How PMO Leaders Get Ready by Doing the Work

You Do Not Become Ready by Waiting 

There is a version of “I’m not ready” that sounds responsible. You care about the outcome, so you want to prepare. You read more, work on the plan, rehearse the conversation, save the training page, and tell yourself you will take the next step when you feel more confident. 

Preparation matters. I am not telling you to walk into a high-stakes executive conversation without understanding the business context or to take a reckless leap because courage sounds good in a podcast episode. Get the training you genuinely need. Ask for support. Practice in a safer environment when the risk calls for it. 

But there is a point where preparation stops preparing you and starts protecting you from the very experience that would make you better. 

That is where a lot of capable PMO and transformation leaders get stuck. 

I Did Not Get Good and Then Start Speaking 

I have delivered keynotes, workshops, panels, and presentations for years. What people see now is the result of a lot of repetitions. They did not see the version of me who was terrified that I would forget what I wanted to say, get a question I could not answer, or discover that nobody had a reason to listen to me. 

One of my early leadership moves was joining the board of a local PMI chapter. Even that required me to act before I felt ready. Later, when I was asked to join a panel about PMOs, my first reaction was absolutely not. I would be on stage in front of hundreds of people answering questions I could not predict. 

I eventually said yes, and then I got serious about preparing. My friend Mike Hannan helped me brainstorm and practice. He asked questions. I practiced answering them. We worked through the situations I was worried about. The preparation became useful because it was pointed at a real commitment I had already made. 

Then I got on the stage. 

When an audience member started talking about how executives should simply understand the value of project managers and the PMO, something changed. I stopped worrying about whether I was saying everything perfectly and leaned into helping. That moment taught me something I could not have learned by rehearsing alone. 

The Repetitions Create the Confidence 

After that first panel, I kept speaking. I paid attention to where people leaned in, where I lost them, which stories helped an idea land, and which explanations made more sense in my head than they did out loud. I adjusted and went again. 

Eventually, people saw confidence. What they could not see were the repetitions, the professional development, the coaching, the practice, the feedback, and the investment behind it. 

That distinction matters because we often compare our beginning to somebody else’s thousandth repetition. Then we use the gap as evidence that we should wait. 

Discomfort is not automatically evidence that you are unprepared. Sometimes it is simply evidence that you are at the beginning of building a new capability. 

When Preparation Becomes the Wait 

I see the same pattern with PMO leaders who know something is not working. Executives are questioning the PMO’s value. Conversations are not going well. The team is overloaded. The leader is still stuck in execution mode trying to hold everything together. 

They know they need help, but they tell themselves they should get a little further first. They want the PMO to be more mature before they join the program designed to help them mature it. They want to solve enough of the problem privately that they will feel ready to ask for support. 

That can become expensive. 

Organizations do not always wait for you to feel ready. Executive trust can erode. People can start working around the PMO. The function can lose influence. In some cases, the leader can lose the role before they ever get the chance to apply what would have changed the trajectory. 

The leadership question is not whether you feel perfectly ready. It is whether you can identify the next responsible move and build the support around yourself to make it well. 

Learn, Apply, Get Feedback, Adjust, Repeat 

If you want to become more confident speaking with executives, you need experience speaking with executives. That does not mean walking in unprepared. Learn a useful structure. Understand the business context. Ask someone you trust to review your approach. Practice. Then have the conversation. 

The real conversation gives you information private preparation cannot. You hear what executives care about. You discover which questions open the discussion and where you need more context. You learn how your thinking holds up when another person responds to it. 

That is how learning becomes judgment. The learning matters, but the practice is how it becomes yours. 

Take the Next Responsible Step While You Still Can 

If you already know something is not working, do not wait for more damage to your credibility before you act. Get the training. Ask for support. Take the first responsible step while you still have time to change the trajectory. 

The work is what makes you ready. 

Press play above to hear the full story, the mistakes and repetitions behind the confidence, and the questions I want you to use when you are tempted to wait a little longer.