The Zen of Hiring and Retaining Top Talent in Silicon Valley – Part 1

Hiring talented people and letting them execute (and not leave) is the only path to success for a startup.  As I said in the “Subtraction = Growth” blogpost, bandwidth is the most critical resource of any startup.  A manager can not afford to waste even a tiny bit of it.  In my career, I hired more talented people onto my teams than I can mention, and while they have gone on to do amazing things after, I rarely lost them while I was still at a company.  Here is the management philosophy that I employed.

I started with an assumption that I learned at Boeing management training:

People want to be successful and help their employer succeed, therefore a manager’s job is to eliminate everything that might prevent that from happening.

This sounds very simple and obvious, but if you really believe it as a primary driver, it is powerful and will change the way you approach your work.  Managers should not need to motivate people, it is already in them.  Managers are hiring people that have been very successful at nearly everything they do, for their whole lives, and they want to continue that trend.  People want to help their company succeed too.  In addition to their own growth, they want to be associated with and meaningfully contribute to a winning company.  This is even more the case at startups, where a win makes you more attractive to your next startup and helps you build your career more quickly.  If a manager hires a Stanford Engineering Masters Grad, who had to get insane test scores on SAT’s as well as GRE’s and insane bachelors degree grades and insane grades in high school and probably had a million extra curricular activities that they worked hard for, and they failed on your team, does a manager really think it is their misfortunate coincidence that the first fail of this sharp successful person’s entire life was working for them?  It sounds crazy when I say it like that, doesn’t it?  And that is how it is.  Starting with this assumption is actually huge, it creates the risk free environment that allows your team to experiment and fail which will lead to winning.  Sean Ellis said at the Agile Marketing Meetup that there is no better indicator of growth than test velocity, and that is consistent with my own experience as well.

A corollary property is that if someone is not thriving, a manager created an environment that is preventing them from doing so.  Common ways managers block people, in order of likelihood, include the following:

  • Lack of success definition clarity: A manager does not clearly communicate what success looks like.  They might have talked about it, but did not reach true concurrence.  Note that it does not matter if the manager thinks they were clear about it, what matters is if the team member and manager are actually in concurrence.  Perception is reality.
  • Lack of prioritization: this is actually a version of not defining success well enough, but it is such an important one that it is worth calling out separately.  Subtracting is one of the more valuable things experience brings a manager.  So many things to do and so little time.  Prioritization is one of the things a manager should review with their team.  It is an efficient application of your experience so long as it is done from the perspective of sharing experience and understanding where the manager has failed in communicating success as opposed to micromanaging.
  • Senior Management Misalignment: A managers version of success is not aligned with other management’s version.  A manager’s team may not be sure which vision of success to achieve.  Do you make your manager happy at the risk of pissing off the CEO or will your manager be happiest if you make the CEO happy?  A manager should cringe at this question entirely.  It is the last thing you want your team worrying about.  Make sure you are aligned so that your team can Subtract this.
  • Role fit: what the company needs from a role is not what the individual provides successfully.  Either it is not enjoyable work to that individual (so they are not good at it perhaps) or perhaps it does not fit in with their career aspirations.  Either way, this is one of the reasons to sometimes hire contractors for skills which you are not 100% sure will be part of your long term strategy until you find out.  This one is most often the manager’s fault too since they hired the skill set and presumably they should know what was needed better than the person interviewing.

Some useful conversations between a manager and their team members will help identify areas where a manager is doing well and also where they are not doing as good a job as they might hope.  A manager is probably blocking team members from success no matter how hard they try, so why not treat discovery and elimination of these areas as a continuous improvement project for the manager?  You can do it as almost a scrum meeting format.

  • A manager can ask what a team member is succeeding at, and what is supporting and allowing this success?  Can we amplify and replicate these things?
  • A manager can ask what is progressing more slowly than hoped?  What is blocking or preventing it from looking like the successful things?  How can we work together to kill these, unblock these, or get them assigned somewhere else where they will be successful?

Applying this as a general framework, I was very successful hiring and retaining some really talented people.  And they strengthened their own careers immensely as well.  Not only were they forever associated with a company that grew very quickly, but they also got to take on as much as they could handle and sometimes more so, as a fast growing startups needs are insatiable.  Proof that it was good for the team is the fact that so many of my team members went on to run huge teams at very fast growing companies subsequent to our working together.  So much so that it was nearly impossible for me to rehire people at a next stop, unless they started in one of my teams very early in their careers.  In my second installment of this blog post, I will review some specific principles and ways to make the most of this kind of environment.


Paul helps companies find balance between what the user needs, the business wants and what resources allow. A keen eye for young companies with huge potential, Paul focuses on mentoring across product, engineering and marketing efforts.


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