Tag: structure

Risk and Support in Leadership

Not long ago I had the pleasure of hosting an old friend in Saratoga (where I live).

Rob and I became colleagues first, by working together in high end coffee in New England, and then eventually friends.

Rob had worked in coffee longer than I had when I joined that industry, and is still a big part of the community in Providence. He was in my neck of the woods visiting clients of his – he’s a coffee trader these days, and sells green unroasted coffee to folks who turn that coffee brown and sell it to the general public.

Over wine and Hatties’ fried chicken, we talked. We talked a lot! We talked about family and career and what it means to live a good life. It was an excellent visit with a great friend.

One of the things that he introduced me to was the idea of thinking about leadership in terms of risk and support. You can imagine these two ideas as different dimensions on a field, like so:

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In a leadership position, the decisions you make will tend to fall into one quadrant most of the time – the way that we can think about these dimensions are in terms of how we work with our team.

Support here means, how well do you as a leader back up the members of your team?

When someone falls down, when something doesn’t work as planned, do you step in, do you take responsibility for the team? Or do you allow the individuals to face scrutiny and take the blame themselves?

If a member of your team tells you that they have a bold career plan, as their lead do you find ways to help move them along that journey, finding or manufacturing opportunities for them? Or do you nod, ask about their day, and let them try to find their own way with neither help nor hindrance from you?

These are both different ways that we can compare high support and low support.

Risk here means, how much risk do you allow or encourage your team to take on? Do you fully insulate them from the winds of your organization’s politics, content with their low amplitude day to day work? Or do you allow them to wander outside your team’s safest places and experience both the opportunity for great work and the chance of failure?

Risk and Support are not always absolutely good or absolutely bad – you can imagine a lead who exposes their team to great risk could create a terrible environment to work in. You can also easily imagine a leader who fully supports her team in all they do, but never offers up any Risk, which means the support isn’t ever really needed.

This is why truly great teams balance the two, and achieve a state of both High Support and High Risk – offering opportunity (and the accordant risk) when appropriate, and doing all they can to also provide support for the decisions made in pursuit of that opportunity.

As far as a guideline for leadership and leadership decisions go – I like this one a lot. I’ve been asking myself, “Am I allowing for some risk? Am I supporting bold choices?” 

This is pretty half baked on my end – there’s a lot here to consider (how much risk is appropriate? Can one over-support? What does high-risk low-support look like? What about low-risk high-support?

Have you heard of this kind of structure before? How does this gel with your own experiences, as a team lead or as a team member?

 

 

Finding Your Own Structure

On the recommendation of my friend and colleague Andrew I recently picked up a leadership book called Extreme Ownership. Here’s his take on it.

There is a lot to talk about in this particular book, but the piece that really stands out to me is the idea that structure and discipline can help an individual to a life of greater freedom. This idea is especially germane to remote workers or folks otherwise enjoying highly flexible schedules and workplaces.

Having travelled in some pretty radical circles, I am familiar with the usual backlash against structure, process, and limitations on behavior – there is definitely a mindset that rejects these things in a wholesale way, and while I don’t agree with it (or find it to be particularly coherent as a political philosophy), there it is.

I can acknowledge that on its face, the idea of adding structure in order to increase personal liberty may sound counterintuitive. Stick with me. We’ll go on this journey together.

When I was studying philosophy one of the works that somehow found its way into all of my other classes was a paper called Two Concepts of Liberty.

If you’re so inclined, and have about sixty pages of time to dedicate, I totally recommend giving it a read in its entirety – it’s dense but brilliant, the kind of work you’ll get through and just nod, because it’s simply intuitively correct, something you understood before you even read it, but put into the very words you never could have.

The TL:DR of Two Concepts is that we can think of liberty as falling into two buckets: Positive Liberty and Negative Liberty. 

Negative liberty is essentially freedom of movement or freedom of choice. If I stop you from eating a donut, I’m infringing on your negative liberty. If I tell you to work on this project and only this project or you’re fired, I’m infringing on your negative liberty.

Positive liberty, Berlin says, is self mastery. Being able to make decisions for yourself in an informed and critical way means you have high levels of positive liberty.

When you answer Berlin’s question, “What, or who, is the source of control or interference that can determine someone to do, or be, this rather than that?” – if the answer is “I am the source of control,” then you’re enjoying positive liberty.

These two ideas are often at odds in ways that will help us to understand my above assertion, that through some structure and some discipline, we can ourselves become more free.

Consider driving. I live in the US, so I’ll be referring to US-based road rules – please substitute whatever is appropriate in your region of the world.

Driving in a car requires following certain rules – you stop at red lights, you drive at an appropriate speed, you stay to the right hand side of the road. These are necessarily restrictions on our behavior and as such, limiting factors of our negative liberty.

However, even as our negative liberty is constrained, we’re able to exercise greater positive liberty, as driving becomes a safe activity, it becomes reasonable to engage in, rather than some sort of Mad Max terror situation. We’re able to effectively self govern.

By creating a more structured environment, we’re all able to thrive more fully and accomplish our personal goals. What is the end goal of liberty if not to accomplish our personal goals?

In Extreme Ownership, they talk about a very serious level of discipline, but they’re also dealing with very serious personal goals; kill or be killed. For somewhat less severe goals (decrease churn, make our customers happier), less serious discipline is probably OK.

One of the things that remote workers gain is an open day. There are pros and cons, and the freedom at hand can be thrilling, to be sure.

When you consider your work, and the way that you approach your work, let me encourage you not to mistake negative liberty for positive liberty. Creating structure around your goals and around your day allows you more freedom, not less.

When you’re your own boss, or when you enjoy the freedom to essentially behave as though you’re your own boss, creating your own schedule, etc, one of the best things you can do is to create some boundaries for yourself, to intentionally limit your own negative liberty.

Maybe that means getting up at 5AM to go to the gym, taking away your own ability to stay in a warm bed. Maybe that means always shutting off the laptop at 5PM, because you know you’ll let work creep into your personal time otherwise.

Self mastery, positive liberty, is best accomplished when you impose your own restrictions on your negative liberty – but you do so intentionally, with an eye to your own broader goals and aspirations. A lack of organization will also surely fill your time, and surely will keep you occupied – but will it move you forward in the right ways?