Having just returned from a few weeks of vacation travel in Europe, I’m now faced with the task of getting back into the groove in terms of my work and daily routines. As we’ve all experienced, the glow from a good vacation can often disappear fairly quickly after return. The memories and insights, however, linger long after the emotional ‘high’ has dissipated – which is what travel is all about.

Funny enough, the memories that often remain top of mind for me, after months and even years have passed, are those where something has gone slightly ‘sideways’ during my travels. I’m referring to unexpected events that are not part of the original itinerary – such as missing a connecting train, leaving behind that just-purchased souvenir, getting lost in the back alleys of a foreign city or having to abandon a reservation at a cherished restaurant.

As long as health and safety aren’t compromised, we can often look back on these events with balance and humour, with the perspective of time, of course. Quite often the sideways element turns into an experience of greater pleasure or interest than that originally planned. That missed train connection leads to the start of a lifelong friendship with someone on the next train or the alternate restaurant serves previously untried dishes that you’ve since incorporated into your dinner parties back at home. Better yet, these anecdotes usually get the best response – and biggest laughs – from family, friends and colleagues.

This same principle plays out in the workplace: You’ll often garner greater interest and deeper learning when you share stories with your team about how things have gone sideways in your work world (assuming, of course, that your efforts to rectify the situation lead to some key learning, the desired outcome or maybe even something better)! A side benefit, or maybe even a key benefit, is that in sharing your vulnerability, you often strengthen your connection with team members.

Here are some suggestions for sharing with team members so that you leverage your own sideways experiences:

1.) Ensure Relevance

Before you even start to share your anecdote, ask yourself if your example is going to provide valuable insight and learnings for your team members. Whatever you share needs to be relevant to the current context in which the team finds itself. If it’s just a chance for you to share an interesting ‘war story’ from your past, it’s best to find another time and venue in which to share the information.

2.) Gauge Interest and Appetite

Determine if your assembled team members are in an appropriate mindset to listen and receive your sideways story and the resulting learnings. If team members aren’t clear on the issue under discussion, team member interests are misaligned around the situation or there’s a sense of real urgency, you’ll want to skip your anecdote this time around.

3.) Set the Context and Be Focused

Be sure to communicate the background context to your story so that team members can better relate your anecdote to the situation that they’re currently addressing. Draw direct links between your previous situation and what the team is facing right now. While you might be tempted to include lots of detail in your story, it’s important to share just the important points.

4.) Summarize Your Learnings

Wrap up your anecdote with a high-level summary of your key observations and insights: what you learned from your experience and how that now influences your approach to similar situations. Encourage discussion among team members to strengthen their understanding, challenge your conclusions and/or add to your insights.

Done well, sharing your key learnings when things have gone ‘sideways’ can be a very effective way to accelerate learning and strengthen engagement within your team. It might also be the spark that enables improved team creativity in capturing an emerging opportunity or addressing a pressing issue.

If you’d like to discuss sideways stories, opportunities for growth or communicating with team members, don’t hesitate to contact me at [email protected] or 250-882-8830 for a conversation regarding the benefits of executive feedback.

Scott Borland, Founder & President of CYGNUS Management Consultants Inc, , is a recognized expert in helping executives host strategic conversations and obtain high impact feedback. He brings insightful perspective and proven strategies to strengthen the alignment between strategy and leadership behaviour. Scott has presented frequently at regional/national conferences and is a regular contributor to online journals/blogs. Follow Scott on Twitter or add him as a connection on LinkedIn.