Plan for the worst, be ready for success

“Don’t seek for everything to happen as you wish it would, but rather wish that everything happens as it actually will.”


How many times have you participated in planning for a new project and it seems like people are just going through the motions? The planning session ends and people go off and do what they have always done, the way they have always done it. Resulting in unclear goals, miscommunication, frustrated teams and unhappy customers.

With new ways of working, these types of issues should no longer exist, right?

For example, in an agile project, you should be set up for success if you apply the method. One key way that can be made true, is by conducting the ritual called sprint planning.

However, you are destined for failure if you don’t plan for it!

In sprint planning a team identifies the work they are going to focus on for the next sprint (normally two weeks). The key outcomes from a sprint planning session include:

  • Clear pieces of work
  • Who will do what
  • Dependencies called out, and
  • A sprint goal.

This goal will represent what the product owner (person that represents the business and helps set priorities) hopes the team will achieve in the sprint. Once set, the team go to work executing the plan that has been laid out.

How this will often go wrong, is that people are told what they will work on by other IT people, or even scrum masters (project managers) that don’t know the business or the technology. Everyone sits, but does not speak up, they listen but don’t pay attention and there is no accountability in the team or business participation. Everyone then leaves planning and goes and does whatever they think is the real priority, regardless of how it fits into the larger picture. This is where there is no strategy, no team focus towards a common agreed goal and the quickest route to failure.

“Strategy without tactics is the slowest route to victory. Tactics without strategy is the noise before defeat” Sun Tzu

So if you want to be a part of successful projects, good planning and goal setting is key. It is the old ways of thinking that should underpin your next planning session.

If Marcus Aurelius was to lead your next planning session, he might start by saying:

“Though no one can go back and make a brand new start, anyone can start from now and make a brand new ending.”

It is important that you don’t dwell on past successes or failures, focus on what is next. There is no way to go back and change what happened, so don’t waste time or energy trying to.

With the team focused on the next steps, planning can begin.

Take advantage of each team members knowledge and expertise. Use your customer’s guidance to help prioritise (build what people want, not what you think they want). Making sure to debate what should be focused on, taking the time to consider everyone’s input. A reminder my uncle (in-law) Niel gave me was:

“Listen to understand, not reply”

Too often we focus on what we want to say next, not what the other person is saying. Make sure you document an estimation of effort and come up with a loose order and sequence of what will be done. Where possible, starting with low hanging fruit.

Once the team has landed on the work that will be tackled, the next big rock is setting a goal for the sprint. This is where I think personal development has some great criteria for goal setting.

A goal should have clarity, achieved by answering the following:

  • What exactly do we want and when?
  • How will we know we have achieved the goal, what will we see or be told?
  • What will this goal mean for the customer or the business?
  • What do we need to achieve it (resources, money, training)?
  • Has anyone else ever completed work like this before (how did they do it and can we re-use it)?
  • What will you gain and lose if the team is successful in reaching the goal?

With the answers to these top of mind, the team should come up with a succinct statement that is used to focus on throughout the sprint.

You will want it to be positive, team initiated (not dependent on another team to start) and ensure it calls out the evidence that shows the goal has been achieved.

Something like this:

It is now________________________________ (future date when it will be delivered)

We have____________(the evidence that lets you know you have achieved the goal)

Now with the teams goal set, Is that it? Are you set up for success? Is it time to start work?


Make sure you have a stretch goal. Extra work, that will push the team up to or past its limits. That everyone accepts may not be achieved, but if it was would be a massive win for the customer, business and team it self. Conor McGregor (UFC fighter) says it best:

“The more you seek the uncomfortable, the more you will become comfortable”

Now with the teams stretch goal set, Is that it? Are you set up for success? Is it time to start work?


Most plans come unstuck when work starts. A team member is sick, there is an unforeseen blocker, something does not work the way it was expected to. Often work is larger or more complex than initially thought. You then have to front up to a manager, the customer or a project board and ‘manage expectations’. The team can’t achieve the goal they set, it will be delayed and it’s going to cost more (money/time).

So what is the treatment for this? What is the way to plan for these future issues, how do you plan for failure? Is there a way to ‘pre-manage expectations’?

Pre-managing expectations is something the stoics were well practiced at. They used a type of negative visualisation they called premeditatio malorum.

To plan for failure, so if something goes wrong, you are ready.

So if Seneca was helping us complete sprint planning, he might say:

“Nothing happens to the wise man (team) against his (their) expectation, nor do all things turn out for him (them) as he (they) wished but as he (they) reckoned – and above all he (they) reckoned that something could block his (their)plans”

To take this from strategy to action (StoA), there is a simple activity that can be run.

The method is:

  • Set the sprint goal
  • Write down (on post-it notes) everything that will go wrong in the sprint
  • Affinity map what the team comes up with
  • Choose 3 of the problems identified
  • Identify 2 ways to prevent the problems (if they happen)
  • Identify 2 ways to adjust the teams approach to solving the problem (if they happen)

This process will result in a plan for dealing with failure, your stakeholders will have their expectations managed from the outset, the team will be able to face issues without surprise and you will be quicker to solve issues if they come up.

So if you have made it this far, you and your team should have:

  • A sprint goal
  • A stretch goal
  • A plan for failure, and
  • Pre-managed expectations

By now I am guessing you want to know, are you set up for success? Is it time to start work?


As the team gets ready to leave the room, Epictetus might say:

“Don’t seek for everything to happen as you wish it would, but rather wish that everything happens as it actually will”

Check out the original article here:

Leave a Reply

%d bloggers like this: