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Leadership Forum: Avoid falling into the “when I was” trap

July 16, 2019
By Matt Pegg

When I am flying somewhere as a passenger, I love that I have time to sit and think and to both read and write. For today’s busy leaders, having time to just think is a true luxury. I wrote this article in cruise at 30,000 feet while flying over Greenland. It was the act of travelling from one place to another that sparked this leadership thought in my mind.

In today’s world, there is more career movement than ever before. In the past, mobility on your resume was viewed as a bad thing, but that is simply not the case today. Today’s leaders, and the executive recruiters that identify and place new leaders, view a reasonable amount of career mobility as a very good thing. Whether that movement is upward or lateral in one organization or is between two or more different organizations, career mobility produces both perspective and exposure that enhance leadership ability.

I am a fan of career mobility, but in this month’s article I would like to share one of the most common pitfalls experienced by leaders who move between positions in one organization or who move between organizations. This one behaviour quickly compromises a leader’s reputation and acceptance within the new organization. This behaviour is what I not so affectionately refer to as “when I was.”

Leaders walk a fine line when attempting to leverage and reference the experience they gained in their former roles, especially those things that brought about positive change and produced results. They risk being quickly, and often silently, dismissed by their new team for being seen as constantly stuck in the “well, when I was” mode.

The tendency to frequently refer to your previous position, team or organization happens naturally and automatically. It sneaks up on you without warning, and all too frequently resides in the leader’s blind spot.

We do this as a result of being outside our comfort zone, in a new culture that we don’t yet understand, and where we silently crave being respected as being competent and worthy by those around us.

Let’s face it, it is more comfortable explaining how things worked or what you did successfully in the role or place you came from than it is engaging your new team within an organizational culture that you have yet to learn. Your new team will be supportive and tolerant for a short period of time, but they will quickly expect you to be a part of their team and not to live in the past.

This is one of the most difficult aspects of integrating into a new team, division or organization. Of course, you never want to disregard the skills, experiences and perspective that your leadership abilities are built on, but how can we leverage our past without alienating ourselves from our new team members?

I recommend learning to use language such as, “In my experience,” and, “Have we considered?” rather than falling into the, “When I was in such and such a place, we did it this way” trap. This provides an effective means of bringing your perspective to the table, without making your new team feel as though they are being subjected to yet another walk down your personal memory lane.

Without any doubt, leaders who ask timely, effective questions are far more successful than those who tend to automatically prescribe the correct answer without seeking to understand the local history and the perspective of the talented people that surround them.

Make no mistake – there will frequently be times when you will be asked specifically about your past experiences, and that information will be immensely valuable to your team. Leaders should never shy away from, nor attempt to “forget” their past experiences, including both past successes and mistakes. However, we owe it to our new team to make every effort to fully integrate into our new role and to be present in today’s reality rather than defaulting to our past.

What everyone wants in a leader is a clear sense of vision, dedication, commitment and engagement. Be that leader. Be the one who seeks to understand how we do this, how we got here, what our team needs and then make it clear that your priority and focus is on the future of this team.

As leaders, our past experiences and stories are like seasoning on food. Using them in moderation enhances the entire experience although using too much can ruin a very good thing.

Avoid falling into the “when I was” trap and your integration into your new leadership role will go much smoother and will be a much more successful and enjoyable experience for both you and your team.


Matthew Pegg is the chief with Toronto Fire Services, having previously served in Georgina, Ajax and Brampton, Ont. Contact Matthew at matthew.pegg@toronto.ca and follow him on Twitter at @ChiefPeggTFS.