Take Initiative

Take Initiative

Dealing with Difficult Conversations

It was one of those awkward moments for everyone – and especially for Jesus, who had to engage two difficult conversations in a matter of minutes.

You’ll find the story in the 20th chapter of Matthew’s Gospel, where we meet the mother of the apostles James and John – perhaps history’s first ever pushy “stage mother.” She’s no fool. As she approaches to ask a favor, we’re told she paid him homage and then indicated she had a question to ask. He invites her to ask it.

Instantly, her tone seems to change from making a request to giving an order. ““Command that these two sons of mine sit, one at your right and the other at your left, in your kingdom,” she tells Jesus.

She wants Jesus to favor her sons – a natural enough thing for a parent to desire. But by pressing her desire publicly she puts Jesus in an awkward position.

Of course, she really doesn’t catch him off guard. He has this incredible awareness about Himself, His role and the environment in which He is imbedded. Thus, He provides us with a model to guide us in our own difficult situations.

The apostles’ mother had approached Jesus only moments after He had had told his disciples: ““Behold, we are going up to Jerusalem, and the Son of Man will be handed over to the chief priests and the scribes, and they will condemn him to death, and hand him over to the Gentiles to be mocked and scourged and crucified, and he will be raised on the third day.”

His challenging forecast apparently didn’t affect her. No matter what happened to Jesus, she was focused on getting the best deal possible for her sons. So, Jesus calls her and her sons to realize the larger picture: “You do not know what you are asking,” He says. Then, to make the picture more complete, He asks them: “Can you drink the cup that I am going to drink?”

The two apostles are naive. They answer without a moment’s hesitation: “We can.”

Jesus confirms that they will drink His cup. But then He adds: “To sit at my right and at my left, this is not mine to give but is for those for whom it has been prepared by my Father.” In effect, such decisions are above His pay grade. His whole life is about serving His Father, and He’s not about to let anyone or anything interfere with that mission

There’s an important lesson in Jesus’ response, one that reminds us to always be mindful of the reality in which we are operating. Sometimes people ask things of us that make us feel uncomfortable, even threatened. Often that’s because we’re not in a position to grant the request even if we wanted to. So we feel powerless in the moment and we react defensively – and in the process we take on more than we should rightfully take on.

We respond that we won’t do what has been requested when that fact is that we can’t do what’s requested, no matter what we would like to do. When we take on the additional burden of refusing to grant a request, our refusal can come off as personal. “Why are you doing this to me?” the other person may ask.

Now the conversation has moved from what we won’t do to something that we are doing – willfully refusing another person’s request. It’s seldom pleasant after that.

It’s true that sometimes we don’t grant people’s requests for our own reasons. When that’s the case, we have to deal with it. We have to take responsibility for our decision and make an effort to get the other person to understand why we are not simply indulging them.

But when we can’t indulge a request – without regard to whether or not we want to – we should do as Jesus did and simply say so. Then if it seems appropriate, we can explain why we can’t give the other what he or she wants. If the discussion continues, we have to be vigilant that it does not move from the issue of can’t to the issue of won’t. That’s one cross you don’t have to carry.

In Jesus’ case, a different challenge presents itself. As Matthew tells us: “When the ten heard this (their mother’s special request), they became indignant at the two brothers.”

Maybe the brothers put their mother up to making her request. Or maybe she did it on her own without consulting them. If that was the case, they were probably shocked and embarrassed to hear her ask Jesus the favor she asked. We’ll never know.

What we do know is that when some members of a group – it might be a family or a work team – ask for special consideration, the other members resent it. The apostles were no different than the rest of us in this regard. No matter whether Jesus granted James and John a special favor, just asking for it crosses a line.

So Jesus has a new problem now. And there’s a lesson for us in how He deals with it.

It’s a lesson that escaped me for many years as I ran newspapers and newspaper groups. Especially when I first started, I had a tendency to ignore festering wounds with the hope that they would just heal and disappear on their own. But as some sage once noted, “Hope is not a strategy.”

As some sage once noted, “Hope is not a strategy.”

What experience should have taught me more quickly than it did is that festering wounds usually don’t heal on their own. Usually they only get worse until someone intervenes. The wound needs to be cleaned. If foreign material is in the wound, say a sliver, it needs to be removed. The wound needs to be disinfected and dressed. And then it needs to be monitored. In some cases, more intervention will be needed before it eventually heals.

Human organizations are bodies – open living systems that need to be served as you would your own body. If festering wounds are not properly attended, they can ultimately prove fatal – if not to the whole organization, then to a significant part of it, say an arm or a leg. If that’s the case, the organism may survive, but it is never the same, never quite as efficacious as it was initially.

Jesus knows all that. So when the 10 become indignant at the other two members of their team, Jesus doesn’t wait with some vague hope that the anger, pain and loss of trust will just heal and go away. Instead, we’re told, Jesus immediately summons them together and makes this crisis a teaching moment.

He uses the moment to explain to His apostles what leadership really means, what it should look like. He tells them: “Whoever wishes to be great among you shall be your servant; whoever wishes to be first among you shall be your slave. Just so, the Son of Man did not come to be served but to serve and to give his life as a ransom for many.” (Matt 20: 26-28)

“Whoever wishes to be great among you shall be your servant" (Matt 20:26)

It wasn’t until I saw a video reenactment of that scene from the Gospels and saw how Jesus handled the festering wound in His ranks that I finally had the insight and the courage to proactively handle festering wounds in my own family and workplace. Now, each time a difficult situation or conversation arises, I remind myself of what Jesus did under the same sort of circumstances.

His example has been a huge help to me, so I can’t bring up the subject now without concluding, “Thank you, Jesus.”



Owen Phelps

Dr. Owen Phelps is Director of the Yeshua Catholic International Leadership Institute and author of the book, The Catholic Vision for Leading Like Jesus: Introducing S3 Leadership — Servant, Steward, and Shepherd. He has presented Lead Like Jesus Encounters in Canada, Uganda and India, as well as all across the U.S.


He formerly served on the faculty of the College of Business & Management at Cardinal Stritch University in Milwaukee, and was a consultant on the U.S. Conference of Catholic Bishops’ Communications Committee for about a decade. He has served as a consultant to church organizations from Vermont to Texas. 


Dr. Phelps was an award-winning writer, columnist, editor and publisher with a multi-state publishing company before he began work in ministry. He has written several articles and contributed chapters to two books devoted to issues of faith-based organizational performance.


He and his wife Jane, a CPA, have been married for 49 years. They live in Durand, Illinois, and Lac du Flambeau, Wisconsin, and they have five grown children and 17 growing grandchildren.