Help! My boss is a digital conservative

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‘My manager doesn’t see the point of Instagram.’

‘My boss says we don’t need to change the website, because we already spent money on it three years ago.’

‘We can’t use emojis in our emails because the CEO doesn’t like it.’

The details may change, but it’s a common form of complaint across the charity sector. Its authors: depressed and unrecognised digital officers. Its villains: Luddite bosses whose views on digital are, at the very least, as eyebrow-raisingly subjective.

And the complaint always ends with the same desperate question: what can I do to make my boss see reason?

What indeed?

In Lisa Welchman’s excellent book Managing Chaos: Digital Governance by Design, she places organisational decision-makers on a spectrum between two polar opposites: ‘digitally conservative’ and ‘digitally progressive’.

Being digitally conservative, she stresses, is not innately a bad thing. Perhaps a digitally conservative boss has a clear understanding of the technological landscape, and good reasons for not wanting to commit to more than your existing digital outputs.

Equally, it’s just as likely that a digitally progressive boss is the one ruining your day by insisting that you live-stream the board of trustees meeting for three hours at a time, because ‘video is big now’.

That said, I think there are several reasons why digital officers at charities — and small charities in particular — might be more likely to end up reporting to someone whose digital conservatism is compulsive and ingrained, rather than informed.

Let’s call them the structural, the personal, and the environmental:

The structural: Your organisation has probably bolted digital onto its existing Comms structure.

Take a look around you.

Are you surrounded solely by press or fundraising officers with their own fully-established working processes? Are your social media and website largely a relaying service for telling your audience about Comms successes or challenge events? Are you exclusively an online echo for offline projects?

If so, it’s likely that your charity’s digital presence has half-heartedly grown out of a side-gig for Comms & Marketing over time (‘The Press Officer is too busy to do tweets in their spare moments any more, so let’s hire someone…’) and has never really had a chance to establish itself on its own terms.

That structure can mean that digital projects aren’t given as much priority as they deserve, but it’s equally likely to mean that you’re forced to accept processes or principles that haven’t been designed with you in mind.

And so you may find yourself told to use wording for social media that seems overly formal (No emojis! No exclamation marks!). Why? Because that’s the tone of voice that appears in your organisation’s press releases.

Or you may be asked to create and maintain a webpage that simply links to PR stories about your charity, counter-productively sending users away from your site.

Again, why? Because your organisational structure means you’re seen as a supplementary service, rather than a content owner in your own right.


Get your colleagues behind the idea that you need to create a set of distinct principles, process guidelines and ToV documents for your digital work.

This may take a long time. It will likely be a struggle to get enough buy-in and involvement that the results can be put into practice (as opposed to the documents being circulated once and then sitting in your shared drive, unread).

But once you’ve agreed on even a basic definition of how digital processes need to work and how digital content needs to look, you’ll be able to back yourself up much more effectively.

The personal: Your boss has probably stepped up from a specialist role into a generalist role.

If you’re working at a charity where Digital has been bolted on to an existing Comms structure, your manager is likely someone with experience that reflects that sense of priority. That is to say, they’ll probably be a PR professional who is now having to learn how to oversee Digital.

This isn’t necessarily a bad thing in itself, but it certainly reflects some bad, commonplace assumptions about the two (it’s assumed that a Comms expert can just ‘pick up’ good digital practice, whereas a digital expert can’t ‘learn’ Comms on the go.)

As result, your boss may be empathetic, thoughtful, and eager to succeed — but nevertheless lack any formal digital training or first-hand experience.

No matter how supportive they’re aiming to be, they may demonstrate unconscious bias towards press work, or shy uncomfortably away from spending budget on digital projects…because they simply don’t know if they’re making the right choice.


Your boss doesn’t need to buy into every aspect of digital, so long as they feel like they can trust in you.

So put any frustrations you might have to one side (easier said than done at times, of course). If you treat your boss like an obstacle or an irritation, your relationship will likely disintegrate — which helps no-one.

When you push back on a bad idea, make sure you’re explaining the problems clearly, without letting emotion get in the way. When you’re forced to accept a bad idea, do it with grace. When something works, show off the results and talk next steps; when something doesn’t work, talk through the failures candidly and without I-told-you-so.

In short, be a digital advocate.

The environmental: Your boss is probably only seeing the broad brushstrokes of digital.

Let’s assume your manager isn’t a digital specialist…but they’re keen to improve their understanding.

With limited time to spare, it’s very possible that they’ll begin by making an informal effort in the corners of their working day: checking out mainstream news articles that mention Facebook, or skimming newsletter stories that talk about the ‘next big innovation for digital’.

I’m not judging, by the way; I’ve done this myself, when I know I should care about an issue but convince myself I’m too busy to investigate it properly.

Unfortunately, this is very much the realm of ‘A little knowledge is a dangerous thing’.

Because your boss will likely end up basing their assumptions about your work on big, bold, at-a-glance statements about the worldwide state of digital media…which are usually incomplete, if not hopelessly irrelevant to you as an organisation.

This problem is both surprisingly widespread and, I’d argue, surprisingly hazardous.

After all, how many charity leaders have privately decided that ‘Facebook isn’t important any more,’ based on January’s headlines about the changing algorithm? And what knock-on effects will that have on decision-making and budget allocation?


Get in front of the problem. Once your boss has accepted bad-but-authoritative information from a mainstream source, it’s already too late; they’ll be far less likely to accept a woolly interjection of ‘Well, actually, it’s more complex than that…’ from a member of their team.

So you have to make sure you’re the first person delivering the big digital news stories to your organisation.

Provide context. Provide nuance. Explain how this latest scandal or story relates to your charity (or explain how it doesn’t).

Be the speedy, entertaining, responsible voice of authority — so your boss already has a clear idea of what they’re looking at once that headline appears in The Guardian.

The structural (again): Your boss is likely being fed digital conservatism from higher up the organisational ladder.

One thing that never quite fails to shock me about the charity sector is how often decision-making isn’t decision-making at all, but rather a reactive drip mechanism based on escalation down the organisational chain.

Here’s a purely hypothetical, but I suspect familiar, example in the field of social media:

You send out a tweet aimed at your younger followers, using a gif, or meme, or jokey contemporary reference. The tweet performs well.

Someone in your board of trustees sees the tweet, and, not understanding it, asks a (gentle) question about it to your CEO during the next meeting.

Your CEO hasn’t seen the tweet, and is caught off-guard. They send a (less gentle) message down the chain asking a senior stakeholder to look into the problem.

Eventually, you’re called into a room by your manager, who is frantic about a complaint that appears to have come down through all the most important people in the organisation.

The tweet is hurriedly deleted, and never spoken of again. At no point do you have the power to point out how well it worked.

Again, I think this kind of drip-effect is particularly prevalent in charity digital for two reasons:

  • Everyday digital decision-making is usually invisible to senior stakeholders, but the everyday results are extremely visible. In the case of trustees, your output may well be the aspect of your charity’s work that they engage with most frequently…which means they’ll have opinions about it, even if they don’t have direct contact with you.
  • Trustee boards, on average, continue to display a worrying lack of digital knowledge. In the 2018 Charity Digital Report from Zoe Amar and David Evans, just 20% of respondents rated their trustees’ digital skills ‘good’ or ‘excellent’; 69% went with ‘low’ or ‘some’, while a further 12% simply didn’t know.

Combined, these issues can create a genuinely toxic situation for you; one where your boss is wary of taking your digital output in new directions not because they don’t want to — but because they’re worried about unanswerable, secondhand criticism coming back at them from further up the ladder.


You need to break out of the downward communication chain, and ensure that your digital advocacy is spreading further than your immediate team.

Talk to the CEO about Twitter. Ask to present to the leadership about your recent email campaign. If you’re feeling brave, suggest the establishment of a new digital trustee.

You’ll want to be careful to ensure your boss doesn’t think you’re going over their head — so work with them closely on this.

If all else fails…

…then reach out to a digital peer.

It can be frustrating, but sometimes a good idea needs to come from an outside source before it’s given proper consideration.

So invite someone else from the sector to come and talk for an hour about their work — in the context of digital best practice — as a voice of external authority.

Organisational complacency is bred in organisational isolation; a bit of healthy, collective insecurity about what others are achieving may do a lot of good.

It’s also a great opportunity for you, personally, to have a coffee, complain a bit, and hear from someone else who is almost certainly facing the same problems with senior stakeholders that you are (or has done so in the past).

We’re all in this together, and the charity world is a small one…so if you’re struggling to talk to your boss about digital, talk to someone else about it first.

Digital comms ’n’ stuff.

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