Walk in the boss’s shoes

This blog post is a part of a larger Success habits collection that demystifies the “secret sauce” expectations that define a high performer at work. In this specific blog post, I illustrate the idea of taking top management perspective, which I defined in an earlier blog post.

Play the boss for a moment

Executives have a long list of expectations, all linked to taking a top management perspective. 

To understand where these expectations come from, let’s play a game: Imagine that you are a very senior executive at a large railway company.  

Take a moment to imagine your office surroundings: the comfortable executive chair, the gorgeous views from your corner office, the smell of the fresh coffee. Can you hear the office chatter behind the doors?

Of course, you have 14 appointments in your very busy day, you are running behind, and you have to squeeze in an emergency meeting instead of lunch. Can you also hear the sounds of your empty stomach?

Your lunchtime meeting

You meet a newly promoted manager who is in charge of a perfectly straight stretch of train tracks in your railway system. He wants you to approve his recommendation to let a fast train pass through the stretch. His argument is very logical: Here you have an empty, straight stretch of rails, why not use it?

As an executive, you consider the recommendation in light of these 3 bigger-picture factors: 

  • Just beyond that rail stretch, there is a busy train track interchange, and if you simply let a fast train pass, it may cause a collision

  • Another train may have to be delayed to give the right of way to the fast train, costing the company money

  • The tracks farther down the road are being replaced today by a different manager’s team, and the fast train would derail if it passes

What is your decision, now that you take a top management perspective rather than the manager’s siloed view? 

Your decision and feedback

Let’s assume that, walking in the boss’s shoes and considering the broader picture, you decide to turn down the proposed recommendation.

And now you, the senior, busy (and hungry) executive, just rejected a recommendation from one of your newly promoted managers. You can see the disappointment on his face, as his argument sounds very logical to him.

But what is on your face? After all, it is not that difficult to proactively consider the bigger-picture reasons that made you reject the recommendation. The manager could have done his homework and stepped out of his silo before he wasted your lunch!

Of course, you are a considerate executive who likes to coach their people and help them grow. So, you take this moment as an opportunity to offer some advice to the manager at the end of the meeting.

“Thank you for coming to this meeting prepared with a clear recommendation and supporting arguments. You are a core part of this rail company. As your responsibilities increase, I suggest that, in the future you,...”

(Complete the sentence. If you need help, read my earlier blog on taking a top management perspective.)

Practice shrewd empathy

Did you enjoy playing the boss at the rail company? For that, you used your empathy: the ability to put yourself in the place of someone else and appreciate how they see a given situation and how they feel about it.

Taking a top management perspective requires you to practice shrewd empathy — my term describing the pragmatic practice of intentionally shifting perspectives and thinking through situations from a different point of view. 

Next time you make recommendations to the decision-makers in your organization, practice shrewd empathy: consider their perspectives and ask bigger-picture questions before you engage them in a conversation.  

Please explore other blog posts in this Success habits series.
Originally written by Aneta Key in February 2016. Last edited December 2018.