In today’s episode of Lessons in Leadership, Dave Anderson continues his powerful series, “Identify and Overcome the Six Temptations of Successful Organizations,” inspired by his book Up Your Business. After tackling complacency in the first installment, he now turns to a second, equally dangerous pitfall: thinking too small because things are going well.
When organizations reach a level of success, many leaders unconsciously slip into “maintenance mode.” They stop pushing boundaries, assuming that good performance is enough. Anderson warns that success should never be the finish line—it should be the platform for even bigger thinking.
Leaders must be willing to challenge themselves, even when current results look strong. It’s easy to settle into comfort, as human nature tends to favor the path of least resistance. However, when we stop reaching, we start regressing.
"This is not a dress rehearsal. We don't get to come back and do a day, a week, or a month over again. Make sure your thinking is right because as the leader, you're supposed to be able to see farther, more, and sooner than your people."
Instead, leaders should pursue goals that stretch their limits by asking, “Do we still have big goals that we’re not equipped to reach yet?” The best goals aren’t the ones that match our current competence; they’re the ones just beyond it. Without that stretch, there’s no genuine growth.
To identify areas of opportunity, Anderson urges leaders to ask themselves: “Are we near our fullest potential?”
Psychological research supports this finding: when a goal is either too easy or too difficult, people tend to disengage. The sweet spot lies just outside the comfort zone, which is challenging enough to warrant new thinking but still achievable with effort.
An additional critical question leaders should ask themselves is, “Where am I playing it too safe?” If current systems and processes can hit the goal without change, the goal isn’t challenging enough.
The most successful leaders are able to see further into the future than their teams. They’re able to see the bigger goal in the distance and encourage their teams to rise to meet the challenge.
Because if not them, then who?
