Moving from strategy to delivery: the “messy middle”.

One of the main issues that companies face, beyond creating a Strategy itself – is the ability to actually implement this.

I’ve been asked this question several times:

“Evie, do you perhaps have an example or template of how large scale corporates handle company strategy to product strategy to epics and features etc.

I am trying to close the gap on the ‘messy middle’.”

It’s one of the topics that I end up working with with every client that I’ve had. 

& it’s something that seems to be widespread across many organisations:

61% of respondents acknowledge that their firms often struggle to bridge the gap between strategy formulation and its day-to-day implementation. (Economist)

Why does the ‘messy middle’ exist?

John Cutler defined the ‘messy middle’ as the 1-3 month or 1-3 quarter areas of work, where topics often get lost / aren’t communicated / people haven’t found the balance between the generic and the specific.

For me, the ‘messy middle’ isn’t just a time-framed problem, but it is all about how we move from direction to execution.

I’ve worked with so many businesses who have created a strategy, communicated it out, but still don’t feel like the teams on the ground are moving in the right direction.

That’s because there’s a huge gap between strategy, and day to day work.

No matter the size of the organisation, there are many layers to get from strategy to execution. However, this becomes so much more important in a larger organisation due to the number of teams and people that need to be coordinated, and receive the same message, with the same clarity – to be moving in the right direction.

For teams on the ground – they often:

  • Already have their own assigned focus: ‘We look after X page and therefore own Y problems”
  • Have their own requests incoming that distract them: bugs, sales requests, stakeholder requests
  • They don’t see how the strategy impacts their work

This is why it is so important to bridge the gap even further, between Strategy and the teams themselves.

How do you achieve this?

Diagram showing the steps from company vision to actual execution.

Product Organisations need to move through each of these steps to make it through the messy middle and really set themselves up for success.

Breaking down the key elements:

Company strategy: If you’re not Product-led, and if Product is just one part of the organisation – it’s likely that the company strategy will be broader than the elements that Product feed into this. If this doesn’t exist – you might be able to solve the gap between your Product strategy and execution, but it’s far harder to align to deliver maximum value to the company as a whole.

Product strategy: There are a tonne of great articles out there on how to do this well. I’ve picked out a few highlights on the essential elements to get right to support with the messy middle:

  • Having a clearly defined overall goal / metric (your North Star) – that everyone in the business can work towards. This really highlights what your priorities are for when teams are making trade-off decisions. They can ask themselves ‘will this help or harm the north star’.
  • You need prioritised strategic pillars. If you have more than 5, you still risk the opportunity for teams to move in a million different directions as they don’t have dedicated focus. These also need to be broken down into the priorities of the initiatives that you will try to deliver over time – to help organise teams based on their importance.
  • You need clear and measurable goals. If your strategic pillars are too broad, then they’re open to different interpretations from different teams, & anything that’s a feature request could potentially feed up to the strategy – so they continue working on what they were working on anyway
  • You need to understand how to structure your Product org for teams to effectively contribute to the strategy. If you know how you’re going to tackle the key pillars, and which areas / skillsets are important to this – you’re in a great place to start tackling the ‘messy middle’, as you can align the right teams around a clear goal.

Organisational set-up: Within set-up it’s important to think broader than just the Product org. 

Product can achieve a lot, but to really deliver maximum value we often need sales, marketing, commercial and more areas involved. It is so important to identify this at an early stage and work as a business to achieve your main goals. 

I therefore recommend assigning the right people from cross-functional departments to these goals. This might take different forms: nuclei teams, working groups, complete squad integration – the model is up to you and the teams to see what works best.

Product Organisation level OKRs:

You already have your strategic pillars, which follow clear and measurable goals. You’ve also worked out in your strategy how you should break these down and prioritise them to deliver. So it should be a relatively straight forward task of converting these into OKRs.

This process helps you to bridge the messy middle by being even clearer on what the top priorities are to focus on at each point in time. Companies often use quarterly OKRs, so they can reflect and plan often – but it might suit you better to keep your organisation OKRs more stable and with a longer timeframe, so you can really measure outcomes.

These are super important, as teams will then be able to set OKRs that feed up into and contribute towards this. This is one of the biggest steps in bridging the gap, as it refines focus, reduces the timeframe and makes the work a little less abstract than a high level strategy.

The beauty of OKRs is that they set the direction, and allow the teams to contribute with the best way to achieve this outcome – to me that is the perfect balance between top-down and bottom up.

I would also strongly advise that communication between leadership and teams on the ground is 2-way and is transparent and frequent, so they can feed into feasibility, approach & learnings. This keeps the whole org aware of what is and isn’t working and allows you to pivot if needed.

Team level OKRs:

You might need to split this to two levels depending on the size of the org – it might be that you need group level OKRs (based on teams aiming for the same strategic goal) and then team level, or the teams just contribute to particular metrics / elements of the OKR. 

The important aspects are:

  • These feed into the Product Org OKRs – so teams are moving in the right direction
  • The right groups of people / teams are aligned on the same OKR and are clear on their contribution towards this

Actual execution: Roadmaps, EPICs, tactics…

With all of the above achieved, then teams should be generated ideas, concepts, roadmaps and insights that are aligned to the overall goals, and across their teams.

This still leaves teams with all of the freedom to identify and define the best way to meet this goal based on their technical and customer understanding – as that is what they should do best.

This is why the open and transparent communication across hierarchies and teams is important – to share learnings, see what is on track and see where it might be more challenging than expected to hit the goals. 

This allows insights that are discovered to influence the team structures, the OKRs and the focus to be adaptive and flexible. It’s unlikely that these insights should change the strategy – as that should be less flexible and more susceptible to broader market changes, but changing customer needs that are uncovered might play a part as teams get into the detail.

& with those 6 steps, you’ve broken down the ‘messy middle’..

As always, this seems like a lot of steps and can seem like a lot of work to move through all of them properly…

However, if the strategy is developed in a really strong manner – then it will be easier to execute on. The following steps outlined above should then cascade from the information that you already have.

My final recommendation, is using continuous planning instead of quarterly planning. This allows for these conversations to take place frequently and doesn’t create a stop-start feeling in the organisation, it means changing when insights mean that it makes sense to do so. This means that you don’t need to go through this whole process every single time. Instead, it means that it is ever evolving to help you to achieve your goals. 

SIMPLE (right?)!

If you have more questions on this topic, please let me know – I’d love to dive a little deeper on the areas of interest and how you can achieve those effectively!

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