How to turn a disappointing conversation with a colleague into a win

By Mike Cook
For the Bellingham Business Journal

I was working with a young manager I have been coaching who had just delivered a tough review to one of his direct reports. In reflecting on how his session had gone he mentioned that the employee’s last manager had stopped by recently and apologized for not previously addressing the employee’s performance shortcomings.

“So why couldn’t he have handled this before now and skipped the apology?” my young colleague quipped. “What good does that apology do me now? So one more time I am left to be the bad guy!”

He may have thought he was asking a rhetorical question, but I decided to provide him an answer, albeit perhaps not one he was looking for.

“So did you hear the invitation in the other manager’s apology?” I asked.


“What do you mean invitation?” he asked.

I responded, “Well you asked why he couldn’t have skipped the apology, how about interpreting the apology as an invitation for some coaching?”

Again the young manager was silent for a bit, then said, “Wouldn’t that seem a bit arrogant on my part, suggesting that maybe he was looking for some coaching?”

So here was a young manager expressing the limits of his vision in much the way philosopher Arthur Schopenhauer a couple of centuries back suggested that we all do:

“Everyman takes the limits of his own field of vision to be the limits of the world.”

I have reached this point time and again with managers I have coached over the years: a failure to look beyond some disappointment they have experienced and create an empowering alternative interpretation of something that has occurred.

So I responded, “Well maybe it would depend on how you asked the question.”

The point I was getting to was that this young manager had a gift to offer the employee’s previous manager. So I went on, “You have spoken to me before about this manager as someone you work well with. What if you went back to him now and asked to talk about the apology again and made him an offer?”

It seemed that I had thrown my colleague a real curveball when, finally, he asked, “Could you tell me how that might go?”

So here now was the request for coaching that had been missing.

OK, I said how about this, you could go back and ask to revisit the conversation. Knowing him as you do I expect he’ll accept the request. Once underway I suggest that you thank him for the apology but let him know that it would be of greater importance to know that he was going to correct this failing and not have a similar situation occur in the future.

You then can offer your own skills and let him know that you’d be more than happy to coach him when the next opportunity comes along for a tough conversation and he is thinking of passing it up.

He’ll either accept the offer or not and let him know that whatever his choice the offer will remain open. I finished off with this question, “Which do you find preferable, leaving things as they are and having your opinion of the other manager damaged or taking this initiative and recognizing that your gifts are to be given not used to make yourself feel superior to those you work with?”

Maybe to you as the reader the answer to my question seems obvious but it is not. For this young manager to accept my suggestion he was going to have to break through one of his own limitations — not wanting to appear arrogant. There was going to be a win in this for everyone involved if it could be pulled off. We’ll see.

Now what about you? Where have you settled for a disappointing result from a conversation?

Let’s face it, most of us are not that great at dealing with disappointing results from a conversation we’ve had with a spouse, superior, direct report or co-worker. We took our best shot and it did not carry the day. How many of us are then willing to re-group — maybe not in that same moment, maybe a day or two later when we’ve had time to gather ourselves — and go back, admit our disappointment and ask for another opportunity to have the conversation?

I’ll tell you a secret … if you labeled that first conversation as not only a disappointment but a loss you will not likely go back because you do not want to face losing twice. If, however, and you need to be honest, your desire is to contribute and create a win/win outcome, then it is worth facing the disappointment again. You have more to gain than to lose.

Mike Cook ‘s columns appear on every other Tuesday. He facilitates a CEO peer advisory group in the Whatcom/Skagit area. He can be reached at He recently published ‘Thriving in the Middle: Why Managers Need to Be Coaching Each Other.”

Note: A version of this column was previously published in the BBJ in 2011.

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