Tag Archives: Heartbreak Hill

Ryan Hall and Greg Mutai on Heartbreak Hill

Catching the Leaders on Heartbreak Hill: 16 Topics for the New Exec

Sixty days into my transition as an exec at Aternity, I feel like a runner just behind, but in sight of the lead pack in a marathon.  Just like the chaser needs to push hard to catch up to the leaders, I’ve been focused on accelerating my ability to add value as a member of the leadership team.

tf90d-book-coverIn “The First 90 Days,” author Michael Watkins lays out an approach to structured learning which helps the new executive determine where to focus their effort.   At this point, I’m about two-thirds of the way through that timeline, and I’m feeling confident about my progress.

With the 118th running of the Boston Marathon this week, it struck me that the two-thirds point of the marathon course is in the middle of the four Newton hills, which culminate between miles 20 and 21 at Heartbreak Hill.  This section of the course is often where leaders are caught.

Boston Marathon Route
Boston Marathon Route

In fact, Heartbreak Hill is so named because of the dramatic finish of the 1936 Boston Marathon.   Defending champion, John Kelley, whose statue now stands at mile 19, overtook Ellison “Tarzan” Brown and gave him a consolatory pat on the shoulder.  This inspired Brown to overtake Kelley and go on to win, thus breaking Kelley’s heart.  Kelley statue before Heartbreak Hill

The new exec shares a similar goal as the chaser of the lead pack at Boston.   Make your move around the two-thirds point, so you catch up to the lead team by Heartbreak Hill.   Just like there are 16 miles to the start of the Newton Hills, there are 16 key points for the new exec to tackle, in order to achieve this goal.

Business Topics

Target market

  1. Market size and growth rates.  Company market share and trends.
  2. Target customer profile and buyer personas.
  3. Industry analyst coverage of the market – size, trends, competitive analysis.

Current customer base and growth  

4.  Revenue, customer count, and average sales price, by customer market segment.
5.  Past and projected growth rates.

Product development

6.  Product revenue and growth, past and projected.

7.  Road maps, key capabilities and competitive advantages.

8.  Access to product demos.


9.  Current and future competitors, based on planned road map.  Their revenue, growth, target customers and buyers.

10.  Strengths and weaknesses.

Partnership ecosystem

11.  Partner categories and leading partners within them.

12.  Business plans and key metrics for measuring success.

Culture Topics

Cultural topics are equally as important as business topics, especially at a small company.

Decision making

12.  Is the culture driven by consensus, top-down management style, or something in between.


13.  What methods of communication are used?  Social media guidelines and key influencers.

Meeting cadence

14.  Regular management team meetings and functional meetings.

Dress code

15.  How formal is the company dress code?

Work practices

16.  Working from home, typical times for arriving and leaving the office.    Social activities like group lunches, happy hours, etc.

What’s missing from my list?  How have you made your move at Heartbreak Hill?  I’m interested to hear about similar or different experiences.   On to Boylston Street!

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