Zach Obront is an Entrepreneurs' Organization (EO) member from Austin, bestselling author and co-founder of Book in a Box, a service that streamlines book writing and publishing processes. As an entrepreneur who recently transitioned into leading this thriving business, Zach shares his strategies for overcoming the challenges of changing jobs.

I've found that most advice given to entrepreneurs focuses on getting a new venture off the ground. There are thousands of articles and books about identifying a business idea, increasing productivity, finding a product-market fit, and earning revenue.

These topics are incredibly important, as the early phases of starting a company are full of many hurdles to overcome.

However, there is a second wave of challenges that catch most entrepreneurs off-guard, and there's far less information available to help during this stage of business. I'm talking about making the transition from "founder mode," when the only goal that matters is hustling and getting things done, to "manager mode," when the goal transforms into building scalable systems and supporting the team's larger objectives.

In theory, it sounds easy: do less yourself, delegate more, read some management books, and focus on helping your team do the work.

But for many founders (especially myself), it's incredibly difficult. In fact, I'd argue that many of the traits that lead to success in "founder mode" make it incredibly difficult to succeed in "manager mode."

This explains why founders often step down from leadership roles as companies grow--I experienced this when my co-founder left our business. After discussing this challenge with dozens of successful founders, CEOs and COOs, I've discovered three useful techniques to master this challenging transition.

1. Ask Leadership Questions

Let's say you own and operate a coffee shop. One day, you arrive to find that one of the letters in the sign above your store is burnt out. You quickly scramble to get it fixed and, two hours later, it's good as new.

As owner of the coffee shop, you're in founder mode. You solved the problem! You can pat yourself on the back, tell yourself how competent you are, and move on.

But what if you're the owner of a chain of coffee shops? What if you run a franchise, with thousands of stores all around the world?

It can be tempting, in a moment of panic, to want to fix the broken sign. It's embarrassing and customers are seeing it.

You think, "Whose fault is this!? Someone get up there and deal with it now!"

Many entrepreneurs thrive on solving problems. As Steve Sisler once told me, "You're so in the zone when you're solving problems, you create more problems just to be at your best."

This mindset is not healthy in a larger organization.

Instead, you can ask yourself one simple question: What system can we put in place so that no letters remain out on any sign, at any of our locations, ever again?

Solving the problem in front of you is important, but it's much more impactful to create a self-correcting system because you won't always be the one standing in front of the coffee shop.

Instead of being frustrated at the current situation, take it as a gift. A problem that gets to you is a notification that your systems aren't handling things adequately. Identify why, and next time, the problem will be solved before you even hear about it.

2. Know How Much to Help

When a team member embarks on a new project, I'm often torn between micro-managing or (if I trust them enough) "under-managing" and leaving them alone to deliver.

Neither technique is very effective. Cameron Herold suggests a different approach.

For each situation, evaluate the person doing the task from two perspectives, measured on a scale from 0-2:

  1. How competent are they in the skills needed? 0, 1 or 2
  2. How interested are they in the task at hand? 0, 1 or 2

Add the resulting numbers, and plug the score into the following framework:

  • 0 - Find someone else to do the job.
  • 1 - Tell them exactly what to do, and supervise as they do it.
  • 2 - Create a detailed plan with them, and have them execute it.
  • 3 - Have them create a detailed plan, and verify it before they start.
  • 4 - Give them an end goal and tell them to ask you for help if they need it.

It's not necessary to follow this system rigidly, but gauging a person's competence lets me consciously decide how involved I should be, rather than trusting my (wildly inaccurate) gut.

3. Change Your Definition of a Successful Day

The first two techniques I've given are tactical; the third is more personal.

Entrepreneurs tend to define themselves by the problems they solve. The more we get done, the better we feel. However, when managing others begins to occupy more of your time, and you stop getting as many small things done, it's easy to feel unproductive.

Here's what you have to understand: When you were the only employee, your personal success was the company's success. Now that your company is the combined vision of many people, it's bigger than you.

You can only define success in terms of what's best for the company, not for you.

Is your goal to lead a thriving organization? Successfully transitioning from founder mode to manager mode--from making to managing--requires a trade-off between doing your own work and supporting others. It represents a crucial change in the way you see and evaluate yourself.

When you succeed in making this transition, your company will take its next step.

Published on: Apr 14, 2017