When you've set the pattern with an employee, you have to be tough to change it

When a manager and direct report have worked together for a long time, both can become complacent. Shaking things up, though, takes both finesse and courage

Dear Bob ...

I run IT for a company that's grown beyond SMB (small to middle-size business) and is now a serious-sized business. I've been trying to coax my two direct reports, the heads of Application Development and Operations, to recognize that the way we've done things in the past isn't going to be good enough for the future. So far they haven't taken the hint.

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I know I have to shake things up. These two have reported to me for more than 10 years, though, and I find I just don't have it in me to tell them they aren't doing the job. We're all too comfortable together and too friendly, I guess.

Please give me an alternative to firing them or demoting them. I'll do it if I have to, but it would just about kill me and would demoralize our employees besides.

- Failed motivator

Dear FM ...

Congratulations. You did exactly what you were supposed to do -- build a strong leadership team with high trust and a strong sense of purpose -- and now you're seeing the downside. This happens more often than you might think. Often, termination or demotion are the result, too, because in the end, you're responsible for the health of the organization before you're responsible for shielding members of the executive team from their own limitations.

Be prepared, because those are the most likely outcomes.

Before you do, announce a strategic planning offsite for the three of you. Your instructions: Each of the three of you is to bring a short list of ways the company has done things in the past that have to change to avoid becoming barriers to the future.

That's it: What it is, how it's done now, how it must change. Everything is on the table -- leadership style, processes and practices, business culture, product portfolio, everything.

Most likely, your two managers will bring small ideas with them, minor tweaks that do more to preserve the status quo than to change it. Challenge them directly in the offsite, making it clear the three of you can't support a 500-person company the way you supported a 50-person company, and you need their best thinking to help you figure out the difference.

One or the other just might pleasantly surprise you.

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If not, there's one other technique you might try, which is to bring in outside help. At the risk of sounding self-serving, sometimes executives like the ones you describe need someone from the outside to tell them what to do differently. In this case, I'd advise bringing in someone who can provide both strategic consulting and executive coaching: the strategic consulting to help these two understand what they need to do differently from an operational perspective, the executive coaching so that they understand how they need to behave differently to lead a larger organization.

The odds still aren't terrific. But if you accomplish nothing else, you'll satisfy yourself that you gave your colleagues every chance to succeed before making a difficult change.

- Bob