How to plan your road map for H2 2018

Paul Roberts
6 min readJul 12, 2018

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Well if the raging heatwave temperatures didn’t give it away we’ve entered peak summer. And with that comes the time to start laying the foundations for planning the second half of the year. Some of you might be well advanced in your preparation while others have realised the year is running away from them. Either way now’s the time to get your house in order and to lay out an effective road map that will take you through to the start of 2019.

I’m supporting numerous teams to craft their road maps between now and Christmas. I’d like to share with you all some tips that will give you road maps that stack up under scrutiny and provide clarity on what you ‘should’ rather than ‘would like’ to deliver.

Let’s start with some top tips

  1. Review what you’ve already achieved so far in 2018. Ask yourself did you bite off more than you could chew? What landed and what crashed and burned? Is there anything you would have done differently?
  2. Look back at programs and projects delivered and assess whether they took longer to implement than you anticipated. Examine the resource profile for each one. Are there projects that sucked up more resources and investment than they should have done?

By asking these questions you’ll get some interesting answers that can help you better plan for H2. You’ll be able to use this historical information to make sure your future judgements and forecasts stack up. You might notice that certain types of effort always require more resources and time that originally stipulated. You might find patterns where certain teams continue to lag behind on delivery. The reasons behind patterns and themes will need further investigation but the insights discovered will help you build a more effective future road map.

Once you’ve evaluated past performance it’s time to start planning for the future.

So where do you start?

  1. Define your Objectives and Key Results (OKRs)

Make sure the items on your road map are aligned with the overall business strategy and high level goals. Be mindful to show how they align to the high level goals you are trying to hit. Using OKRs are a great way to do this. Items on your road map should be grouped by OKRs to show how they deliver on the overall strategy and are responsible for delivering against specific metrics.

2. Identify and stack rank your Big Bets

Work with colleagues to identify and stack rank your top 5 ‘Big Bets’. By ‘Big Bets’, we mean those programs that have the potential to delivery high returns but come with increased risk. Make sure you limit the number of Big Bets depending on your teams capacity. Again, look back to the past to see how many complex and high risk programs you think you can typically pick off in any 6 month period.

After you’ve done this add smaller items into the list but again in stack rank order. You’ll eventually have to start cutting back to get to your final list.

Stack ranking is great for driving team debate on trade offs!

3. Leave room for BAU

Remember that there will be programs and projects continuing from early 2018 into your new road map. There may also be work that is required for regulatory reasons or simply to keep the show on the road. Your road map should have a good balance between Big Bets and BAU.

4. Be willing to cut things out of H2

Looking back at in-flight effort are there programs or projects that haven’t delivered the benefits as intended? Is there an opportunity to tackle the fear of sunk costs and re-deploy resources onto newer and more certain opportunities. Don’t be afraid to tell your team something is getting culled with effort given to delivering something else.

5. Embrace agile and waterfall

Yes some work still needs waterfall planning. For a Big Bet you want to land in December you’ll need to start planning back from that date to build out your road map. Make sure you leave at least a 10–15% flex in your road map and capacity plan to allow for the elimination of operational and technical debt. Once you start shipping product and service elements you might discover improvement opportunities that need to be exploited rapidly. Having this buffer will allow you room to complete this work.

6. Link dependencies.

Most items on your road map will have interdependencies elsewhere. A new CMS system might require new content. Make sure you clearly label where there are dependencies. It sounds obvious but I’ve been in too many meetings where the cart is delivered before the horse.

7. Forecast impact (as best you can).

Do your best to forecast the business impact or return on investment items on your road map will give back. Imagine you’re spending $20M on a single Big Bet, you’ll need to demonstrate what you expect the return to be. This figure should already be in your business case so just cut and paste.

8. Be clear on benefit realisation.

Something landing in September might not actually deliver benefits to the business for several months. Make sure you make it clear on a road map when something goes into operation vs. when it’s expected to deliver the forecasted benefits. There’s nothing worse than a senior leadership team thinking something has failed because an item in Q3 wasn’t actually expected to deliver benefits until Q4.

9. Highlight resource footprint.

For each item on the road map predict the human effort required to deliver the work. It might require a sprint team for 5 months or a ring-fenced operational team for 3 weeks. Doing this will help you with capacity planning.

10. Split your road map to give more focus.

If everything on your road map is BAU then you have a problem. You’ll find yourself basically standing still. With no innovation ideas, you’ll fail to progress. On a recent assignment we helped a client map out a road map that reserved 60% of resources for Big Bets, 25% BAU and tackling technical debt, 15% for moonshots.

11. Think about tradeoffs.

Avoid starting out with the best intentions only to fill your road map with all manner of requests. Stick to your guns in being clear about what you can and can’t deliver. Having a structure and framework for how you develop your road map will help you. Put a relentless focus on those programs and projects that will deliver most business benefit. Everything else push it aside.

And finally…

Make sure you only have one road map no matter the number of teams. It’s confusing to have multiple road maps that aren’t linked and worst of all following different designs, taxonomy and labelling. It lowers efficiency as colleagues waste hours trying to find out interdependencies between different road maps.

At Strategy Activist we work with clients to improve their planning. We help clients build effective road maps that focus on delivering real change within constraints. To learn more about how we can help your business visit us at www.strategyactivist.com or call us on +44 7786063053.

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Paul Roberts
Paul Roberts

Written by Paul Roberts

Work in travel tech. A fan of applying disruptive thinking to age old problems. Passions include writing, reading, ski touring and travel. Opinions are mine.

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