Be prepared to fail if you want to succeed
Let me tell you something important: despite all your best intentions and efforts, your transformation projects will go wrong. Often. In a number of different ways. Not only is that okay, but it is to be expected. Even with the best planning in the world, it is impossible to foresee how a complex environment such as an entire organization's ecosystem will react to your transformation. Such problems may occur because you made a mistake or missed a critical step in the planning phase, or because someone misunderstood what was said and passed down incorrect information. Other times, issues may be caused by something else completely outside your control, such as a pandemic or a war. Either way, you can’t expect perfection.
So, should you accept defeat before you even start? No - you should expect things to go wrong and prepare yourself to deal with them, as explained by the old adage: “it is not what happens to you, it is how you respond to it”. If the CEO sees every failure as the end of the world, things will go south pretty quickly. Whether they realize it or not, employees around them constantly take cues from their verbal expressions, body language, and reactions.
“it is not what happens to you, it is how you respond to it”
I once worked with a CEO who was overseeing a massive IT overhaul in a global company. The project was running way over budget and had already missed several milestones. I joined him in a few meetings, and his message was clear: stop bringing him problems and fix the project - after all, that was the reason the team had a job. Unsurprisingly, people stopped bringing problems to him, and things didn’t get any better. Problems were pushed down the organization to employees who didn’t have the view of the whole situation. They knew they had to deliver results within budget and within the plan - and that is exactly what they set out to do. However, to reach their goal, they cut back the scope of the project so much that at the end of two years, the new tool would have had even less functionalities than the current one. Again, not surprisingly, business unit leaders became so frustrated that they started a crusade against IT. The stalemate brooded for weeks until the situation was brought to the attention of the CEO, who then had to address a much bigger problem.
If you are serious about transforming, you must make friends with the failures that happen along the way. You need to welcome bad news and treat each issue as an opportunity to model the behavior you want your team to demonstrate. You must ask questions, understand what went wrong and why, problem solve with the team for alternatives they may have missed, document and share the lessons learned, and then ensure the team leaves with clear direction and an adjusted plan to go execute.
Last, you want to make sure the team is really pushing itself - after all, this is a transformation. You need to spend the time needed to make them believe they can deliver on the company’s goals - and that you are by their side through it all, even if that requires having to roll up your sleeves to show them what you expect.
You need to learn to enjoy the “sausage making” process knowing that, at the end of it all, not only will the desired outcomes be delivered, but you will have a much stronger and more engaged team to work with.