In a recent “Art of Managing” post, I focused on the challenges that almost all organizations face when trying to move beyond the successes of a fading past towards new markets and new ways of doing business. In the excellent book that prompted the article, "Escape Velocity," by Geoffrey Moore, the author raises the idea of Breakaway Leadership, but leaves us groping in the dark a bit, wondering just what this leadership looks like in the wild.

If you’ve lived through a successful migration of a business from a legacy market to a new world, you know that it’s a sometimes messy, often emotionally turbo-charged experience laced with a fair amount of doubt and fear. It’s also a time rich in experimentation and learning filled with a whole lot of “new” in the form of new people, new customers, new offerings, new products, new partners and so on.

I’ve personally been a part of exactly two of these that worked in a big way, and I’ve counseled clients who have ultimately pulled it off. I’ve also been around colleagues and clients who failed to execute. Earlier in my career, I was along for the ride when the train ran off the rails on a collapsing bridge over a big waterfall that emptied into a lake filled with alligators and sharks. At least that’s what it felt like.

While sensitive to stepping all over the fundamental attribution error when looking in the rear-view mirror, I can tell you there were and are leadership behavior differences that made a difference in the outcomes in my opinion. For this post, let’s explore some of the behaviors that supported a failure to Breakaway.

8 Leadership Tripping Points that Destroyed Attempts at Breaking Away:

1. Cloistered Cockpit Control. The senior management team assumed the responsibility for the change efforts (good), but failed to adequately involve anyone not seated on Mahogany Row (bad). They worked unceasingly to think through the change, but fundamentally lost track of what the people doing the work needed in the form of context, support and motivation.

2. Left the Legacy Behind. The painful reality is that what got you here won’t take you forward, but when you alienate the good people working hard to optimize outcomes outside of the spotlight, the culture shift crashes. The fact that the legacy business is paying the way for the investment in the future makes it all the more critical to both lead and manage this part of the organization with care and concern.

3. Only the Cool Kids Got to Play. Yes, it takes new people with new schools to facilitate a successful market shift, but it’s a huge mistake to not bring legacy talent along through opportunities, education and immersion.

4. A Shortage of Courage and It Wilted Under Pressure. As Moore points out, the worst of all economic outcomes is an attempt at building the future that wilts due to pressure part-way through the process. Leading major change is not for the faint of heart or the short-on-courage type individuals.

5. Taking a Lazy Approach to Strategy. When senior managers fail to hold themselves accountable to properly defining their new opportunity in the context of audience, problem/solution, competitor set, ecosystem and all those other vexing strategy issues, the lack of clarity creates a brutal case of mission drift.

6. The Royals Arrived and the Dictators Emerged. I’ve observed leaders take on an almost royal or in some cases dictatorial persona, with all of the attendant hubris, arrogance and carnage. Followers who remain take the leader’s every utterance as something between a royal decree and the law of the land, and every discussion in every meeting focuses on what people perceive the leader wants. I observed this in a Good to Great firm (Collins) that is no longer great and arguably not good. It was fascinating and horrifying to watch as good people deserted, messengers of market truths were regularly executed and the remaining shell of the organization was held hostage by one person.

7. Flailing and then Failing. Much like Jim Collins describes in his book, How the Mighty Fall, at least one of the steps on the road to ruin is an undisciplined pursuit of more. In the failed transformations I’ve observed, this malady is present in all circumstances. Frustrated over the lack of quick results, senior managers lash out in pursuit of new initiatives. Projects are started and abruptly stopped and new projects are heaped upon the existing overload of work. Eventually the organization grinds to a halt.

8. Trust Took a Holiday at the Top of the Organization Chart. A creeping lack of trust between a firm’s senior leaders is nearly almost fatal, and nothing kills trust faster than a team that has not linked arms around a direction and a set of choices. There’s no more heated time in a senior leadership group’s lifecycle than a major change initiative and the trend is towards entropy instead of order. Always fatal as it unfolds like a Kabuki Play on a stage that all employees can see. My least favorite senior leadership team ended up refusing to ever meet as a group in large part due to their not so secret contempt for each other.

The Bottom-Line for Now:

While the focus in this post is on large organizational transformation, the same issues and same behaviors emerge in attempts at team, unit or functional transformations. There’s a group of leadership behaviors that suck the critical energy out of any attempt to breakaway no matter the size or scale. And while part of the answer is to “do the opposite” of the above, life, business and organizational change are never that simple. For now, beware the tendencies described above and plan on a return visit for Part 2, where I’ll explore the behaviors that support success in Breakaway situations.

This post originally appeared at Published with permission.