We are terrible at quantifying and understanding risk. More often than not, we err on the side of positive outcomes, especially if we think something is pretty likely to happen. You can explore this deeply in the classic Thinking, Fast and Slow, but today we’ll look at risk vs optimism in software development planning.

If something is complex, novel or collaborative, then it’s really hard to plan, with software, it’s all three! Previously we’ve looked at the reasons why we use agile methods, and why launching early is important to the creative endeavour, and why “When” is a bad question. Now we’ll bring some number to the party. Exciting!

Sometimes we need to hit a particular date or milestone, usually when there’s an external requirement (think a new law coming in to force, or an immovable date like Christmas). How can we understand the risk we are facing, and also report them out accurately?

Optimism is not our friend in these circumstances. There are a number of ways to be optimistic when planning against these fixed dates, here are the top three:

  1. This is an easy problem to solve
  2. We’ll get faster as we go
  3. Nothing unexpected will happen

A new or na├»ve planner will come up against all of these, but might not recognise them. They will look at the requirements, split them up, estimate them and slot them into your preferred timeboxes. Almost certainly this means your plan will slip and you’ll miss your target.

Imagine that you hit sprint commitments 90% of the time. That’s pretty good! However, that means within five sprints, you have more than 40% chance of missing a commitment. As soon as you miss one, you are playing catch-up, and experience shows us that never actually happens.

Being right 90% of the time is also massively unlikely, but it’s a nice round number that’s pretty comforting in planning world. If you only really are spot on 75% of the time, then after 5 sprints you’ll have missed at least once move than 76% of the time!

To beat this optimism, put some evidence into your thinking. Track two things. First off, how hard you thought something would be at the start. Second, the end-to-end time to complete it (which includes everything to get it really and truly done and out into the world).

Generally, we’ll perform about as well as we did last time. Maybe a little better, possibly a bit worse, but tracking these two numbers mean you’ll be able to get good confidence in how often you hit those commitments.

Next up, grab some contingency. If you have a fixed date, then aiming at that time is the high risk approach. Remember, you are super likely to slip up, even if you are right 90% of the time.

Assuming that 90% figure, if you extend that five sprint timeline to six, then the chance that you miss commitments twice is only 18%. That’s over 80% confidence of success, much better than your 60% working to 5 sprints exactly.

These calculations can be performed with the help of a binomial distribution. It’s all pretty theoretical, but it can help to shed some light on unexpected outcomes.

Finally, do the things that are most important first. That’s a key part of success in the agile world, and it still helps even with the fixed commitment.

It’s not always the hardest things, but the ones that matter most. If there’s a feature you simply must have or else risk breaking the law, then do that first. If it’s nice to have, or a general solution to the problem, or something else that’s not vital, put it to the back of the queue.

This means that even if you do end up missing more than expected, at least you’ve done the biggest bits first. When a deadline is looming and you’ve got the ‘Musts’ done, then the ‘Maybe’ quite often just falls by the wayside.

These techniques help you overcome optimism, plan better, be more agile and keep more of the commitments you make.

Measure the difference between your estimates and the actual time taken, grab contingency and do the important things first!

Coaching Leadership


Effective delegation is a vital skill to scale your efforts as a leader.

As with any skill, it takes practice to get right, and it’s certainly something you can get wrong. Bad delegation is an abrogation of responsibility, it leaves people confused and uncertain, and it’s a super quick way to confirm any rumours that management is ‘out of touch’.

Good delegation is a powerful way to develop people in your organisation, and to get them ready to take on aspects of your role, so you can step up to the next level yourself.

Look out for opportunities that align to the development needs of the person you wish to delegate to. That could be their strengths to take to the next level, or it could be a gap where they need to show stronger competencies on a wider stage.

Early on, it can be hard to let go. Use the 70% rule. If you think the person is going to be at least 70% as effective as you, then they are ready to take on the delegation. Don’t wait until they are 100% ready, especially if you lean towards perfectionism. This is because your judgement is going to be somewhat off, if you think 70%, it’s more likely they are just about there, and if you think they are 100%, then it’s likely they were really ready a long time ago.

Also, start small. Don’t delegate a year long project, start with something that runs for a few weeks at most. It’ll be easier to track progress, and failure here is likely to be less than catastrophic.

To ensure a good delegation experience, you need to set solid expectations, you need to show trust and you need to verify what’s going on. It’ll be rocky the first few times, so check-in on these as you go, and don’t be afraid to reflect and correct.

  • Expectation – This sets clear boundaries, you explain what the goals are, what the parameter are and especially what success and failure looks like.
  • Trust – You then need to give space to the person to achieve the outcome. They won’t do it like you would, so don’t micromanage
  • Verify – Trust the process, check-in on the progress. Agree when you’ll do this as part of the expectation setting, and scale it based on the importance and duration of the task. Daily check-ins on a yearlong project are probably too often, but might not be for a week long effort. Make sure it’s close enough together to enable easy course correction, but far enough apart to avoid constraining creativity.

Use these techniques, and you are much more likely to turn delegation into a great development opportunity rather than an abrogation of responsibility.

Coaching Leadership

Point to Point

Different messages need different types of communication. Big broadcasts will not always cut it, sometimes you need to think about when it’s right to use methods when there are only a couple of people in the conversation.

Going point-to-point is great when the conversation is nuanced, any time that you need to discuss something in a back and forth way. That might be having a difficult conversation about development, or when you need to discover more information before making a decision.

It’s also great if the topic only affects a few people, or if there’s an outsized impact of a change on a small group of people. For example, if you are going to make a change to how a process is run, it’s almost certainly going to be a broadcast message. However, if there are a few people who will be negatively impacted, you should communicate that directly and personally in an individual setting. This is especially relevant for times when the changes are impacting people slightly differently, you use the capacity for back and forth to understand the impact on them, and make sure you are acknowledging that impact.

You might go point-to-point to build up support for an idea or change before sharing the big broadcast. Similarly to the way you look at people who are negatively impacted, here you look for people who will have an outsized positive change. These will be big supporters, so get them onside before you go public.

Not every communication in your working life will be best served with a Slack message, an email blast or a shout out in the all hands. Look out for times when you need the personal touch, and go point-to-point when the time is right