2025's Biggest Leadership Challenge

The biggest problem I see now can be summarised in a single, overused, misunderstood word.

2025's Biggest Leadership Challenge
Photo by Jukan Tateisi / Unsplash

One of the benefits of working with leaders across the world is that you get to spot patterns. You get to connect the dots across industries and time zones and levels of seniority. Well, you do if you listen carefully.

In 2023, the biggest challenge leaders faced was recovery from the pandemic. No, I haven't got my dates mixed up. This was the unseen thing. We were all still struggling to recover from what happened in 2020-21. On the surface, we'd all moved on, but psychologically and physiologically we hadn't.

And so, one of the biggest acts of service I was able to provide was to help my clients to see this and then to handle it. For themselves and others.

This isn't a problem I see much these days. The biggest problem I see now can be summarised in a single, overused, misunderstood word.

That word is "woke".

The Oxford English Dictionary defines the word like this:

Progressive or left-wing attitudes or practices, esp. those opposing social injustice or discrimination, that are viewed as doctrinaire, self-righteous, pernicious, or insincere. Hence: such attitudes or practices seen as constituting a collective social movement or agenda.

I am choosing the words that I write today very carefully. And I have no intention of taking sides on any issues. That's not my role.

But I see the cultural debates (wars?) having a real impact in businesses and organisations across the world. This shows up in two main ways:

  • People (often older) who are confused about what they can/can't/should/shouldn't say. This leads to fear, silence and anger.
  • People (often younger) who are confused about why the world of work doesn't seem to match the values they have. This leads to confusion, silence and anger.

Here are two questions I've helped people with in the last few months:

  • Can I discipline someone who tells me they struggle with mental health?
  • Can I ask my manager for some flexibility without seeming flaky?

Honestly, in both cases, in the confidential coaching space, the questions were phrased differently with more sweary words and frustration.

So what's the answer?

Well it isn't (in my opinion) to wade into the rights and wrongs of different perspectives, or to start demanding other people see the world the way we do.

The answer is to learn the lost art of adult-to-adult conversations.

Once you do that, you can remove the fear and say the things you want to say in a way that is likely to be heard and respected. Even if it isn't agreed with.

Which is what we all want, right?

I know it is, because I regularly run a workshop called "How to Talk to Adults" that helps people and teams to improve their workplace communication. If you want to research some of the ideas in that, I'd suggest you look into:

  • The Parent/Adult/Child model from Transactional Analysis.
  • The Drama Triangle and how to avoid it.

Or, drop me a message and I'll tell you more about it myself.

Have a great day, Stephen


Every Friday I run HeRO Hour. It's group coaching for professionals all over the world. Each week we alternate between personal and professional development. This week the topic is: How Teams Can Make Better Decisions.

Soon I'll be launching a way for people to automatically subscribe to these sessions. But if you can't wait, drop me a reply and I'll tell you how you can join us.