After doing in product management over the last 20,000+ office hours, I still find there are some things that are extremely difficult to do consistently well as a software product management leader.
So this post is for all of you hot shot PM's a few years out of b-school who wonder what things might slow down your career progression once you've nailed the fundementals. (Many of these might be applicable for leaders outside of product management as well.)
Below are five tough challenges and some color on why I think they're hard. In the future, I'll probably do some posts on lessons I've learned and potential approaches worth considering for each of these areas. Feel free to share thoughts and advice in the comments. I need all the help I can get ;-)
1. Hiring
Everyone knows the most important thing in any business is hiring great people. Pulling that off is at least 1/2 of my job. Here are some reasons building out a world-class team is a pain in the butt.
A lot of good people you want to hire to work for you would love to have your job (which is a good thing). They're usually kicking butt wherever they are, have a long track record, and solid credentials -- which is why you're recruiting them in the first place. Unfortunately, many of those same A candidates find anything less (working for you versus being you) beneath them even if their current job is less challenging than the one you're offering. That's not a dig on them, it just makes it hard since you ideally want someone who's ambitious but also fired up to do the job for which you're hiring today.
Unless you're recruiting for the company du jour, the candidates you want may not know about your firm or at least the opportunity you're trying to fill so you may not be interviewing the right people. Let's face it, there's only a few hot companies in tech each year. A few years ago it might have been Myspace, Plaxo, and Yahoo. Then it might have been Google, Facebook, and Zynga. Next year, it will be a whole new crop. If you're like 99.9% of hiring managers, you're not from one of the two or three "it" companies of the year (of course we all believe we're the next one) so you have to hunt versus gather.
Most people are not a good fit and to make matters worse, the interviewing process is like weather prediction. It's better than guessing but wrong enough that it can feel like that. Case interviews, behavioral interviews, reference checks, etc. are most good at evaluating a candidates interviewing and personal marketing skills. Trying to figure out how someone will actually grow long term in your Company versus talk about performing may be akin to picking stocks -- shades of improvement over random. To be fair, it's a bit more achievable to pick people who can do the job you're hiring for today, it's the growth ceiling that's harder to forecast.