Manager guide for creating calm waters with new direct reports

New Manager Career Deep Dive

Discussion and activity guides to help managers onboarding and inheriting new direct reports. Try these activities that go beyond question and answer to learn their career highlights and lowlights, their happy workplace, and their personal needs from a manager.

Schedule

1. Week 1: ☕️ Informal Coffee Hang
2. Week 2: 🤿 Career Deep Dive (Sketch Your Career Milestones & Sketch Your Happy Workplace)
3. Week 3: 🗒️ Working Together Discussion

1. Informal Coffee Hang

Schedule an informal coffee a week before the Career Deep Dive
Before kicking off the Career Milestone activity, have at least one casual coffee chat style one on one. Here’s how I describe it in the calendar invite:

☕️ Designer / Nina
Time for us to hang out and get to know each other. Calls with snacks, coffee, tea, hanging in the backyard or pets are all welcome! My calendar is up to date and this invite is modifiable by so please move this around to work best for your schedule and deep work time!

Uncover the bright points and career shadows they may be bringing into your working relationship

2. Career Deep Dive

Calendar Invite Template

Title: 🤿 [Name] Career Deep Dive
Duration: 50 Minutes

Description: Now that we’ve had time to get to know each other on a personal level, I’d like to learn about your your experience working at [Company]. During this activity you’ll be sketching a timeline of your time at Faire, tracking major milestones, both the highs and lows, and daydreaming about your fantasy dream happy workplace. You don’t need to prepare any materials in advance, but it may help to review recent performance reviews and 1:1 notes as guideposts.

Setup: 10 Min
Meetings tend to start late so realistically set aside 5 minutes for that and another 5 to settle in, lay out supplies, ‘elevator/weather chat’.

Introduction (5 Minutes)

Now that we’ve had time to get to know each other on a personal level, I’d like to learn about your your experience working [‘at this company’ or ‘at your last job’]. I’ll be looking to learn about your major milestones at Faire and what is your happiest workplace. The primary goal of this activity is for me to learn about your experience not to evaluate your performance, or you as an artist.

Why are we sketching? Sketching activates visual, kinesthetic, auditory, and linguistic skills. Since we’re activating multiple parts of your mind, you’ll have different outputs than having a conversation, typing, or writing on sticky notes. And sharpies and letter paper are also intentionally imprecise!

Reflection on the highs and lows of their career

2a. Career Milestone Activity Guide (20 Minutes)

1. Draw a horizontal line across the page. Mark your start date on the left, and today on the right

2. Draw a smiley face above the line and a sad or frustrated face below the line

3. Draw 3 dots on your timeline and label them above the timeline with your top 3 big wins at Faire — they can be product launches, ah-ha moments, customer insights, team activity, or even day you had a hilarious moment with a work best friend!

4. Now draw 3 more dots on your timeline and label them below the timeline. These are low, challenging, frustrating, or deeply tiring moments. This lets me anticipate needs for you so we don’t repeat those in the future!

5. Discuss

If you could work anywhere, in any way, what would it be?

2b. Sketch Your Happy Workplace (20 Minutes)

The next activity is a futurespective in which individuals on your team sketch themselves happiest at work. By imagining the future, this helps individuals implicitly create a response from current pains, unmet desires, and explicitly shows the future matters. Sketching also brings a relaxing and expressive activity for teams that usually talk, listen, or write during meetings. See also the Sketch Your Happy Workplace facilitation guide to run this activity for large teams.

1. Present the sketching prompt

Now we’ll take out a new sheet of paper. We’re going to do an activity where you get to think about yourself happiest at work. By the end we’ll have a better shared idea of what you need on this team. The only constraints are this sheet of paper and a sharpie. You can be as fantastical as you want. You can be in underwater or in outer space! I’m going to set a timer for 10 minutes.

Use this time to draw yourself happiest at work. Where are you? Who are you with? What’s on your desk? Do you even have have a desk? What’s on your desk? Do you have a desk? What do you hear? What do you see around you? What are you thinking about? What are you working on?

2. Set a timer for 10 minutes
I schedule in a buffer time here so they can take an extra 5 minutes if needed. I like to play some relaxing music during this time. Sometimes I even step away.

3. Discuss
Invite your new hire to share their drawing with you. Use the visuals as probes to understand their ideal working styles.

2c. Reflection

Set aside time to put sharpies down and reflect on both activities. As a manager reflect back what you learned and heard to help both of you internalize the insights. Then, each person should take a photo of each sheet of paper for their personal archives.

How were those activities for you? Is there anything you think we didn’t cover that we should talk about next time? In our next one-on-ones I’ll be learning more about how you like to work and be supported, so we’ll have plenty of time to get to that.

Bring all the experiences from the past together with the present

3. Followup ‘Working Together’ Discussion

Setup time the following week to get to know each other on a professional level. If you have a personal ‘readme’ document, this is a great pre-read to send out before your Working Together meeting.

Title: 🗒️ [Designer/ Nina — Working Together]
Duration: 30Minutes
Description: time to get to know each other in a work context:
Nina’s “housekeeping topics”
What do you want/need from a manager at [Company]?
Your experiences with managers in the past (good, bad, confusing)
How do you like to get feedback?
Your questions for me

Preread: Working with Nina
This doc is an aspirational description of how I’d like to lead my teams and work toward’s my company’s mission. You, the designers on my team, are the audience. I hope this doc helps you know what I’m striving for and so you can give me feedback to help me get there. I’m interested in all ways I can raise the quality bar of my own work to serve you better.