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  • Jessie Brennan, MPH

Using Hindsight to See the Path Forward: Tapping into Staff Self-Awareness for Career Development

Updated: Apr 29, 2022

The truth that we cannot separate our work selves from our personal selves was made very clear to all of us over the past two years, as work and personal lives collided. As leaders, you were asked to support employees through the full range of their work-life issues, including job flexibility, remote work, hybrid work, and child care challenges- and you did it, despite facing all of those challenges yourself. I hope that you and your teams are still endlessly proud of yourselves for continuing your incredibly important work through some truly hard times.

If you are like me, you developed a love/hate relationship with Zoom over this period. Hours-long meetings on camera never got easier, but I will always appreciate the humanity the cameras caught during those meetings. I personally enjoyed every moment of household chaos that we caught a glimpse of- dogs barking, kids climbing into laps, household members trying to quickly get out of frame. You can’t help but bring your whole self to work when work is happening in your kitchen.

The importance of being able to bring your “whole self” to work has become a hot topic in the management literature. It turns out that being able to present your true, authentic, whole self in the workplace is one of the keys to workplace engagement. How do we develop workplaces that honor each employee’s whole self? It starts with developing our employees themselves.

Career development conversations are key to helping employees develop both themselves, and their roles, in a way that highlights their strengths, interests, and values. Bringing this invaluable information to the surface involves facilitating hindsight conversations. A hindsight conversation is a look backward to develop an understanding of such things as where employees have been, what they love, and what they’re good at.

Hindsight Conversations

Hindsight conversations are based around past experiences, but shine a light on the future. They are designed to spark thinking, encourage connections, and promote discovery. They provide invaluable information about the path forward to both the employee and you. Where have they been? What do they value? What gets them to work every day?

Clarity around these key factors is the foundation of career development:

  • Skills and strengths—what they’re good at

  • Values—what’s most important

  • Interests—what keeps them engaged

  • Dislikes—what they want to steer clear of

  • Preferences—how they like to work

  • Weaknesses—what they struggle with

Helping your staff members look back (and inward) provides a wealth of information that they may not have been consciously aware of. As an understanding about these things grows, people start to see a clearer picture of their lives and who they are. This allows them to move forward and toward their career goals in intentional ways that will produce satisfying results.

The benefits of these conversations go beyond team members developing new, more intentional goals. They satisfy a fundamental human need to know ourselves and be known by others. Greater personal insight can’t help but spill over into day-to-day work, improving relationships, performance, and results. It starts to seep out into one’s personal life—enhancing that as well.

Hindsight conversations are good for the whole person.


Hindsight conversations don’t need to be long or take a lot of planning time. One approach is to close out every quarter with brief employee checkups or check-ins. The purpose of these conversations is not to evaluate performance over the past quarter, rather, the goal is to diagnose what’s going on in the employee’s heart and head.

Put performance entirely aside and ask questions like these:

  • What was the best part of the quarter for you?

  • What work did you find most satisfying?

  • How often were you stretched, and how did that feel?

  • At what points did you feel your energy and engagement lagging?

I suggest providing these questions to staff members ahead of time, so that they are able to really reflect on the answers before your conversation. Make this a habit, and at least four times each year you’ll help employees turn their day-to-day experiences into profound self-awareness that can inform career decisions—and a lot more.


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