It’s pretty common to be making plans for the year ahead about now. I’ve always been fascinated by planning – and its tension with reality. There are plenty of classic quotes ranging from the generic “if you fail to plan, you are planning to fail”… to “everybody has a plan until they get punched in the mouth”.
Over the years, I’ve experimented with endless planning approaches. I grew up in a family that designs and builds things – which means being curious about how things work, creatively finding patterns to bring order to chaos, and also working out how to make the change real. That means planning – especially in a creative process.
My path in the corporate world was focused on designing, building, delivering, and leading innovation and strategic change. That means projects – and planning. I started out as a project analyst in a bank in the early 90s and over time progressed to managing projects, then large programs and portfolios. I did this because it’s how you get things done in large complex organisations… but I was actually in it so I could work on interesting problems and design solutions that gave people better processes, tools, and experiences. I was usually an architect as well as the program manager.
This context gave me an interesting relationship to planning. Everyone wants a plan. Perceived certainty through complexity and change. Sometimes the beautifully crafted project and change plan became the deliverable more so than the actual project. This was mostly back in the days when everything was done waterfall.
At the same time, I was also working on startups – usually with little to no detailed planning.
With that context…
What I’ve Learnt
Time Horizons Matter
There’s a big difference in planning the next fortnight and planning the next three years. Unfortunately, a lot of traditional planning approaches treat these time horizons the same or in very similar ways.
In my experience, the longer the time horizon and the more complexity and uncertainty I’m working in, the more the planning needs to focus on intent and direction – and less on detailed plans full of untested assumptions, tasks, and dates.
It can be easy to give up on planning when you feel uncertain – like being in a pandemic. I think it’s a time when doing some planning focused on intent and direction is even more important. It can help give hope and a future to work toward. It’s also important to not let the things we can’t do stop us doing what we can do.
Now’s a good time to think about what the next few years might look like. There’s a lot we don’t know, but reflecting on our individual and organisational purpose, the direction we want to go, and how we want to spend our time – both now and in the coming years, is a helpful way to stay in a positive headspace.
It’s funny how things start coming together as we get more clarity on our intent and direction. With a clear sense of direction, we can start planning the detail in shorter time horizons (fortnights and quarters) with more certainty – and it allows us to refine our plans as we learn. The trick is to keep a strong connection between longer-term planning focused on intent and direction with short-term planning focused on getting stuff done.
Reflect & Refine
No plan exists in a vacuum. The world has changed and is changing. With any plan over any time horizon, it’s important to regularly reflect on how the context is changing, what trends are emerging or playing out – and how’s it relevant to our strategy and plan.
This is where a lot of planning goes wrong. Too often planning is approached by pretending we know everything before we’ve even started – and the plan is rigid and absolute. It doesn’t allow for learning and refinement. This is a key reason a lot of plans are out of date before they’re even complete.
In this time of great uncertainty and change, it becomes even more important to make our assumptions explicit and have a clear plan to test them. Because the context has changed so rapidly and dramatically, a key risky assumption to test is the belief that what was working well for us pre-pandemic – will continue to work well as we move forward. It might… but it might not. It’s worth testing.
A consistent theme is the pandemic has accelerated a lot of trends that were already in play – and it has highlighted and exacerbated inequalities in the system. What’s that mean for our plans?
I find reflecting regularly on how things are going really valuable. Every fortnight I spend some time reviewing the past fortnight – what went well, not so well, and what I’m going to keep doing or do differently over the next fortnight. I connect this to my strategic direction and make ongoing refinements. I reflect on all aspects of my life – not just Dynamic4. I then cast forward and set the direction for the next fortnight. I use this same approach quarterly and annually to make sure I’m always learning and refining how I do things.
Another thing I find really important as part of regular reflection is to celebrate the wins. And celebrate the wins as they happen. There’s always more to be done, and it can be easy to fixate on the next thing rather than taking a moment to pause and recognise what’s already been achieved. This is a key reason I really like Objectives & Key Results (OKRs) as a goal setting and tracking approach – I find the non-binary approach much better for my headspace. A rabbit hole I’ll resist diving down right now.
Freedom Through Structure
Planning is valuable… but often the plan isn’t. The thinking and conversations involved in planning the future you’re working toward and how to make it happen is where the real value is. Understanding different perspectives and expectations, making assumptions explicit, building a collective… these are the things that set you up for success.
We need to capture the key elements of this to come up with an agreed approach and boundaries. The type of documentation and level of detail needed varies depending on the time horizon, people, and context. It’s important to have a record to refer to and to use to communicate and build momentum.
Finding the right level of structure that’s not too rigid but provides enough certainty normally takes some experimentation… but when you find it, and it becomes part of your workflow, you’ll be amazed at how much freedom it provides. The interesting juxtaposition of freedom through structure.
I sometimes still feel the need to create a polished detailed plan and put a bow on it, but I know this is usually a distraction and maybe a seemingly valid way to procrastinate. I do my best to be aware of this and instead focus on planning to the right level of detail for the time horizon, make sure I’ve got clarity on intent and direction… and do just enough planning to provide freedom through structure.
2021 Update: In Solve Problems That Matter, I go into a lot more detail on how I approach planning – in line with your purpose, vision, and theory of change.
Dynamic4: The 20th Year
It seems a good time to reflect on the journey so far and some key things I’ve learnt on the way. This is Part 3 in a blog series as we count down to our 20th birthday on 1 October 2021.
