Complexity is the enemy of success 

When I was running Classy I had this terrible moment of panic around 200 employees. I realized that I was spending more time on HR, investor and legal related matters than I was spending on customer problems. Somehow an insane level of complexity had seeped in around me – and I didn’t even see it coming! 

Turns out this same thing happens to many well-intentioned leaders. Why? Because organizational complexity is like an invasive weed. If you’re not actively pruning it, the entire place gets overrun. As the leader, you need to fight back. I literally picture myself with a machete whacking the tangled vines that are choking the company’s creativity, innovation and pace. Too extreme? I think not. 

So if complexity is the enemy of success, is simplicity the answer? Yes and no. Simplicity without value is just complexity in disguise. What we’d call ‘waste’ in my lean six sigma days. The real antidote for complexity is focus. Identifying what truly matters and stripping away everything else. 

But focus doesn’t come naturally to most leaders. And it becomes harder with every new person you add to the company. This was me at 200 employees. I was bogged down with non-essentials – a bunch of stuff that didn’t add value to our customers. So I forced myself to go back to the basics and refocus everything that I (and the company) was doing. Perhaps unsurprisingly, the team thrived with less baggage and an extra level of clarity. Financial results followed. 

Leading like a minimalist 

My minimalist approach was inspired by the founder of Patagonia, Yvonne Chouinard, and his incredible book Let My People Go Surfing. Luckily I got a copy early enough to realize that leadership didn’t need to be so complicated. It was about identifying the essentials and doing them amazingly well. Better than anyone in the world. That became our new bar.

But like anything worthwhile, it takes effort to stay on the right path. Especially as your company goes from stage to stage. This article started as a reminder on my phone when I felt myself getting off track. When I felt complexity starting to creep in. I’d pull out my phone, read the three notes (below) and ask myself the following question:

Is the company focused enough?

The answer is almost always no, but you learn quickly that continuous calibration is necessary for even the best companies. So regardless of where you’re at in your leadership journey, use this article as a reminder to keep things simple, clear and actionable at your own company.

1. Refocus your energy 

If you’re not focused as the leader, no one else will be. But how do you prioritize where you spend your energy? 

Start with this very basic exercise. You have three main stakeholders that compete for your energy: your customers, your people, and your shareholders. You should spend the most energy on your customers, then your people, then your shareholders. Here’s what this looks like: 

• Customer Bucket: Spending time driving results for your customers – like product, experience, service, etc. – falls in the customer bucket. This time can be spent solo or with your team.
  
• People Bucket: Spending time on individual people issues – like careers, performance, conflict, etc. – falls in the “people” bucket”.
  
• Shareholder Bucket: Spending time on new & existing shareholders – like investor updates, Board meetings, fundraising, etc. – falls in the “shareholder” bucket. 

Do a calendar audit. Where are you spending most of your time & energy? Put a percentage behind each bucket. How do you put more energy into the customer bucket? 

Don’t get me wrong, the people and the shareholder buckets are important, but not at the expense of your customers. When you focus on the customer, the rest of the stuff tends to work itself out with less energy.

2. Refocus your PDP

PDP is an acronym for Purpose, Direction & Progress. Three questions that every leader, and team should be able to answer with absolute clarity:

• Purpose: Why are we here?
  
• Direction: Where are we going?
  
• Progress: How are we doing? 

The answers to the PDP serve as a map for the team. If the map is fuzzy, or missing altogether, the team will be lost. This makes the organization far more susceptible to complexity because everyone’s moving in different directions. 

I strongly suggest taking the PDP test as a baseline. How clear are you on these three questions? Then make your leadership team take the test as well. Don’t leave the room until everyone is on the exact same page. Warning: this is MUCH harder than it seems.

The PDP is a fundamental part of the operating system we teach in Highland – my private community for founders & CEOs. I call it the Northstar Operating system, and you can use our template to consolidate your PDP in one single slide. Then roll this out to your company and you’ll be amazed at the clarity it brings to your team – it’s like turning a light on in a dark room. 

I’ve also written a few articles that might help you strengthen your company’s PDP: 

• How to write a great mission statement (+50 examples)
• How to create values people actually care about
• How to create a company vision people want to follow
• 7 essential rules of goal setting 

3. Refocus your rhythm 

Your operating rhythm is like a routine you set for the entire company. It helps define how and when the team comes together to put the PDP into action. It’s typically a well-understood set of meetings, reviews and analytics that holds the team accountable to the desired outcomes. 

But the relationship between operations and minimalism is delicate. Too little structure and you’re flooding the team with an unworkable amount of chaos and confusion. Too much structure, on the other hand, and you’ll slow the team down and suffocate creativity and innovation. You have to strike the right balance as you move through each stage of company growth. 

Similar to your personal calendar, you should do an audit of your company’s operating rhythm at least annually with that same question in mind: Are we focused enough as a company? 

Here are some reflection questions that might help:

• Are the company’s top 3 priorities front & center and discussed weekly?
• Does the full team understand how you’re doing against priorities?
• Which meetings reinforce priorities, which do not? Can you cut any?
• Do your dashboards & analytics give insights into the priorities? 
• Are you holding leaders accountable to these priorities in the right way? 
• Does the current system force cross-team alignment against priorities? 

Keep refining your operating rhythm until the answer to all of these questions is ‘yes’.

How I can help you… 

Are you a founder, executive, or manager? I’d love to support your professional growth. 

Here are three ways: 

1. Connect on LinkedIn, X, and Instagram – where I post practical tips about leadership and startups every day.

2. Subscribe to my free newsletter – where I dive deep into a variety of management and operations topics that will make you a better leader & operator. 

Join Highland – my executive coaching program for founders, where we help you become a top-tier CEO who can scale into the tens of millions & beyond.