The Urgent vs. Important Paradox — CEO Gut Check

Over 10 years of starting and scaling companies, one of the most important skills is time management. No matter what type of company you are building, there is never enough hours in the day.

I have found that analyzing my time spent per week can be extremely helpful in assessing the strength of my business, and as I invest in more companies, I am finding this analysis is helping the CEOs I work with.

Here is the headline:

· Great CEOs are able to spend most of their day on Important tasks.

· Surviving CEOs spend most of their day on urgent tasks.

· CEOs focused on neither have a fundamental business problem.

Urgent vs. Important is not a new concept or one that applies only to the CEO, but this concept is uniquely tested as the leader of a high-growth organization.

When running Kahuna as it was scaling rapidly, I was always busy — the opportunity was too exciting not to live and breathe the job. That said, looking back I noticed two very different types of busy.

Every morning I start my day by listing my ‘to-do’s’ for the day. For each task, I score it in terms of urgent and important. I then look at the list and put a page break below the items I have to do. The idea is I’d rather do the three most important tasks instead of being overwhelmed by 30 tasks.

Every Friday I look back at my calendar and review where I spent my time. You are in the tornado when you are scaling a company and taking 10 minutes at the end of the week can help you see the forest for the trees.

Upon reflection, during the scale phase, I found that most weeks I was in Quadrant 1 or Quadrant 4. The big questions were why, and where should I be?

Why you are in each quadrant

Let’s knock out the easiest one first: Quadrant 2. Note that I am breaking the cardinal rule of the 2x2 matrix: the top right quadrant is not the answer. That is because no person can or should try to always live doing Urgent and Important things — there just isn’t that many of them that truly pop up. Examples of Urgent and Important things include:

· Sending wire instructions to get $10M+ wired to your bank account.

· The final hours before closing a $1M+ customer.

· Taking a VP Engineering candidate out to a ‘sell dinner,’ where at the end you expect her to sign an offer letter.

As you can see above, these tasks don’t come up every day. Recognize when they arise and focus on them, but they are never the majority of your time.

The Urgent vs. Important paradox is named so because you can’t spend 50–80 hours a week doing only urgent and important tasks. The goal is to create enough time to work on important items.

Next, let’s tackle Quadrant 1. Whenever you ask a CEO how she is doing and she says “I’m so busy,” it is typically because she is in Quadrant 1. You are in Quadrant 1 because of a laundry list of urgent tasks that take over your life.

The most poignant times when I fell into Quadrant 1 is when I had Customer Success issues. Most organizations value customers highly, hence when a customer has an issue it becomes urgent. If multiple customers have issues, suddenly your entire day is consumed by firefighting.

Living in Quadrant 1 is unsustainable and not fruitful. You find yourself working hard just to break even.

If you find yourself in Quadrant 1, trying to identify what are the deeper issues that are creating all the urgent tasks and go fix them. It might cause consternation, but in the end making the hard changes enable you to be more successful.

The most depressing state is to be in Quadrant 3. You still might be working hard and be in Quadrant 3, but you are not really doing urgent or important things. Great examples of Quadrant 3 tasks:

· Speaking at a conference.

· VC cocktail events

· Bookkeeping

By all means, do Quadrant 3 things, just don’t make them the majority of your week.

The businesses that are doing the best have CEOs living in Quadrant 4. The CEOs are not running around frantically, rather spending quality time on very important tasks.

When I ask these CEOs what they are working on, the answers are thoughtful, and the tasks feel important. A CEO can only be in Quadrant 4 if other team members are sharing the responsibility for urgent tasks.

Quadrant 4 tasks are proactive and might not have immediate payoff but set the company up for success.

Great examples of Quadrant 4 tasks include:

· Refining product roadmap for increased competitive differentiation.

· Customer meetings to further refine product/market fit.

· Listening to employees and making sure culture is sound and the team is aligned.

Your business metrics can still look amazing while you are outside Quadrant 4, but Quadrant 4 tasks are vital to the long-term success of your business. At different times Kahuna was growing quickly but I was not in Quadrant 4, and I always paid the tax. If you find yourself not in Quadrant 4 but still growing, I am happy to help diagnose and brainstorm ways to get there!

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Adam Marchick

Investor & 3x Founder —Active Investor (15+ private investments); Founder/CEO Alpine.AI (through acq. by Headspace Health); Founder/CEO Kahuna; Founder/ED Glow.