For nearly four decades Ken Nolan has been invited into rooms that he had no business being in.

It started before he had graduated college when he decided to apply for an engineering job that required a professional license and ten years of experience, and he got the job.

It continued over the next three decades while he worked for two successive utility executives that valued judgement over experience.  Eventually he obtained a reputation as “the fixer” and  “ Barb’s Bulldog” in reference to his mentor and Burlington Electric Department General Manager Barb Grimes.  Barb and Ken’s former manager, Bill Gallagher, did not hesitate to put Ken in situations where he had responsibility but no authority and was often dealing with counterparts residing high above his position in the org. chart.

Those experiences led a 28-year old Ken to seek elected office in his hometown of Milton, Vermont where he ended up serving 15-years on the Selectboard, 10-years as Chair, and at one point chaired the Selectboard while simultaneously representing Milton on three county boards.  That involvement earned him the unofficial moniker “Mayor of Milton”.

Ken often found himself representing organizations or stakeholders with fewer resources, less influence, or smaller constituencies than the people across the table and routinely found himself looking for the leverage points in discussions that would move the needle in his side’s favor.  He slowly built the skills, and reputation, for identifying issues others were missing and changing the trajectory of discussions.

Eventually, the CEO of one of the company’s where Ken sits on the board mentioned casually over lunch that he had started having his staff run presentations through “The Ken Test” before board meetings in an attempt to anticipate questions/comments Ken would have.  Completely independently one of the managers working with Ken mentioned that his staff had a “Ken Test” before bringing issues to him for discussion.  Both comments were meant tongue in cheek, but they struck a chord.  Obviously, others were seeing a pattern in how Ken reacted to their work, and were trying to mimic his thinking.

After decades of similar experiences Ken has recently begun reflecting on those “Ken Test” comments and his learning from the many unusual situations he’s encountered.  He started writing brief essays and case studies as training materials for his staff, but quickly realized those documents represented a way of thinking, or framework, that is broadly applicable across a wide range of organizations.

The essays and case studies collected here are not about utilities, local government, or public policy, although many of the stories come from those worlds. They are about strategic judgment: understanding what problem is actually being solved, what assumptions are being accepted, who bears the risk, and what questions need to be asked before important decisions are made.