How to influence senior leaders to invest in digital maturity

My Digital Maturity Assessment is used by clients to assess their digital operations. We establish whether they are making the best use of digital technology and its associated culture and ways of working in everything they do.

So far, relatively straightforward.

Once they’ve got their results, the next stage for many of the people I work with is to create a digital transformation strategy. This helps them focus their attention on the changes needed in areas where digital will bring most value to their mission. And often involves making the case to senior leaders for investment.

Not quite so simple.

For us digital folk, influencing senior stakeholders is a core part of the job. Change needs changemakers, and changemakers need cheerleaders. Here are some tips for how to take those at the top with you on a journey of digital change.

1. Speak your leaders’ language

It’s time to put your audience hat on. Yes, senior leaders are an audience too!

My first tip for influencing senior leadership is to use the same skills that you use every day as a digital practitioner: start with the audience.

Where do you think your senior leaders are at, and what kind of information will they need to reach the point you want them to get to? What are your CEO’s hopes and dreams for the organisation? What are their expectations when it comes to digital strategy and digital operations? It’s only by understanding people’s motivations and aspirations that you can figure out what you need to say to take them to the next step.

Then, paint a picture of the future. Be enthusiastic. Be organised and prepared, and to the point.

2. Tailor your delivery style

Do you know how your senior leaders prefer to take in information? If not, can you find out?

I had leaders who only wanted information in presentation style with loads of graphs and minimal number of words. Others wanted absolutely everything written down in minute detail so that they can examine it carefully. And some others wanted me to take them through it bit by bit t face to face.

3. Mobilise your allies

Prime your allies, whether they are your peers, your manager or a board member, to vocally support your proposal in advance. Even better if you can win over someone on the senior management team ahead of time. As a board member, I was approached to play this role a couple of times and it does work!

Here’s another thought. Consider that you might not be the best messenger to deliver your proposal. Could it sound stronger coming from one of your allies instead?

4. Link everything to your organisational goals…

Last month, I discussed how to reach clarity of vision using a strategy house. You can use it to identify what you’re trying to achieve and where digital can make the most difference.

In the context of persuading senior leaders, clarity of vision means pinpointing how your digital strategy, and its implementation, would help your organisation meet its objectives.

How will this work serve the organisation in two to three years from now?

For example, Barnardo’s and Parkinson’s UK prioritised digitally transforming their service delivery, because it was strategically vital for them in the context of growing numbers of people needing their support. On the other hand, charities like Greenpeace and Save the Children have focused their digital efforts on building a movement of people who will take action and support their work financially. It’s all about the overarching goals.

5. …Especially your data

We digital experts love a bit of data. But pause before you pull out an elephant-sized report packed with analytics to show your CEO.

Presenting data without giving proper context or guiding your audience is a bit like sticking them in a boat without any oars and expecting them to row.

Catch my drift?

6. Get everyone on the same page

I’ve run a lot of workshops. One thing I’ve learned? Never assume that your group’s level of understanding is the same.

Just because senior staff in the room have approved the meeting, it doesn’t mean that everyone’s speaking the same language. Someone who works in recruitment once said to me: “As I understand it, digital transformation means AI”. In another workshop, an IT person told me they thought it was about making the whole team redundant.

So check in. Explain what the purpose of the process is. And explain key concepts and terms, such as digital maturity and digital transformation. Remember the audience and address any concerns head-on.

I often use a definition of digital transformation that puts it in the centre of a Venn diagram where business purpose and organisational strategy, customer or supporter experience, and staff experience overlap.

So it doesn’t start with technology! Technology is a solution to a problem you are trying to solve in one of these areas. Skills and processes are essential too. Look out for another article going into this in more from me soon.

7. Drip feed slowly

You’re probably bursting with enthusiasm and can’t wait to get everything out. But try to take it slow. Drip feed information so your leaders can absorb it.

For example, in my experience, it’s better to hold two one-hour workshops a week apart, rather than hold one two-hour session. That way people have time to digest the information from the first workshop before they join the next one.

Within one workshop, you could have a presentation at the beginning, but leave proportionally more time for group work and discussions. Because many people learn and absorb information through discussion and interaction with other colleagues.

8. Adapt as you go

A tip about workshops and group discussions: if you’re running more than one in succession, adapt future sessions depending on how previous ones go.

At the end of every session, ask for feedback, and ask each person for their main takeaway. You’ll garner an understanding of different mindsets and priorities.

Adjust the next session accordingly.

9. Always be two steps ahead

This is a game of chess. You constantly have to think about your next move. Sometimes it’s the small things, like making sure documents that need to be shared ahead of a workshop get seen by the right people at the right time.

After meetings and workshops, follow up immediately. Follow-up communications should include your main points and list of actions, as well as what happens next. Keep repeating the ultimate destination on the journey, and the next milestone.

10. Look for quick wins

If you feel stuck, look for low hanging fruit. Many people assume that technology is going to solve all their problems. But much more often it’s about ways of working. Changes to processes, such as how you plan and approve new work, can bring quick wins and resolve frustrations. Use these to show progress and keep people on your side.

If you need a hand assessing your digital maturity or convincing your senior leaders to take it seriously, get in touch.