The New Leader’s Journal: Milestone update I

Well, that was an ugly meeting. No one circulated their updates in advance. People didn’t follow the meeting format.  It ended up being a free-flowing conversation instead of an update.  I thought I had set the direction in advance.  But they weren’t seeing things the way I did.

Part of me expected this to happen because I know it generally takes a couple of milestone update meetings to establish a rhythm. I know we have to get through these bad meetings early on to get to the good ones later and consistently moving forward, but it  did seem like a waste of time.

We did a good job at the end agreeing on what was particularly valuable about the meeting.  (And there were some valuable conversations.)  Then we agreed what would make these meetings even better going forward.  Step-by-step.

Reflections

Milestone management is a process, not a one-time event.  In some ways, the 100-day action plans are really about jump-starting the strategic, operational, and organizational processes.  Milestone management is a core operational process.  Hugely valuable.  Requires persistence to get operating right.

Had a good conversation with my boss, Jack, earlier this week.  I’m so glad I took him through the plan early on and have been keeping him up to date with how it’s working.  He definitely bought into the “go slow at first” approach, but is even more pleased now that we’re moving things forward.  He was particularly pleased with the output from our imperative workshop and heard good things from some of the participants.


The New Leader’s Journal is a fictional exercise illustrating the prescriptions and tools in the 3rd edition of The New Leader’s 100-Day Action PlanClick here to request an executive summary of the book.  Click here to order a copy.

Read More Articles

Argentina flag with the body shape of the country in soccer field.
Strategic Adaptation in Leadership: Lessons from the Argentina–England World Cup Semi-Final

The Argentina–England World Cup semi-final was not just a game; it was a live case study in how leaders deploy strategy and tactics—and what happens when they fail to adjust…

Read Article
Confident executive standing on a modern stage, delivering a presentation
Act Like You’re Already Successful to Jump-Start Success

Success doesn’t start when you “make it.” It starts when you behave like you already have. The best leaders - whether they are taking on a new CEO role, launching…

Read Article
Picture of the Allies Normandy World War II amphibious assault D‑Day
Why Leaders Get the Followers and Decisions They Deserve

Leaders don’t simply get the followers they deserve; they get the decisions they design for. When leaders understand the different ways people create value - artistically, scientifically, and interpersonally -…

Read Article
Primegenesis Operational Leadership
The Underappreciated Power of Operational Leadership

Operational leadership is the undervalued fulcrum between theory and reality. It is where strategy stops living in slide decks, where culture becomes observable behavior, and where tactics gain the coherence…

Read Article
NBA Champions game
The Stockdale Paradox: Preparing Your Leadership Team for Adversity

Down 29 points in the third quarter of Game 4 of the 2026 NBA Finals, the New York Knicks did something that had never been done in Finals history. With…

Read Article
Building Accountability in High-Performing Teams: From Slogan to Commitment

Turning empowerment from a slogan into a mutual agreement and engagement from an attitude into observable commitment  Almost every leader says they want empowered people. Almost every employee says they…

Read Article