Are you planning or building a plan and hoping for the best?
“In preparing for battle I have always found that plans are useless, but planning is indispensable.” — Dwight D. Eisenhower
We like knowing, as humans, we don’t like surprises — we want certainty. So much so that we often get obsessed with predicting the future.
Don’t believe me? How many times have you checked the weather forecast this week? Ever been upset when the forecast was incorrect? — I have, “I thought it was supposed to be sunny today!”
Often this obsession makes its way into how we deliver products — we devise a plan, the perfect plan, often with the shortest timeframe and everything fitting perfectly together. We then crossed our fingers, shut your eyes and hope nothing goes wrong — but we know something always goes wrong! (Murphy’s Law after all — don’t blame me, I just inherited the name)
Breaking the ‘Perfect Plan Trap’
There are things that we know and things that we don’t know, but there are equally things that we know might happen.
The idea with planning and what Eisenhower was getting at with his famous quote is that through the act of planning we can anticipate potential setbacks and plan for them — what are we going to do if we can’t get our hands on something before a particular date? What about if our solution isn’t fit for purpose? What’s our plan B, C, and D?
This is planning. We will never cover all possibilities, nor would we want too as there is a diminishing return on investment (think over-planning), but we can anticipate and prepare for things to not go according to plan — because they never do.
A plan to planning 🤔
Going all ‘Inception’ on this, with a four step plan-to-planning — hurts my head just saying that!
- Come up with your perfect plan
- Wargame it — pre-mortem’s are a great technique for this
- Prioritise and mitigate risks
- Develop alternatives, aka “mini-plans”
Step 1: Come up with your perfect plan
No need to reinvent the wheel to start with, it’s easiest to just do as you always would and come up with the perfect plan like you normally would.
Step 2: Wargame it with a Pre-mortem
Wargaming is something I learned in the army. What would usually happen is as a commander you would develop your initial plan, once done you will present it to a group, usually your commander, peers, other impacted parties and your team. At which point they will proceed to rip your plan to pieces. This can be a shock for some who are not used to receiving such brutal feedback but it’s constructive. They’re not attacking you or your planning ability, it’s about strengthening the plan.
This is very similar to running a pre-mortem — if you aren’t familiar with a pre-mortem it is an activity where a team and relevant parties attempt to predict all the things which could go wrong on a project and then work backwards by looking at ways in which they could mitigate those things from happening.
Step 3: Prioritise and remove high risk
A framework that I find quite useful to use in my pre-motrems and for prioritising risks is a ‘likelihood’ vs ‘impact’ matrix.
The idea being, that we cannot possibly remove all risk but rather we can take a risk-based approach. Basically a simple prioritisation framework allowing one to focus on the high likelihood, high impact items first, whereas low impact, low likelihood last.
A framework I then like to overlay the matrix with is ‘Avoid-Reduce-Share-Accept’ for managing the risks in each quadrant. This essentially informs the cause of action that you are likely to take for the items in each quadrant based on a loose cost-benefit tradeoff — high likelihood + high risk items = should be avoided altogether. Whereas low impact + low likelihood = can be accepted (not worth the effort to do anything about them).
This overlay isn’t a hard and fast rule — if anything I think of it as more of a de-escalation method.
- First ideally I want to start by trying to avoid the risk altogether.
- Failing to achieve that I want to reduce it — either in likelihood or in impact (this should theoretically move it to another quadrant).
- After trying to reduce, look at the possibility of sharing the risk — this is a way of mitigation we spread the risk across multiple places, perhaps even paying a 3rd party to take on most of the risk.
- And finally, ignore it — because it’s either too low impact and likelihood or there’s nothing we can do about it, like a meteor strike.
Step 4: Develop alternatives paths
This is something the military does very well too — they not only look to mitigate the things which may occur but they also develop predetermined ways in which they intend to respond when something goes wrong. These responses are referred to as “actions-on”.
Think of actions-on like “mini-plans” — what cause of action are we going to take if ‘such-and-such’ happens? Rather than hoping for the best, expect the worst and plan for it.
I like to think of it this way, we typically plan for the best and just cross our fingers and hope nothing goes wrong — rather what I noticed whilst in the army was that they then to plan for the worst and hope for the best — there’s a strong lesson there.
You’re never going to be able to create a ‘mini-plan’ for every possibility but the idea is to cover anything we believe is likely to happen. Many will say but that is a waste of time, any planning above what is needed at that moment is a waste because it may not occur — and I’m all for JIT (just-in-time) planning — but there is a trade off.
I’ll give you two arguments for doing a bit more planning upfront and anticipating possibilities and having alternate paths for them — flow and psychological comfort.
- Flow: Every time something new occurs that requires planning the team's flow is broken. We need to notify the team, stop them doing what they are doing and re-plan. Having pre-determined mini-plans before something occurs allows that event to unfold without breaking the teams flow, the event happens, they respond by changing course based on their “min-plan” whilst all staying in alignment because we had aligned earlier — a common thing that happens when plans have to change is misalignment this for most cases solves that issue as the need to communicate any plan changes is no longer — we have already decided how we will respond so even without telling me I know that the plan has changed and we are now executing “mini-plan-A”.
- Psychological comfort: I mentioned at the beginning of the post that we don’t like surprises, we don’t like uncertainty. Planning for the unplanned can alleviate the anticipation of the unknown — I’ve often felt it helps put the team's minds at ease, that we have considered potential events and have a reasonable response for them. This allows them to leave the room feeling comfortable with what's ahead rather than apprehensive about all the things they are thinking about which could go wrong.
Clarity, psychological comfort, alignment and speed of execution are the benefits of creating mini-plans upfront — let’s be honest the JIT planning concept is not completely true, I think yes if things don’t change much then sure it makes total sense to not worry about it until it happens, but how often do things go according to plan? — not often.
I think of it this way, how much a) risk are you willing to take and b) how much unknown is there? In a complex world, like war, we expect a lot of unknown — after all, Helmuth van Moltke famously said “No plan survives first contact with the enemy”. Which makes the investment of coming up with mini-plans worth it. But if there is a low amount of unknown and you are willing to accept the risk, then going with JIT planning makes total sense.
It may seem counter intuitive to spend time planning for things that may not occur, but from my experience the benefits you not only get from psychological comfort and alignment but also on the speed of decision making and adaptability through predetermined mini-plans is well worth the investment.
A word of caution however there is a cost benefit ratio that needs to be maintained — don’t fall into the trap of analysis paralysis, possibly time-box the activity or prioritise the likely outcomes and tackle the top 3–5. Anything beyond that and the cost of upfront planning no longer outweighs the benefits.
A story to finish things off
I’ve run many pre-mortems in my time and one which I will always remember was a few years back at a client, we were kicking off a new team and planning a significant product pivot. Being such a ‘big bet’ we decided it would be best to wargame our plan and have a look at all the things that could go wrong with the product pivot. My college, a brilliant designer, crafted this fantastic newspaper front page mockup which read — “[client] in hot water. Customers run for the hills after the latest product release”.
We spent a solid four hours doing a pre-mortem — a first for the client— a very traditional company they had never once gone through an activity like this before — victims to the “perfect plan trap”. Exhausted by the four hour long pre-mortem we finished with a check-out, among our normal check-out I wanted to gauge how they felt conducting a new activity like this — so I asked “what did you think?” — I’d never forget the response I got — one of them sat there looking shattered, it had been a long day, they simply look up at me and said “I think it was all a bit depressing, very negative. I didn’t much enjoy it, it’s not a good feeling talking about things that could go wrong. It just felt too negative!”
Wow, what an honest answer — safe to say I didn’t expect that. I followed up on the response and they all overall agreed that it was a valuable activity albeit a massive shock for them. A shock to do something so vastly different than what they are used too — safe to say they got out of their comfort zone that day.
Upon reflection I think I got two lessons from that experience for those of you trying this out for the first time:
- Some people aren’t used to thinking negatively and seeing it as a positive thing, this may be a large mindset shift for some — particularly those who have been doing the “perfect plan trap” for many years.
- Pre-mortems can be grueling and not super enjoyable for some, this is where leadership is important — bring energy to the room, remind them that it’s ok to feel such a way but this will lead to better outcomes and the more we do it the better we’ll get at it.
