Anna Shipman : JFDI

Strategic technology leadership: fireside chat

11 July 2023 / Strategy / Speaking

I keynoted the second day of CTO Craft Con: The Strategic CTO. The topic was strategic technology leadership. This is a write-up; you can watch the video here.

It was a fireside chat

I was in conversation with the excellent Emma Hopkinson-Spark.

Emma kicked it off by asking what strategy actually is, and how it’s different from roadmaps, initiatives, tactics etc. That gave me an opportunity to define strategy as diagnosis, vision and a plan, and recommend the excellent Good Strategy, Bad Strategy.

We talked about communication. The most important aspect of strategy is communication: the point of a strategy is to execute on it, so people need to understand what they need to do.

It needs to be simple enough for people to understand; communication needs to be verbal, visual and written because people absorb information in different ways, and you need to keep repeating it, far more than you might think.

You must carve out time for strategy

There were also questions from the audience. One was “How do you break out of the delivery whirlwind to set your strategy?” and I was unequivocal on this: as CTO it is your job to set and lead on that strategy, so you have to make time. That could be blocking out time, setting meetings with people to work on it, Away Days, or whatever works for you.

When you make time for strategy, the reactive demands decrease because you have more systemic approaches. I also taked about rocks, pebbles and sand; strategy must be one of the rocks.

It can be really difficult to carve time out to begin with, but once you have, you will start to see the benefits.

I favour transparency

Another question was: “what’s the best approach for course correction and how do you tell the difficult story to the board when it’s a drastic change?”

Talking to the board, you should operate on the principle of “no surprises”, so when you see things heading off track, have the conversation as soon as you can.

This led into a discussion how to have that conversation. Emma asked how you change your style if you are communicating upwards, to the board; and one thing I shared was that it’s a good idea to create artefacts (diagrams, documents, progress indicators) and use the same artefacts for everyone: for the board, for your peers, and for your reports, so that everyone knows you are talking about the same thing.

People are incentivised by working on important things

Another question from the audience was “how do you directly incentivise people at all levels around a common strategy?”

This was an interesting question because I don’t think of it like that. Part of the work of strategy is inspiring people with the vision. When you are working on the plan, the more you can involve people, the more bought in they will be.

I don’t think about separately incentivising people, because I find they are motivated by working towards the vision they’ve (hopefully) bought into, with some actions they’ve helped figure out. People like to be involved in delivering something good.

How to get started

Emma then asked for suggestions on how to actually get started on strategy work.

I said:

We discussed a lot of other topics

There were a lot of other great questions, like how OKRs and strategy can work together, aspiring to have an elevator pitch for your strategy, and thinking about strategy mistakes I’ve made.

You can watch the full conversation here.

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