Having Career Conversations

“What’s your 3-5 year plan?  Where do you see yourself in a few years?  What do you want to accomplish?”  Unless you’re in a massively trusting setting (e.g. a spouse or best friend), who wants to answer these kinds of questions?  You might feel put on the spot.  You might feel ashamed at not having an answer or that the answer might somehow be graded.  Am I ambitious enough?  Am I humble enough?  Is it ok to say “If it were open I’d like to have your job”?  Is it ok to say I want to start my own business even though that may imply leaving the company?  Stumbling for an answer you might mutter a platitude such as “I see myself seeking gradually increasing levels of responsibility while maximizing my positive impact on the dynamics of the business...” (zzzz)  So on the receiving end, we see these conversations as challenging.  When we ask these questions of those that we mentor or manage is it any wonder that they don’t always go so well?

What is the desired outcome of exploratory discussions related to someone’s career development?  A good outcome should (eventually) include:

  • Goal(s)
  • An understanding of the motivations that underlie the goal(s)

I have often found that it is tempting but dangerous to focus only on #1.  “I want to be a Tech Lead within 5 years”.  “Check - we’re done!  That was easy.  Great discussion.”  The problem is that we don’t know what is motivating the goal.  It can be a tricky a combination of such factors as:

  • Desire to influence
  • Desire for authority
  • Desire for prestige / acknowledgement / appreciation / status
  • Desire for growth & mastery
  • Desire for autonomy
  • Desire to do something meaningful
  • Compensation
  • Guessing (just pick the next rung on the ladder!)  :-)

Picking the next rung on the ladder may work fine for a time, especially if one is new to the ecosystem.  Do good work, enjoy it, get more responsibility and iterate.  But the algorithm may eventually break down and may take some time, pain and mistakes before the realization that it’s time to chart a new course.  Understanding what lies beneath our goals affords us the option of making more strategic choices.

But how do we get the desired outcome of goals and motivations?  If it were easy we’d all download the app and be done with it.  But it’s not easy and what works for one mentor/mentee combination might not work for the next.  Nevertheless there are some essential ingredients the absence of which will make for a bad meal:

  • The mentee must trust the mentor. The mentee has to have confidence that the mentor will not use the information against them or push them into a path that is not necessarily in their best interest.  Such trust takes time and patience to build.
  • The mentor must trust the mentee to some degree. The mentor has to have the confidence to brainstorm, share anecdotes and be frank in discussions.  And as noted above trust takes time.
  • There must be mutual agreement on how discussions will be treated with respect to confidentiality.  For example, the mentee’s manager will have limits on what can be kept fully confidential whereas a more informal mentor might not.
  • Trust facilitates openness and honesty.  Add in some hard work and there’s a very good chance that the process will yield fruit.

But what is “the process” and how do we go about this concretely?  There is no one right way to do this and the best process will likely be a function of the mentor/mentee combination as well as cultural and organizational dynamics.  And we won’t employ the “best process” because we’re human and will make mistakes.  We will learn from trial and error.  What’s most important is that we learn and consider career coaching to be a foundational part of our job.

Some concrete suggestions to consider:

  • Focus first on building mutual trust.  The first step in this is forming a relationship which will create opportunities for trust to be built up incrementally.
  • Try to be explicit about expectations up front including roles, logistics, level of confidentiality, etc.
  • One way to build trust is to be vulnerable. Share personal anecdotes especially those that are embarrassing and induce a good belly laugh. It sends the message that we’re all human and make mistakes.
  • Be mindful of other things that build trust like keeping your commitments and apologizing when you make a mistake.
  • Accept that there are limits to trust that may be specific to the mentee and beyond your control.
  • Accept that there are limits to trust based on cultural and organizational factors. For example, the mentee’s manager should always help with career coaching. But some people might need additional mentor(s) outside their reporting chain to feel completely comfortable.  It is perfectly normal for a mentee to seek multiple mentors.
  • Try to remove any shame or embarrassment attached to having lofty financial goals. Such goals are often tied up with a sense of safety, well-being, supporting a family or earning enough money to fulfill a lifelong dream.  In addition, compensation growth can be important in order to feel valued and appreciated.  To some it is also a concrete measurement of growth.
  • Try to remove any shame or embarrassment attached to having career goals that would be best fulfilled in a different part of the organization or outside the organization altogether.
  • Try to remove any shame or embarrassment attached to being ambitious.  What if they want your job?  Or your boss’s job?  Ask the mentee the following question: “Imagine everyone in the company (except you) won the lottery and on the same day decided to resign to spend time with their family and friends.  Whose job would you want and why?  Whose job wouldn’t you want and why?”
  • If they can answer the question above, ask what they think the job would entail.  This can help illuminate whether they’re reading the organization accurately.
  • When trying to get to underlying motivations keep trying to get to “why” (perhaps in a subtle way) until you hit bedrock.  Bedrock is not “I want to be a Tech Lead” but things like “I love working on the hardest problems because it keeps me from getting bored” or “I love helping people”.  Bedrock statements tend to be about our core needs, beliefs or interests.  They’re often very simple.  They don’t tend to be industry-specific or job-specific and they don’t change overnight.
  • Try to tease out desires for influence and desires for authority.  They are not always mutually exclusive.  Some combinations can be rooted in a desire for impact.  Other combinations can be rooted in a desire for control.
  • Try to uncover passions.  The mentee may or may not be able to connect their work back to their passions.  If someone can’t identify their passions, observe their tone when they talk about different things in relaxed or social settings.  People tend to get excited about or want to talk about things that tie back to their passions.  Passions are often driven from values and purpose.
  • When trying to uncover passions, point out the fact that doing so is a win-win if you’re their manager.  “If we can get you working on something you're passionate about, I can be more effective as a manager.”
  • Look for the overlap between interests (passions are basically strong interests), strengths and the needs of the company - this is the sweet spot for growth within the company.  But don’t forget to allow for the possibility that their interests may be best served outside the company.
  • Refrain from judging the fitness of their interests or goals.
  • Don’t advise unless explicitly asked to and even then consider whether you should.  Be transparent that you’re trying to refrain from advice.  (This is very difficult for those of us who love solving problems!)  Listen intently, play things back, confirm things, ask provocative questions, expose underlying assumptions, etc.  Listen much more than you speak.  Generally you are trying to help them come to their own conclusions, not reach conclusions on their behalf.
  • Integrate career discussions into daily work over time.  If you are their manager, seek assignments and opportunities for the mentee that reflect your support of these goals.  Make sure the mentee sees that you understand their career goals and are mindful of them.
  • Experiment and leave room for error.  They may come to and act on a conclusion that turns out to be wrong.  For example if someone wants to be a tech lead they might try to lead a small project effort.  After leading that effort they might reach the conclusion that they were way off!  Perhaps they like owning a slice of functionality as a senior developer but trying to influence others without authority is not their cup of tea.
  • Talk to others that mentor and manage people.  Share ideas and experiences with one another.  Write them down.  Contribute to the collective wisdom.
  • Be patient and persistent.  This is not a single conversation.  Rather it’s a conversational theme that you’ll have to chip away at over time and it may involve receiving and passing the torch to other mentors.  Don’t think days or weeks.  Think months or years.

Wow!  That sounds like a lot of work.  Why are we doing this again?  Because great people will be nurtured or will find new homes.  Because career coaching is an essential component of engaging the best and brightest.  And because the quality of its people is the foundation of an organization's success.