Make work a place for dreams with career conversations

Robert Holma
Daresay
Published in
6 min readAug 25, 2022

I am a Team Lead for engineers at Daresay, a business area at Knightec, focusing on customer driven digital service and product development. I am proud of our innovation culture where it is safe try and fail. Also when it comes to leadership practices I like to take this approach. Try new ideas and learn from success and failure. It makes the manager role more fun and motivating. This is one of my favourite learnings from this year.

Life stories, dreams and life goals at work

Time and time again for the yearly employee dialogue I always felt it’s hard, both my own and as a manager helping my team, to set motivating goals for the coming year(s).

  • It’s easy to identify short term competence development goals, closely align with ones current role and assignments. Usually these goals are reached by growing in the daily work, great but only within a limited horizon. They will happen or not, but isn’t very inspiring.
  • I find it much harder to identify long term goals that truly motivates to challenge one self, or really inspires to take big steps in competence or career. I haven’t met many with a clear five year plan or life goals. Those people impress and probably need less coaching.

Gladly, while reading Kim Scott’s book Radical Candor, I was inspired to try a new approach when conducting my teams yearly employee goal talk. Inspired to put personal growth and organisational goals into the context of individual life stories and dreams. Called a Career Conversation. This felt like a method that, without too much effort, could give an opportunity to identify goals that inspires and matters in the employees life and career.

This is how we did it and what we learnt.

Career Conversation

Helping each person on your team grow in the direction of their dreams is part of being a kick-ass boss, and it’s the key to successful growth management.

Kim Scott

Instead of just having one goal talk, we split into three;

  • The life story of the employee
  • Dreams for the future
  • Goals for the coming year

To not force anyone into this new format, I sold it as an experiment and made it optional. Almost everyone gave it a shot 👏🏻

1. Life story

The first talk, where employees share their life story was really exciting as a manager. Understanding the life choices people make and why, gives a deeper understanding of what they find valuable in life. Knowing this is great in future growth dialogues.

This was the meeting invite:

Career Conversations Part 1: The life story conversation

Preparation: Reflect on your life story focusing on

– What choices have you made in your life that have had impact on your career and life situation?

– Why did you make these choices?

If you want to I can share my life story as well for equal openness in our conversation. Please let me know ahead of the meeting if you want this.

After the talk, I summarised each team members life story in a timeline using pictures and emojis, like below. This was an appreciated gift and good memory support for the coming talks.

The authors life story in pictures and emojis
An example life story, actually the authors.

2. Dreams

For the second talk we dived into dreams. A challenging topic, since many of us don’t have clear dreams. But some do, and what is a dream? Big and small things. Private and professionally or a balance between both. They will probably also change over time. But by having the talk, we at least start reflecting on this and allow ourselves to start dreaming.

The meeting invite:

Career Conversations Part 2: The dreams conversation

Preparation, reflect on:

– What dreams do you have?

– What do you want to achieve in your life?

– Where do you want to be for life to be great?

– What skills and conditions would you need to reach your dreams?

Dreams can be big and small, one or many. Allow yourself to dream high. What would make you proud to achieve? If no big dreams arise, think of the smaller things that would make your life and career great.

To document the dreams shared in the session, I added them in the life story visualisation.

Dreams described in emojis attached to the persons life story.
Dreams described in emojis attached to life story.

3. Goals

The third talk, more or less the regular goal talk. But now with an input that felt much more relevant and fun to collaborate on finding goals. We use inspiration from SMART goals as a baseline for the goal setting. The goal setting is still something I want to improve and focus more on in the future. So far I really like the goal pyramid to set goals on different levels (dreams in the top!). Also consider different types of goals, like; outcome based — what do you want to achieve or process based ones — how do you get there.

Lessons learned

  • I really enjoyed listening to all different life stories in my team. I wish I had done it earlier. From now on I will ask for a life story from all new members of my team already during their onboarding. It’s such a great way to get to know someone more in depth and it improves the opportunity to be a better coach. Also, parts of my team are remote and it’s much harder to learn about each others life when not bumping into each other by the coffee machine on a daily basis. Our regular 1:1´s (most on video) doesn’t give enough room for this.
  • Not everyone had clear dreams, many people might not be dreaming much when in the middle of their career (didn’t you dream more as a kid?). But what a lovely position it is to be the employer where an employee started dreaming again and got support to move in the direction of their dreams.
  • For next year, I will re-visit the life stories and ask everyone to picture how their last year been in context of their life and dreams.
  • The simple timeline was a great way to visualise life stories and dreams and it really helped in setting relevant and motivating goals.

Impressions from the team

My team really appreciated this experiment and the way their life story was visualised. We both felt that we had more relevant background when setting goals, it will be exiting to follow which goals they achieve ahead.

One interesting team reflection was that; just by having this formal and personal way of caring for an employees life and career, makes one feel truly valued and seen. This might be an even bigger gain for well-being and retention than the actual insights found in the conversation.

Most employees won’t stay forever, but they will probably stay longer if they feel that they are on a place caring about both their long term career and private goals.

Personal dreams are important to be aware of as well. If one get support to reach them in their current workplace, that will probably stand out.

I truly recommend others to give it a try. Please share if you have any experiences with this yourself.

More reading:

Radical Candor, Kim Scott — Especially Chapter 6: Creating Growth Plans With Your Employees.

The Dream Manager, Matthew Kelly — A story about a fictional company that supports their employees personal dreams. Some food for thought.

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Robert Holma
Daresay
Editor for

Developer and Team Lead at Daresay by Knightec