I cannot claim to be excellent at picking great jobs for myself; in fact, my track record is pretty poor.  With the benefit of 20/20 hindsight and from my mid-career perch, I’d say that I’ve made the right choice 4 out of the 7 full-time jobs I’ve held since college.  Of course, it’s hard to say if things would have been worse had I gone elsewhere, and the criteria for ‘right’ is a little fuzzy, but generally consists of:  1) my overall happiness, 2) my productivity, 3) my learning/growth, and 4) the quality of the opportunities I got afterwards.

Not knowing my spotty track record, many unwitting folks — former colleagues, people in my network, and students from my alma maters — reach out to me for career advice and guidance on job selection.  So I’m attempting here to come up with a methodology for job selection.  Consider using this at your own peril!!  😏

Method #1:  What You Want v. What You Get

For major decisions in my life, I’ve tended to use what I’ll call the What I Want v. What I Get model for evaluating multiple options.  It starts with a series of questions:

• For my next job, what are the things I want to have?  I typically dive deeply into the following areas:
  • Nature of the role
  • Characteristics of the company
  • Business stability and viability
  • People and relationships (esp. Manager traits)
  • Financial considerations
  • Future opportunities
• Rate each of these conditions from 1-5 in terms of importance to me.  5=deal-breaker; 1= important enough to be considered in aggregate with other characteristics
• Considering each opportunity, rate from 1-5 how close it is to satisfying my conditions.  5=is beyond what I want; 4=satisfies what I want; 1=far from what I want

With these inputs, I run a series of calculations that weigh each opportunity against the conditions I want.  This simple model spits out a sum that shows which job, in aggregate, satisfies my conditions the best.  Here is a fake example to illustrate this:

		How well are these conditions met?
What I want	Importance to me	Opportunity 1	Opportunity 2
Full autonomy in running the People team	5	4	5
Strong incumbent team members	2	5	1
Commute that is <20 minutes	3	1	4
Free lunch and snacks	4	1	5
High salary	5	4	3
Unlimited PTO	2	5	5
	Weighted sum	67	84

The challenge with this approach is that it appears super-objective, but relies tremendously on self-awareness and being very truthful with yourself about what matters, even if what matters is something you don’t like mattering.  

The ultimate answer that this model spits out isn’t the important outcome — it’s how you feel when you see the ultimate answer being spat out.  If you are happy with it, it’s probably the right answer.  If your mind jumps to, “Wait a minute, what if I tweak X…?” then it probably isn’t the right answer.  

Despite my attempts at being super analytical and data-driven, I believe that my heart is wiser than my head when it comes to making the most difficult decisions.  And when I think about those 3 wrong job choices, they all involved me convincing myself that I was picking the best choice given the data presented.

Method #2:  Magnifying the Unknowns

Here’s another process that I’m just making up as I’m typing.  Basically, I’m realizing that the biggest blindspots for me when making a decision among several options is that I underweight the unknowns.  I fall into the same trap that we all do when confronting something exciting and new — we fill in the information gaps with endless (but mostly positive) possibilities.  Selection bias also doesn’t help; I tend to hear what I want to hear and, rather than asking clarifying questions, I make assumptions about what is meant.

Unfortunately, those unknowns are often the very things that determine our day-to-day job satisfaction — what our relationship with our manager is like; how well we’ll get along with the incumbent team; the culture of the company.

So here is an idea that I’m drawing from our ideal recruiting process:  after several rounds of interviews with a candidate, we compile all of the unknowns and potentially negative views, and use these to grill references for data that supports or refutes.  Remaining unknowns after the reference checks are considered carefully through several scenarios, and we consider whether they may be deal-breakers.

Could I do the same with job selection?  

First, I would basically go through the same steps as in Method #1:  list out conditions, weigh them, and evaluate each opportunity across these traits.  

Next, I would rate my level of certainty about my evaluation, likely from 1 to 5.  For things that are cut-and-dry like “Free lunch and snacks” and “salary” and “commute”, I can give a 5 and separate these traits out as ‘known knowns’.  For things that  are not, such as “strong incumbent team members” or “full autonomy”, I would rate much lower and group them into traits that are ‘known unknowns’.  (See exhibit below.)

Then I’d examine what my top conditions are, and how they relate to areas of uncertainty.  Any condition that is a 4-5 in importance that has a “certainty score” of <4, I should create a set of open-ended questions and get them answered before making any decisions.  I can update my scores after these discussions, and hopefully end up making a much more informed choice.  

		Opportunity 1		Opportunity 2
What I want	Importance to me	How well are these conditions met?	Certainty score	How well are these conditions met?	Certainty score
Full autonomy in running the People team	5	4	2	5	3
Trust-based relationship with manager	5	4	2	3	3
Strong incumbent team members	2	5	3	1	4
Commute that is <20 minutes	3	1	5	4	5
Free lunch and snacks	4	1	5	5	5
High salary	5	4	5	3	5
Unlimited PTO	2	5	5	5	5
	Wgtd knowns	37		57
	Wgtd unknowns	50		42

This is definitely not a tried-and-true method.  But it does help force me to think about my conviction about a particular opportunity, and to probe to learn more.