What are some key challenges when hiring for leadership roles?

If you're looking for someone to take on a leadership role, your candidates have already accomplished some things, but it’s as if the experience that they have is not taken into account when they start the interviewing process. It always seems like you're taking the lowest common denominator and starting from the assumption that even though the person might be well-regarded outside the company, they're a nobody in this context, so they’re still going to start at the bottom. That sends the wrong message and it's disrespectful for people who've been in the field for a number of years and have already established themselves.

I had some roles come to me that seemed fantastic until I read the last two lines, where they’d list hands-on development among the duties. I'm pretty decent with Python and all the other languages used today, but that's not why you're hiring me. If you want me to do code reviews at this level, that's not going to happen. How do you expect me to do the top 95% of the work if you also want me to code and run scripts?

For my current role, I had six interviews over three days because that was one of my stipulations. I’d told them, "I'm not dealing with two months of interviews. Please get everybody at the table so we can try to cram this in." I couldn't deal with yet another assessment test or white board, so I said, "You either trust the 30 years of experience that I have in delivering or you don't, because I don't have time to be micro-analyzed. I'm not going to sit through 600 hours of interviews to see if I'm a cultural fit."