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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. 

You can be awesome at strategy, insights, requirements, and tradeoffs and still be collosal failure if you can't get the entire organization aligned culturally, philosophically, and personally.

By virtue of their chosen profession and the values of their own teams, most functional groups are not naturally aligned.  Some groups feel passionately about process and comraderie, others are most passionate about financial performance, and others are passionate about customer satisfaction.  In theory, those are not mutually exclusive but invariably, choices about prioritization, resource allocation, and success metrics show the gaps between these overlapping world views.

Not only are functional folks often wired different and colored by their personal experience, they are often compensated and promoted based on non-aligned goals (if only everyone were paid completely in equity).  Some are bonused on sales, some on media mentions, some on hires, some on customer satisfaction, some on absolute usage, etc.  This isn't necessarily because their employer is neurotic but often because it often makes sense to compensate people based on the levers they have most control over and equity values are hard to move quarter to quarter (some would say year to year) no matter how good an individual really is.

Everyone isn't at work for the same reasons.  Some are looking to prove something.  Some are passionate about the customer problem.  Some are looking to pay their kids' college tuition.  Then there are some who are not the right fit but you don't know it.  At any rate, people's personal situations and arc of life make it such that unless we're all being invaded by the British, we're a motley crew with divergent priorities and motivations in life that impacts how we are at the office.

3. Personal Scale

You may have kicked butt as an IC or manager or group manager but getting more enterprise impact can be increasingly challenging as you attempt to get closer to running the whole show.

One challenge is you have less and less direct control over decisions, work product, conversations etc.  At one extreme, if you've got the juice, you can be a great IC.  If you can find people with the juice, you can be a solid manager.  Getting beyond that introduces increasing degrees of challenge such as cross-group cultural issues (see #2 above), increasing levels of high beta decisions (all the easy ones get made before they reach you), and further dillution of your individual activities from the trenches (i.e. layers of people between you and the people who do stuff).

This is where work-life balance also takes a hit since Type A people tend to compensate for this by working harder, "rolling up our sleaves" more, and looking for blind spots in every direction, color, and shape.  This is usually a good thing (that's why your boss likes you) but at some point, it's a bit like driving a sports car at high speeds constantly where your mind, body, and soul get taxed to a point where the enterprise will take as much as you can give it and always want more.  Unlike your earlier IC jobs, you will never be in full control.  You need to accept that and try to get your 8 hours of sleep and be present for your family if you want to be a player for the long haul.

4. Winning Products

Picking winning product ideas is even harder than hiring.  Predicting what customers will want, need, pay for, use, recommend, generate growing revenue, retain competitive advantage, and stick with is no walk in the park.  And let's not forget making sure you can build such a thing better than your competitors is kind of hard as well.   Most of us can come up with ideas that meet some of those criteria but it's hard to nail all of them.

If picking, designing, building, launching, evolving, and scaling winning products was easy, Microsoft would have had a kick ass phone back in 2005, Google would have figured out social, and Amazon would have figured out mobile advertising.  I'm sure all of those places have been trying to do that kind of thing for many years now but somehow others who had similar talent, money, and time nailed it (at least social and mobile). 

To make matters more challenging, unless you have a monopoly or close to one, you usually don't have enough resources to place as many bets as you'd like to place.  We've all seen the academic articles about innovation pipelines and there's hundreds of dots on the left hand side of the pipeline and a few emerge as winning products.  In reality, most of us work at places where we can only flare so much beyond brainstorming and soon after we need to figure out which few prototypes to build and even fewer alphas to ship.  So as much as we'd like to load up with buck shot in the morning sun, most of us are dealing with bolt-action rifles in the moonlight.

5. Team bar raising

Hiring a great team is hard enough (as per #2) but growing it's capabilities beyond just adding more people is a different ball game.  If you're doing your job, your company is probably growing and going after increasingly competitive, demanding, and/or growing markets. By definition, for you to be as successful as you were last year, your team needs to improve at at least the same rate that your company's goals are scaling.  I.e., last year's A team can't just rinse and repeat next year if the Company has big growth ambitions. Your team needs to be better, smarter, and faster. 

Surely, adding more varsity players is critical to raising the team's capacity and mojo.  However, raising the game of every existing team player (yourself included) is the fastest way to sustainably increase output, especially as the team gets big.  Figuring out how to unlock unrealized potential in people and helping them get there is a huge challenge for varsity teams since everyone should already be performing at a high level.  Inevitably, you may determine that some people are capable of a lot more than you thought (awesome outcome) but you may also find some people are peaking.  In that latter case, knowing for sure when you've reached that point, making sure you've been fair and transparent and supportive to disprove this assumption, and making a call on if that's an ok long-term proposition can really seperate leaders from managers.

Summary

 If you're in a PM role and wondering if you'll be as challenged in a few years as you were a few years ago, I think the answer is yes.  

-Tom 

Hiring top talent is hard.  Check out this video to see the lengths people will go to attract the interest of great product managers.