It turns out I plan backwards

I was raised to be resilient, grateful, persistent and willing to make the best of things as they are rather than complain about how they should be.

Having this constantly reinforced has been a real strength during my life – giving me a optimism and a pragmatic acceptance of the challenges I face from time to time. It also gave me the ability to keep taking small steps when a goal seemed to be a long way off and to respond to setbacks in a pragmatic way.

Every strength is a weakness though, just as every weakness is likely to be hiding a hidden strength. So the weakness I grew up with was sometimes to put up with things longer than I should and to accept things as OK when they were not necessary and less awesome than they could be.

So what does that have to do with planning?

Impact on planning

When I was first introduced to serious work planning, I took quickly to planning my day as an administrator. Partly because I was never overwhelmed and also partly because I was happy to start at the beginning and then get through what I could.

My contingency though, was often to work late to get through things. I did that for too long when I could have challenged my workload and, more importantly, found better ways of getting things done. But what always helped me cope was that I naturally started at the end and the worked backwards to see what had to happen. I would sometimes take short-cuts and sometimes pause to make sure I nailed the important things, without worrying about “noise and distractions.”

Sadly I sometimes made my own assumptions about what was important and what was a distraction, but I had good mentors who taught me to prioritise on group needs rather than my own perception. That simple concept has remained a key reason I succeed/survive when stressed – I remember to share thinking and take on ideas and then pivot.

But then I moved to bigger pieces of work – projects and quarterly goals. I learned that you have to “plan the work and then work the plan”. I didn’t really learn that though – I learned that you do a lot of planning and then you let your fresh, ripe plans slowly decay like old fruit.

Meanwhile I would start a the end and work out what mattered. Then a series of crises or urgent deadlines would emerge, forcing me to rise to the occasion and get enough done to meet what people needed. It was a bit erratic and stressful, but actually that matched perfectly with the way I was raised – I wanted to be good in a crisis and coping under pressure.

It also played to my weakness when I would accept that we had to do the ceremonial (but not always useful) planning up front and then move to crises management and stakeholder negotiation. I think it was great that my strengths got me through the day, but my willingness to treat this as normal wasted a lot of my time, and a lot of other people’s time/stress levels.

One day I was speaking to a group of experienced project managers and one of them referred to me as “a lucky project manager.” He said that some project managers always do the “right things” but seem to always be unlucky, while others, like me, seem to always deliver but don’t follow the rules.

I took it as a compliment, though maybe it was also a warning that relying on luck is not the best way to manage large budgets and risk endeavours. What works in the movies does not always work well in the real world.

Some time later though, I learned that it was not about luck, it was about planning. I was speaking to another group when one of them actually listened to what I was saying and started asking me open, curious questions.

I told her I am not very good at planning, but that I seem to deliver on time with good quality. She asked how and eventually I concluded that I always think about quality, but more as something the stakeholders needed than a set of requirements. I also focuses on planning for risks and expecting impediments and having arguments along the way.

Her key insight stuck with me ever since – I was not someone who didn’t plan, I was someone who planned differently to many others.

How do I plan then?

I always ask what the goal is before getting into the planning. I then come back again and again to ask whether the goal has shifted or whether it is still the same.

I instinctively thought everyone did this, until I was involved in process re-engineering. I always started my process models with the end state, then added a start and then worked backwards from the end to the start. This confused a lot of people who, while they clarified the end state, they then wanted to work from beginning to end.

My natural instinctive approach to work backwards carried over to projects too, and even my daily planning in administration type work.

When I learned to be persistent, I was always taught to be pragmatic and not bloody minded. My family, my teachers and my early work mentors all hammered into me that it is the impediments and unexpected twists that will test you – not the steps you planned to take.

So when I planned the tasks up front on a project, it was unnatural to me. Planning for a single, expected future always seemed, somehow, wrong.

Better project managers planned better than I did. They treated the planned steps and dependencies as a hypothesis, that they provided as best guess (or best, worst and likely guess). Doing so allowed them to set initial expectations and to see/manage changes. My gap was that I saw the plan as an unlikely outcome, and therefore it was really an explanation of “what will probably not happen.”

Spending a lot of time explaining what will, likely, never happen always seemed like a waste of time. Or, I saw it as a marketing thing to get initial agreement before the chaos began.

But I was actually planning “properly”, I was just planning differently, after I finished the paperwork.

So, how do I plan then?

Backwards planning

Where my planning actually starts is not with the steps on the journey but on the gaps between me and the destination. Let’s say I was going to plan a party, this is what would happen.

Start with the goal –

“We are overdue to celebrate our thing, so let’s get together with some good food somewhere to mark the occasion.”

I then share my goal, sometimes making sure it is the scope I want (good food) and sometimes just testing the idea, open to what others say (let’s go to a pub instead, lets go to a gallery and then discuss fine art).

Logically, I think, most people would then ask “what should we do to organise the party?”. This is forward planning and will lead to the necessary steps to get there.

My next step though is to ask a negative version of the same question. I want to know what is stopping us from achieving our goal:

Why aren’t we already at the party now? What is stopping us from having the party in about 15 minutes from now?

The question may seem a bit less sensible, but it is just how I think. Now instead of the steps needed to get there, I find out the impediments stopping us from getting there. Then the milestones become the points where we overcome each impediment.

So what is stopping me from organising the party:

  • We have not asked people if they are available
  • We don’t know where to go. Even if we did, we don’t know if we will get a booking
  • We don’t know if people will like the food. They might even have allergies
  • I don’t think people are available right now, even if they knew it was on
  • Some people might not want to pay much, while others might want fine dining at any price
  • I suck at organising social things and will almost certainly procrastinate for days instead of getting on with it.

I now have a list of complaints, worries and things that are stopping us. This might seem negative to some people, but it motivates my view of myself as a persistent and resilient person who will over come all of these issues.

It also helps me to connect things to each other. For example, there is no point in asking about allergies before finding out who might come and there might be a waste of time if I book in a venue before finding out what people’s tastes and budget it.

Most importantly though, I like to then explore alternatives before planning too many steps. For example:

  • Budget might be an issue for some people – but will the company pay? Is there place that is reasonable cost but has something unique about it?
  • I suck at planning social events – Should I just admit that and stop pretending I will do it? Should I ask a friend to organise it? Should I take a small easy step like sending an email to create a crisis so that I am forced to take the next step?

Once I do this then I find I can work backwards until I have a plan, with key risk mitigations or milestones to see if I am on track.

If needed that list can become a mind map, a prioritised (evolving) backlog, gant chart, a run sheet or a todo list, but it is a plan that makes sense to me and that I will actually track. I can also do estimates based on estimating each impediment (which seems to confuse some people) and I can work out where to really focus my efforts right now.

So my plan evolves as success becomes more likely, each milestone making me more confident and each unexpected challenge becoming part of the plan.


I know people who are great at execution and always deliver, who start where we are and then map out the steps, thinking forwards. I also know that I and some others do our best planning working backwards.

Finally I know that I need to communicate with people who visualise things differently to me, because I have confused people or left them nervous when my plan looks like a list of complaints and concerns, rather than a “plan”.

Or do I know those things? Do you think I am unusual in that I plan backwards, or do you think it is actually what most people do?

Also – do you think I really need to spend time talking about how I plan so that forward thinkers don’t have a different plan, or do you think that we all come to the same plan anyway, just from different directions?


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