Be unreasonable; break through arbitrary barriers

Welcome to the "The Catalyst," Kevin Noble's weekly newsletter about becoming a more effective leader.

Past newsletters can be found online here.

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Quick Note

I’m looking for a better calendar solution.

I’ve been using Hey.com for several months. It’s attractive and has some neat features, but is built for a casual user.

Small example, but if you have two events at the same time, it hides one behind the other. Not useful when you’re managing multiple family events, or even just tracking something like a football game!

I'm in the middle of a debate with myself about going back to Google Calendar. The biggest barrier is my concern on privacy, but otherwise it does what I'm looking for.

Also, the integrations with Google are also so common! Most of the CRM or other advanced tools I look at only integrate with Google 😒. Do I trade privacy for convenience and productivity?

Are you an advanced calendar user? What do you use to keep track of everything? Whether you love your solution or not, let me know at heykev@kevinnoble.xyz.

Kevin 😁

A Quote

“ When we conceive an enterprise and commit to it in the face of our fears, something wonderful happens. A crack appears in the membrane. Like the first craze when a chick pecks at the inside of its shell. Angel midwives congregate around us; they assist as we give birth to ourselves, to that person we were born to be, to the one whose destiny was encoded in our soul, our daimon, our genius. — Steven Pressfield in "The War of Art"

Three Things

1 - 👷‍♂️ Justin Willis on Acquiring Minds - A friend from college was recently on the Acquiring Minds podcast to share a cautionary tale for buying a business. Justin liquidated his $1M 401k to acquire a construction business, and then everything went wrong, including sabotage by the seller. In the end he may even lose his house! I love the strength of Justin’s character throughout. Lots of Stoic ideas in there while dealing with a difficult time.

2 - 📅 Morgen Calendar/Task App - I signed up for the free tier of Morgen as an experiment in solving calendar and task management issues. Bring all your calendars together alongside your tasks. It integrates with ToDoist and Obsidian! You can schedule with other people through booking page and scheduling links. It’s $9/month for the advanced features. Video review here.

3 - 🎚️ Salvatore Ganacci, Step-Grandma - Is there a genre for dark comedy music videos? If so, Salvatore Ganacci, a Bosnian-Swedish DJ, is the undisputed king. Watch this visual short story play out behind his equally good electronic music.

Deep Dive on Breaking Limits

How do you know whether a limit is truly a limit? You test it.

This is how kids learn about the world around them. They’re constantly testing boundaries. Over time, they learn what’s okay and what’s not okay.

Kids turn into adults, and somewhere along the way they stop testing boundaries altogether. We become somewhat blind to the possibility that limits can be moved. We go along to get along.

Not pushing boundaries is a form of learned helplessness. Like when a dog is in a cage with the door open, but won’t leave.

We are agents in the world, and in order to achieve our goals, we have to bend the world around us. Just because someone set a policy or a budget or a course of action doesn’t mean it’s unalterable in perpetuity.

In fact, this is often seen as a key distinction between leadership and management. Leaders create their environment, and managers react to their environment. To be leaders, we have to push against perceived barriers.

I like the analogy in that quote! Am I setting the temperature for the team? Or am I recording the temperature of the team?

Today I’ll share my thoughts on why I think breaking limits is an important skill for a leader, examples of where to put this in action, how to model it, while also keeping it in balance.

Let’s break our limits.

Let’s escape the cage.

Let’s set the temperature for the team.

You with me?

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The Importance of Challenging our Constraints

As leaders we’re creating a vision of the future that doesn’t exist yet. We have to make the seemingly impossible, possible. By definition we’ll need to break the limits of what’s believed to be possible.

At a more micro - and less grandiose! - level, we need to make sure we’re taking care of our team. You may encounter an edge case that requires a policy to shift in order to do the right thing.

You don’t want to be a bureaucrat who tells someone on your team, “Well, that’s the policy” and watch them eventually leave.

We have to fight against the natural tendency for a system to settle into a solid form! Policies, procedures, and processes often start out as a best effort MVP and somehow turn into inviolable decrees over time.

We know that systems are powerful; good people operating in a bad system create bad outcomes. A system that doesn’t change with the environment is probably no longer an effective system. A leader will be needed to break those barriers and create a new system.

The operating system in your business is there to serve you. Change it as necessary.

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Examples of Areas to Challenge

The barriers in our life are a funny illusion; they all seem firm and solid at first glance, but when you get closer, some are just holograms, some are made of paper, some of Jello, and just a few are made of steel.

I like the “coffee test” that Noah Kagan uses. To help people in starting a business and asking for what they need, he has them go into their coffee shop and ask for a 10% discount.

Most people are horrified! (me included)

“Retail prices are set! You can’t just get a discount! What will they think of me if I ask for one?!”

Guess what? Even retail prices are flexible.

What are other types of barriers we can push against? Here’s just a few for you to think about:

Budgets
These are just numbers on a spreadsheet. You can ask for more. You can take less. You can add a new line item. You can ask for another to be deleted. You can change the overall approach from “90% likely to hit” to “50% likely to hit” (or vice versa).

Ask for what you need.

Resourcing
There was a planning process that determined how many people will be working on an initiative you’re driving. And while the methodology might’ve been sound, that’s not the end of the story.

How many people do you need to be successful? You won’t get it if you don’t ask.

Compensation
Twice I spent more than six months actively making a case for why the compensation ranges of an entire function reporting to me were off and needed to shift upward. It was difficult, as all challenges to established methods are, but it was the “right” answer for the team each time.

HR would explain the process by which salaries were set, and I’d have to argue how the underlying assumptions were incorrect. I eventually succeeded in making my case.

Your own compensation, and that of your team, are not set in stone.

Policies
Policies may be well-intentioned, but they often over-constrain an organization. Someone writes a policy and then it lives on the company intranet forever.

Challenge the policy if it’s no longer the right answer.

Time
As a leader I’ve been guilty of throwing out a timeline to a team only to have it treated as permanent. It was just a suggestion!

Many timelines are like that. They feel like they roll down the hill to a team who looks at it and thinks, “What are they smoking?!”

If the timetable is inaccurate, push back. Advocate for what’s needed and why.

Strategic Choices
Which problems you choose to solve, and how you intend to solve them, are variables, not fixed. If you see a better path to an outcome, make the case for why you should take a different path.

Armed with all these possible limits to go challenge, what’s needed and how do you model this?

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What’s Needed, and How To Model This

There are two big things that influence the difficulty of challenging barriers - culture and accountability.

Culture - or, “how we do things around here” - can make this much harder or much easier. A culture that encourages and supports people in challenging the status quo will be much easier to work within than one that doesn’t.

There are many leaders who opt for a “command control” style of leadership which propagates throughout the org. (see your org. looks like you). In that organization there’s not much flexibility. Barriers will be harder and more costly to break.

As a leader, work to create a culture that supports breaking barriers.

It’s also much easier to challenge barriers when there is clear accountability and ownership. Meaning, who do you talk to, and what’s the process?

When accountability is diffuse, that looks like the policy document with no owner and no process for periodic review. You may know the policy needs to change, but how exactly do you go about doing it? It’s very hard to push back when there’s nothing to push back against.

As a leader, make sure you have clear accountability and processes to challenge things. What’s the budget review process and who decides? Who’s the owner of the strategic choices and what’s the ritual to discuss them?

So far I’ve been pretty one-sided. Breaking limits is generally good, yes, but is there a limit to its usefulness? Are there any costs associated with it?

On Balance and Modeling

Imagine a world in which every barrier is removed. Everything is up for grabs. People can choose do whatever they want, whenever they want, for as long as they want.

Chaos!

That means breaking limits isn’t a universal good. As usual, we’re working in the gray. There’s a balance to this.

You want to break limits, and a team that can break limits, but it has to be within reason.

How do you create the balance? By modeling it.

Show your team where and how you push against limits outside of the team. Teach them the nuance of when to challenge and when to comply.

Have open forums where you discuss what’s working and what’s not. Be sure you don’t “shoot the messenger” and be mindful of power dynamics. How you respond to someone challenging the status quo will affect the rest of the team’s willingness to do so.

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The Costs

Breaking limits is not without cost, or it would be more common!

The biggest cost is your time and energy. Ugh, it can be real pain in the butt to fight the system.

You honestly won’t have the energy to fight everything, so don’t try. Be strategic in what you choose to expend energy on.

The other big costs are social and political capital. There will be other humans involved in every one of your attempts to break through limits. Those people will often be driven by emotion, power, and ego.

While you might be rational and doing the right thing, do it too often and with the wrong people, and your brand will literally turn into the “unreasonable man.” It’ll make it that much harder to do your day-to-day job, much less break through barriers.

Be mindful of the costs. Play the long game. Expend your energy where it’ll be put to best use.

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Call to Action

Consider this newsletter to be a set of “barrier-busting glasses” for you. Put these new glasses on at work this week.

What’s made of paper? What’s made of Jello?

What’s made of steel, but might be worth the cost to change?

Start talking about this with your peers and your team. Start to influence the culture and model how to do this well.

Good luck and have fun! And as always, let me know what you think, and what you try! I’d love to hear about it. Email me at heykev@kevinnoble.xyz.

Kevin 😄

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