Some of you were blown away by the plenary session that Paul Gaffney, currently Chief Digital Officer for Omni Logistics. Previously, he was the head of software for The Home Depot, CTO of Dick’s Sporting Goods, and CTO and head of supply chain at Kohl’s.

Paul had made the observation that many technology leaders might be doing their subordinates’ jobs instead of their boss’s jobs. So during the breakout, I asked him to do a role-play he did with Jeff Gallimore, where Jeff played his boss, who wasn’t very interested in having Paul do his job.

It was an amazing demonstration of modeling how one starts that conversation, and what to do when there are clearly issues that need to be fixed beforehand.

At GeneCon, Paul and I did another role-play, where I was the boss presenting his annual performance review, and the main advice he got was, “Keep doing what you’re doing.” This is not particularly helpful advice and certainly doesn’t help advance one’s career.

In the role-play, Paul again wonderfully models taking responsibility for getting the feedback he needs even if it might be hard for him to hear, making it possible for his boss to share it, and gets some surprising feedback.