Some Thoughts on Leadership: Do Less to Achieve More

Paradoxical productivity advice for aspiring leaders.

It’s Sunday, second cup of coffee o’clock, and I’m making a list of possible topics to write about for this post for tomorrow (which is now today, as you read these words). The list is pretty long, and could win me a bunch of woke awards for its exceptional diversity – here is everything from Pareto’s Law in practice, to octopus intelligence (!), alchemy, career hacking, over-managing your life, and the joy of missing out.

But the only topic on the list written in all caps is LEADERSHIP, because that’s what’s on my mind and on top of my list of Kindle books at the moment. So let’s start there and see where we end up.

Beware though – this post will probably become a stream-of-consciousness-style, fairly self-centered ramble in text form. You have been warned.

From Founder to Leader – From Doing More to Doing Less

We just signed our 9th employee in Braver (and looking for one more). Less than a year ago, we were literally three dudes in a garage-looking office, and now we’re a capital T Team. Exciting times ahead!

These days, I’m reflecting on what my own role in this emerging Team should be going forwards. For the last 3.5 years I’ve been doing stuff continuously. Checking off tasks. Creating systems. Making slides. Holding webinars. Watering the plants at the office… It’s been an operational day-to-day life, with some time slots to think squeezed in between all the doing.

That’s all well and fine. I’m pretty good at it. It creates decent results. It’s fun. But – there’s always a but – it doesn’t scale. As any entrepreneur will tell you, sooner or later (ideally sooner), you have to transition away from doing towards something else – leading.

At some point, your job is no longer to do everything yourself, but to empower other people to do great work.

Problems are no longer yours to solve alone, and often not yours to solve at all. They are yours to pass on to other people to solve, using their good judgment rather than your own.

In the wise words of the author of The E-Myth Revisited, “you have to work less in the business, and work more on the business”.

At that point, you no longer get paid to do. You get Paid to Think (great book by the way), and paid to lead.

Making this transition is long overdue for yours truly. This post is, more than anything else, an attempt to solidify some things I’ve read lately about how to make that transition, and what to focus on going forwards. Beyond being an effective reflection exercise for myself, I hope it will be valuable for others in similar situations.

The Only Four Things that Matter

I already know that most things in life don’t matter. Don’t sweat the small stuff, as they say. Pareto said the same thing – find the 20% of inputs that produce 80% of the results, then focus exclusively on those twenty and disregard everything else.

When I say I already know that, I mean I understand it intellectually. Living it out in practice is a whole other story. I don’t follow said advice nearly as much as I’d like, but I’ve committed to focus on doing more high-leverage stuff going forwards.

What might such stuff be? Well, as a tiny company grows, semi-conventional wisdom says that the founders should focus more and more of their time and energy on the only things that really matter:

  1. Talking to customers.
  2. Controlling cash flow.
  3. Recruiting and hiring.
  4. Communicating the vision and direction to everyone all the time.

My co-founder mostly deals with the first, and I deal with the second. The last two we must take shared responsibility for.

Regarding the third point, I think we’ll get pretty good at hiring. Not because we have much experience yet, but because we’re looking for a distinct type of person whenever we’re hiring for the Braver team. These human beings are hard to find, but they’re easy to spot when we encounter one.

This leaves me with the fourth point, which stands out as the most difficult by far. Not objectively so, but the most difficult for me personally.

I generally prefer to work on things that have a defined end date, something that can be completed or resolved or fixed once and for all. I also generally prefer working on my own – to close the door, block off all possible distractions, and go deep into flow states for hours (or days, or weeks!) on end.

Communicating the vision and direction of a company is the opposite of both those things.

It’s something that will never end. It’s never “done” – you never check off the vision task in Asana. In the lingo of last week’s post, it’s an infinite game.

It’s also at odds with closing the door, literally and metaphorically. Communicating the vision must, by its very definition, be done to and with others (duh!).

This is energy and time consuming work. Therefore, it needs dedicated headspace and time in the calendar. To find some of that, I’ll need to practice something else in tandem, something that might be equally difficult and equally worthwhile: letting go.

I’ve developed a set of professional habits that center around being operational, on doing stuff, on solving problems, on being busy. I now have to practise letting go of these habits, and replace them with new ones.

But more importantly, or more fundamentally if you will, I have to let go of something else: the identity of being a doer and a fixer.

That’s the fundamental change that needs to happen, and it is also the most difficult change to make. The reason why it’s difficult can be found by answering a very deep question I’ve heard business coach Jerry Colonna ask on several podcasts:

“How am I complicit in creating the conditions I say I don’t want?”




(Here is a pause for you to reflect on Jerry’s question in the context of your own life)




For example, I might say I don’t want to have too many responsibilities and too full a calendar at work. But in answering Jerry’s question, it becomes immenently clear that I am complicit in, or practically 100% responsible for, every aspect of the conditions that lead my calendar to fill up like a world class Tetris game week after week.

This is great news. Since I have created these conditions, it is clearly also in my power to change them. That’s what I’ll focus on over the next few weeks (if anyone has advice on how, please reply to this email!)

Role vs Behaviour: What Comes First?

As I’m about to wrap up this ramble of a post, I can’t help but reflect on one final question – what comes first on the path to becoming a great leader?

Is it being appointed (or self-appointed) to a leadership role, or is it exhibiting leadership behaviour?

Do you first become a leader on paper and then in practice, or is it the opposite way around? Does the designation of a leadership role inspire leadership action, or does action tend to come first?

I believe it can work both ways, but I’m most bullish on leadership in the form of actions. Leadership, as far as I understand it, is essentially just a mindset and a way of acting that is available to all, regardless of role and rank. Act more as a leader, and you might suddenly find yourself being one.

Best of luck.


📚 Further Reading

For more on similar themes, see these books:

  • The E-Myth Revisited, by Michael Gerber.
  • Traction, by Gino Wickman (also: Rocket Fuel, by the same author)
  • Extreme Ownership, by Jocko Willinck.

Also published on Medium.