In our blog post from February 2 entitled, 10 Must-Dos to Be Among the 25% of Companies That Succeed in Business Transformation, we mentioned the need to deal aggressively with the skeptics—those who can’t or won’t get on board for business transformation. We failed to mention, however, that this is the single most difficult task most CEOs face (avoid, for that matter). While it’s pretty clear what needs to happen when a leader fails to deliver results or commits some kind of egregious error, it’s much less clear how to handle it when someone can’t or won’t get on board with a significant transformation.

We’re not talking about the leader who grumbles about having to learn a new online HR system or report T&E expenses differently; we’re talking about the executive who actively or passively opposes the strategic transformation you are trying to effect. By tolerating this kind of obstacle, you put your entire agenda at risk.

You may rationalize that the leader is talented and has contributed a great deal to the company in the past. The challenge here is that past performance does not guarantee future success. Not in the stock market and not in the leadership market. You must be more concerned about whether this leader has the emotional wherewithal and resilience to handle the ambiguous and uncertain future; not only for themselves but also for those whom they lead. Depending on the scope of responsibility, the ripple effect of just one executive’s recalcitrance can be devastating.

If you suspect that you are dealing with an executive who is more of an obstacle to change than an agent of change, here are some suggestions on how to move forward:

1. Talk to them. Share your observations of his or her attitude and/or behavior and the impact it has had on you, their peers and their team. Describe the kind of impact you need from this leader and the changes required to make it happen.
2. Ask them to reflect on what you have described and determine if they are willing and capable of making these changes. Suggest that this reflection take place over the course of a few days versus responding right away.
3. Talk about what they’ve reflected on and determine the best course of action:
   • If they are willing to and capable of making the changes, agree upon a time frame and what success looks like. Give them the time to make the change and come back together to evaluate at the end of the time frame.
   • If they are willing but incapable, determine if coaching or mentoring can close the gap. If so, give them the support they need and evaluate progress. If it is doubtful that the gap can be closed, discuss how to exit them from the organization in a way that is consistent with your culture and values and preserves their dignity.
   • If they are unwilling to make the change, discuss how to exit them from the organization.

You are not alone if the very thought of this approach causes heart palpitations. But you don’t need to go it alone. While it may be a first for you, The Bailey Group has helped many CEOs address similar challenges. We can help you, too.