Welcome back to our 5 Top Challenges for Digital Leaders series!

(If you missed it, you can catch up on last week’s effort here: The Burning Platform Death Spiral and Other Digital Adoption Strategies).

We’re now moving on to the final challenge of Building Trust and Credibility and this week’s topic – creating your digital strategy – is a beautiful segue.

A few years ago, I saw tech legend Claudia Batten talk about her career journey and her experience with a squiggly career path, rather than a linear one.

“Squiggling is creation in pursuit of one’s ambition that follow’s a non-linear progression”.

I think that squiggling is also how we should approach digital strategies.

Broadly you know where you’re going but how you get there is by no means a straight line.
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There are changes in direction in response to organisational need, customer demand, and innovation in how we think and the tools we use.

As a transformation leader you may be a pioneer in your own organisation, having to make bold calls, try new ways of doing things and convince others to come along with you.

Transformation is not for the faint-hearted or the quiet-spoken.

If you want to succeed you need to win the support of your teams, colleagues and the Board. And the most common way of doing this is through your digital strategy.

But sadly, too often the act of putting that strategy on paper (or a powerpoint) actually stifles the creativity and spontaneity you need.

The boldness and joie de vivre that comes from leading an amazing digital programme gets beaten out of you as you commit to a linear and safe roadmap.

And, by the way it’s practically impossible to write a three to five year digital strategy that remains relevant over that time.
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So how best to approach your digital strategy? Here’s some practical tips to help you live a more squiggly life:

There is great power in helping your stakeholders believe in a bold new world.

A short, entertaining video of a radically transformed customer journey is much more engaging than a 30-page strategy document.

The best ones I’ve seen have been animated and from the customer’s perspective. You walk a mile in your customer’s shoes and feel that anything is possible in this brave new world.

Boldness is key here. Paint a picture of how the world could be, not how it will be one or two years down the track.
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This vision of the future becomes your beacon on the hill, your ambition, or your MTP (massive transformative purpose). It’s aspirational, you are not meant to be able to attain it during your three-year strategy, but you are creating that future as you progress.

It may seem obvious but it’s really important that you can demonstrate a clear line of sight between your digital beacon on the hill and your organisation’s aspirations and focus.
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A disconnect between digital aspirations and the organisation as a whole can only have two possible outcomes - either the digital team is successful at convincing the wider organisation of their vision for the future and that becomes the organisation’s strategy. Or the transformation programme is starved for funds and prioritisation, and digital folks leave and take their vision elsewhere.

Think about your own digital journey. I bet right now your teams are working on things that you hadn’t considered (or in fact might not even have existed) when you wrote your digital strategy three years ago.

Don’t tie your roadmap to what you know about now. Say “we’re going to solve this problem” rather than we’re going to “update platform X” or “build new capability Y”.
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The specifics of what you are actually going to do for the next six months can be managed via a one page roadmap, which will continually evolve. 

One of the biggest drivers of change to your strategy will be adapting to the lessons you have learned along the way.

A great squiggly strategy builds flex for learning into your plans. This means not being too prescriptive about the steps you take; building room for trials, pilots and proof of concepts; and allowing for things that don’t succeed.

For example, an innovation programme needs to build in an allowance for a high failure rate – if we want to have three successful partnerships in three years’ time then we probably need to be signing at least ten or fifteen deals this year.

A focus on accelerating your rate of learning is a great way to deliver more transformational thinking for your organisation. Your strategy should focus on building the capabilities that encourage learning, rather than doing the learning itself.
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Good luck!