart people leave companies and go to other companies to be smart in. Maybe that’s why they’re so smart, they’re always looking for new opportunities, new failures, and they love to share those experiences. The problem with smart people left alone too long is that they generally become SMEs, or as I like to call them, SPOFs (single points of failure) or BFO1s (bus factors of 1). The key is to make sure they’re not gauged singularly by their individual contributions, but how successful they are in cloning themselves.

A bus factor of 1.

As “The Phoenix Project” points out, every company has their own “Brent.” There’s nothing wrong inherently with being a Brent, or in my case I’ll say a Davis, a Lior, a Shaun, a John, an Andrea, a Viral, a Nilesh, etc. It only becomes a problem if that BFO1 doesn’t clone themselves, doesn’t succeed in cross-training, knowledge-sharing, creating new little mini-me’s. If they’ve not succeeded in cloning themselves, then when they decide to part ways and look for that new opportunity in a company far, far away, you’ll be left holding the short end of the stick and your life will become a living hell.

Make sure your teams are aggressively working to remove BFO1s, SPOFs, or whatever you may call them. Get that knowledge shared across pairs, teams, and leaders. And make sure your leaders are approaching success the same way. Individual contributions are great, but if they remain that, then they become nothing but waste and shackles.

FIN/ACK

In the spirit of telling you what I’m about to tell you, telling you, then telling you what I just told you, here’s the summary.

TL;DR Take your teams and leaders seriously. Help them achieve free, agile mindsets. And help them know they shouldn’t be victims, and should work to achieve a “whole team” career strategy. Ask the right questions and look for the right characteristics, or lack of, so you can help grow them.

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Mark Fowler

Continuous learner & technologist currently focused on building healthcare entities with forward-thinking partners. Passionate about all things Cloud.