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hament@skillionvision.com

Program Management & Issue Avoidance: Real Lessons from the Virtual Trenches

Managing a program is never just about tasks and timelines—it’s about people. And in a world where remote work, different time zones, and cultural differences are the norm, those people challenges only get trickier.

Let me tell you a story.

We once brought on a new salesperson—let’s call him Simon. Veteran in sales, tons of experience, and full of confidence. But after a couple of months, there were still no sales. I started joining his video calls, just to see what was happening.

And what did I see? Ten-minute monologues. No breaks. Simon would go on about everything under the sun—his research, product thoughts, lead opinions, strategies, even some philosophical takes on the market. It was a stream of consciousness, and while it sounded insightful, it completely skipped the one thing we needed to hear: how many leads he was generating.

Spoiler: not many.

So what was going on?

It was clear Simon wanted to show he was engaged—but he was also dodging real accountability. It wasn’t malicious. We’ve all been there. Talking can make us feel heard and in control. But in this case, it was a problem. We weren’t moving forward, and the rest of the team was starting to lose clarity too.

How do you deal with it?

You don’t have to be a tyrant to steer things back on course. Here are some things that worked for us:

Interrupt—politely but firmly.
If someone’s veering off course, jump in. I’d say something like, “Simon, can we pause and go back to the lead generation issue for a sec?” It puts the spotlight where it belongs.

Name the issue.
By calling it “the lead generation issue,” I framed it as a real, solvable problem. It helped Simon—and everyone else—treat it seriously.

Ask direct, measurable questions.
“How many leads did you find yesterday?” It’s amazing what clarity a simple number can bring.

Don’t underestimate one-on-one chats.
Taking things offline helps cut the noise and politics. We had Charles (our sales manager) meet with Simon separately to unpack how he was approaching lead sourcing. It worked.

Use your tools.
We backed everything up with Agile principles, Jira boards, and simple project docs. When expectations are written down and visible, there’s less room for confusion—or excuses.

Bottom it out.
This is one of my favorite techniques. It means really digging into a problem until you get to the heart of it. In Simon’s case, we found switching from cold Google searches to using LinkedIn InMail (and our networks) boosted lead quality—and volume—almost overnight.

Culture is contagious

One unchecked behavior can spread. If monologues become the norm, so does avoiding responsibility. That quiet inner voice that says, “It’s not my fault” or “this company just isn’t set up right” starts to echo in the team. Your job as a Program Manager is to catch that early—and cut it off.

Final thoughts

The truth is, no playbook will cover every scenario. But if you stay present, stay curious, and stay focused on the goals, you can guide your team through almost anything. Interrupt when you need to. Ask for the numbers. Set the tone.

Because the small stuff? It’s usually not that small.

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