Be Like Zappos’ Tony Hsieh – Answer Three Key Onboarding Due Diligence Questions

For Zappos CEO Tony Hsieh, the most important decision is where to play. He learned that playing poker. He applied it at Zappos. It’s critical for onboarding. In Hsieh’s words:

Through reading poker books and practicing by playing, I spent a lot of time learning about the best strategy to play once I was actually sitting down at a table. My big ‘ah-ha!’ moment came when I finally learned that the game started even before I sat down in a seat.

In a poker room at a casino, there are usually many different choices of tables. Each table has different stakes, different players, and different dynamics that change as the players come and go, and as players get excited, upset, or tired.

I learned that the most important decision I could make was which table to sit at. (1)

40 Percent of New Leaders Fail

40 percent of new leaders fail in their first 18 months. (2) Many of these failures are the result of choosing the wrong table and stepping on an organization, role, or personal land mine that should have been seen before accepting the job.

Three Questions Leading to the Right Table

The ability and willingness to assess and deal with risk is often a critical differentiator between success and failure. Once you’ve been offered the job—and only after you’ve successfully dealt with the only three interview questions—do in-depth due diligence to make sure it is right for you. This involves mitigating organizational, role, and personal risks by answering three questions:

  1. What is the organization’s sustainable competitive advantage? (To get at organizational risk.)
  2. Did anyone have concerns about this role; and, if so, what was done to mitigate them? (To get at role risk.)
  3. What, specifically, about me, led the organization to offer me the job? (To get at personal risk.)

Organizational Risk

When looking to mitigate organizational risk, be sure to assess risk elements across the 5Cs: Customers, Collaborators, Capabilities, Competitors and Conditions. The good news is that you probably have a significant head start on understanding many of these or you wouldn’t even have been considered for the job. But do not rely on what you think you know. Invest the effort to see what new things you can learn. As Christopher Frank and Paul Magnone describe in their book, “Drinking from the Fire Hose,” pay special attention to what surprised you. In particular, you need to understand all these in the light of the specific job you’ve been offered.

Role Risk

To mitigate role risk (internal concerns about the role), you should:

  • Find the people who had concerns.
  • Understand those concerns.
  • Understand what has changed to make those concerns go away.
  • Believe that those people will support the role (and you) going forward.

In particular, look hard at peers. In general, your new boss and subordinates will understand the role. The most likely place for there to be issues are peers who think your new job overlaps with parts of theirs.

Personal Risk

The goal in mitigating personal risk is to find out if your strengths, motivation and fit are a match for what is required to deliver the expected results. Knowing what you know, would you hire yourself for the job? If there are significant differences, probe and explore and keep the option of walking away open in your mind. Not taking a job due to lack of fit is usually one of the best career moves a leader can make.

Now What?

With those answers in hand, you can then decide if you have a low level of risk that requires no extraordinary actions, manageable risk that you’ll manage as you go, mission-crippling risk that you must resolve before going forward, or insurmountable barriers requiring you to walk away.

This is a critical part of step 1 of The New Leader’s PlaybookPosition Yourself for Success

There are several components of this including positioning yourself for a leadership role, selling before you buy, mapping and avoiding the most common land mines, uncovering hidden risks in the organization, role, and fit, and choosing the right approach for your transition type.

Click here to read about each step in the playbook

Click here for YouTube videos highlighting each step

Read More Articles

A large crowd of people seated closely together, viewed from behind, attending an event or presentation in a dimly lit venue.
The Stakeholders You’re Not Thinking About – And Why They Can Derail Your First 100 Days

Cracker Barrel made headlines when its relatively new CEO departed after less than two years in the role they were hired to transform. The reasons were complex, but one thread…

Read Article
A person holding a clipboard with a blank sheet of paper and a pen poised to write
Outcome-Based Governance: Aligning Policies, Guidelines, and Principles

Policies channel compliance. Guidelines invite contribution. Principles earn commitment. Start with how you want people to behave at work and then design your governance stack to reinforce, not inhibit that.  Three…

Read Article
Concept image of human brain made of blue and gray paint brushes
The Neuroscience of Leadership: Accelerating Growth Mindset and Enterprise Performance

Organizations’ futures depend less on what their people know today than on how fast they can learn, adapt, and execute tomorrow. Building on Carol Dweck’s Growth Mindset – the idea that abilities can be…

Read Article
A group of professionals collaborating.
Everything Communicates: Especially As and To an Executive Onboarding into a New Role

Everything communicates. Everything you say and don’t say, do and don’t do, and the order in which you say and do it sends a message. The same is true for everyone around you. As an executive onboarding into a…

Read Article
Group team working in a office.
Designing The Right Offsites for Different Leadership Levels

Offsites can be rocket fuel or expensive theater. One difference is whether you design each for the kind of leadership each level needs to provide: cultural, strategic, operational, or tactical. When you nest your offsites to fit those roles, you…

Read Article
Argentina flag with the body shape of the country in soccer field.
Strategic Adaptation in Leadership: Lessons from the Argentina–England World Cup Semi-Final

The Argentina–England World Cup semi-final was not just a game; it was a live case study in how leaders deploy strategy and tactics—and what happens when they fail to adjust…

Read Article