Talking to Senior Leaders When Things Aren’t Going Well

When a project is struggling, gaining confidence from senior leaders is important. What senior leaders want to know is the extent of the business risk, whether someone’s on top of it, and whether what was promised will be delivered. Your job is to answer those questions in their language, not PM-speak. Here’s how:

• Don’t name the problem as a lack of discipline

Walking into an executive conversation and describing the issue as ‘low project management maturity’ rarely lands well. Focus instead on the business symptoms: missed timelines, unclear deliverables, decisions getting reversed, teams not aligned. You can work together to draw conclusions about the root cause, then quickly shift to how you will address it.

• Translate technical problems into business exposure

When technical teams raise issues, they rarely describe them in business terms.  Your value in those moments is being the person who can explain what the technical problem actually means for the business — what it costs, what it delays, what it puts at risk. If you can’t articulate that clearly, the executive can’t make a good decision. Get comfortable being the translator.

• Ask what they think the problem is before offering a solution

When you’re brought in to manage a struggling project, one of the most useful things you can do is ask the assigning manager what they think went wrong. Their answer can shed light on the real constraints, what’s political, and where they’re prepared to give you room to operate. It also gives you an entry point to talk about what you’d do differently without sounding like you’re criticizing what came before.

• Focus forward, not on what happened

When a project is struggling, briefly share what went wrong, but don’t drag out the details. The primary focus of your reports should be on what should happen next to address the issues. That approach tends to get people working together rather than ducking blame.

• Give executives what they want: predictability

At the senior level, confidence in a project often comes down to one thing — predictability. Can you tell them what’s happening, what’s at risk, and what you’re doing about it, in terms they can relay to their own stakeholders? If the answer is yes, you’ll earn the latitude to keep introducing the practices that make that predictability possible in the first place.