Success in delegating depends in a large degree on a leader’s ability to manage milestones. Recall that in my earlier piece on “Work Less, Create More Value – The Art of Delegating” I suggested six levels of delegation:

    1. Do well yourself
    2. Do yourself, but just well enough
    3. Delegate and supervise
    4. Delegate and trust
    5. Do later
    6. Do never

Milestone management is a critical skill when it comes to level three: delegate and supervise. Different people in different situations require different levels of supervision. In every case milestones help. The difference comes in leash management – how long you’re going to let those you are supervising go between milestone check-ins. The more confidence you have in their ability to execute, the more leash you can give them.

Here’s an example from The New Leader’s 100-Day Action Plan:

Imagine that you set a goal of getting from London to Paris in 5.5 hours. Now imagine that you choose to drive.

You set off on your journey.

It takes you 45 minutes to get from Central London to the outskirts of London.

Thirty minutes after that, you wonder: “How’s the trip going so far?”

You have no clue.

You might be on track. You might be behind schedule. But it’s early in the trip so you probably think that you can make up time later if you need to. So you’re not worried.

If, on the other hand, you had set the following milestones, you would be thinking differently:

  • Central London to outskirts of London: 30 minutes.
  • Outskirts of London to Folkestone: 70 minutes.
  • Channel Crossing: load: 20 minutes; cross: 20 minutes; unload: 20 minutes.
  • Calais to Paris: 3 hours.

If you had set a milestone of getting to the outskirts of London in 30 minutes and it took you 45 minutes, you would know you were behind schedule. Knowing that you were behind schedule, you could then take action on alternative options. The milestone would make you immediately aware of the need to adjust to still reach your overall goal.

The people you supervise are going to miss milestones. It is not necessary for them to hit all their milestones. What is essential is that you and your team have put in place a mechanism to identify reasonable milestones with checkpoints that allow you to anticipate and adjust along the way.

Back to our London to Paris example. If you have a lot of confidence in the person doing the driving, you might have only one checkpoint – at the channel crossing. If you have less confidence, you might check in at each of the milestones.

In team management settings, some senior leadership teams do milestone check-ins quarterly and some monthly. Middle management teams often do weekly milestone check-ins. Some front line managers have daily milestone check-ins. And crisis managers check-in several times each day as they work with their teams to make sense of ever-evolving situations together.

Remember, of course, that milestones don’t get delivered by themselves. As part of managing milestones, make sure someone – ideally some one individual – has accountability for delivery. Don’t expect anything to happen unless there’s a commitment to what’s going to get done, by when, by whom, with what resources and support. Saying all are responsible is frighteningly close to saying no one is responsible.

Back to the point about level three delegation. If you don’t delegate accountability to a specific person, you’re still accountable. Unfortunately, it’s not enough for you to delegate. The person being delegated to must accept accountability.

There is no one right timing and no one right process. However, it is abundantly clear that knowing what’s going on earlier rather than later is often the difference between delegating and supervising well and a failure to hit goals.

Put milestones in place.

Put a process in place to manage those milestones as a team.

Shorten or lengthen the time between checkpoints based on how things are going.