The most effective senior leaders pay attention to strategy, organization and operations, driving what to do and why, who’s going to do it, and how to get it done. While the first two are essential, they are useless without the third. High performing organizations rely on a strong milestone management process to ensure things get done when they are supposed to get done. However, for a senior leader, “pay attention” is not the same as “manage.”

Consider the difference between leaders and managers. The best leaders spend their time inspiring and enabling others to do their absolute best together to realize a meaningful and rewarding shared purpose. The strongest managers spend their time directing and coordinating the actions of others.

As described in my earlier article on Managing Milestones – The Key to Level Three Delegation, milestone management is a critical tool in delegating accountability for delivery. Don’t expect anything to happen unless there’s a commitment by an individual to what’s going to get done, by when, by whom, with what resources and support.

Get it? Milestone management is a management exercise, not a leadership exercise.

On the one hand, lower-level managers toggle between leading and managing frequently. But at senior levels, so many people are watching everything leaders do and say, toggling runs the risk of sending mixed messages. A better approach is for senior leaders to delegate management of the milestone process to someone else.

Milestone Process

The core of a milestone process is agreeing what’s going to get done by whom by when and then following up to make sure that gets done.

We have a relatively straightforward tool for this with a neat twist. Happy to send it (free) to anyone who clicks here to ask for it. Here are the steps:


  1. Lay out the steps on the way to delivering strategic priorities with an accountable owner and date for each step.
  2. Schedule regular milestone management meetings.
  3. Prior to each meeting, each team member submits their updates and the designated person or milestone process manager compiles and circulates updated milestone tracking in advance of the meeting.
  4. In the first part of the meeting, each team member gives a five-minute update in the following format: most important wins, most important learnings, areas where they need help.
  5. At the mid-point of the meeting, the manager orders topics for discussion in order of priority.
  6. In the second part of the meeting, the group discusses priority topics in order, spending as much time as necessary on each topic.
  7. The remaining topics are deferred to the next milestones management meeting or a separate meeting. Key items are updated and communicated.


A couple of tips:

Anticipation is the key, At first, milestones will go from “on track” to “oops we missed” with no steps in between. You’ll know the process is working well when people are surfacing areas they “might miss” if they don’t get help from others. Focus your love and attention on these “might miss” items to get the team to help. It will make people feel good about surfacing issues and will encourage them to bring future issues to the group for help.

Banish the first-come, first-served mentality. This milestone process is easy to deploy for disciplined people and teams. It is hard for less disciplined people because they want to work items first-come, first-served. Resist that. Follow the process.

Integrate across instead of managing down. The milestone meetings are great forums for making connections across groups. The further you rise in the organization, the more time you’ll spend integrating across and the less time you’ll spend managing down. Most don’t like to be tightly managed or have their decision rights compromised, but everyone appreciates improved information flows and linking projects and priorities across groups.

By letting someone else direct and coordinate the mechanics of the milestone management process, senior leaders can spend more time focused on people and content – inspiring and enabling.

Click here for a list of my Forbes articles and a summary of my book on executive onboarding: The New Leader’s 100-Day Action Plan.