A few months ago, I had dinner with a friend who was being asked to take a new job with a big team. At the beginning of our conversation I asked him, “You do realize you’re not ready to do this job, right?” He looked at me like he was offended. I really meant no offense at all, and thankfully he was gracious enough to listen as I explained that I was simply reflecting what I’ve learned throughout my professional life. Whether you are leading a small team for the first time or taking your first CEO role, no matter how much preparation and training you do, you’re never ready for what is coming.

My first real management role involved running the eight-person marketing team on Microsoft Excel. When I was offered the job, I was very excited because I thought it played to my strengths. I’d always considered myself a leader – in the classroom, on the tennis court, and on the job, I naturally gravitated to the role of organizing the group and making sure things got done. Lord knows I’d been selected for every “leadership experience” possible in school and had been “trained” a-plenty. And yet I must report I was a miserable leader of that Excel team…and want to officially apologize to them for the experience I put them through. Sadly, eight years later when I was asked to lead the Xbox business, I once again thought I was ready – and once again punished my team in the process.

Whether you think “leadership” is a nature or nurture characteristic (and it is almost certainly a bit of both), why is it that even those that should be well prepared usually run the ship up on the rocks before they make it out of the harbor?

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