How will you know when you’re winning?

The answer is in the strategy, not the Gantt chart

Everybody has a plan until they get punched in the mouth” Mike Tyson told a reporter nearly four decades ago. His straightforward wisdom tells us something we knew even then: plans are fragile things that barely survive contact with oxygen, let alone the enemy.

When the plan gets shredded, you rely on the strategy to come back fighting. Because the strategy is a separate thing from the plan, right? It is. So why do people show me Gantt charts when I ask them about their strategy?

Plans vs strategies

If you cannot imagine why plans and strategies are separate but related ideas, take a look at the excellent works by Simon Wardley and John Cutler.

Simon Wardley makes the separation of strategy and plan obvious. Before making any plans, you need to understand your context in terms of landscape, climate, and doctrine. Once you understand that, you have a rationale -a strategy- to go back to when reality hits.

But most of us don’t create strategy from scratch. Most likely, your company already has a strategy, probably depicted by a Greek temple-looking thing or a layered pyramid. It appears meaningful, but you’re not quite sure how to translate it for your team. Yet you’re expected to respond to the image – politely, too.

Creating some kind of plan seems the right thing to do, even when you know that strategy-on-a-slide isn’t going be much of a “Northstar” when reality floors your plans. Cutler knows exactly what that’s like.

I learnt a lot from these masters of perspective and want to add two practical pieces of advice to help you get more value from your plan – and put you back on your feet when the punch in the mouth happens.

Rolling with the punches

In a perfect world, you have an expansion of the corporate strategy made relevant to your team. But if you find yourself with a roadmap instead, you are not alone. You need to think about how to make the most of what you have and be ready for what the future will throw at you. The following two points help you prepare.

1 – How will you know when you’re winning?

That’s my favourite way of making a rude and negative question sound polite and positive. What I’m really asking is, “Why do you have a plan but no measures?”

Corporate strategy comes pre-chewed and linked to enterprise-level KPIs. By reflex, we crank out a plan and define success as completing milestones. We do that even when we understand plans are delicate and punchable.

Leverage that instinct – and the pressure. Look at your plans and do the following exercise.

  • Think of someone who will experience the outcome of your roadmap. A paying customer if possible, or an actual colleague if not.
  • Imagine describing to them how their world will be different.
  • And them not believing your claims.
  • Now figure out how to convince them: what proof do they need? Quantify that in measures.

The exercise does three useful things. First, you think in terms of outcome – not output. Second, you get ready to talk to your stakeholders about what they need – rather than your plan. Last, you come equipped with measures. While measures are not indestructible, they hold up better than plans

2 – Your plans might make your boss happy, but can hurt your team

That pressure you feel to produce a plan comes from a good place. You’re filling someone else’s need for certainty – at minimum enough to allocate some money.

Plans like yours culminate in the annual budgeting process: we aggregate layers of uncertainties, creating just enough consensus to allocate packets of investment. That budget becomes the foundation of our actions.

Some teams are allowed to call their plans a forecast, but the further you get from the customer, the less we hear this word. And that’s where the damage can happen.

Forecasts are best guesses, subject to review when new information surfaces. Plans, on the other hand, feel like commitments.

The more technical the team, the more they anchor on the plan. But the plan will fall apart and the lofty purpose/vision/strategy slide will be too high-level to be useful. Your team will struggle to adapt if all they have is a plan. So give them a little more.

  • Be honest about what the plan really is. It’s the first draft of a guess.
  • Be sceptical of roadmaps that have the same level of detail for the near term and the long term. The further out you plan, the wilder the guessing.
  • Be careful setting targets for yourself and your team based on the roadmap. Use the measures you get from the exercise in point 1 instead.
Final round

High-level corporate strategy makes us feel that a Gantt of some sort is the only correct response. And maybe it is.

After all, we do need to create roadmaps for enterprise-level certainty. But we also need to hold them lightly – and teach our teams to do the same.

Reverse engineering stakeholder analysis and metrics from roadmaps is not ideal, but it is a pragmatic compromise.

So, with little choice, how do we stay on our feet? The key is translating the wider corporate strategy into a meaningful version for your team – and not disguise a forecast as fact.


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