When I’m managing or mentoring somebody, this is one of my favorite questions.  It’s a good way to crawl into their heads a bit, understand their motivations, and figure out how I can help them.  It’s also not a bad question to ask yourself!

Framing

There are different ways to approach the answer – you might base it on:

• A particular person’s abilities: code like Guy Steele, move an audience like Meryl Streep, or paint like Raphael.
• A particular job: be the VP of your division, the CEO of a Fortune 500 company, or the founder of a growing startup.
• An achievement:  win an Olympic gold medal in swimming, design a piece of software that millions of people adopt, or take a company public.
• A state of being: be crazy passionate about your job, feel that you are living in perfect alignment with your principles, or devote your life to serving the community.

How somebody chooses to answer will tell you a lot about their values, ambitions, and self-image.  Be careful about guiding them too much .. we’re talking about their dreams, not yours.

Cheerleader or Critic?

In doing this exercise with many people, it’s usually at least imaginable that they might achieve their ambitions with hard work and some (or a lot) of luck.  However, now and then somebody will come up with a goal where you have to struggle a bit to keep a straight face.  Often it’s about personality and passion – if you are impatient and can’t stay focused on your own, writing novels might not be your best bet.  So what do you do when someone who hates math wants a Nobel Prize in physics?

I try to be a “pragmatic cheerleader”.  I don’t want to be a dream buzzkill – most people are surrounded by plenty of those already.  But I also don’t want to be mindlessly encouraging.  The next question often helps to get things more grounded in reality.

What Does it Take to Achieve That Goal?

Dreaming big is great, but you have to break down the goal and figure out what it takes to achieve it.  One approach I like: if the person wants to be an X, I get them to write down a description of what the absolutely perfect X would be like.  For example, when I was running a relatively large team, I came up with what I thought a perfect team leader should do .. I wrote about that here.

Often, the person doesn’t have a great answer.  They are attracted to the idea of being a CEO, but they don’t actually know much about what the day to day life of a CEO looks like.  After some discussion, we can usually rough out an outline of the skills and qualities needed, but we often agree that a key next step is to validate that list with people who actually have that role or are more familiar with it than we are.  That’s a great practical step forward on the journey.

How Do You Stack Up Today?  How Do You WANT to Stack Up?

The next thing I do is have them assess themselves against those ideal qualities or skills.  At this point, people sometimes realize that their supposed goal doesn’t actually make a lot of sense for them.  I was talking to one person who thought they wanted to be the CFO of a public company.  We talked about the skills you’d need to be a fantastic CFO, and then she thought about when in her work life she had been really happy and why.  And she realized that the things that really did make her passionate and inspired were not the key activities of that job at all.  So I think that was a helpful moment of self-revelation.

This exercise also tests self-awareness.  Sometimes, they are confident that they have some needed quality .. and you think they are wrong.  It’s tricky to handle this.  I tend to tread pretty lightly – the goal here is self-revelation, not a lecture on their weaknesses, which tends to bring the discussion to a halt in a hurry.

But if people have at least a basic level of clue about their true nature and abilities, this exercise can have quite a profound impact.  I’ve watched people realize that they were carrying around outmoded ideals foisted on them by authority figures from their youth, and realize that they have an inspiring path open to them in a quite different direction.  That’s what you hope for – an opportunity to enable somebody to achieve a profound moment of self-discovery.

How Does One Actually Get That Job?

Next, I like to consider how people actually get the job or the opportunity to achieve the goal in question.  If it is a well-defined role, then the answer is usually straight-forward, but many people don’t think about it very practically.  I’ve repeatedly asked, “how do you become a VP” (or whatever).  People go on about a demonstrated track record, a well rounded set of skills, and all sorts of worthy things … but none of those are the real answer.

The actual answer is, “somebody who hires VPs chooses you”!  Now why would they do that?  All these ideas about skills and roundedness are fine, but often the true reason is that the hiring manager has confidence in you to do a great job and trusts you.  They’ll almost always pick somebody with strong skills, whom they deeply trust, over an unknown with a potentially stronger resume but who might be a whacko.  And they trust you because they know you over a long period of time, and have watched how you handle many different situations.  So one of the things that might be necessary to achieve your goal is to deeply commit to a particular team or company for an extended period of time, rather than bouncing around all the time.

Alternatively, the goal might be something that has to be created rather than granted – becoming the CEO of a new startup is self-elected (!).  But they need to have enough money to survive without an income and perhaps to fund the company for a while.  They may need a network of people they can hire.  And so forth.  Pretty much any ambitious goal will require something in order to open up the opportunity.

What Are Your Next Steps?

Now they have identified the goal, what it takes to get that opportunity, what they need to be successful, and where they stand now.  For each skill or ability where they aren’t already strong and experienced, I’ll brainstorm with them about a specific action that will develop it.  For example,  they can often build up skills that aren’t a direct part of their job by volunteering for extra projects – what I like to call “hobbies”.  I’ve learned a ton from hobbies – helping to organize and run a large developer conference, participating in working groups considering radical new directions to take the team, teaching classes, etc.  None of those had much to do with my core job, but I practiced new skills, learned about new areas, met really cool people .. and had a lot of fun.

The goal is to finish the discussion by identifying very concrete steps that will build the skills they need to achieve their dreams.  And if you have an ongoing relationship, hold them to it.  If you can really help somebody achieve their dreams, that is one of the best feelings in the world!