I want to tell you a story about Jack. You couldn’t meet a nicer bloke. His heart is in the right place, he’s a great operator and CEO, and has a reputation amongst his peers that we can all but strive for. But you wouldn’t want to have been in his shoes. So let’s learn from him.
It looks like your dream team.
Jack thought he had the dream team. Jill, John, Jacquie, Justin and Jim (I never use real names). And with his dream team in place he had his dream plan – to retire early (in three years time) leaving a legacy he’s proud of.
Just one problem. Confirmation bias. Jack was so wedded to the idea that he had everything sorted that he failed to notice the hairline cracks. Hairline cracks don’t get better without treatment, and unfortunately for Jack, he didn’t believe they were there. Not until it was too late.
First, Jill leaves.
One of Jill’s superpowers is that she’s a canary in the corporate culture coal mine. She knew trouble was on the horizon. In this case, Jack’s plan was far from dreamy for those he’d be leaving behind—old systems no longer fit for purpose, running too lean, and unfilled positions. The usual suspects.
But when she’d raise these issues with Jack, and the toll they were taking on her team for starters, he didn’t take her seriously. They’d gotten this far with the status quo. He couldn’t see a reason to change.
After many months of self-doubt and ridiculous hours, Jill had had enough. She resigned.
Jack was devastated. He cared about Jill. He valued her. She was on his dream team. She’d been part of his plan. He lamented:
Why didn’t Jill say how big the problems were?
She thought she had. Many times, and in many ways. Perhaps she didn’t say it in a way that he could hear. But what should she have done? Rant and rave, start to cry, create a scene? The concerns and solutions she presented fell on deaf ears.
Then John makes a big mistake.
With Jill gone, and her shoes being hard to fill, the other dream team members had to step up and fill some of the gaps while the job hunt was on. John was the obvious contender for one aspect of her role, and so he took it on. A good idea in theory.
In practice, he already had a very busy job. Now it was crazy busy. John was stretched, stressed and, inevitably, after some months, not at his best. It was probably just a matter of time before he made a mistake. In this case, a big, potentially very expensive one.
Then you discover your part in it.
Let’s not fall into the trap of not solving for the right problem. It’s clear Jack would have done better with Jill, if he’d been more attuned. That is, listened and really heard what she was saying so that he could take action to remedy the situation. But he wasn’t the least bit curious. He simply didn’t believe her until she left. Only then did the penny finally drop.
It’s not so clear cut with John. It turns out that part of the reason for the big mistake was that John had avoided a difficult conversation.
For years now, John has avoided difficult conversations and Jack has avoided helping him step up out of his comfort zone. Instead, Jack would step in for John and have those difficult conversations for him. Jack used to think he and John complimented each other so well. That they made a great team by filling in for each other’s gaps.
But now, with Jack intending to move on, he can see how he unwittingly colluded with John’s desire to avoid those conversations. In the end, Jack hasn’t helped John at all. He’s held him back.
Attuned leaders don’t just listen. They also help people see and close their gaps so that they grow. John will need to learn how to have those difficult conversations, and Jack has work to do, too.
It’s more than solving for the busyness, fixing the systems and finding staff. He has to address what he’s avoided with John for all these years.
Dream teams can kill dreams
These are hard lessons. Jack’s coming to the end of a very successful career. It may have been good while the ‘dream team’ lasted (at least in his mind), but things have clearly changed. As he said:
Work’s not fun right now.
To his credit, Jack started focusing on solving for where he let his people, the business, and ultimately himself, down. And that’s what made him such a joy to work with.
Facing reality is better than a dream
There are so many lessons to be learned from Jack. For me, I think the main one is that it’s better to face reality, sooner rather than later. And so, I’ve been asking myself:
What am I avoiding?
The challenge is that it’s not always easy to see. I guess, then, a dream team is the team who can help you do just that.
What’s the main lesson learned for you? What are you avoiding?
Image by Keith Johnston from Pixabay
