The Journey: 16 Swing and a Miss

There’s a first time for everything.

I’ll never forget my first board meeting as a new VP when I was presented with my first-ever board-owned revenue target.

Looking at the number, it was clear it would be a stretch.

But based on the data I had at the time, there was no obvious reason why we couldn’t hit it.

I was still new and like many new leaders, I didn’t know what I didn’t know.

So I assumed if this was the target they set, it must be achievable.

Who was I to question it?

We wrapped up the meeting. I left feeling optimistic. Excited. Ready to prove myself.

Then the quarter began.

Month 1: Some early warning signs. But I stayed positive, after all, bumps in the road were normal, right?

Month 2: Those bumps got bigger.

Month 3: Reality hit.

We weren’t just going to miss the target, we were going to miss it by more than I was comfortable admitting.

The last day of the month and the quarter came and went.

Just as I feared, we missed.

And then came the second "first" of my VP career:

Marching back into a board meeting to explain why.

What I Learned (The Hard Way)

Missing a board revenue target early in your VP journey can feel like a gut punch.

But honestly?

It was one of the most important leadership lessons of my career.

If you ever find yourself in a similar situation (and at some point, you probably will), here’s what I recommend:

1. Communicate Early and Often

If you spot risk, don’t sit on it. Raise it. Talk about it. Document it. Board members don’t expect perfection but they expect visibility. It’s far better to show up proactive than reactive.

2. Rebuild Trust with Insights, Not Excuses

When you miss, your credibility is tested. What rebuilds it isn’t blame or excuses it’s insights. Bring a real understanding of why you missed, what the data now tells you, and how you're applying those lessons going forward.

3. Run a Post-Mortem

You owe it to yourself, your team, and the business to dig deep. Where were the breakdowns? Were the targets realistic? Was there a forecasting issue, a process issue, a product issue, a people issue? Post-mortems turn a failure into a blueprint for future success.

4. Create a Clear Action Plan

Don't just say you'll "do better." Map out the steps. Outline the initiatives, shifts, and reinforcements you're putting in place. Confidence comes from a clear plan not vague promises.

Looking Back . . .

Today, I realize that blindly accepting that number wasn’t a show of loyalty, it was a missed opportunity for real leadership.

Real leaders don't just accept goals.

They question, validate, pressure-test, and advocate for what they know can be achieved based on reality, not just hope.

I wasn’t ready to do that yet.

But missing that target was the wake-up call I needed to level up.

And if you’re reading this and nodding along ... maybe it's the reminder you need too.