How Leaders Can Upskill Their Team

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Being Proactive in the Workplace


Sean: When do we need to start doing that? Is it when we bump someone up to be a leader of a team of four or five like we mentioned earlier? Or is it when they’re managing a team of ten like two teams at the same time? Because that is a really good thing. That is a fantastic thing to do, develop your team’s decision making skills and maybe telling them own up to it. If it fails, it fails. That’s going to be your decision. It’s your head on the chopping block and I support you when you make mistakes. I’ll pay for your tuition fee, no problem. But how do you know when to involve them in your think tank? In your decision making process? In your ideas on the wall?

Michael: It’s a great question. When they manage a team at ten feels too late for me, and I think it actually comes much earlier than when they’re even managing a team of four or five. You can build people’s capacity to be independent thinkers, decision makers. Earlier on, you can have a leader who’s managing a team of three and have that leader building that team’s decision making skills. You know, their willingness to engage in in tough conversations, their willingness to speak their minds and freely share their ideas. And so then when those people get promoted, if they do, it’s already embedded in the DNA. I mean, the question I would ask you to ask yourself, Sean, and for any listeners who are in a similar bucket, is like is the thing you’re trying to cultivate at the leadership level embedded in the DNA of the entire organization? Meaning does everybody at every level feel empowered to make these really tough decisions and to have their voice be heard? Now you can’t have – everybody can’t be the boss. And that’s not what I’m saying, I am suggesting that whatever you want to cultivate at the leadership level is embedded in the DNA of the organization. So you are not starting from scratch every time somebody gets promoted.

Michael: I will say this, I’m going to give you some feedback, even though I’m not your coach and you can cut this out if you like. You may have just been saying this as a throwaway line on the podcast, but telling people that their heads on the chopping block, if they make a decision that doesn’t work out, is not going to encourage people to make those tough decisions. Right. There’s an opportunity there to say, ‘even if I have your back, hey, if this doesn’t work out, it doesn’t work out. The most important thing here is that you’re running lead on this.’ Right. And that’s a different message to somebody, even if that’s just a throwaway line. You cast a huge shadow as a leader. If somebody in your team hears that, they’re going to be more hesitant regardless.

Sean: Yeah, for sure. For sure. I mean, perhaps I’m too deep into being the leader, you know, that’s what I think about every day. My head’s on the chopping block if I decide this and that. So yeah, for sure.

Michael: But I know it. I’m with you. I’m in your shoes, man.

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