Knowing When and How To Challenge Others

I had some feedback from a coaching client recently that prompted this post. At the end of each of my coaching sessions I usually ask how the session went and whether there is anything that I could do that would make our work together more effective.  Feedback isn’t always offered, but when it is it usually hits home.  This time was no exception.

What the client asked was that I challenge him more.  I took this to mean that, when necessary, I need to push him into places of discovery, places where it might not be comfortable to go.  Our coaching school refers to this as “courage to challenge”, because not only is it uncomfortable for the client to enter some of these places, it is uncomfortable for the coach to ask them to go there.

This is one of my areas of development as a coach, so when it was presented as feedback I started thinking about it right away.  One of the things that came to mind for me was how this same learning edge appears for me elsewhere in life.  It helped me understand my part in another challenge I’ve been having that I’d like to share as an example.

A work group I am part of is working on a new approach for a client I am responsible for.  We have been meeting regularly and had hit a critical decision.  The solution the group was moving toward wasn’t the one I was favoring, but I didn’t challenge it.  I can recall my own internal dialogue at the time. I told myself that I can be too zealous about my own approach and that I should sit back and allow other possibilities to unfold.  I participated, and asked questions, but the solution remained as proposed, I accepted it and agreed to present it to our client.

After our meeting I sat with it and realized that I didn’t have enough personal commitment to the solution that would allow me to propose it with conviction to our client. So at the next meeting, where the group was asking if everything was ready to go, I then spoke my mind and said I wasn’t committed to it. I caused quite a stir in the group, because they quite rightly expected that everything was moving ahead, and here I was causing them to go back over old ground.  We did end up with a solution that I could align behind, but only after taking another whole meeting to get through the decision again.

If I had had the courage to challenge the group in the moment during the first meeting, we would likely have arrived at this same place sooner, and without me creating a situation where our group dynamics became a concern.

Scenarios like this have caused me to dig deep to figure out what I can do better. Here are four key questions I came up with for myself on how and when to challenge.

Is it Important?

There are always things we see and hear that we don’t agree with or want to do differently. But if we always had to get our way it would be very difficult to maintain relationships (do you know someone like that?)  So when we encounter a situation where we might want to challenge, we first have to do a quick assessment of how important it is.  Ask this on two levels.  How important is it to me?  If the answer here is “not so much” then move on.  If the answer is “pretty important” then ask how important it is to the objectives of the team. Often we will find this as an opportunity for us to re-align ourselves with these objectives.

Is this the right time?

Timing is often everything.   From one angle, feedback is best delivered in the moment so if a challenge is to be offered it is best to do it when it arises.  On the other hand, it is important to be mindful of the other parties involved as well.  Often our need to challenge takes some time to process internally, and by the time we are ready the conversation may have moved past a point where it would make sense to offer it.  Likewise, if we are in a group setting and our challenge is only for one member of the group then it might be more appropriate to wait for an opportunity to have a one-on-one discussion.  Pick a time as close to the moment that gave rise to the need to challenge that honours the situation fully.

How do I challenge respectfully?

This might be the most important question of the four.  Nobody ever sets out to put a bad idea on the table, so challenging it with respect is paramount.  I like to think of the principles offered in the book Crucial Conversations by Kerry Patterson et al. First, make sure your challenge is aligned with the mutual purpose of the relationship. Second, follow a progression that starts with stating the facts (making sure that what we call facts are not a part of our internal story), telling our side of how we see the issue and then inviting others to share their thoughts on the issue.  As we do this, we need to be careful to talk tentatively, avoiding bold language and statements while experimenting with possible outcomes.

When shouldn’t I challenge?

I can think of two times that I know I shouldn’t challenge anything.  The first is when I’m being challenged already, and the second is when my emotions are elevated.  Often these two conditions exist at the same time, making it doubly sensitive.  Others have the right to challenge us as well, and as long as it is done respectfully, deserves our attention before moving on to our concern.  Dealing with elevated emotions is often much more difficult because emotions can hi-jack intellect.  Watch for the physical signs in your body of fear, anger, anxiety and shame so you can stay on top of your emotions. And if you catch yourself in the midst of delivering an emotion-charged challenge, just stop and reset by bringing yourself back to the first three questions.
All aspects of our lives are built on relationships.  It is a part of being human as we are a social species.  I also believe that relationships can only grow when they are challenged, although it is more comfortable for us to want to keep the status quo, because we know how to behave.

Leadership is all about relationships too, and just like coaching, these relationships are ones where it is our responsibility to help others grow.  How do you, as a leader, use this capacity to challenge to develop those you support?

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Ian Munro @

Ian Munro is a leadership and vitality coach with a primary passion for working with senior professionals who wish to improve their connection to and vitality in their career, or who wish to make a transition to a meaningful and rewarding retirement. His methods are focused on helping clients understand why they present as they do in day-to-day life, discover their authentic self and give themselves permission to build a meaningful and rewarding future, both professional and personal. Ian’s love for this work has developed naturally as he built his career as an executive and leader in the IT services industry, serving in many roles and facets of this industry over 25 years. As he reached the pinnacle of his career he began to search more deeply for meaning and alternate rewards from his own career and to begin to plan for his own “first retirement”.

11 thoughts on “Knowing When and How To Challenge Others

  1. It’s very important to give room for others to differ with us. we learn in the process and grow in leadership. It is also important to challenge others so that we can get ample feedback on their choices.

  2. A very thoughtful and vulnerable post Ian. When to challenge, when not to challenge, this is the question. I think you nailed it for me when you suggested the question, “How important is this?”

    So glad you’re enjoying and growing through your coaching practice. ❤
    Diana xo

  3. This is an excellent post and is me all over. I always need time to process first before I challenge. I feel this is better than flippant and impulsive challenges that may not be right. However, where this causes upset is when it appears that I have changed my mind. What I try to do now is to respectfully delay my input, rather than to seemingly agree – when my internal dialogue is saying ‘wait-and-think-about-it’.

  4. Great timing. It is an area of growth for me, not because I’m afraid to challenge (my reputation in general is quite the opposite and mostly appreciated) but haven’t brought it forward as fully in coaching. I am tackling this opportunity with renewed energy and appreciate the reminders about considering importance, timing and respect. Thanks!

  5. Great reflections and insight Ian.
    On the other hand …
    I’m not sure if what I am hearing resonates fully with me Ian. I sense there may be something left unsaid…

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