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Five Skills for Leading Strategic Conversations

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Leadership used to be a pretty straightforward affair. The boss knew all the things, and told all the people who worked for them what to do.

Nice. Simple. Clear.

With the explosion of knowledge work, it’s not quite this easy anymore. Leaders aren’t always the experts - and nor should they be.

Who’s the expert now?

Peter Drucker describes a knowledge worker as “people who know more about what they are doing than their boss does.

When you’re leading people who know more about their job than you, you can’t just tell them what to do. So the whole ‘leader-as-expert’ paradigm doesn’t work anymore. As an expert, your job was to have the answers. As a leader, your job is to enable your team to find the answers.

Which is hard, because actually - expertise does matter. Leaders without domain-specific expertise generally have to work harder to gain the respect of their teams. General managers and sector-hoppers can struggle to understand context, design suitable systems and motivate and reward people effectively. For commercial managers in fields like law, medicine or engineering, this can be double-tough if all the SMEs you lead turn up their nose.

When you’ve got domain-specific expertise, it’s easier to hold your team to account, to deliver first-rate technical performance and to communicate internally. So, yeah. What you know counts.

But you can’t know it all. Besides, the more senior you are, the more you’d have to know. No-one expects the CEO to be a marketing whiz, IT guru, legal boff, technical expert and communications visionary all in one (or at least, they shouldn’t) but they do expect you to know enough to ask the right questions.

Enter: the strategic conversation leader.

The strategic conversation leader

Finding the expertise/leadership sweet spot lies in knowing enough to ask good questions. If you can ask good questions, it doesn’t matter whether you understand the technical aspects of someone else's job. Because your role isn’t to do the work - or even to direct it. It’s to enable it.

I might be biased here - I’m a career facilitator after all - but I’m convinced that the leaders who’ve mastered the skill of leading strategic conversations have a huge edge on those who don’t. In one of my favourite books on the topic - Moments of Impact - Ertel & Solomon argue that leading strategic conversations that drive change is the most important leadership skill that you’ve never been taught. I couldn’t agree more.

Strategic conversation leaders are the ones who can marshall and mobilise their teams in the right direction, to draw insight from the clever people they hire, and to build ownership and engagement that sustains.

Sure, you can just work on your communication skills instead. You can find the right way to tell, persuade, command or manipulate people into doing what you think is right. But if that’s the goal, why bother having a team of clever people at all?

Strategic conversation leaders know better. They know that setting direction or rolling out change needs them to harness the collective power of talented individuals, so that those people can get out there and make good things happen.

Basic facilitation won’t cut it

Here’s where it gets tricky, though. Regular facilitation training is unlikely to help you.

You’re not just a facilitator. Traditional facilitation, like early leadership, was a clearly defined task.

An objective, process-driven person would rock in with a handy-dandy toolbox full of exercises, remain totally detached from the outcome, and make sure a group delivered an outcome.

They had no skin in the game, and the responsibility for making conversations a reality stayed with the people in the room.

When you’re the leader, it’s a bit murkier. You’ve got responsibility here. The outcomes of your conversations - and the change they inspire - rest on your shoulders. You’re holding a strong sense of vision and direction, and your teams look to you for that. So, what do you do?

You learn to ask tricky questions. You take your ego out of the game. You slowly and consistently build a reputation for being onto-it, but open. You genuinely open yourself up to the brilliance of your people, and master the art of supporting them to succeed and holding them accountable, in equal measure.

Five strategic conversation leadership skills

For a long time, we assumed that if you were a technical expert, and you did more of the same, you’d be successful. An MBA would give you all the add-ons - finance, marketing, accounting, operations management - and you’d be away laughing.

My upcoming book You Don’t Need An MBA, busts that myth. In the new world of work, those things can be outsourced. But there’s some five critical areas that can’t be, and each of them comes into play here...

Skill one: flexibility

You need to be flexible - aware of your environment, open to new ideas and ready to change course while the world shifts around you. In a facilitation context, that means putting away your preconceptions and cultivating a sense of consistent and compassionate curiosity about what’s possible.

Skill two: decisions

You need to know how to make good decisions - which is all about the process, not the outcome. In a facilitation context, that means putting your attention into structuring the conversation - the right people, at the right time, talking about the right thing, with the right attitude - rather than attaching to an outcome.

Skill three: systems

You need to think in systems - which is all about perspective. Rather than focusing on the symptoms of your problem, you encourage others to zoom out and work together to see how the puzzle pieces fit together, and what the underlying issues are.

Skill four: performance

You need to understand the true drivers of performance - which is all about focus and empowerment. Rather than getting entangled in the work yourself, or bulldozing your way to the finish, you help others to narrow their focus to what matters the most, and create the conditions where they are able to make those priorities a reality.

Skill five: influence

You need to prioritise influence - which is all about mobilising others to action. Rather than worrying about how to communicate, or what to put on your slides, put your energy into building a coalition of enthusiastic collaborators who feel heard and seen.

Do these things, and you’re not the know-it-all leader, but you’re not the know-nothing facilitator, either.

You’re a strategic conversation leader, drawing on your expertise to mobilise others and drive change… outside of the room.

And who doesn’t want to be that?